Lenny's Podcast: Product | Career | Growth

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad). In our in-depth conversation, Keith shares: 1. The barrels vs. ammunition hiring framework (and how to spot barrels) 2. Why talking to customers is actively harmful for consumer products 3. How to identify undiscovered talent 4. Why the PM role is dying 5. The three traits of the best-performing companies right now 6. The specific interview question he asks every senior candidate 7. Why CMOs (not engineers) are becoming the #1 consumer of tokens — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Keith Rabois: • X: https://x.com/rabois • LinkedIn: linkedin.com/in/keith • Website: https://www.khoslaventures.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Keith Rabois (01:59) Why Keith hasn’t used a computer since 2010 (04:52) The team you build is the company you build (07:40) How Keith learned to identify talent at PayPal (10:05) Tactics for getting better at hiring (15:31) The barrels vs. ammunition framework (18:52) What makes someone a barrel (22:36) How to attract the best talent (26:18) Building companies on undiscovered talent (27:53) Why better performance requires more pressure (32:36) Career advice in the age of AI (35:14) The future of the product triad (41:03) Why design and code are merging (49:35) What practicing law taught Keith about entrepreneurship (51:22) Contrarian takes on customer feedback (1:02:33) Identifying great AI opportunities (1:05:13) Advice for evaluating statrups  (1:12:36) Criticizing in public vs. private (1:15:05) Failure corner (1:17:29) Lightning round — Referenced: • Square: https://squareup.com • Jack Dorsey on X: https://x.com/jack • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • Simon Willison’s Weblog: https://simonwillison.net • Vinod Khosla on X: https://x.com/vkhosla • Peter Thiel on X: https://x.com/peterthiel • Max Levchin on X: https://x.com/mlevchin • David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks • Tony Xu on X: https://x.com/t_xu • David Sze on X: https://x.com/davidsze • Faire: https://www.faire.com • Max Rhodes on X: https://x.com/MaxRhodesOK • Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson • Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois • Lattice: https://lattice.com • Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640 • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights • Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs) • Eric Glyman on X: https://x.com/eglyman • Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177 • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html • Opendoor: https://www.opendoor.com • The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q • Lovable: https://lovable.dev • The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Jeremy Stoppelman on X: https://x.com/jeremys • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol • Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms • Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway • William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare • Evan Moore on X: https://x.com/evancharles • Andrew Mason on X: https://x.com/andrewmason • Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941 • The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16 • How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden • Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred • Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000 • Jon Chu on X: https://x.com/jonchu • Kanu Gulati on X: https://x.com/KanuGulati • Rogo: https://rogo.ai • Profound: https://www.tryprofound.com • Basis: https://www.getbasis.ai • Spellbook: https://www.spellbook.legal • Roelof Botha on X: https://x.com/roelofbotha • Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742 • Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1 • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp • Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4 • Eight Sleep: https://www.eightsleep.com • “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224 — Recommended books: • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012 • The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666 • The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Amol Avasare is Head of Growth at Anthropic, which is going through the most unprecedented growth trajectory in history—scaling from $1 billion to over $19 billion in ARR in just 14 months. Previously, Amol worked on the growth teams at Mercury and MasterClass. Before that he was a founder, and he cold emailed his way into the Anthropic role when no job listing existed. Most remarkably, he overcame a traumatic brain injury from a Muay Thai match that meant he couldn't work for nearly a year. In our in-depth discussion, Amol shares: 1. How Amol landed his role by cold emailing Anthropic’s CPO Mike Krieger 2. How Anthropic is automating growth experiments with Claude (their internal tool called “CASH”) 3. Why the ratio of PMs to engineers might need to flip (more PMs than engineers) as AI makes engineers exponentially more productive 4. Why activation is the single highest-leverage growth problem in AI 5. Why Anthropic indexes 70/30 toward big bets (the opposite of most growth teams) 6. How he uses Cowork to detect team misalignment in Slack 7. How the company’s focus on AI coding created a research flywheel that accelerated their models — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Amol Avasare: • X: https://x.com/TheAmolAvasare • LinkedIn: https://www.linkedin.com/in/amolavasare — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Amol and Anthropic’s growth (03:15) The story of cold emailing Mike Krieger to get the job (08:28) What it’s like leading growth at the fastest-growing company ever (10:46) What the growth team actually does at Anthropic (12:16) The concept of “success disasters” (13:55) Why activation is the biggest challenge in AI products (18:05) Improving Mercury’s onboarding experience (20:57) The importance of adding the right kind of friction (25:10) Anthropic’s org structure (27:06) Why Anthropic focuses on big bets over micro-optimizations (33:34) Automating growth experiments with Claude (CASH) (38:20) How AI is starting to identify what experiments to run (41:07) The future of PM, engineering, and design roles (47:19) Why you might need more PMs as engineers get more productive (51:13) How Amol uses AI to prototype ideas and skip PRDs (58:10) Amol’s morning routine: AI analyzes 20 to 25 charts automatically (1:03:31) Getting coaching from an AI version of your manager (1:06:27) How Anthropic’s focus on coding and B2B drove their success (1:12:10) Balancing growth with AI safety as a core mission (1:18:09) Advice for thriving in an AI-first future (1:22:53) Anthropic’s culture and the “notebook channels” on Slack (1:35:12) Failure corner: Shutting down his startup after raising money (1:38:25) The traumatic brain injury that changed everything (1:46:49) Lightning round — References: https://www.lennysnewsletter.com/p/anthropics-1b-to-19b-growth-run — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Simon Willison is a prolific independent software developer, a blogger, and one of the most visible and trusted voices on the impact AI is having on builders. He co-created Django, the web framework that powers Instagram, Pinterest, and tens of thousands of other websites. He coined the term “prompt injection,” popularized the terms “AI slop” and “agentic engineering,” and has built over 100 open source projects, including Datasette, a data analysis tool used by investigative journalists worldwide. What makes Simon unique is that he’s made the leap from traditional software engineering to AI-native development more fully and visibly than almost anyone—and he’s been documenting everything he learns in real time on his blog, SimonWillison.net. In our in-depth conversation, Simon shares: 1. Why November 2025 was the inflection point when AI coding agents crossed from “mostly works” to “actually works” 2. How Simon writes 95% of his code from his phone now and why he’s mentally exhausted by 11 a.m. 3. Why mid-career engineers (not juniors) are most at risk right now 4. The three agentic engineering patterns Simon uses daily (red/green TDD, templates, hoarding) 5. The next leap: the “dark factory” pattern where nobody writes or reviews code and AI does its own QA 6. Why prompt injection is an unsolved security problem and the “lethal trifecta” that will likely lead to an AI Challenger disaster 7. Why the pelican riding a bicycle became the unofficial benchmark for AI model quality — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Simon Willison: • X: https://x.com/simonw • LinkedIn: https://www.linkedin.com/in/simonwillison • Website: https://simonwillison.net • Agentic Engineering Patterns: https://simonwillison.net/guides/agentic-engineering-patterns — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Simon Willison (02:40) The November 2025 inflection point (08:01) What’s possible now with AI coding (10:42) Vibe coding vs. agentic engineering (13:57) The dark-factory pattern (20:41) Where bottlenecks have shifted (23:36) Where human brains will continue to be valuable (25:32) Defending of software engineers (29:12) Why experienced engineers get better results (30:48) Advice for avoiding the permanent underclass (33:52) Leaning into AI to amplify your skills (35:12) Why Simon says he’s working harder than ever (37:23) The market for pre-2022 human-written code (40:01) Prediction: 50% of engineers writing 95% AI code by the end of 2026 (44:34) The impact of cheap code (48:27) Simon’s AI stack (54:08) Using AI for research (55:12) The pelican-riding-a-bicycle benchmark (59:01) The inherent ridiculousness of AI (1:00:52) Hoarding things you know how to do (1:08:21) Red/green TDD pattern for better AI code (1:14:43) Starting projects with good templates (1:16:31) The lethal trifecta and prompt injection (1:21:53) Why 97% effectiveness is a failing grade (1:25:19) The normalization of deviance (1:28:32) OpenClaw: the security nightmare everyone is looking past (1:34:22) What’s next for Simon (1:36:47) Zero-deliverable consulting (1:38:05) Good news about Kakapo parrots — References: https://www.lennysnewsletter.com/p/an-ai-state-of-the-union — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Claire Vo is the host of our sister podcast, “How I AI,” a former product executive and engineer, and founder of an AI startup called ChatPRD. Claire now runs her business, podcast, and family life with the help of nine OpenClaw agents running on multiple Mac Minis and old laptops. In this episode, Claire shares her journey from OpenClaw skeptic (it deleted her family calendar the first time she tried it) to true believer, and gives a masterclass in using AI agents in real life. We discuss: 1. The exact step-by-step process to install and set up OpenClaw (it’s easier than you think) 2. How to avoid the biggest OpenClaw mistakes (don’t install it on your main computer) 3. Actual use cases that have changed Claire’s life (e.g. family scheduling, inbound sales, podcast prep, and course management) 4. Why multiple specialized agents beat one general-purpose agent 5. The security risks everyone worries about—and how to handle them 6. Browser limitations, memory issues, and practical workarounds — Brought to you by: Mercury—Radically different banking Omni—AI analytics your customers can trust Orkes—The enterprise platform for reliable applications and agentic workflows — Where to find Claire Vo: • X: https://x.com/clairevo • LinkedIn: https://www.linkedin.com/in/clairevo • Podcast: https://www.youtube.com/@howiaipodcast • Website: https://clairevo.com • ChatPRD: https://www.chatprd.ai — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Claire and OpenClaw (08:00) The journey from OpenClaw skeptic to believer (11:50) What OpenClaw actually does that’s useful (13:35) OpenClaw vs. other AI agent products (17:05) How to actually install OpenClaw: the basics (18:49) Setting up like you’d onboard a real assistant (20:41) Security and privacy considerations (24:53) Live demo: Installing OpenClaw step-by-step (28:47) Setting up Q: an agent for her kids’ homework (34:08) Understanding “soul,” “identity,” and “memory” (40:40) The unlock: multiple agents, not just one (45:02) How to run multiple agents on one machine (47:28) Jesse Genet’s homeschooling use case (49:58) Real examples and use cases (56:41) Finn, Claire’s family agent (1:00:05) Sage the Course Bot (1:02:15) Common issues and workarounds (1:08:08) The Exa/Perplexity web search workaround (1:09:29) Memory management and context overload (1:12:09) Pro tip: Screen sharing to manage Mac Minis (1:14:18) Using Google Workspace for agent collaboration (1:16:24) What makes OpenClaw special (1:20:15) The “yappers API” and ramble mode (1:22:04) Using Claude Code as your OpenClaw brain surgeon (1:25:16) Bringing management skills to AI agents (1:29:32) Why this matters (1:32:37) Lightning round and final thoughts — Referenced: • OpenClaw: https://openclaw.ai • Claude Cowork: https://claude.com/product/cowork • Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics • Peter Steinberger on LinkedIn: https://www.linkedin.com/in/steipete • Telegram: https://telegram.org • WhatsApp: https://www.whatsapp.com • Fin: https://fin.ai • Why OpenClaw feels alive even though it’s not (this AI has a heartbeat but not a brain): https://x.com/clairevo/status/2017741569521271175 • 5 OpenClaw agents run my home, finances, and code | Jesse Genet: https://www.youtube.com/watch?v=96Vl8s3EQhk • Executive Playbook for AI in Engineering, Product, and Design: https://maven.com/clairevo/ai-native-epd-org • Zach Davis on LinkedIn: https://www.linkedin.com/in/zach-m-davis/ • ChatGPT Atlas: https://chatgpt.com/atlas • Perplexity Comet: https://www.perplexity.ai/comet • Browser (OpenClaw-managed): https://docs.openclaw.ai/tools/browser • Buffer: https://buffer.com • Brave: https://brave.com/search/api/ • Exa: https://exa.ai • Hilary Gridley on X: https://x.com/yourgirlhils • How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with • How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.youtube.com/watch?v=xDMkkOC-EhI • How to debug a team that isn’t working: the Waterline Model: https://www.lennysnewsletter.com/p/how-to-debug-a-team-that-isnt-working • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang • How I built a 1M+ subscriber newsletter and top 10 tech podcast | Lenny Rachitsky: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter • Age of Attraction on Netflix: https://www.netflix.com/title/81779095 • Oura Ring: https://ouraring.com/ • Eight Sleep: https://www.eightsleep.com • Hoopsalytics: https://hoopsalytics.com • DJI Osmo smartphone gimbal: https://www.amazon.com/DJI-Stabilizer-Tracking-Extension-Stabilization/dp/B0FJ2L67HJ?ref_=ast_sto_dp • Silent basketball: https://www.amazon.com/Rzkipdy-Silent-Basketball-Size-27-5/dp/B0FHFSQWPP/ref=sr_1_9 • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom — Recommended books: • Treasure Island: https://www.amazon.com/Treasure-Island-Robert-Louis-Stevenson/dp/1505297400 • Alice’s Adventures in Wonderland: https://www.amazon.com/Alices-Adventures-Wonderland-Illustrated-Illustrations/dp/991673268X • Charts for Babies: A Picture Book: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process. We discuss: 1. Why great ideas often don’t get buy-in 2. Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much 3. Why executives are usually optimizing for a global maximum while you are often optimizing locally 4. The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?” 5. Why you should go in to learn, not to convince 6. Why showing only one option is a mistake 7. Why AI will make influence more important, not less — Brought to you by: Omni—AI analytics your customers can trust Lovable—Build apps by simply chatting with AI Vanta—Automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-art-of-influence-jessica-fain — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jessica Fain: • LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jessica Fain (03:53) Why influence is the highest-leverage skill in product (04:47) Why great ideas fail without executive buy-in (06:00) How executives actually think (09:05) The fundamentals: context-setting, communication, and empathy (10:22) Stop pitching for approval—start co-creating with execs (12:59) Influence vs. politics (and why people get it wrong) (15:44) How to disagree with execs without losing trust (17:20) Going in to learn, not to convince (19:08) How to present ideas (26:05) The Minto-style approach and tailoring your communication to each exec (28:22) Why Jessica doesn’t like the question “What’s top of mind for you?” (30:24) Understanding incentives to unlock buy-in (32:10) Aligning product work with company strategy (35:10) Quick summary (37:31) Disarming the executive (40:49) Speed matters: why fast follow-up builds momentum (43:32) How to run high-impact meetings (the 60-second rule) (47:00) Why influencing execs is part of your job (49:15) Asking for more resources and thinking in 10x bets (52:23) What to do when your idea gets rejected (54:18) Clarifying information (56:50) How to build trust and make ideas stick (58:30) Shrinking big ideas into experiments (01:02:27) Common mistakes people make when influencing leaders (01:06:00) How to grow into your next role (01:09:32) How AI is changing influence and product work (01:17:55) Using AI to simulate exec feedback and improve pitches (01:21:15) Protecting our brains from overwhelm (01:22:44) Lightning round and final thoughts — Referenced: • Box: https://www.box.com • Slack: https://slack.com • Brightwheel: https://mybrightwheel.com • Webflow: https://webflow.com • April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood • Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua • Atlassian: https://www.atlassian.com • Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid • Calendly: https://calendly.com • Glassdoor: https://www.glassdoor.co.in/index.htm • The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai • Ethan Eismann on X: https://x.com/eeismann • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield • Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank • Checkr: https://checkr.com • Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl • Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan • How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief • Barbara Minto’s website: https://www.barbaraminto.com • How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2 • Casa: https://getcasa.com • Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix • Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles) — Recommended books: • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061 • A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243 • The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jacob Warwick is an executive negotiation coach who helps senior operators negotiate better salary, equity, titles, and severance packages. He has worked with leaders across tech and Hollywood, was previously a founder and CEO himself, and has helped clients secure millions in additional compensation. His approach focuses on collaboration over confrontation, understanding motivations, and treating job searches like enterprise sales processes. We discuss: 1. Why a simple “What’s the chance there’s a little more here?” often unlocks a 20% bump 2. Why Jacob sees 40% average movement when negotiations are run well 3. When negotiation actually starts (hint: it’s much earlier than you think) 4. Why information + timing create power 5. The biggest mistakes people make when negotiating 6. How to navigate the important “What’s your comp expectation?” question without anchoring too low 7. Why the best interviews feel more like discovery calls than interrogations — Brought to you by: Orkes—The enterprise platform for reliable applications and agentic workflows Mercury—Radically different banking Omni—AI analytics your customers can trust — Episode transcript: https://www.lennysnewsletter.com/p/the-tactical-playbook-for-getting-more-comp — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jacob Warwick: • Substack: https://www.execsandthecity.com • YouTube: https://www.youtube.com/@ExecsandtheCity • Website: https://www.thinkwarwick.com • Complete Job Search Course: https://www.execsandthecity.com/p/complete-job-search-course — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jacob Warwick (04:12) How much comp people leave on the table (07:52) Why you shouldn’t feel greedy asking for more (09:45) What founders should know about negotiation (13:03) How Jacob works behind the scenes (15:35) The biggest mistakes people make when negotiating (19:30) Home-field advantage and controlling the conversation (23:02) The step-by-step approach to negotiating an offer (30:17) Jacob’s passion and why these tips don’t work on kids (32:04) Who should speak first about compensation (35:36) Understanding power (39:52) Breaking out of salary bands by focusing on pain points (45:45) Brief summary (47:20) Selling the vacation: How to visualize success (50:07) Controlling the narrative and planting seeds (59:01) Jacob’s role as hype man (01:01:05) Positioning yourself like a product (01:02:49) Making the process frictionless for hiring managers (01:06:20) Flipping the interview to extract information (01:12:17) Five tactical tips for negotiating comp (01:21:45) What to do when negotiations fall apart (01:25:05) Why negotiation is different for every individual (01:28:55) Why outcomes aren’t predetermined (01:32:52) Wild Hollywood negotiation stories (01:37:35) The first step you should take after getting an offer (01:40:30) Jacob’s personal mission (01:44:42) Lightning round and final thoughts — Referenced: • The ultimate guide to negotiating your comp: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-negotiating • Sam Altman on X: https://x.com/sama • Tom Brady on X: https://x.com/TomBrady • Career Huddle: Interview & Negotiation Master Class with Jacob Warwick: https://www.youtube.com/watch?v=TgjWTiSj8E8 • Salesforce: https://www.salesforce.com • Julia Roberts: https://en.wikipedia.org/wiki/Julia_Roberts • Matt Damon: https://en.wikipedia.org/wiki/Matt_Damon • Steven Spielberg: https://en.wikipedia.org/wiki/Steven_Spielberg • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Chris Voss’s quote: https://www.goodreads.com/quotes/10181396-remember-never-be-so-sure-of-what-you-want-that • Chris Voss on X: https://x.com/fbinegotiator • Werewolf: https://playwerewolf.co • Modes of persuasion: https://en.wikipedia.org/wiki/Modes_of_persuasion • How to use tactical empathy: https://www.linkedin.com/posts/christophervoss_tacticalempathy-negotiation-customerexperience-activity-7361004118808670212-oeRy • ZOPA, BATNA and Win-Win in Negotiation: https://www.parallelprojecttraining.com/blog/zopa-batna-and-win-win-in-negotiation • Marvel: https://www.marvel.com • Negotiation Made Simple podcast: https://www.buzzsprout.com/2227030 • Luca on Disney+: https://www.disneyplus.com/browse/entity-f28b825f-c207-406b-923a-67f85e6d90e0 • Minuscule: https://www.youtube.com/user/Minuscule • Claude Cowork: https://claude.com/product/cowork • Macrofactor: https://macrofactor.com • Whoop: https://www.whoop.com • Gemini: https://gemini.google.com/app • The Cody Dieruf Foundation: https://breathinisbelievin.org • Cystic Fibrosis Foundation: https://www.cff.org — Recommended books: • Negotiation Games: https://www.amazon.com/Negotiation-Games-Routledge-Advances-Theory/dp/0415308941 • Influence: The Psychology of Persuasion: https://www.amazon.com/Influence-Psychology-Persuasion-Robert-Cialdini/dp/006124189X • You Can Negotiate Anything: How to Get What You Want: https://www.amazon.com/You-Negotiate-Anything-Herb-Cohen/dp/0806541229 • Negotiation Made Simple: A Practical Guide for Solving Problems, Building Relationships, and Delivering the Deal: https://www.amazon.com/Negotiation-Made-Simple-Relationships-Delivering/dp/1400336325 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

People have been asking me to sit on the other side of the mic for a long time. With my wife’s debut children’s book, Charts for Babies, coming out next month, we figured: why not do it together? What followed was one of the most honest conversations I’ve had on this podcast. Michelle asked things no one else would think to ask—and many things I’ve never shared publicly. You’ll hear about the specific moments that pushed me to start the newsletter, how I think about quality and iteration, what most stresses me out, and the scariest moment of my life. This was so fun, and so special, and I hope you like it. We discuss: 1. The collection of moments that led me to what I do now 2. When I added a paywall, and how I knew it was working 3. The hidden treadmill behind shipping a newsletter post and podcast episode every week 4. The most stressful moments I’ve had in business and in life 5. How I think about stress, consistency, and keeping the business small — Pre-order Charts for Babies: https://www.amazon.com/Charts-Babies-Picture-Book/dp/1419785184 — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Metaview—The AI platform for recruiting: https://metaview.ai/lenny DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Michelle Rial: • X: https://x.com/TheRialMichelle • LinkedIn: https://www.linkedin.com/in/michellerial • Website: https://www.michellerial.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction and role reversal (04:06) What would Lenny be doing without the newsletter? (07:20) The moments that led to starting the newsletter (09:58) Does Lenny still enjoy the work? (12:42) Stress management and misophonia (14:00) The psychedelic trip that changed everything (15:45) Online happiness course and baseline optimization (17:30) Thunder round: Lenny’s misophonia worst sounds (20:20) What makes Michelle’s charts so shareable (23:55) Where chart ideas come from (and why meditation helps) (26:59) Where does “Lenny” come from? (28:54) Being recognized in public (31:24) Early projects (36:30) Michelle and Lenny’s yin and yang (37:49) Missing office culture (but not really) (39:37) Lenny’s face blindness (40:47) The $100M fraud attack story (42:50) Michelle’s childbirth emergency (47:22) Michelle’s creative process (51:58) Lenny’s favorite children’s books (54:00) Product management lessons in parenting (55:31) Defining product management in five words (58:23) Why Michelle pivoted to children’s books (01:01:30) The power of iteration and real experience — Resources and episode mentions: https://www.lennysnewsletter.com/p/how-i-built-a-1m-subscriber-newsletter — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. To hear more, visit www.lennysnewsletter.com

Qasar Younis is the co-founder and CEO of Applied Intuition, a $15 billion AI company that adds intelligence to cars, tractors, planes, submarines, and other vehicles—essentially, Tesla or Waymo without the hardware. He was previously COO of Y Combinator, started his career as an engineer at GM and Bosch, and was born on a farm in Pakistan. We discuss: 1. Why the biggest AI revolution will play out in mining, farming, construction, and trucking over the next 5 to 10 years, not in software 2. Why Qasar intentionally stayed under the radar for nearly a decade while building Applied Intuition, and why most founders shouldn’t do that 3. The truth about China’s AI capabilities and why comparisons to American companies are fundamentally flawed 4. The company values that drive Applied Intuition: speed above everything, laugh a lot, half the work is follow-up, never disappoint the customer 5. The biggest lessons from Qasar’s stint as YC’s COO, including that the most successful companies show traction very early 6. How reading old books is the best way to build taste — Brought to you by: Omni—AI analytics your customers can trust Vanta—Automate compliance. Simplify security. Lovable—Build apps by simply chatting with AI — Episode transcript: https://www.lennysnewsletter.com/p/the-most-successful-ai-company-youve-never-heard-of — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Qasar Younis: • X: https://x.com/qasar • LinkedIn: https://www.linkedin.com/in/qasar • Website: https://qy.co • Reading list: https://qy.co/books — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Qasar and Applied Intuition (04:01) The optimistic vision: How AI will create abundance (08:49) Why anxiety about AI comes from misunderstanding—and how to fight fear with knowledge (12:58) The market sell-off explained (16:31) Self-driving cars: Why 30,000 annual deaths prove we need autonomy now (20:22) The spectrum of physical AI (28:00) How AI is coming just in time (33:26) Why comparing Chinese AI companies to American AI companies is a category error (39:12) Why Qasar finally joined Twitter after staying silent for a decade (45:08) Why successful companies almost always show early signs of traction (50:40) Applied Intuition’s core values (56:00) Why the company cleans its own office—and never spent a dollar of raised capital (58:50) Quasar’s reading philosophy (01:06:14) How to operationalize listening to naysayers (01:12:53) The importance of decisiveness (01:14:55) Removing emotions from decisions (01:19:02) Why most Silicon Valley CEOs don’t have great taste—and how to develop it — Referenced: • Applied Intuition: https://www.appliedintuition.com • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Elad Gil’s website: https://eladgil.com • Bosch: https://www.bosch.com • Berkshire Hathaway: https://www.berkshirehathaway.com • Naval Ravikant on X: https://x.com/naval • Y Combinator: https://www.ycombinator.com • Waymo: https://waymo.com/ • Tesla: https://www.tesla.com • DeepSeek: https://www.deepseek.com • Rivian: https://rivian.com • Crate & Barrel: https://www.crateandbarrel.com • OpenClaw: https://openclaw.ai • Sam Altman on X: https://x.com/sama • Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig • What Steve Jobs really meant when he said ‘Good artists copy; great artists steal’: https://www.cnet.com/tech/tech-industry/what-steve-jobs-really-meant-when-he-said-good-artists-copy-great-artists-steal • 7 quotes on the power of reading from Charlie Munger: https://www.neil.blog/articles/7-quotes-power-reading-charlie-munger • Andreessen Horowitz: https://a16z.com • John Doerr on LinkedIn: https://www.linkedin.com/in/john-doerr-03248211 • Gandhi’s quote: https://www.azquotes.com/author/5308-Mahatma_Gandhi/tag/truth#google_vignette • Steve Ballmer on X: https://x.com/Steven_Ballmer • General Motors: https://www.gm.com — Recommended books: • House of Huawei: The Secret History of China’s Most Powerful Company: https://www.amazon.com/House-Huawei-History-Powerful-Company/dp/0593544633 • Maintenance: Of Everything, Part One: https://press.stripe.com/maintenance-part-one • The Autobiography of Malcolm X: As Told to Alex Haley: https://www.amazon.com/Autobiography-Malcolm-Told-Alex-Haley/dp/0345350685 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916 • Made in America: https://www.amazon.com/Sam-Walton-Made-America/dp/0553562835 • My American Journey: https://www.amazon.com/American-Journey-Autobiography-Colin-Powell/dp/0679432965 • Guns, Germs, and Steel: The Fates of Human Societies: https://www.amazon.com/Guns-Germs-Steel-Fates-Societies/dp/0393317552 • Collapse: How Societies Choose to Fail or Succeed: https://www.amazon.com/Collapse-Societies-Choose-Succeed-Revised/dp/0143117009 • SPQR: A History of Ancient Rome: https://www.amazon.com/SPQR-History-Ancient-Mary-Beard/dp/0871404230 • A World Appears: A Journey into Consciousness: https://www.amazon.com/World-Appears-Journey-into-Consciousness/dp/198488199X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jenny Wen leads design for Claude at Anthropic. Prior to this, she was Director of Design at Figma, where she led the teams behind FigJam and Slides. Before that, she was a designer at Dropbox, Square, and Shopify. — We discuss: 1. Why the classic discovery → mock → iterate design process is becoming obsolete 2. What a day in the life of a designer at Anthropic looks like, including her AI tool stack 3. Whether AI will eventually surpass humans in taste and judgment 4. Why Jenny left a director role at Figma to return to IC work at Anthropic 5. The three archetypes Jenny is hiring for now 6. Why chatbot interfaces may be more durable than most people expect — Brought to you by: Mercury—Radically different banking: https://mercury.com/?utm_source=lennys&utm_medium=sponsored_newsletter&utm_campaign=26q1_brand_campaign Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Omni—AI analytics your customers can trust: https://omni.co/lenny — Episode transcript: https://www.lennysnewsletter.com/p/the-design-process-is-dead — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jenny Wen: • X: https://x.com/jenny_wen • LinkedIn: https://www.linkedin.com/in/jennywen • Substack: https://jennywen.substack.com • Website: https://jennywen.ca — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jenny Wen (04:23) Why the traditional design process is dead (06:33) The two new types of design work (10:00) How widespread this shift will be (13:00) Day-to-day life as a designer at Anthropic (18:45) Jenny’s AI stack (20:03) Why Figma still matters for exploration (22:25) Advice for working with engineers (24:19) How to maintain craft, quality, and trust in the AI era (27:35) Will AI ever have “taste”? (31:38) The future of chatbot interfaces (35:33) Moving from director back to IC (41:00) The 10-day build of Claude Cowork (46:06) Hiring: the three archetypes (50:44) Advice for new and senior designers (54:42) The value of “low leverage” tasks for managers (57:52) Why the best teams roast each other (01:01:45) The legibility framework (01:07:22) Lightning round and final thoughts — Referenced: • Figma: https://www.figma.com • Anthropic: https://www.anthropic.com • v0: https://v0.app • Navigating a Design Career with Jenny Wen | Figma at Waterloo: https://www.youtube.com/watch?v=OHcBPMh2ivk • Claude Cowork: https://claude.com/product/cowork • Use Claude Code in VS Code: https://code.claude.com/docs/en/vs-code • Claude Code in Slack: https://code.claude.com/docs/en/slack • Lex Fridman’s website: https://lexfridman.com • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • OpenClaw: https://openclaw.ai • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Socratica: https://www.socratica.info • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Evan Tana’s ‘legibility matrix’ on X: https://x.com/evantana/status/1927404374252269667 • How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early • Palantir: https://www.palantir.com • Stripe: https://stripe.com • Linear: https://linear.app • Notion: https://www.notion.com • Julie Zhuo’s website: https://www.juliezhuo.com • Sentimental Value: https://www.imdb.com/title/tt27714581 • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Noah Wyle: https://en.wikipedia.org/wiki/Noah_Wyle • ER on Prime Video: https://www.amazon.com/gp/video/detail/B0FWZSDYRP • Retro: https://retro.app • Granola: https://www.granola.ai — Recommended books: • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • The Power Broker: Robert Moses and the Fall of New York: https://www.amazon.com/Power-Broker-Robert-Moses-Fall/dp/0394480767 • Insomniac City: New York, Oliver Sacks, and Me: https://www.amazon.com/Insomniac-City-New-York-Oliver/dp/162040494X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jeetu Patel is the president and chief product officer at Cisco, where he leads a team of 30,000 people and is playing a central role in the massive AI infrastructure buildout happening right now. Previously, he spent five years as CPO at Box and 17 years running his own startup. Recently Jeetu organized an AI summit featuring industry leaders like Jensen Huang, Sam Altman, Marc Andreessen, and Fei-Fei Li. We discuss: 1. How Cisco went AI-first across 90,000 employees 2. His six-part framework for building great companies: timing, market, team, product, brand, distribution 3. Why he says he couldn’t have done this job without AI 4. His “right to win” strategic framework 5. His communication framework for preventing “packet loss” across an organization 6. Why he flips “praise in public, criticize in private” and does the exact opposite 7. The important communication lesson his mother taught him — Brought to you by: Sentry—Code breaks, fix it faster: https://sentry.io/lenny Framer—Build better websites faster: https://framer.com/lenny Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jeetu Patel: • X: https://x.com/jpatel41 • LinkedIn: https://www.linkedin.com/in/jeetupatel • Website: https://blogs.cisco.com/author/jeetupatel — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction and welcome (04:15) Insights from Cisco’s Al summit (08:45) Transforming Cisco into an Al-first company (15:33) What Cisco actually does in the Al infrastructure stack (19:09) The future of Al (24:36) Raising kids in the AI era (29:46) “Permission to play” framework (36:50) Lessons from great CEOs (42:02) Leading at scale (50:54) Why Jeetu inverts the ‘praise in public, criticize in private’ rule (57:45) Surrounding yourself with good human beings (58:35) Lessons from loss (01:03:21) Career advice: platforms, hunger, and preparation (01:10:21) The six-part framework for building great companies (01:19:05) Lightning round and final thoughts — Resources and episode mentions: https://www.lennysnewsletter.com/p/ai-is-critical-for-humanitys-survival — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Boris Cherny is the creator and head of Claude Code at Anthropic. What began as a simple terminal-based prototype just a year ago has transformed the role of software engineering and is increasingly transforming all professional work. We discuss: 1. How Claude Code grew from a quick hack to 4% of public GitHub commits, with daily active users doubling last month 2. The counterintuitive product principles that drove Claude Code’s success 3. Why Boris believes coding is “solved” 4. The latent demand that shaped Claude Code and Cowork 5. Practical tips for getting the most out of Claude Code and Cowork 6. How underfunding teams and giving them unlimited tokens leads to better AI products 7. Why Boris briefly left Anthropic for Cursor, then returned after just two weeks 8. Three principles Boris shares with every new team member — Brought to you by: DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Sentry—Code breaks, fix it faster: https://sentry.io/lenny Metaview—The AI platform for recruiting: https://metaview.ai/lenny — Episode transcript: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Boris Cherny: • X: https://x.com/bcherny • LinkedIn: https://www.linkedin.com/in/bcherny • Website: https://borischerny.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Boris and Claude Code (03:45) Why Boris briefly left Anthropic for Cursor (and what brought him back) (05:35) One year of Claude Code (08:41) The origin story of Claude Code (13:29) How fast AI is transforming software development (15:01) The importance of experimentation in AI innovation (16:17) Boris’s current coding workflow (100% AI-written) (17:32) The next frontier (22:24) The downside of rapid innovation  (24:02) Principles for the Claude Code team (26:48) Why you should give engineers unlimited tokens (27:55) Will coding skills still matter in the future? (32:15) The printing press analogy for AI’s impact (36:01) Which roles will AI transform next? (40:41) Tips for succeeding in the AI era (44:37) Poll: Which roles are enjoying their jobs more with AI (46:32) The principle of latent demand in product development (51:53) How Cowork was built in just 10 days (54:04) The three layers of AI safety at Anthropic (59:35) Anxiety when AI agents aren’t working (01:02:25) Boris’s Ukrainian roots (01:03:21) Advice for building AI products (01:08:38) Pro tips for using Claude Code effectively (01:11:16) Thoughts on Codex (01:12:13) Boris’s post-AGI plans (01:14:02) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brian Halligan co-founded HubSpot, ran it as CEO for about 15 years, and now coaches Sequoia’s fastest-growing founders as their in-house CEO coach. We discuss: 1. His LOCKS framework for evaluating founders 2. Why you should build your team like the 2004 Red Sox 3. Why hiring “spicy” candidates beats consensus picks 4. Why enterprise sales will be the last white-collar job AI replaces 5. Some of my favorite “Halliganisms” — Brought to you by: Sentry—Code breaks, fix it faster: http://sentry.io/lenny Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/sequoia-ceo-coach-why-its-never-been — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Brian Halligan • X: https://x.com/bhalligan • LinkedIn: linkedin.com/in/brianhalligan • Delphi: https://www.delphi.ai/bhalligan • Podcast: https://sequoiacap.com/series/long-strange-trip — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Brian Halligan (03:56) The perpetual state of constructive dissatisfaction (05:25) Coaching CEOs (07:49) The art of interviewing and hiring (11:21) Getting the most out of reference calls (13:10) Homegrown talent vs. big company hires (16:31) Traits of successful CEOs (19:40) Brian’s LOCKS framework for evaluating founders (21:34) Are great CEO’s born or made? (23:41) Giving effective feedback (25:54) The future of go-to-market strategies (31:56) Understanding forward deployed engineers (34:17) How the CEO role has evolved over the last 20 years (38:10) Halliganisms (01:01:18) The CEO’s role in scaling a company (01:02:41) Lightning round and final thoughts — Referenced: • Dev Ittycheria on LinkedIn: https://www.linkedin.com/in/dittycheria • HubSpot: https://www.hubspot.com • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad • McKinsey & Company: https://www.mckinsey.com • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang • Winston Weinberg on LinkedIn: https://www.linkedin.com/in/winston-weinberg • James Cadwallader on LinkedIn: https://www.linkedin.com/in/jsca • Gabriel Stengel on LinkedIn: https://www.linkedin.com/in/gabestengel • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Scaling Entrepreneurial Ventures: https://orbit.mit.edu/classes/scaling-entrepreneurial-ventures-15.392 • OpenClaw: https://openclaw.ai • Ruth Porat on LinkedIn: https://www.linkedin.com/in/ruth-porat • Mike Krzyzewski: https://goduke.com/sports/mens-basketball/roster/coaches/mike-krzyzewski/4159 • Dalai Lama’s 18 Rules for Living: https://www.prm.nau.edu/prm205/Dalai-Lama-18-rules-for-living.htm • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Kareem Amin on LinkedIn: https://www.linkedin.com/in/kareemamin • Glassdoor: https://www.glassdoor.com • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Katie Burke on LinkedIn: https://www.linkedin.com/in/katie-burke-965767a • Jerry Garcia: https://en.wikipedia.org/wiki/Jerry_Garcia • Bob Weir: https://en.wikipedia.org/wiki/Bob_Weir • Phil Lesh: https://en.wikipedia.org/wiki/Phil_Lesh • Ron “Pigpen” McKernan: https://en.wikipedia.org/wiki/Ron_%22Pigpen%22_McKernan • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • The American Revolution: https://www.pbs.org/kenburns/the-american-revolution • Delphi: https://www.delphi.ai • Sonos: https://www.sonos.com • Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan • The Boston Red Sox: https://www.mlb.com/redsox — Recommended book: • Marketing Lessons from the Grateful Dead: What Every Business Can Learn from the Most Iconic Band in History: https://www.amazon.com/Marketing-Lessons-Grateful-Dead-Business/dp/0470900520 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Sherwin Wu leads engineering for OpenAI’s API platform, where roughly 95% of engineers use Codex, often working with fleets of 10 to 20 parallel AI agents. We discuss: 1. What OpenAI did to cut code review times from 10-15 minutes to 2-3 minutes 2. How AI is changing the role of managers 3. Why the productivity gap between AI power users and everyone else is widening 4. Why “models will eat your scaffolding for breakfast” 5. Why the next 12 to 24 months are a rare window where engineers can leap ahead before the role fully transforms — Brought to you by: DX—The developer intelligence platform designed by leading researchers Sentry—Code breaks, fix it faster Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Episode transcript: https://www.lennysnewsletter.com/p/engineers-are-becoming-sorcerers — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Sherwin Wu: • X: https://x.com/sherwinwu • LinkedIn: https://www.linkedin.com/in/sherwinwu1 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sherwin Wu (03:10) AI’s role in coding at OpenAI (06:53) The future of software engineering with AI (12:26) The stress of managing agents (15:07) Codex and code review automation (19:29) The changing role of engineering managers (24:14) The one-person billion-dollar startup (31:40) Management lessons (37:28) Challenges and best practices in AI deployment (43:56) Hot takes on AI and customer feedback (48:57) Building for future AI capabilities (50:16) Where models are headed in the next 18 months (53:35) Business process automation (57:22) OpenAI’s ecosystem and platform strategy (01:00:50) OpenAI’s mission and global impact (01:05:21) Building on OpenAI’s API and tools (01:08:16) Lightning round and final thoughts — Referenced: • Codex: https://openai.com/codex • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • OpenClaw: https://openclaw.ai • The creator of Clawd: “I ship code I don’t read”: https://newsletter.pragmaticengineer.com/p/the-creator-of-clawd-i-ship-code • The Sorcerer’s Apprentice: https://en.wikipedia.org/wiki/The_Sorcerer%27s_Apprentice_(Dukas) • Quora: https://www.quora.com • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Sarah Friar on LinkedIn: https://www.linkedin.com/in/sarah-friar • Sam Altman on X: https://x.com/sama • Nicolas Bustamante’s “LLMs Eat Scaffolding for Breakfast” post on X: https://x.com/nicbstme/status/2015795605524901957 • The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html • Overton window: https://en.wikipedia.org/wiki/Overton_window • Developers can now submit apps to ChatGPT: https://openai.com/index/developers-can-now-submit-apps-to-chatgpt • Responses: https://platform.openai.com/docs/api-reference/responses • Agents SDK: https://platform.openai.com/docs/guides/agents-sdk • AgentKit: https://openai.com/index/introducing-agentkit • Ubiquiti: https://ui.com • Jujutsu Kaisen on Crunchyroll: https://www.crunchyroll.com/series/GRDV0019R/jujutsu-kaisen?srsltid=AfmBOoqvfzKQ6SZOgzyJwNQ43eceaJTQA2nUxTQfjA1Ko4OxlpUoBNRB • eero: https://eero.com • Opendoor: https://www.opendoor.com — Recommended books: • Structure and Interpretation of Computer Programs: https://www.amazon.com/Structure-Interpretation-Computer-Programs-Engineering/dp/0262510871 • The Mythical Man-Month: Essays on Software Engineering: https://www.amazon.com/Mythical-Man-Month-Software-Engineering-Anniversary/dp/0201835959 • There Is No Antimemetics Division: A Novel: https://www.amazon.com/There-No-Antimemetics-Division-Novel/dp/0593983750 • Breakneck: China’s Quest to Engineer the Future: https://www.amazon.com/Breakneck-Chinas-Quest-Engineer-Future/dp/1324106034 • Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Lazar Jovanovic is a full-time professional vibe coder at Lovable. His job is to build both internal tools and customer-facing products purely using AI, while not having a coding background. In this conversation, he breaks down the tactics, workflows, and framework that let him ship production-quality products using only AI. We discuss: 1. Why having no coding background can be an advantage when building with AI 2. Why most of your time should go to planning and chat mode, not prompting 3. What to do when you get stuck: his 4x4 debugging workflow 4. The PRD and Markdown file system that keeps AI agents aligned across complex builds 5. Why kicking off four or five parallel prototypes is the best way to clarify your thinking 6. Why design skills and taste are going to be the most important skills in the future 7. His “genie and three wishes” mental model for making the most of AI’s limitations 8. How product, engineering, and design roles are converging—and what that means for your career — Brought to you by: Strella—The AI-powered customer research platform: https://strella.io/lenny Samsara—Saving lives with AI built for physical operations: https://samsara.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Lazar Jovanovic: • X: https://x.com/lakikentaki • LinkedIn: https://www.linkedin.com/in/lazar-jovanovic • YouTube: https://www.youtube.com/@50in50challenge • Starter Story course: https://build.starterstory.com/build/ai-build-accelerator?via=lazar (code LAZAR15 for 15% off) — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Lazar and professional vibe coding (04:53) What a professional vibe coder actually does day-to-day (09:26) Why non-technical backgrounds can be an advantage (12:24) The importance of self-awareness (14:42) His “genie and three wishes” mental model (17:43) Developing taste and judgment in the age of AI (21:46) The parallel project approach for better outcomes (29:30) Creating dynamic context windows with PRDs (36:56) Why elite vibe coders focus on planning, not coding (44:43) Creating MD files to guide AI development (50:57) Why prototyping still matters (56:50) Why “good enough” is no longer good enough (01:00:53) The future of engineering in an AI world (01:05:14) What to do when you get stuck: his 4x4 debugging workflow (01:14:27) Helping agents learn from their mistakes (01:15:35) Why watching agent output is more important than code (01:19:08) The incredible pace of AI development (01:22:55) Why emotional intelligence will become more valuable (01:28:30) How to become a professional vibe coder (01:30:10) Why building in public is the fastest path to opportunities (01:37:03) Final thoughts on focusing on quality over tech stack — Referenced: • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna • Lovable: https://lovable.dev • Lovable + Shopify: https://lovable.dev/shopify • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Mobbin: https://mobbin.com • Dribbble: https://dribbble.com • 21st.dev: https://21st.dev • Lovable base prompt generator: https://chatgpt.com/g/g-67e1da2c9c988191b52b61084438e8ee-lovable-base-prompt • Lovable PRD generator: https://chatgpt.com/g/g-67e1e85fbeac8191a69b95c6d5c42ef6-lovable-prd-generator • Felix Haas’s newsletter: https://designplusai.com • Bauhaus: https://en.wikipedia.org/wiki/Bauhaus • Glassmorphism: https://www.figma.com/community/plugin/1197106608665398190/glassmorphism • UI style guide: http://uistyle.lovable.app • Cloudflare: https://www.cloudflare.com • Ben Tossell on X: https://x.com/bentossell • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Peter Thiel says AI will be ‘worse’ for math nerds than for writers: https://www.businessinsider.com/peter-thiel-ai-worse-for-math-professionals-than-writers-2024-4 • Andrej Karpathy on X: https://x.com/karpathy • The 100-person AI lab that became Anthropic and Google’s secret weapon | Edwin Chen (Surge AI): https://www.lennysnewsletter.com/p/surge-ai-edwin-chen • Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody • Slumdog Millionaire: https://www.imdb.com/title/tt1010048 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dr. Becky Kennedy is a clinical psychologist, the bestselling author of Good Inside, and the founder of a parenting platform used by millions. Known for her practical, psychology-based approach to parenting, Dr. Becky shares how the same principles that help parents raise resilient children can make you a much more effective leader. In this conversation, she breaks down why all human systems—whether families or companies—operate on the same fundamental principles, and how understanding these dynamics can make you more effective in every relationship. We discuss: 1. Why repair—not perfection—defines strong leadership 2. Why you need to connect before you correct to build cooperation and trust 3. The “most generous interpretation” framework for handling difficult behaviors 4. How to correctly set boundaries (vs. making requests) 5. The power of “I believe you, and I believe in you” 6. What it looks like to be a “sturdy” leader — Brought to you by: Merge—Fast, secure integrations for your products and agents: https://merge.dev/lenny Metaview—The AI platform for recruiting: https://metaview.ai/lenny Framer—Builder better websites faster: https://framer.com/lenny — Episode transcript: https://www.lennysnewsletter.com/p/dr-becky-on-the-surprising-overlap — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Dr. Becky Kennedy: • X: https://x.com/GoodInside • LinkedIn: https://www.linkedin.com/in/drbecky • Instagram: https://www.instagram.com/drbeckyatgoodinside • TikTok: https://www.tiktok.com/@drbeckyatgoodinside • Website: https://www.goodinside.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dr. Becky Kennedy (05:14) Connecting parenting and leadership (08:40) The power of repair (11:05) Connecting before correcting (17:45) Good Inside framework at work (22:08) The most generous interpretation (MGI) (25:46) Curiosity over judgment (27:07) Understanding behavior change (31:08) What potty training can teach us about workplace behavior (34:40) Naming your intention (35:41) Sturdy leadership (40:52) How to set boundaries well (46:33) The role of leadership and consensus (50:50) The importance of being “locatable” (52:40) A powerful story of betrayal and realization (57:12) Building resilience over happiness (01:00:34) The power of the phrase “I believe you, and I believe in you.” (01:09:08) The Good Inside community and resources (01:16:22) AI corner (01:19:52) Good Inside’s mission (01:22:26) Lightning round and final thoughts — Referenced: • Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng • Punch: https://en.wikipedia.org/wiki/Punch_(play) • Figma: https://www.figma.com • Andrew Hogan on LinkedIn: https://www.linkedin.com/in/ahhogan • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Claude: https://claude.ai • ChatGPT: https://chatgpt.com • Secrets We Keep on Netflix: https://www.netflix.com/title/81697668 • K Pop Demon Hunters on Netflix: https://www.netflix.com/title/81498621 • Liberty puzzles: https://libertypuzzles.com — Recommended books: • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375 • Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481 • Leave Me Alone!: A Good Inside Story About Deeply Feeling Kids: https://www.amazon.com/Leave-Me-Alone-Inside-Feeling/dp/1250413117 • The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765/ • The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture: https://www.amazon.com/Messy-Middle-Finding-Through-Hardest/dp/0735218072 • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Marc Andreessen is a founder, investor, and co-founder of Netscape, as well as co-founder of the venture capital firm Andreessen Horowitz (a16z). In this conversation, we dig into why we’re living through a unique and one of the most incredible times in history, and what comes next. We discuss: 1. Why AI is arriving at the perfect moment to counter demographic collapse and declining productivity 2. How Marc has raised his 10-year-old kid to thrive in an AI-driven world 3. What’s actually going to happen with AI and jobs (spoiler: he thinks the panic is “totally off base”) 4. The “Mexican standoff” that’s happening between product managers, designers, and engineers 5. Why you should still learn to code (even with AI) 6. How to develop an “E-shaped” career that combines multiple skills, with AI as a force multiplier 7. The career advice he keeps coming back to (“Don’t be fungible”) 8. How AI can democratize one-on-one tutoring, potentially transforming education 9. His media diet: X and old books, nothing in between — Brought to you by: DX—The developer intelligence platform designed by leading researchers Brex—The banking solution for startups Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Episode transcript: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Marc Andreessen: • X: https://x.com/pmarca • Substack: https://pmarca.substack.com • Andreessen Horowitz’s website: https://a16z.com • Andreessen Horowitz’s YouTube channel: https://www.youtube.com/@a16z — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Marc Andreessen (04:27) The historic moment we’re living in (06:52) The impact of AI on society (11:14) AI’s role in education and parenting (22:15) The future of jobs in an AI-driven world (30:15) Marc's past predictions (35:35) The Mexican standoff of tech roles (39:28) Adapting to changing job tasks (42:15) The shift to scripting languages (44:50) The importance of understanding code (51:37) The value of design in the AI era (53:30) The T-shaped skill strategy (01:02:05) AI’s impact on founders and companies (01:05:58) The concept of one-person billion-dollar companies (01:08:33) Debating AI moats and market dynamics (01:14:39) The rapid evolution of AI models (01:18:05) Indeterminate optimism in venture capital (01:22:17) The concept of AGI and its implications (01:30:00) Marc's media diet (01:36:18) Favorite movies and AI voice technology (01:39:24) Marc's product diet (01:43:16) Closing thoughts and recommendations — Referenced: • Linus Torvalds on LinkedIn: https://www.linkedin.com/in/linustorvalds • The philosopher’s stone: https://en.wikipedia.org/wiki/Philosopher%27s_stone • Alexander the Great: https://en.wikipedia.org/wiki/Alexander_the_Great • Aristotle: https://en.wikipedia.org/wiki/Aristotle • Bloom’s 2 sigma problem: https://en.wikipedia.org/wiki/Bloom%27s_2_sigma_problem • Alpha School: https://alpha.school • In Tech We Trust? A Debate with Peter Thiel and Marc Andreessen: https://a16z.com/in-tech-we-trust-a-debate-with-peter-thiel-and-marc-andreessen • John Woo: https://en.wikipedia.org/wiki/John_Woo • Assembly: https://en.wikipedia.org/wiki/Assembly_language • C programming language: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org • Netscape: https://en.wikipedia.org/wiki/Netscape • Perl: https://www.perl.org • Scott Adams: https://en.wikipedia.org/wiki/Scott_Adams • Larry Summers’s website: https://larrysummers.com • Nano Banana: https://gemini.google/overview/image-generation • Bitcoin: https://bitcoin.org • Ethereum: https://ethereum.org • Satoshi Nakamoto: https://en.wikipedia.org/wiki/Satoshi_Nakamoto • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • Inside Google’s AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search): https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year • DeepSeek: https://www.deepseek.com • Cowork: https://support.claude.com/en/articles/13345190-getting-started-with-cowork • Definite vs. indefinite thinking: Notes from Zero to One by Peter Thiel: https://boxkitemachine.net/posts/zero-to-one-peter-thiel-definite-vs-indefinite-thinking • Henry Ford: https://www.thehenryford.org/explore/stories-of-innovation/visionaries/henry-ford • Lex Fridman Podcast: https://lexfridman.com/podcast • $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz • Eddington: https://www.imdb.com/title/tt31176520 • Joaquin Phoenix: https://en.wikipedia.org/wiki/Joaquin_Phoenix • Pedro Pascal: https://en.wikipedia.org/wiki/Pedro_Pascal • George Floyd: https://en.wikipedia.org/wiki/George_Floyd • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Grok Bad Rudi: https://grok.com/badrudi • Wispr Flow: https://wisprflow.ai • Star Trek: The Next Generation: https://www.imdb.com/title/tt0092455 • Star Trek: Starfleet Academy: https://www.imdb.com/title/tt8622160 • a16z: The Power Brokers: https://www.notboring.co/p/a16z-the-power-brokers — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team. We discuss: 1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market 2. A small tweak that’ll double response rates on your cancellation surveys 3. Why “it’s too expensive” is almost never the real reason customers cancel 4. The “elephant curve” of growth 5. How repositioning the same product can increase revenue 8x 6. When to reconsider if growth is even the right goal for your business — Brought to you by: 10Web—Vibe coding platform as an API Strella—The AI-powered customer research platform Brex—The banking solution for startups — Episode transcript: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Jason Cohen: • Preorder Jason’s book: https://preorder.hiddenmultipliers.com/ • X: https://x.com/asmartbear • LinkedIn: https://www.linkedin.com/in/jasoncohen • Blog: https://longform.asmartbear.com • Website: https://wpengine.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Cohen (05:19) Jason’s writing journey (08:25) Questions to ask when your product stops growing (18:17) Getting real customer feedback (20:27) Analyzing cancellation reasons (26:54) Onboarding and activation (29:35) Quick summary (35:46) Revisiting pricing strategies (41:46) Positioning strategies (47:52) Why pricing is inseparable from your strategy (52:06) The importance of net revenue retention (NRR) (01:00:25) Asking whether or not this is good for the customer (01:04:34) Leveraging existing customers (01:06:42) Are your acquisition channels saturated? The “elephant curve” (1:09:41) Why all marketing channels eventually decline (01:12:04) Direct vs. indirect marketing channels (1:13:36) Getting creative with new channels (01:19:04) Do you actually need to grow? (01:25:57) Deciding when to quit (01:29:27) Book announcement (01:33:21) AI corner (01:34:35) Contrarian corner (01:37:43) Lightning round and final thoughts — Referenced: • Tyler Cowen’s website: https://tylercowen.com • How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn • Linear: https://linear.app • Jira: https://www.atlassian.com/software/jira • Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942 • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy • M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • Buffer: https://buffer.com • AG1: https://drinkag1.com • How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng • How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth • The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth • HubSpot: https://www.hubspot.com • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/ • Ecosystem is the next big growth channel: https://www.lennysnewsletter.com/p/ecosystem-is-the-next-big-growth • ChatGPT apps are about to be the next big distribution channel: Here’s how to build one: https://www.lennysnewsletter.com/p/chatgpt-apps-are-about-to-be-the • 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths • Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead • ER on Prime Video: https://www.amazon.com/ER-Season-1/dp/B0FWK5WJQ4 • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Wispr Flow: https://wisprflow.ai • Anker: https://www.anker.com — Recommended books: • Will: https://www.amazon.com/Will-Smith/dp/1984877925 • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Hidden Multipliers: Small Things That Accelerate Growth: https://preorder.hiddenmultipliers.com • On Writing Well: The Essential Guide to Mastering Nonfiction Writing and Effective Communication: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548 • Crossing the Chasm, 3rd Edition: The Updated Version of the Insightful Guide on Bringing Cutting-Edge Products to the Mainstream: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Zevi Arnovitz is a product manager at Meta with no technical background who has figured out how to build and ship real products using AI. His engineering team at Meta asks him to teach them how he does what he does. In this episode, Zevi breaks down his complete AI workflow that allows non-technical people to build sophisticated products with Cursor. We discuss: 1. The complete AI workflow that lets non-technical people build real products in Cursor 2. How to use multiple AI models for different tasks (Claude for planning, Gemini for UI) 3. Using slash commands to automate prompts 4. Zevi’s “peer review” technique, which uses different AI models to review each other’s code 5. Why this might be the best time to be a junior in tech, despite the challenging job market 6. How Zevi used AI to prepare for his Meta PM interviews — Brought to you by: 10Web—Vibe coding platform as an API DX—The developer intelligence platform designed by leading researchers Framer—Build better websites faster — Zevi's Slash Command Bank for Claude: ⁠https://zeviarnovitz.com/⁠ — Episode transcript: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Zevi Arnovitz • X: https://x.com/ArnovitzZevi • LinkedIn: https://www.linkedin.com/in/zev-arnovitz • Website: https://zeviarnovitz.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Zevi Arnovitz (04:48) Zevi’s background and journey into AI (07:41) Overview of Zevi’s AI workflow (14:41) Screenshare: Exploring Zevi’s workflow in detail (17:18) Building a feature live: StudyMate app (30:52) Executing the plan with Cursor (38:32) Using multiple AI models for code review (40:40) Personifying AI models (43:37) Peer review process (45:40) The importance of postmortems (51:05) Integrating AI in large companies (53:42) How AI has impacted the PM role (57:02) How to improve AI outputs (58:15) AI-assisted job interviews (01:02:57) Failure corner (01:06:20) Lightning round and final thoughts — Referenced: • Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Product Lead at Riverside): https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv • Wix: https://www.wix.com • Building AI Apps: From Idea to Viral in 30 Days: https://www.youtube.com/watch?v=j2w4y7pDi8w • Riley Brown on YouTube: https://www.youtube.com/channel/UCMcoud_ZW7cfxeIugBflSBw • Greg Isenberg on YouTube: https://www.youtube.com/@GregIsenberg • Bolt: https://bolt.new • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • StudyMate: https://studymate.live • Dibur2text: https://dibur2text.app • Claude: https://claude.ai • Everyone should be using Claude Code more: https://www.lennysnewsletter.com/p/everyone-should-be-using-claude-code • Bun: https://bun.com • Zustand: https://zustand.docs.pmnd.rs/getting-started/introduction • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Wispr Flow: https://wisprflow.ai • Linear: https://linear.app • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Cursor Composer: https://cursor.com/blog/composer • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Base44: https://base44.com • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • v0: https://v0.app • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Cursor Browser mode: https://cursor.com/docs/agent/browser • Google Antigravity: https://antigravity.google • Grok: https://grok.com • Zapier: https://zapier.com • Airtable: https://www.airtable.com • Build Your Personal PM Productivity System & AI Copilot: https://maven.com/tal-raviv/product-manager-productivity-system • The definitive guide to mastering analytical thinking interviews: https://www.lennysnewsletter.com/p/the-definitive-guide-to-mastering-f81 • AI tools are overdelivering: results from our large-scale AI productivity survey: https://www.lennysnewsletter.com/p/ai-tools-are-overdelivering-results-c08 • Yaara Asaf on LinkedIn: https://www.linkedin.com/in/yaarasaf • The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD • Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx • Loom: https://www.loom.com • Cap: https://cap.so • Supercut: https://supercut.ai ...References continued at: https://www.lennysnewsletter.com/p/the-non-technical-pms-guide-to-building-with-cursor — Recommended books: • The Fountainhead: https://www.amazon.com/Fountainhead-Ayn-Rand/dp/0451191153 • Shoe Dog: A Memoir by the Creator of Nike: https://www.amazon.com/Shoe-Dog-Memoir-Creator-Nike/dp/1501135910 • Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Sam Lessin is a partner at Slow Ventures, a former VP of Product at Facebook, and a two-time founder who’s now teaching etiquette to Silicon Valley’s founders. In this unconventional episode, Sam explains why proper etiquette has become a vital skill for founders in 2026—especially as technology becomes more central to society and trust becomes harder to build. His etiquette book and courses have become surprisingly popular, teaching founders how to “show up in a room with a low heart rate” and quickly build trust. We discuss: 1. Why etiquette matters 2. Sam’s framework for showing up confidently, with a low heart rate, in any room 3. How to navigate introductions, small talk, meetings, and meals like a pro 4. Simple hacks for remembering names and handling awkward social situations 5. 30+ specific etiquette tips — Brought to you by: 10Web—Vibe-coding platform as an API DX—The developer intelligence platform designed by leading researchers WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs — Episode transcript: https://www.lennysnewsletter.com/p/silicon-valleys-missing-etiquette-playbook — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Sam Lessin: • X: https://x.com/lessin • LinkedIn: https://www.linkedin.com/in/wlessin • Website: https://www.wlessin.com • Podcast: https://moreorlesspod.com • Lettermeme: https://lettermeme.com/lessin — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sam’s background (04:18) The role of etiquette in business success (09:30) Introductions and entering a room (16:20) Engaging conversations and building relationships (23:55) Hygiene and dress code essentials (33:42) Dining etiquette (37:15) Tipping etiquette (41:36) The “B&D trick” (43:05) Humor in social settings (45:18) Self-deprecating humor (47:42) Winding down conversations (49:20) Scheduling etiquette (55:23) Communication and email etiquette (01:02:28) Meeting etiquette tips (01:04:03) Virtual meeting best practices (01:05:15) The importance of cleaning up after yourself (01:05:58) Exiting and follow-up etiquette (01:07:24) Final thoughts (01:09:20) AI corner (01:11:13) Contrarian corner (01:16:25) Lightning round — Referenced: • Y Combinator: https://www.ycombinator.com • Kleiner Perkins: https://www.kleinerperkins.com • “Lose Yourself” by Eminem on Spotify: https://open.spotify.com/track/7MJQ9Nfxzh8LPZ9e9u68Fq • Alison Gopnik on Childhood Learning, AI as a Cultural Technology, and Rethinking Nature vs. Nurture: https://conversationswithtyler.com/episodes/alison-gopnik • Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan • Bain & Company: https://www.bain.com • Evernote: https://evernote.com • Calendly: https://calendly.com • Morning Brew: https://www.morningbrew.com • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • DigitalOcean: https://www.digitalocean.com • Cloudflare: https://www.cloudflare.com • SpaceX: https://www.spacex.com • Marc Andreessen on X: https://x.com/pmarca • Landman on Prime Video: https://www.amazon.com/Landman-Season-1/dp/B0D4D8RTMD • Dave Morin on X: https://x.com/davemorin — Recommended books: • Modern Etiquette in Technology, Finance, Society, and at Home: A Slow Ventures Handbook: https://www.amazon.com/Modern-Etiquette-Technology-Finance-Society-ebook/dp/B0G4HSKSY5 • Life, the Universe and Everything: https://www.amazon.com/Universe-Everything-Hitchhikers-Guide-Galaxy-ebook/dp/B001ODEQ7A • The Ancient City: A Study on the Religion, Laws, and Institutions of Greece and Rome: https://www.amazon.com/Ancient-City-Religion-Institutions-Greece/dp/0801823048 • Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl-ebook/dp/B009U9S6FI • Area 51: An Uncensored History of America’s Top Secret Military Base: https://www.amazon.com/Area-51-Uncensored-Americas-Military-ebook/dp/B004THU68Q • The Lessons of History: https://www.amazon.com/Lessons-History-Will-Durant/dp/143914995X • The Fish That Ate the Whale: The Life and Times of America’s Banana King: https://www.amazon.com/Fish-That-Ate-Whale-Americas/dp/1250033314 • The Last Kings of Shanghai: The Rival Jewish Dynasties That Helped Create Modern China: https://www.amazon.com/Last-Kings-Shanghai-Jewish-Dynasties/dp/0735224439 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Aishwarya Naresh Reganti and Kiriti Badam have helped build and launch more than 50 enterprise AI products across companies like OpenAI, Google, Amazon, and Databricks. Based on these experiences, they’ve developed a small set of best practices for building and scaling successful AI products. The goal of this conversation is to save you and your team a lot of pain and suffering. We discuss: 1. Two key ways AI products differ from traditional software, and why that fundamentally changes how they should be built 2. Common patterns and anti-patterns in companies that build strong AI products versus those that struggle 3. A framework they developed from real-world experience to iteratively build AI products that create a flywheel of improvement 4. Why obsessing about customer trust and reliability is an underrated driver of successful AI products 5. Why evals aren’t a cure-all, and the most common misconceptions people have about them 6. The skills that matter most for builders in the AI era — Brought to you by: Merge—The fastest way to ship 220+ integrations: https://merge.dev/lenny Strella—The AI-powered customer research platform: https://strella.io/lenny Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs — Transcript: https://www.lennysnewsletter.com/p/what-openai-and-google-engineers-learned — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/183007822/referenced — Get 15% off Aishwarya and Kiriti’s Maven course, Building Agentic AI Applications with a Problem-First Approach, using this link: https://bit.ly/3V5XJFp — Where to find Aishwarya Naresh Reganti: • LinkedIn: https://www.linkedin.com/in/areganti • GitHub: https://github.com/aishwaryanr/awesome-generative-ai-guide • X: https://x.com/aish_reganti — Where to find Kiriti Badam: • LinkedIn: https://www.linkedin.com/in/sai-kiriti-badam • X: https://x.com/kiritibadam — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Aishwarya and Kiriti (05:03) Challenges in AI product development (07:36) Key differences between AI and traditional software (13:19) Building AI products: start small and scale (15:23) The importance of human control in AI systems (22:38) Avoiding prompt injection and jailbreaking (25:18) Patterns for successful AI product development (33:20) The debate on evals and production monitoring (41:27) Codex team’s approach to evals and customer feedback (45:41) Continuous calibration, continuous development (CC/CD) framework (58:07) Emerging patterns and calibration (01:01:24) Overhyped and under-hyped AI concepts (01:05:17) The future of AI (01:08:41) Skills and best practices for building AI products (01:14:04) Lightning round and final thoughts — Referenced: • LevelUp Labs: https://levelup-labs.ai/ • Why your AI product needs a different development lifecycle: https://www.lennysnewsletter.com/p/why-your-ai-product-needs-a-different • Booking.com: https://www.booking.com • Research paper on agents in production (by Matei Zaharia’s lab): https://arxiv.org/pdf/2512.04123 • Matei Zaharia’s research on Google Scholar: https://scholar.google.com/citations?user=I1EvjZsAAAAJ&hl=en • The coming AI security crisis (and what to do about it) | Sander Schulhoff: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis • Gajen Kandiah on LinkedIn: https://www.linkedin.com/in/gajenkandiah • Rackspace: https://www.rackspace.com • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Semantic Diffusion: https://martinfowler.com/bliki/SemanticDiffusion.html • LMArena: https://lmarena.ai • Artificial Analysis: https://artificialanalysis.ai/leaderboards/providers • Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead): https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck • Airline held liable for its chatbot giving passenger bad advice—what this means for travellers: https://www.bbc.com/travel/article/20240222-air-canada-chatbot-misinformation-what-travellers-should-know • Demis Hassabis on LinkedIn: https://www.linkedin.com/in/demishassabis • We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents • Socrates’s quote: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living • Noah Smith’s newsletter: https://www.noahpinion.blog • Silicon Valley on HBO Max: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d • Clair Obscur: Expedition 33: https://store.steampowered.com/app/1903340/Clair_Obscur_Expedition_33/ • Wisprflow: https://wisprflow.ai • Raycast: https://www.raycast.com • Steve Jobs’s quote: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only — Recommended books: •  When Breath Becomes Air: https://www.amazon.com/When-Breath-Becomes-Paul-Kalanithi/dp/081298840X • The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032 • A Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Molly Graham has worked for some of tech’s most effective leaders, including Mark Zuckerberg, Sheryl Sandberg, Chamath Palihapitiya, and Bret Taylor. Today she leads Glue Club, a community for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models for leading through hypergrowth. We discuss: 1. “Give away your Legos”: a framework for scaling yourself as a leader 2. “J-curves vs. stairs”: the two paths of career growth, and why you should pick the scarier path 3. “The waterline model” for diagnosing team problems (and why you should “snorkel before you scuba”) 4. Six rules for creating effective goals (and aligning everyone around them) 5. Rules of thumb for leading through rapid scale and change 6. Her biggest leadership lessons from Mark Zuckerberg, Sergey Brin, Larry Page, Sheryl Sandberg, and Bret Taylor — Brought to you by: DX—The developer intelligence platform designed by leading researchers Brex—The banking solution for startups GoFundMe Giving Funds—Make helping a habit — Transcript: https://www.lennysnewsletter.com/p/the-high-growth-handbook-molly-graham — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182877855/my-biggest-takeaways-from-this-conversation — Where to find Molly Graham: • X: https://x.com/molly_g • LinkedIn: https://www.linkedin.com/in/mograham • Substack: https://mollyg.substack.com • Website: https://glueclub.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Molly Graham (04:28) Molly’s background at Google, Facebook, Quip, and CZI (11:29) The “Give away your Legos” framework (16:44) Managing your inner monster (19:49) When not to give away your Legos (21:28) Embracing a long career (23:25) The J-curve vs. stairs approach to career growth (32:00) The gift of knowing yourself (34:28) Learning to be a professional idiot (38:30) The waterline model: snorkel before you scuba (47:16) Six rules for creating strong alignment around goals (57:15) Rules of thumb for leading through rapid scale (01:07:49) Investing in high performers vs. low performers (01:10:54) Lessons from Zuckerberg, Sandberg, and Bret Taylor (1:21:15) Pivoting from ambition to purpose (1:26:32) Finding stability in instability (01:29:44) Final thoughts — Referenced: • Making an impact through authenticity and curiosity | Ami Vora (CPO at Faire, ex-WhatsApp, FB, IG): https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 • Elliot Schrage on LinkedIn: https://www.linkedin.com/in/elliotschrage • Quip: https://quip.com • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Chan Zuckerberg Initiative: https://chanzuckerberg.com • 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths • ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups • The Muppets: https://muppets.disney.com • Sara Caldwell on LinkedIn: https://www.linkedin.com/in/saramcaldwell • J-Curves vs. Stairs: Two Approaches to Career Growth: https://mollyg.substack.com/p/j-curve • Forget the corporate ladder—winners take risks: https://www.ted.com/talks/molly_graham_forget_the_corporate_ladder_winners_take_risks • Chamath Palihapitiya on LinkedIn: https://www.linkedin.com/in/chamath • Lori Goler on LinkedIn: https://www.linkedin.com/in/lori-goler-6b96921 • Joseph Campbell’s quote: https://www.goodreads.com/quotes/192665-the-cave-you-fear-to-enter-holds-the-treasure-you • Zevi Arnovitz on LinkedIn: https://www.linkedin.com/in/zev-arnovitz • Peopling 101: The Waterline Model: https://christinehaskell.com/blog/peopling-101-the-waterline-model • Introduction to NVC: https://www.cnvc.org/learn/what-is-nvc • I hate OKRs... and other thoughts about goal setting: https://mollyg.substack.com/p/i-hate-okrs-and-other-thoughts-about • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • James Clear’s quote: https://www.goodreads.com/quotes/9614600-problem-1-winners-and-losers-have-the-same-goals • Founder mode: https://paulgraham.com/foundermode.html • Stripe: https://stripe.com • Patrick Collison on X: https://www.linkedin.com/in/patrickcollison • John Collison on X: https://x.com/collision • Seth Godin’s best tactics for building remarkable products, strategies, brands and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products • Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow — Recommended books: • The Artist’s Way: https://www.amazon.com/Artists-Way-25th-Anniversary/dp/0143129252 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new operating model, where 20 AI agents managed by just 1.2 humans now do the work previously handled by a team of 10 SDRs and AEs. In this conversation, Jason shares his hands-on experience implementing AI to run his sales org, including what works, what doesn’t, and how the GTM landscape is quickly being transformed. We discuss: 1. How AI is fundamentally changing the sales function 2. Why most SDRs and BDRs will be “extinct” within a year 3. What Jason is observing across his portfolio about AI adoption in GTM 4. How to become “hyper-employable” in the age of AI 5. The specific AI tools and tactics he’s using that have been working best 6. Practical frameworks for integrating AI into your sales motion without losing what works 7. Jason’s 2026 predictions on where SaaS and GTM are heading next — Brought to you by: DX—The developer intelligence platform designed by leading researchers Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web Datadog—Now home to Eppo, the leading experimentation and feature flagging platform — Transcript: https://www.lennysnewsletter.com/p/we-replaced-our-sales-team-with-20-ai-agents — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/182902716/my-biggest-takeaways-from-this-conversation — Where to find Jason Lemkin: • X: https://x.com/jasonlk • LinkedIn: https://www.linkedin.com/in/jasonmlemkin • Website: https://www.saastr.com • Substack: https://substack.com/@cloud — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Lemkin (04:36) What SaaStr does (07:13) AI’s impact on sales teams (10:11) How SaaStr's AI agents work and their performance (14:18) How go-to-market is changing in the AI era (19:19) The future of SDRs, BDRs, and AEs in sales (22:03) Why leadership roles are safe (23:43) How to be in the 20% who thrive in the AI sales future (28:40) Why you shouldn't build your own AI tools (30:10) Specific AI agents and their applications (36:40) Challenges and learnings in AI deployment (42:11) Making AI-generated emails good (not just acceptable) (47:31) When humans still beat AI in sales (52:39) An overview of SaaStr's org (53:50) The role of human oversight in AI operations (58:37) Advice for salespeople and founders in the AI era (01:05:40) Forward-deployed engineers (01:08:08) What's changing and what's staying the same in sales (01:16:21) Why AI is creating more work, not less (01:19:32) Why Jason says these are magical times (01:25:25) The "incognito mode test" for finding AI opportunities (01:27:19) The impact of AI on jobs (01:30:18) Lightning round and final thoughts — Referenced: • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • SaaStr Annual: https://www.saastrannual.com • Delphi: https://www.delphi.ai/saastr/talk • Amelia Lerutte on LinkedIn: https://www.linkedin.com/in/amelialerutte/ • Vercel: https://vercel.com • What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google): https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Replit: https://replit.com • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • ElevenLabs: https://elevenlabs.io • The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack • Bolt: https://bolt.new • Lovable: https://lovable.dev • Harvey: https://www.harvey.ai • Samsara: https://www.samsara.com/products/platform/ai-samsara-intelligence • UiPath: https://www.uipath.com • Denise Dresser on LinkedIn: https://www.linkedin.com/in/denisedresser • Agentforce: https://www.salesforce.com/form/agentforce • SaaStr’s AI Agent Playbook: https://saastr.ai/agents • Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan • Brian Halligan’s AI: https://www.delphi.ai/minds/bhalligan • Sierra: https://sierra.ai • Fin: https://fin.ai • Deccan: https://www.deccan.ai • Artisan: https://www.artisan.co • Qualified: https://www.qualified.com • Claude: https://claude.ai • HubSpot: https://www.hubspot.com • Gamma: https://gamma.app • Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b • Brex: https://www.brex.com • Outreach: https://www.outreach.io • Gong: https://www.gong.io • Salesloft: https://www.salesloft.com • Mixmax: https://www.mixmax.com • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • Clay: https://www.clay.com • Owner: https://www.owner.com • Momentum: https://www.momentum.io • Attention: https://www.attention.com • Granola: https://www.granola.ai • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Palantir: https://www.palantir.com • Databricks: https://www.databricks.com • Garry Tan on LinkedIn: https://www.linkedin.com/in/garrytan • Rippling: https://www.rippling.com • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth): https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna • Pluribus on AppleTV+: https://tv.apple.com/us/show/pluribus/umc.cmc.37axgovs2yozlyh3c2cmwzlza • Sora: https://openai.com/sora • Reve: https://app.reve.com • Everything That Breaks on the Way to $1B ARR, with Mailchimp Co-Founder Ben Chestnut: https://www.saastr.com/everything-that-breaks-on-the-way-to-1b-arr-with-mailchimp-co-founder-ben-chestnut/ • The Revenue Playbook: Rippling’s Top 3 Growth Tactics at Scale, with Rippling CRO Matt Plank: https://www.youtube.com/watch?v=h3eYtzBpjRw • 10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling): https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. We discuss: 1. Why “extraordinary results demand extraordinary efforts” 2. Why you should deliberately understaff projects, and how to know when you’ve gone too far 3. Matt’s transition from COO to CPO and what surprised him about leading product 4. The “high alpha, low beta” framework for evaluating people, processes, and products 5. When founders should quit their startups (hint: much earlier than VCs want you to) 6. How to fight entropy in your organization through relentless energy and intensity — Brought to you by: Google Gemini—Your everyday AI assistant: https://ai.dev/ Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny — Transcript: https://www.lennysnewsletter.com/p/10-contrarian-leadership-truths — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181916584/my-biggest-takeaways-from-this-conversation — Where to find Matt MacInnis: • X: https://x.com/stanine • LinkedIn: https://www.linkedin.com/in/macinnis • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt MacInnis and Rippling (04:38) The importance of extraordinary efforts (08:37) The challenges and rewards of relentless effort (10:11) Your job as a leader is to preserve intensity (12:39) You learn far more from success than failure (16:34) Transitioning to chief product officer (19:54) Fixing product management at Rippling (25:27) The “high alpha, low beta” framework (28:55) The PQL framework (35:16) Hiring frameworks and team dynamics (36:52) A helpful interview tactic (40:00) Leading as a COO vs. a CPO (42:34) The reality of product-market fit (46:38) The problem with venture capital (49:29) When founders should quit their startups (41:48) The immutable market (54:13) Lessons from Notion’s success (57:43) Investment strategies and narrative violations (01:00:42) The power of compounding, power law, and entropy (01:07:02) Maintaining intensity and fighting entropy (01:11:33) The importance of feedback and escalations (01:14:31) Rippling’s vision and success (01:17:48) AI’s impact on SaaS and business software (01:23:42) AI corner (01:26:23) Final thoughts and lightning round — Referenced: • Rippling: https://www.rippling.com • Sunil Raman on LinkedIn: https://www.linkedin.com/in/sunilraman • Dan Gill on LinkedIn: https://www.linkedin.com/in/dangill • Carvana: https://www.carvana.com • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad • Inkling: https://www.inkling.com • Akshay Kothari on LinkedIn: https://www.linkedin.com/in/akothari • Notion: https://www.notion.com • Conway’s law: https://en.wikipedia.org/wiki/Conway%27s_law • Seeking Alpha: https://seekingalpha.com • Dennis Rodman’s website: https://dennisrodman.com • Dancing pickle emoji: https://slackmojis.com/emojis/456-dancing_pickle • Pickle Rick: https://en.wikipedia.org/wiki/Pickle_Rick • SPOTAK: The Six Traits I Look for When I’m Hiring: https://finance.yahoo.com/news/spotak-six-traits-look-m-181335267.html • Geoff Lewis on LinkedIn: https://www.linkedin.com/in/geofflewis1 • Zenefits: https://en.wikipedia.org/wiki/TriNet_Zenefits • New banking records prove Deel paid thief who stole trade secrets from Rippling: https://www.rippling.com/blog/new-banking-records-prove-deel-paid-thief-who-stole-trade-secrets-from-rippling • Workday: https://www.workday.com • Matic robots: https://maticrobots.com • Wall-E: https://www.imdb.com/title/tt0910970 • Conviction: https://www.conviction.com • Mike Vernal on X: https://x.com/mvernal • Sarah Guo on X: https://x.com/saranormous • No Priors: https://linktr.ee/nopriors • Gemini: https://gemini.google.com • ChatGPT: https://chatgpt.com • Claude: https://claude.ai • Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier • Heated Rivalry on HBO Max: https://www.hbomax.com/shows/heated-rivalry/50cd4e99-04ee-427b-a3b4-da721ed05d9c • Fellow coffee maker: https://fellowproducts.com/products/aiden-precision-coffee-maker — Recommended books: • Pale Blue Dot: A Vision of the Human Future in Space: https://www.amazon.com/Pale-Blue-Dot-Vision-Future/dp/0345376595 • Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020 • Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 • The Effective Executive: The Definitive Guide to Getting the Right Things Done: https://www.amazon.com/Effective-Executive-Definitive-Harperbusiness-Essentials/dp/0060833459 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Sander Schulhoff is an AI researcher specializing in AI security, prompt injection, and red teaming. He wrote the first comprehensive guide on prompt engineering and ran the first-ever prompt injection competition, working with top AI labs and companies. His dataset is now used by Fortune 500 companies to benchmark their AI systems security, he’s spent more time than anyone alive studying how attackers break AI systems, and what he’s found isn’t reassuring: the guardrails companies are buying don’t actually work, and we’ve been lucky we haven’t seen more harm so far, only because AI agents aren’t capable enough yet to do real damage. We discuss: 1. The difference between jailbreaking and prompt injection attacks on AI systems 2. Why AI guardrails don’t work 3. Why we haven’t seen major AI security incidents yet (but soon will) 4. Why AI browser agents are vulnerable to hidden attacks embedded in webpages 5. The practical steps organizations should take instead of buying ineffective security tools 6. Why solving this requires merging classical cybersecurity expertise with AI knowledge — Brought to you by: Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Metronome—Monetization infrastructure for modern software companies: https://metronome.com/ GoFundMe Giving Funds—Make year-end giving easy: http://gofundme.com/lenny — Transcript: https://www.lennysnewsletter.com/p/the-coming-ai-security-crisis — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/181089452/my-biggest-takeaways-from-this-conversation — Where to find Sander Schulhoff: • X: https://x.com/sanderschulhoff • LinkedIn: https://www.linkedin.com/in/sander-schulhoff • Website: https://sanderschulhoff.com • AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sander Schulhoff and AI security (05:14) Understanding AI vulnerabilities (11:42) Real-world examples of AI security breaches (17:55) The impact of intelligent agents (19:44) The rise of AI security solutions (21:09) Red teaming and guardrails (23:44) Adversarial robustness (27:52) Why guardrails fail (38:22) The lack of resources addressing this problem (44:44) Practical advice for addressing AI security (55:49) Why you shouldn’t spend your time on guardrails (59:06) Prompt injection and agentic systems (01:09:15) Education and awareness in AI security (01:11:47) Challenges and future directions in AI security (01:17:52) Companies that are doing this well (01:21:57) Final thoughts and recommendations — Referenced: • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff • The AI Security Industry is B******t: https://sanderschulhoff.substack.com/p/the-ai-security-industry-is-b******t • The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0 • OpenAI: https://openai.com • Scale: https://scale.com • Hugging Face: https://huggingface.co • Ignore This Title and HackAPrompt: Exposing Systemic Vulnerabilities of LLMs through a Global Scale Prompt Hacking Competition: https://www.semanticscholar.org/paper/Ignore-This-Title-and-HackAPrompt%3A-Exposing-of-LLMs-Schulhoff-Pinto/f3de6ea08e2464190673c0ec8f78e5ec1cd08642 • Simon Willison’s Weblog: https://simonwillison.net • ServiceNow: https://www.servicenow.com • ServiceNow AI Agents Can Be Tricked Into Acting Against Each Other via Second-Order Prompts: https://thehackernews.com/2025/11/servicenow-ai-agents-can-be-tricked.html • Alex Komoroske on X: https://x.com/komorama • Twitter pranksters derail GPT-3 bot with newly discovered “prompt injection” hack: https://arstechnica.com/information-technology/2022/09/twitter-pranksters-derail-gpt-3-bot-with-newly-discovered-prompt-injection-hack • MathGPT: https://math-gpt.org • 2025 Las Vegas Cybertruck explosion: https://en.wikipedia.org/wiki/2025_Las_Vegas_Cybertruck_explosion • Disrupting the first reported AI-orchestrated cyber espionage campaign: https://www.anthropic.com/news/disrupting-AI-espionage • Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske • Prompt Optimization and Evaluation for LLM Automated Red Teaming: https://arxiv.org/abs/2507.22133 • MATS Research: https://substack.com/@matsresearch • CBRN: https://en.wikipedia.org/wiki/CBRN_defense • CaMeL offers a promising new direction for mitigating prompt injection attacks: https://simonwillison.net/2025/Apr/11/camel • Trustible: https://trustible.ai • Repello: https://repello.ai • Do not write that jailbreak paper: https://javirando.com/blog/2024/jailbreaks — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Elena Verna is the head of growth at Lovable, the leading AI-powered app builder that hit $200 million in annual recurring revenue in under a year with just 100 employees. In this record fourth appearance on the podcast, Elena shares how the traditional growth playbook has been completely rewritten for AI companies. She explains why Lovable focuses on innovation over optimization, how they’ve shifted from activation to building new features, and why giving away their product for free has become their most powerful growth strategy. We discuss: 1. Why 60% to 70% of traditional growth tactics no longer apply in AI 2. Why you have to re-find product-market fit every 3 months 3. The specific growth tactics driving Lovable’s unprecedented growth 4. Why giving away product is a growth strategy that beats paid ads 5. “Minimum lovable product” as the new standard (not minimum viable product) 6. Why activation now belongs to product teams, not growth teams 7. Whether you should join an AI startup (honest tradeoffs) — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vercel—Your collaborative AI assistant to design, iterate, and scale full-stack applications for the web Persona—A global leader in digital identity verification — Transcript: ⁠https://www.lennysnewsletter.com/p/the-new-ai-growth-playbook-for-2026-elena-verna⁠ — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/181207556/my-biggest-takeaways-from-this-conversation⁠ — Where to find Elena Verna: • X: https://x.com/elenaverna • LinkedIn: https://www.linkedin.com/in/elenaverna • Newsletter: https://www.elenaverna.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Elena Verna (05:19) The scale and growth of Lovable (08:55) Confidence in Lovable as a business (12:17) Retention at Lovable (15:02) Lovable’s unique growth levers (28:13) The role of marketing in Lovable’s success (38:09) Launching new features (40:59) Hiring and team dynamics (43:17) The value of vibe coding (49:46) The importance of community (51:47) Giving away your product for free (56:26) Tripling their company size (01:00:23) Product-market-fit challenges (01:08:50) Advice for joining AI companies (01:12:00) Work-life balance (01:15:20) What it’s like to work at Lovable (01:19:45) Women in tech (01:25:29) Final thoughts and lightning round — Referenced: • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey): https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Stripe: https://stripe.com • What differentiates the highest-performing product teams | John Cutler (Amplitude, The Beautiful Mess): https://www.lennysnewsletter.com/p/what-differentiates-the-highest-performing • How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra • “Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO): https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn • Eric Ries on LinkedIn: https://www.linkedin.com/in/eries • Elena’s post on LinkedIn about Lovable Missions: https://www.linkedin.com/posts/elenaverna_everythingispossible-lovableway-activity-7401627519646474242-hn6e • SheBuilds: https://shebuilds.lovable.app • Shopify + Lovable: https://lovable.dev/shopify • The Product-Market Fit Treadmill: Why every AI company is sprinting just to stay in place: https://www.elenaverna.com/p/the-product-market-fit-treadmill • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba • The adjacent user: https://brianbalfour.com/quick-takes/the-adjacent-user • Granola: https://www.granola.ai • Wispr Flow: https://wisprflow.ai • I’m worried about women in tech: https://www.elenaverna.com/p/im-worried-about-women-in-tech • Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Alexander Embiricos leads product on Codex, OpenAI’s powerful coding agent, which has grown 20x since August and now serves trillions of tokens weekly. Before joining OpenAI, Alexander spent five years building a pair programming product for engineers. He now works at the frontier of AI-led software development, building what he describes as a software engineering teammate—an AI agent designed to participate across the entire development lifecycle. We discuss: 1. Why Codex has grown 20x since launch and what product decisions unlocked this growth 2. How OpenAI built the Sora Android app in just 18 days using Codex 3. Why the real bottleneck to AGI-level productivity isn’t model capability—it’s human typing speed 4. The vision of AI as a proactive teammate, not just a tool you prompt 5. The bottleneck shifting from building to reviewing AI-generated work 6. Why coding will be a core competency for every AI agent—because writing code is how agents use computers best — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc — Transcript: https://www.lennysnewsletter.com/p/why-humans-are-ais-biggest-bottleneck — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180365355/my-biggest-takeaways-from-this-conversation — Where to find Alexander Embiricos: • X: https://x.com/embirico • LinkedIn: https://www.linkedin.com/in/embirico — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Alexander Embiricos  (05:13) The speed and ambition at OpenAI (11:34) Codex: OpenAI’s coding agent (15:43) Codex’s explosive growth (24:59) The future of AI and coding agents (33:11) The impact of AI on engineering (44:08) How Codex has impacted the way PMs operate (45:40) Throwaway code and ubiquitous coding (47:10) Shipping the Sora Android app (49:01) Building the Atlas browser (53:34) Codex’s impact on productivity (55:35) Measuring progress on Codex (58:09) Why they are building a web browser (01:01:58) Non-engineering use cases for Codex (01:02:53) Codex’s capabilities (01:04:49) Tips for getting started with Codex (01:05:37) Skills to lean into in the AI age (01:10:36) How far are we from a human version of AI? (01:13:31) Hiring and team growth at Codex (01:15:47) Lightning round and final thoughts — Referenced: • OpenAI: https://openai.com • Codex: https://openai.com/codex • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Dropbox: http://dropbox.com • Datadog: https://www.datadoghq.com • Andrej Karpathy on X: https://x.com/karpathy • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Atlas: https://openai.com/index/introducing-chatgpt-atlas • How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna: https://www.lennysnewsletter.com/p/how-block-is-becoming-the-most-ai-native • Goose: https://block.xyz/inside/block-open-source-introduces-codename-goose • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennysnewsletter.com/p/lessons-on-building-product-sense • Sora Android app: https://play.google.com/store/apps/details?id=com.openai.sora&hl=en_US&pli=1 • The OpenAI Podcast—ChatGPT Atlas and the next era of web browsing: https://www.youtube.com/watch?v=WdbgNC80PMw&list=PLOXw6I10VTv9GAOCZjUAAkSVyW2cDXs4u&index=2 • How to measure AI developer productivity in 2025 | Nicole Forsgren: https://www.lennysnewsletter.com/p/how-to-measure-ai-developer-productivity • Compiling: https://3d.xkcd.com/303 • Jujutsu Kaisen on Netflix: https://www.netflix.com/title/81278456 • Tesla: https://www.tesla.com • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Andreas Embirikos: https://en.wikipedia.org/wiki/Andreas_Embirikos • George Embiricos: https://en.wikipedia.org/wiki/George_Embiricos: https://en.wikipedia.org/wiki/George_Embiricos — Recommended books: • Culture series: https://www.amazon.com/dp/B07WLZZ9WV • The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411 • A Fire Upon the Deep (Zones of Thought series Book 1): https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/1250237750 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge, Edwin was a research scientist at Google, Facebook, and Twitter and studied mathematics, computer science, and linguistics at MIT. We discuss: 1. How Surge reached over $1 billion in revenue with fewer than 100 people by obsessing over quality 2. The story behind how Claude Code got so good at coding and writing 3. The problems with AI benchmarks and why they’re pushing AI in the wrong direction 4. How RL environments are the next frontier in AI training 5. Why Edwin believes we’re still a decade away from AGI 6. Why taste and human judgment shape which AI models become industry leaders 7. His contrarian approach to company building that rejects Silicon Valley’s “pivot and blitzscale” playbook 8. How AI models will become increasingly differentiated based on the values of the companies building them — Brought to you by: Vanta—Automate compliance. Simplify security. WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Coda—The all-in-one collaborative workspace — Transcript: https://www.lennysnewsletter.com/p/surge-ai-edwin-chen — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180055059/my-biggest-takeaways-from-this-conversation — Where to find Edwin Chen: • X: https://x.com/echen • LinkedIn: https://www.linkedin.com/in/edwinzchen • Surge’s blog: https://surgehq.ai/blog — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Edwin Chen (04:48) AI’s role in business efficiency (07:08) Building a contrarian company (08:55) An explanation of what Surge AI does (09:36) The importance of high-quality data (13:31) How Claude Code has stayed ahead (17:37) Edwin’s skepticism toward benchmarks (21:54) AGI timelines and industry trends (28:33) The Silicon Valley machine (33:07) Reinforcement learning and future AI training (39:37) Understanding model trajectories (41:11) How models have advanced and will continue to advance (42:55) Adapting to industry needs (44:39) Surge’s research approach (48:07) Predictions for the next few years in AI (50:43) What’s underhyped and overhyped in AI (52:55) The story of founding Surge AI (01:02:18) Lightning round and final thoughts — Referenced: • Surge: https://surgehq.ai • Surge’s product page: https://surgehq.ai/products • Claude Code: https://www.claude.com/product/claude-code • Gemini 3: https://aistudio.google.com/models/gemini-3 • Sora: https://openai.com/sora • Terrence Rohan on LinkedIn: https://www.linkedin.com/in/terrencerohan • Richard Sutton—Father of RL thinks LLMs are a dead end: https://www.dwarkesh.com/p/richard-sutton • The Bitter Lesson: http://www.incompleteideas.net/IncIdeas/BitterLesson.html • Reinforcement learning: https://en.wikipedia.org/wiki/Reinforcement_learning • Grok: https://grok.com • Warren Buffett on X: https://x.com/WarrenBuffett • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong • Interstellar on Prime Video: https://www.amazon.com/Interstellar-Matthew-McConaughey/dp/B00TU9UFTS • Arrival on Prime Video: https://www.amazon.com/Arrival-Amy-Adams/dp/B01M2C4NP8 • Travelers on Netflix: https://www.netflix.com/title/80105699 • Waymo: https://waymo.com • Soda versus pop: https://flowingdata.com/2012/07/09/soda-versus-pop-on-twitter — Recommended books: • Stories of Your Life and Others: https://www.amazon.com/Stories-Your-Life-Others-Chiang/dp/1101972122 • The Myth of Sisyphus: https://www.amazon.com/Myth-Sisyphus-Vintage-International/dp/0525564454 • Le Ton Beau de Marot: In Praise of the Music of Language: https://www.amazon.com/dp/0465086454 • Gödel, Escher, Bach: An Eternal Golden Braid: https://www.amazon.com/G%C3%B6del-Escher-Bach-Eternal-Golden/dp/0465026567 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Tomer Cohen is the longtime chief product officer at LinkedIn, where he’s pioneering the Full Stack Builder program, a radical new approach to product development that fully embraces what AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder program that teaches coding, design, and PM skills together. He’s also introduced a formal “Full Stack Builder” title and career ladder, enabling anyone from any function to take products from idea to launch. In this conversation, Tomer explains why product development has become too complex at most companies and how LinkedIn is building an AI-powered product team that can move faster, adapt more quickly, and do more with less. We discuss: 1. How 70% of the skills needed for jobs will change by 2030 2. The broken traditional model: organizational bloat slows features to a six-month cycle 3. The Full Stack Builder model 4. Three pillars of making FSB work: platform, agents, and culture (culture matters most) 5. Building specialized agents that critique ideas and find vulnerabilities 6. Why off-the-shelf AI tools never work on enterprise code without customization 7. Top performers adopt AI tools fastest, contrary to expectations about leveling effects 8. Change management tactics: celebrating wins, making tools exclusive, updating performance reviews — Brought to you by: Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Miro—The AI Innovation Workspace where teams discover, plan, and ship breakthrough products: https://miro.com/lenny — Transcript: https://www.lennysnewsletter.com/p/why-linkedin-is-replacing-pms — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/180042347/my-takeaways-from-this-conversation — Where to find Tomer Cohen: • LinkedIn: https://www.linkedin.com/in/tomercohen • Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Tomer Cohen (04:42) The need for change in product development (11:52) The full-stack builder model explained (16:03) Implementing AI and automation in product development (19:17) Building and customizing AI tools (27:51) The timeline to launch (31:46) Pilot program and early results (37:04) Feedback from top talent (39:48) Change management and adoption (46:53) Encouraging people to play with AI tools (41:21) Performance reviews and full-stack builders (48:00) Challenges and specialization (50:05) Finding talent (52:46) Tips for implementing in your own company (56:43) Lightning round and final thoughts — Referenced: • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen • LinkedIn: https://www.linkedin.com • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Devin: https://devin.ai • Figma: https://www.figma.com • Microsoft Copilot: https://copilot.microsoft.com • Windsurf: https://windsurf.com • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Lovable: https://lovable.dev • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • APB program at LinkedIn: https://careers.linkedin.com/pathways-programs/entry-level/apb • Naval Ravikant on X: https://x.com/naval • One Song podcast: https://podcasts.apple.com/us/podcast/%D7%A9%D7%99%D7%A8-%D7%90%D7%97%D7%93-one-song/id1201883177 • Song Exploder podcast: https://songexploder.net • Grok on Tesla: https://www.tesla.com/support/grok • Reid Hoffman on X: https://x.com/reidhoffman — Recommended books: • Why Nations Fail: The Origins of Power, Prosperity, and Poverty: https://www.amazon.com/Why-Nations-Fail-Origins-Prosperity/dp/0307719227 • Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599 • The Beginning of Infinity: Explanations That Transform the World: https://www.amazon.com/Beginning-Infinity-Explanations-Transform-World/dp/0143121359 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. We discuss: 1. Why GTM is becoming more strategically important in the AI era 2. The rise of the GTM engineer 3. A primer on segmentation 4. How to build a sales org that engineers and product teams respect 5. The changing calculus of build vs. buy for go-to-market tools in the AI era 6. Why most customers buy to avoid pain rather than to gain upside — Brought to you by: Datadog—Now home to Eppo, the leading experimentation and feature flagging platform: https://www.datadoghq.com/lenny Lovable—Build apps by simply chatting with AI: https://lovable.dev/ Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ — Transcript: https://www.lennysnewsletter.com/p/what-the-best-gtm-teams-do-differently — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/179503137/my-biggest-takeaways-from-this-conversation — Where to find Jeanne DeWitt Grosser: • X: https://x.com/jdewitt29 • LinkedIn: https://www.linkedin.com/in/jeannedewitt — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jeanne DeWitt Grosser (05:26) Defining go-to-market (08:43) The evolution of go-to-market roles (11:23) The rise of the go-to-market engineer (14:21) Implementing AI in sales processes (15:28) Optimizing sales with AI agents (23:47) Defining sales roles: SDRs and AEs (26:04) When to hire a GTM engineer (29:04) Hiring and scaling sales teams (30:50) The ideal go-to-market engineer (34:24) The go-to-market tool stack (40:39) Advice on building a great sales bot (44:34) Vercel’s unfair advantage (46:37) Go-to-market as a product (47:04) Innovative sales tactics at Stripe (52:38) Effective go-to-market tactics (01:00:37) Segmentation strategies (01:09:31) Building a sales org that engineers love (01:14:00) Thoughts on PLG and pricing (01:16:44) Sales compensation and hiring (01:19:24) Lightning round and final thoughts — Referenced: • Vercel: https://vercel.com • Stripe: https://stripe.com • Rosalind Franklin: https://en.wikipedia.org/wiki/Rosalind_Franklin • Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman • SDK: https://ai-sdk.dev/docs/introduction • Gong: https://www.gong.io • Lyft: https://www.lyft.com • Instacart: https://www.instacart.com • DoorDash: https://www.instacart.com • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Kate Jensen on LinkedIn: https://www.linkedin.com/in/kateearle • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Atlassian: atlassian.com — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Rachel Lockett is a sought-after executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me. We discuss: * When to coach and when to just tell people what to do [09:00] * The GROW technique for helping people figure out a solution for themselves [18:37] * Techniques for making difficult conversations less difficult [01:20:28] * Avoiding burnout and designing a more energizing career [41:55] * Building and sustaining a healthy co-founder relationship [01:06:50] * Creating a one-page plan that aligns your entire company [01:31:47] * Practical ways AI is transforming executive coaching and leadership development [01:36:50] * Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55] Also on Spotify and Apple Podcasts Brought to you by: Stripe—Helping companies of all sizes grow revenue Vanta—Automate compliance. Simplify security. Persona—A global leader in digital identity verification Where to find Rachel Lockett: • LinkedIn: https://www.linkedin.com/in/rhlockett/ • Website: https://www.lockettcoaching.com Referenced: • One-page plan template: https://www.lockettcoaching.com/#resources • Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0 • Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/ • First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0 • Coinbase: https://www.coinbase.com • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to • Patrick Collison on X: https://x.com/patrickc • Stripe: https://stripe.com • Remind: https://www.remind.com • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams • Brex: https://www.brex.com • Bridge: https://www.bridge.xyz • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • The Enneagram Institute: https://www.enneagraminstitute.com • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst • How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver • Granola: https://www.granola.ai • KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621 • Loom: https://www.loom.com • Joseph Campbell’s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front • Wes Anderson’s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-films Recommended books: • Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904 • Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321 • Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Stewart Butterfield is the co-founder of Slack and Flickr, two of the most influential products in internet history. After selling Slack to Salesforce in one of tech’s biggest acquisitions, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principles that most contributed to his success. From “utility curves” to “the owner’s delusion” to “hyper-realistic work-like activities,” his thoughts on craft, strategy, and leadership apply to anyone building products or leading teams. We discuss: 1. Hyper-realistic work-like activities 2. The owner’s delusion 3. Utility curves 4. “Don’t make me think” 5. “We don’t sell saddles here” 6. Tilting your umbrella 7. When to pivot — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Metronome—Monetization infrastructure for modern software companies Lovable—Build apps by simply chatting with AI — Transcript: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178320649/my-biggest-takeaways-from-this-conversation — Where to find Stewart Butterfield: • X: https://x.com/stewart • LinkedIn: https://www.linkedin.com/in/butterfield — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Stewart Butterfield (04:58) Stewart’s current life and reflections (06:44) Understanding utility curves (10:13) The concept of divine discontent (15:11) The importance of taste in product design (19:03) Tilting your umbrella (28:32) Balancing friction and comprehension (45:07) The value of constant dissatisfaction (47:06) Embracing continuous improvement (50:03) The complexity of making things work (54:27) Parkinson’s law and organizational growth (01:03:17) Hyper-realistic work-like activities (01:13:23) Advice on when to pivot (01:18:36) The importance of generosity in leadership (01:26:34) The owner’s delusion — Referenced: • Slack: https://slack.com • Flickr: https://www.flickr.com • Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal • Blok: https://blok.so • Brandon Velestuk on LinkedIn: https://www.linkedin.com/in/brandon-velestuk-6018721b • Magic Link: https://en.wikipedia.org/wiki/Magic_Link • Ticketmaster: https://www.ticketmaster.com • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai • Three Questions with Slack’s CEO: https://www.technologyreview.com/2014/11/21/170330/three-questions-with-slacks-ceo • Six Sigma: https://www.6sigma.us • What is kaizen and how does Toyota use it?: https://mag.toyota.co.uk/kaizen-toyota-production-system • John Collison’s post on X about passion projects: https://x.com/collision/status/1529452415346302976 • Parkinson’s law: https://www.economist.com/news/1955/11/19/parkinsons-law • We Don’t Sell Saddles Here: https://medium.com/@stewart/we-dont-sell-saddles-here-4c59524d650d • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • IRC: https://en.wikipedia.org/wiki/IRC • This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke • The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins: https://www.lennysnewsletter.com/p/the-making-of-canva • Prisoner’s dilemma: https://en.wikipedia.org/wiki/Prisoner%27s_dilemma • Stewart Little: https://en.wikipedia.org/wiki/Stuart_Little • Dharma and Greg: https://en.wikipedia.org/wiki/Dharma_%26_Greg • Stewart’s post on X referencing “the owner’s delusion”: https://x.com/stewart/status/1223286626991796224 — Recommended books: • Principles: Life and Work: https://www.amazon.com/Principles-Life-Work-Ray-Dalio/dp/1501124021 • Why Nothing Works: Who Killed Progress―and How to Bring It Back: https://www.amazon.com/Why-Nothing-Works-Killed-Progress_and/dp/154170021X • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s Institute for Human-Centered AI. In this conversation, Fei-Fei shares the rarely told history of how we got here—including the wild fact that just nine years ago, calling yourself an AI company was basically a death sentence. We discuss: 1. How ImageNet helped spark the AI explosion we’re living through 2. Why world models and spatial intelligence represent the next frontier in AI, beyond large language models 3. Why Fei-Fei believes AI won’t replace humans but will require us to take responsibility for ourselves 4. The surprising applications of Marble, from movie production to psychological research 5. Why robotics faces unique challenges compared with language models and what’s needed to overcome them 6. How to participate in AI regardless of your role — Brought to you by: Figma Make—A prompt-to-code tool for making ideas real Justworks—The all-in-one HR solution for managing your small business with confidence Sinch—Build messaging, email, and calling into your product — Transcript: https://www.lennysnewsletter.com/p/the-godmother-of-ai — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/178223233/my-biggest-takeaways-from-this-conversation — Where to find Dr. Fei-Fei Li • X: https://x.com/drfeifei • LinkedIn: https://www.linkedin.com/in/fei-fei-li-4541247 • World Labs: https://www.worldlabs.ai — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dr. Fei-Fei Li (05:31) The evolution of AI (09:37) The birth of ImageNet (17:25) The rise of deep learning (23:53) The future of AI and AGI (29:51) Introduction to world models (40:45) The bitter lesson in AI and robotics (48:02) Introducing Marble, a revolutionary product (51:00) Applications and use cases of Marble (01:01:01) The founder’s journey and insights (01:10:05) Human-centered AI at Stanford (01:14:24) The role of AI in various professions (01:18:16) Conclusion and final thoughts — References: https://www.lennysnewsletter.com/p/the-godmother-of-ai — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable for most of its history, has not raised significant funding, and they built a massive business in a category most investors dismissed. In fact, one investor told Grant his idea was “the dumbest idea he had ever heard.” We discuss: • How Gamma found product-market fit by rethinking their onboarding • Their process for building a “word-of-mouth machine” • How they leveraged more than 1,000 micro-influencers instead of big names • Why focusing on the “first 30 seconds” transformed their business • Their approach to pricing that led to profitability within months • How Grant thinks about building a durable “GPT wrapper” business — Brought to you by: Vanta—Automate compliance. Simplify security. Justworks—The all-in-one HR solution for managing your small business with confidence Miro—A collaborative visual platform where your best work comes to life — Where to find Grant Lee: • X: https://x.com/thisisgrantlee • LinkedIn: https://www.linkedin.com/in/grantslee — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Grant Lee and Gamma (05:59) The founding story of Gamma (09:52) Achieving product-market fit (15:43) Self-awareness as a founder (17:17) The power of onboarding (20:41) The original insight that led to Gamma (22:42) Founder-led marketing and growth tactics (29:20) Sharing online (37:40) Getting to $100M ARR (41:19) Influencer marketing as a growth strategy (54:08) Virality is not an accident (58:30) Investing in brand before paid ads (01:02:04) Tips for getting started with performance marketing (01:04:49) Prototyping and user feedback (01:16:12) Adapting and moving quickly (01:19:21) The concept of GPT wrapper companies (01:22:16) Deep dive into workflow and model utilization (01:29:06) Pricing strategies (01:34:53) Hiring philosophy and practices (01:43:24) Betting big on high performers (01:45:03) Final thoughts and lightning round — References: https://www.lennysnewsletter.com/p/how-50-people-built-a-profitable-ai-unicorn — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on the skills founders need to learn to go from $1M to $10M ARR. We discuss: 1. Why the “mid-market” doesn’t exist 2. Why tier-one logos like Stripe and Tesla counterintuitively make the best early customers 3. The dangers of pricing your product at $10K-$20K 4. Why you need to vision-cast instead of problem-solve to win enterprise deals 5. Why services are the fastest way to get your foot in the door with enterprises 6. How to find and work with design partners 7. When to hire your first salesperson and what profile to look for — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Lovable—Build apps by simply chatting with AI Coda—The all-in-one collaborative workspace — Where to find Jen Abel: • X: https://x.com/jjen_abel • LinkedIn: https://www.linkedin.com/in/earlystagesales • Website: https://www.jjellyfish.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Jen! (04:38) The myth of the mid-market (08:08) Targeting tier-one logos (10:50) Vision-casting vs. problem-selling (15:35) The importance of high ACVs (20:45)  Don’t play the small business game with an enterprise company (25:09) Design partners: the double-edged sword (28:11) Finding the right company (36:55) Enterprise sales: the art of the deal (43:21) The problem with channel partnerships (44:41) Quick summary (50:24) Hiring the right enterprise salespeople (56:49) Structuring sales compensation (01:01:01) Building relationships in enterprise sales (01:02:07) The art of cold outreach (01:07:31) Outbound tooling and AI (01:14:08) Lightning round and final thoughts — Referenced: • The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH): https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel • Mario meme: https://www.linkedin.com/pulse/missing-meme-led-me-woman-johann-van-tonder-im6df • Kathy Sierra: https://en.wikipedia.org/wiki/Kathy_Sierra • Cursor: https://cursor.com • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Justin Lawson on X: https://x.com/jjustin_lawson • Stripe: https://stripe.com • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Linear: https://linear.app • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Gemini: https://gemini.google.com • Microsoft Copilot: https://copilot.microsoft.com • How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi • McKinsey & Company: https://www.mckinsey.com • Deloitte: https://www.deloitte.com • Accenture: https://www.accenture.com • Building a world-class sales org | Jason Lemkin (SaaStr): https://www.lennysnewsletter.com/p/building-a-world-class-sales-org • Peter Dedene on X: https://x.com/peterdedene • Hang Huang on X: https://x.com/HH_HangHuang • Hugo Alves on X: https://x.com/Ugo_alves • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Clay: https://www.clay.com • Apollo: https://www.apollo.io • Jason Lemkin on X: https://x.com/jasonlk • Gavin Baker on X: https://x.com/GavinSBaker • Jason Cohen on X: https://x.com/asmartbear • Baywatch on Prime Video: https://www.primevideo.com/detail/Baywatch/0NU9YS8WWRNQO1NZD5DOQ3I8W6 • Playground: https://www.tryplayground.com • ClassDojo: https://www.classdojo.com • Jason Lemkin’s post about Replit: https://x.com/jasonlk/status/1946069562723897802 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Melanie Perkins is CEO and co-founder of Canva, currently valued at over $42 billion, generating over $3 billion in annual revenue, with more than 240 million monthly active users and, incredibly, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising round, her team spent two years without being able to ship a new feature during a technical rewrite, and the company pivoted early from a yearbook publishing platform to become the design powerhouse it is today. Through it all, she maintained what she calls “column B” thinking: building toward a dream future rather than just using the bricks around you. We discuss: 1. How “column B” thinking helped Melanie build Canva, by starting with an impossible vision rather than existing constraints 2. The power of setting “crazy big goals” 3. How Canva survived a painful two-year period without shipping any new features while rewriting their codebase 4. How Melanie pushed through 100 investor rejections, and how she used each rejection to strengthen her pitch 5. Canva’s “two-step plan”: build one of the world’s most valuable companies, then do the most good possible 6. Melanie’s vision for 2050 and why she believes imagination is the first step toward a better world — Brought to you by: Vanta—Automate compliance. Simplify security. https://vanta.com/lenny Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com — Transcript: ⁠https://www.lennysnewsletter.com/p/the-making-of-canva⁠⁠ — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/176082995/my-biggest-takeaways-from-this-conversation — Where to find Melanie Perkins: • X: https://x.com/melaniecanva • LinkedIn: https://www.linkedin.com/in/melanieperkins/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Melanie Perkins and Canva (04:44) Building a “column B” company (06:36) Operationalizing big visions (13:13) Crazy big goals and celebrations (22:00) Challenges and setbacks in Canva’s journey (26:30) Fundraising and investor rejections (29:36) Leadership and growth lessons (34:38) Canva’s goal-driven structure (35:46) Balancing work and personal life (38:02) Community-driven product development (40:37) The two-step plan for global impact (45:04) Canva’s biggest launch yet (48:10) How Canva approaches product expansion (52:37) AI integration in Canva (53:56) AI corner (55:22) Melanie’s vision for 2050 and beyond (01:00:07) Lightning round and final thoughts — Referenced: • Canva: https://www.canva.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennysnewsletter.com/p/building-high-performing-teams-melissa • UserTesting: https://www.usertesting.com/ • Figma: https://www.figma.com/ • Adobe: https://www.adobe.com/ • Calm: https://www.calm.com/ • Gandhi’s quote about happiness: https://www.brainyquote.com/quotes/mahatma_gandhi_105593 • Help us improve Canva: https://www.canva.com/help/get-in-touch/general-feedback/ — Recommended books: • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/ • The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898/ • The Power of Moments: Why Certain Experiences Have Extraordinary Impact: https://www.amazon.com/Power-Moments-Certain-Experiences-Extraordinary/dp/1501147765 • Designing the Obvious: A Common Sense Approach to Web and Mobile Application Design: https://www.amazon.com/Designing-Obvious-Common-Approach-Application/dp/0321749855 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dhanji R. Prasanna is the chief technology officer at Block (formerly Square), where he’s managed more than 4,000 engineers over the past two years. Under his leadership, Block has become one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transformation (and his promotion to CTO). We discuss: 1. How Block’s internal open-source agent, called Goose, is saving employees 8 to 10 hours weekly 2. How the company measures AI productivity gains across technical and non-technical teams 3. Which teams are benefiting most from AI (it’s not engineering) 4. The boring organizational change that boosted productivity even more than AI tools 5. Why code quality has almost nothing to do with product success 6. How to drive AI adoption throughout an organization (hint: leadership needs to use the tools daily) 7. Lessons from building Google Wave, Google+, and other failed products — Brought to you by: Sinch—Build messaging, email, and calling into your product: https://sinch.com/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Persona—A global leader in digital identity verification: https://withpersona.com/lenny — Where to find Dhanji R. Prasanna: • LinkedIn: https://www.linkedin.com/in/dhanji/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dhanji (05:26) The AI manifesto: convincing Jack Dorsey (07:33) Transforming into a more AI-native company (12:05) How engineering teams work differently today (15:24) Goose: Block’s open-source AI agent (20:18) Measuring AI productivity gains across teams (21:38) What Goose is and how it works (32:15) The future of AI in engineering and productivity (37:42) The importance of human taste (40:10) Building vs. buying software (44:08) How AI is changing hiring and team structure (53:45) The importance of using AI tools yourself before deploying them (55:13) How Goose helped solve a personal problem with receipts (58:01) What makes Goose unique (59:57) What Dhanji wishes he knew before becoming CTO (01:01:49) Counterintuitive lessons in product development (01:04:56) Why controlled chaos can be good for engineering teams (01:08:07) Core leadership lessons (01:13:36) Failure corner (01:15:50) Lightning round and final thoughts — Referenced: • Jack Dorsey on X: https://x.com/jack • Block: https://block.xyz/ • Square: https://squareup.com/ • Cash App: https://cash.app/ • What is Conway’s Law?: https://www.microsoft.com/en-us/microsoft-365-life-hacks/organization/what-is-conways-law# • Goose: https://github.com/block/goose • Gosling: https://github.com/block/goose-mobile • Salesforce: https://www.salesforce.com/ • Snowflake: https://www.snowflake.com/ • Claude: https://claude.ai/ • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • OpenAI: https://openai.com/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Llama: https://www.llama.com/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Top Gun: https://www.imdb.com/title/tt0092099/ • Lenny’s vibe-coded Lovable app: https://gdoc-images-grab.lovable.app/ • Afterpay: https://github.com/afterpay • Bitkey: https://bitkey.world/ • Proto: https://github.com/proto-at-block • Brad Axen on LinkedIn: https://www.linkedin.com/in/bradleyaxen/ • Databricks: https://www.databricks.com/ • Carl Sagan’s quote: https://www.goodreads.com/quotes/32952-if-you-wish-to-make-an-apple-pie-from-scratch • Google Wave: https://en.wikipedia.org/wiki/Google_Wave • Google Video: https://en.wikipedia.org/wiki/Google_Video • Secret: https://en.wikipedia.org/wiki/Secret_(app) • Alien Earth on FX: https://www.fxnetworks.com/shows/alien-earth • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Fargo TV series on Prime Video: https://www.amazon.com/Fargo-Season-1/dp/B09QGRGH6M • Steam Deck OLED display: https://www.steamdeck.com/en/oled • Doc Brown: https://backtothefuture.fandom.com/wiki/Emmett_Brown — Recommended books: • The Master and Margarita: https://www.amazon.com/Master-Margarita-Mikhail-Bulgakov/dp/0802130119 • Tennyson Poems: https://www.amazon.com/Tennyson-Poems-Everymans-Library-Pocket/dp/1400041872/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Chip Huyen is a core developer on Nvidia’s Nemo platform, a former AI researcher at Netflix, and taught machine learning at Stanford. She’s a two-time founder and the author of two widely read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has built multiple successful AI products and platforms and works directly with enterprises on their AI strategies, giving her unique visibility into what’s actually happening inside companies building AI products. We discuss: 1. What people think makes AI apps better vs. what actually makes AI apps better 2. What pre-training vs. post-training is, and why fine-tuning should be your last resort 3. How RLHF (reinforcement learning from human feedback) actually works 4. Why data quality matters more than which vector database you choose 5. Why high performers are seeing the most gains from AI coding tools 6. Why most AI problems are actually UX issues — Brought to you by: Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/ Justworks—The all-in-one HR solution for managing your small business with confidence: https://www.justworks.com Persona—A global leader in digital identity verification: https://withpersona.com/lenny — Where to find Chip Huyen: • X: https://x.com/chipro • LinkedIn: https://www.linkedin.com/in/chiphuyen/ • Website: https://huyenchip.com/ • Substack: https://substack.com/@chiphuyen — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Chip Huyen (04:28) Chip’s viral LinkedIn post (07:05) Understanding AI training: pre-training vs. post-training (08:50) Language modeling explained (13:55) The importance of post-training (15:20) Reinforcement learning and human feedback (22:23) The importance of evals in AI development (31:55) Retrieval augmented generation (RAG) explained (38:50) Challenges in AI tool adoption (43:19) Challenges in measuring productivity (45:20) The three-bucket test (49:10) The future of engineering roles (55:31) ML Engineers vs. AI engineers (57:12) Looking forward: the impact of AI (01:05:48) Model capabilities vs. perceived performance (01:08:23) Lightning round and final thoughts — Referenced: • Chip’s LinkedIn post on what actually improves AI apps: https://www.linkedin.com/posts/chiphuyen_aiapplications-aiengineering-activity-7358971409227792384-y0mf/ • Prediction and Entropy of Printed English: https://www.princeton.edu/~wbialek/rome/refs/shannon_51.pdf • Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody •Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO): https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord • First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course): https://www.lennysnewsletter.com/p/why-ai-evals-are-the-hottest-new-skill • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Stanford webinar—How AI Is Changing Coding and Education, Andrew Ng & Mehran Sahami: https://www.youtube.com/watch?v=J91_npj0Nfw • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • Lenny’s vibe-coded app made on Lovable: https://gdoc-images-grab.lovable.app/ • Story of Yanxi Palace: https://www.imdb.com/title/tt8865016/ • Steve Jobs’s quote: https://www.goodreads.com/quotes/427317-remembering-that-i-ll-be-dead-soon-is-the-most-important — Recommended books: • The Complete Sherlock Holmes: https://www.amazon.com/Complete-Sherlock-Holmes-Volumes/dp/0553328255 • AI Engineering: Building Applications with Foundation Models: https://www.amazon.com/AI-Engineering-Building-Applications-Foundation/dp/1098166302 • The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152 • From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Nicole Forsgren created the most widely used frameworks for measuring developer productivity—DORA and SPACE. She wrote the foundational book Accelerate and is about to release her newest book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google. We discuss: 1. Why most productivity metrics are a lie 2. Signs that your engineering team could be moving much faster 3. Why AI accelerates coding but developers aren’t speeding up as much as you think 4. AI’s impact on engineers getting into “flow” 5. Her framework for building and scaling a developer experience team 6. The three components of developer experience: flow state, cognitive load, and feedback loops — Brought to you by: Mercury—The art of simplified finances: https://mercury.com/ WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny — Where to find Nicole Forsgren: • Twitter: https://twitter.com/nicolefv • LinkedIn: https://www.linkedin.com/in/nicolefv/ • Website: https://nicolefv.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nicole Forsgren (05:09) The concept of developer experience (DevEx) (08:33) Flow state and cognitive load in the age of AI (12:02) Challenges in measuring productivity with AI (21:19) The importance of developer experience for business value (22:20) Common issues and solutions in developer experience (26:49) Signs your eng team is moving too slow (29:52) How AI is improving productivity (33:32) Real examples of productivity improvements (36:35) Introducing her new book, Frictionless (43:40) How to get started building a DevEx team (45:15) The impact of forming developer experience teams (46:15)  How to measure the impact of DevEx teams (48:53) Measuring the impact of AI tools on productivity (55:16) Survey design for developer experience (57:59) Popular AI tools for developers (59:08) Bringing a product mindset to DevEx improvements (01:00:40) AI corner (01:02:33) Lightning round and final thoughts — Referenced: • How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennysnewsletter.com/p/how-to-measure-and-improve-developer • DORA: https://dora.dev/ • The SPACE framework: A comprehensive guide to developer productivity: https://getdx.com/blog/space-metrics/ • Measuring developer productivity with the DX Core 4: https://getdx.com/research/measuring-developer-productivity-with-the-dx-core-4/ • Gloria Mark’s website: https://gloriamark.com/ • Taking Flight with Copilot: https://dl.acm.org/doi/10.1145/3589996 • DevEx in Action: https://spawn-queue.acm.org/doi/10.1145/3639443 • CodeX: https://openai.com/codex/ • Devin: https://devin.ai/ • Abi Noda on LinkedIn: https://www.linkedin.com/in/abinoda/ • DX is joining Atlassian: https://getdx.com/blog/dx-is-joining-atlassian/ • GitHub Copilot: https://github.com/features/copilot • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Gemini Code Assist: https://codeassist.google/ • Claude Code: https://www.claude.com/product/claude-code • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Love Is Blind on Netflix: https://www.netflix.com/title/80996601 • Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking/umc.cmc.apzybj6eqf6pzccd97kev7bs • Ninja Creami: https://www.amazon.com/Ninja-NC301-CREAMi-Containers-Bundle/dp/B0BLGR5JPV/ • Jura coffee maker: https://www.amazon.com/Jura-Nordic-Automatic-Coffee-Machine/dp/B0CF65BFZ1/ — Recommended books: • Frictionless: https://developerexperiencebook.com/ • DevEx Workbook: https://developerexperiencebook.com/#workbook • Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599 • Back Mechanic: https://www.amazon.com/Back-Mechanic-Stuart-McGill-2015-09-30/dp/B01FKSGJYC • How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/ • The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/dp/B01KBM82M4/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the company to a successful IPO in 2025. What you’ll learn: • How Dylan kept internal morale up after the Adobe acquisition fell through • His approach to maintaining pace and a sense of urgency 13 years in • How to systematically develop taste • How Figma decides which product lines to add • Why Dylan obsesses over “time to value” • How AI is making design more valuable — Brought to you by: Stripe—Helping companies of all sizes grow revenue — Transcript: ⁠https://www.lennysnewsletter.com/p/why-ai-makes-design-craft-and-quality-the-new-moat⁠ — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175569466/my-biggest-takeaways-from-this-conversation⁠ — Where to find Dylan Field: • X: https://x.com/zoink • LinkedIn: https://www.linkedin.com/in/dylanfield/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dylan Field (03:58) The Adobe deal fallout (05:50) Maintaining team morale post-deal (09:13) Strategies for sustaining high performance (13:37) Maintaining Figma’s unique company culture (16:22) Dylan’s leadership evolution (21:03) How to improve clarity as a leader (24:40) The controversy behind FigJam (31:06) Lessons from expanding Figma’s core product line (39:32) Time-to-value (45:14) Introduction to Figma Make (48:26) AI app prototyping and the future of Figma Make (53:38) Lessons from Figma’s AI product launch (57:47) The importance of craft (59:54) Developing good taste (01:05:35) The future of product development (01:10:32) Why AI won’t steal your job (01:14:37) AI corner (01:18:32) Lightning round and final thoughts — Referenced: • Dylan Field live at Config: Intuition, simplicity, and the future of design: https://www.lennysnewsletter.com/p/dylan-field-live-at-config • Figma: https://www.figma.com/ • Adobe: https://www.adobe.com/ • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao • $46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder): https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz • FigJam: https://www.figma.com/figjam/ • Cursor chat: https://help.figma.com/hc/en-us/articles/4403130802199-Use-cursor-chat-in-Figma-Design • Figma Slides: https://www.figma.com/slides/ • Figma Sites: https://www.figma.com/sites/ • Figma Buzz: https://www.figma.com/buzz/ • Figma Draw: https://www.figma.com/draw/ • Figma Design: https://www.figma.com/design/ • Dev Mode: https://www.figma.com/dev-mode/ • Figma Make: https://www.figma.com/make/ • Zach Lloyd on X: https://x.com/zachlloydtweets • Warp: https://www.warp.dev/ • Dylan’s post on X about Figma on an AI product leaderboard: https://x.com/zoink/status/1968588014935801884 • Kurt Cobain: https://en.wikipedia.org/wiki/Kurt_Cobain • Damien Correll on LinkedIn: https://www.linkedin.com/in/damiencorrell/ • Marcin Wichary on LinkedIn: https://www.linkedin.com/in/mwichary/ • Loredana Crisan on LinkedIn: https://www.linkedin.com/in/loredanacrisan/ • Amber Bravo on LinkedIn: https://www.linkedin.com/in/amberbravo/ • Figma’s 2025 AI report: Perspectives from designers and developers: https://www.figma.com/blog/figma-2025-ai-report-perspectives/ • Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox#Energy_conservation_policy • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff • Pantheon: https://www.imdb.com/title/tt11680642/ • Retro: https://retro.app/ • Thiel Fellowship: https://thielfellowship.org/ — Recommended books: • Understanding Comics: The Invisible Art: https://www.amazon.com/Understanding-Comics-Invisible-Scott-McCloud/dp/006097625X • The Spy and the Traitor: The Greatest Espionage Story of the Cold War: https://www.amazon.com/Spy-Traitor-Greatest-Espionage-Story/dp/1101904216 • Codex Seraphinianus: https://www.amazon.com/Codex-Seraphinianus-Anniversary-Luigi-Serafini/dp/0847871045 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Robby Stein is VP of Product at Google, where he oversees the core products of Google Search—including the new AI Overviews, AI Mode, search ranking, Google Lens, and more. Previously, he led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions. — What you’ll learn: Why Google’s AI products are suddenly taking off after years of perceived stagnation  How AI is expanding Search rather than replacing it, contrary to what many predicted  The three core product principles that have helped Robby build multiple billion-user products  Inside Instagram’s decision to build its own version of Snapchat Stories  His mantra of “relentless improvement”  How Google developed AI Mode from concept to launch in just one year  Why most teams give up too early on potentially transformative products  — Brought to you by: Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny/?utm_source=lennypodcast&utm_medium=paid-audio&utm_campaign=fy24q1-jpd-imc Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ — Transcript: https://www.lennysnewsletter.com/p/how-google-built-ai-mode-in-under-a-year — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/175041217/my-biggest-takeaways-from-this-conversation⁠ — Where to find Robby Stein: • X: https://x.com/rmstein • LinkedIn: https://www.linkedin.com/in/robbystein/ — Referenced: • Google Gemini: https://gemini.google.com/app • Nano Banana: https://aistudio.google.com/models/gemini-2-5-flash-image • Chat GPT: https://chatgpt.com/ • Perplexity: https://www.perplexity.ai/ • Google Lens: https://lens.google/ • AI Google search: https://www.google.com/ai • Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge): https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour • Alex Rampell on X: https://x.com/arampell • A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype): https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products • Look broader, look closer, think younger: Tony Fadell speaks at TED2015: https://blog.ted.com/look-broader-look-closer-think-younger-tony-fadell-speaks-at-ted2015/ • Jobs to Be Done: https://www.christenseninstitute.org/theory/jobs-to-be-done/ • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • Rinstagram or Finstagram? The curious duality of the modern Instagram user: https://www.theguardian.com/technology/2016/sep/26/rinstagram-finstagram-instagram-accounts • V03: https://v03ai.com/ • Pirate GPT: https://www.kickstarter.com/projects/silentmeditation/pirate-gpt/ • The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f • Dune on HBO Max: https://www.hbomax.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7 • Top Gun: Maverick: https://www.imdb.com/title/tt1745960/ • Purple pillows: https://purple.com/pillows • Avocado pillow: https://www.avocadogreenmattress.com/products/green-pillow • Justin Bieber’s website: https://www.justinbiebermusic.com/ • Scooter Braun’s website: https://scooterbraun.com/ — Recommended books: • Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612 • The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654 • Aurora: https://www.amazon.com/Aurora-High-Stakes-Survival-Navigate-Darkness/dp/0062916475 • Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135202 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwich ingredients, and over 25 years of launching transformative technology businesses. What you’ll learn: What actually happened with Meta’s $14 billion investment in Scale AI Why AI models still need human experts to improve, and how that relationship is evolving How AI models learn from experts building websites and debugging code The business lessons from building Uber Eats from zero to $20 billion Why most enterprise data is useless for AI models today Why urgent daily problems beat super-valuable occasional problems when building products How to think independently when building new products and businesses — Brought to you by: Merge—The fastest way to ship 220+ integrations: http://merge.dev/lenny Figma Make—A prompt-to-code tool for making ideas real: https://www.figma.com/lenny/ Mercury—The art of simplified finances: https://mercury.com/ — Transcript: https://www.lennysnewsletter.com/p/first-interview-with-scale-ais-ceo-jason-droege — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174979621/my-biggest-takeaways-from-this-conversation — Where to find Jason Droege: • X: https://x.com/jdroege • LinkedIn: https://www.linkedin.com/in/jasondroege/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jason Droege (06:01) Jason’s early career and lessons learned (10:27) The current state of Scale AI (12:37) The shift to expert data labeling (17:02) Challenges and strategies in finding experts (18:48) Reinforcement learning and AI environments (28:18) The future of AI and human involvement (31:21) The role of evals (35:25) What AI models will look like in the next few years (41:43) Building Uber Eats and understanding customer needs (48:19) The importance of independent thinking (50:45) Setting high standards for new businesses (53:03) Exploring and selecting business ideas (57:07) The McDonald’s story (01:00:13) The role of gross margins in business feasibility (01:04:49) Why Jason says, “Not losing is a precursor to winning” (01:09:12) Hiring and building teams (01:12:11) AI corner (01:14:47) Lightning round and final thoughts — Referenced: • Travis Kalanick on X: https://x.com/travisk • Scour: https://en.wikipedia.org/wiki/Scour_Inc. • Scale: https://scale.com/ • Alexandr Wang on X: https://x.com/alexandr_wang • Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor): https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody • Brendan Foody’s post on X about knowledge work changing: https://x.com/BrendanFoody/status/1970163503702188048 • MIT Finds 95% of GenAI Pilots Fail Because Companies Avoid Friction: https://www.forbes.com/sites/jasonsnyder/2025/08/26/mit-finds-95-of-genai-pilots-fail-because-companies-avoid-friction/ • Uber Eats: https://www.ubereats.com/ • Stephen Chau on X: https://x.com/thestephenchau • a16z Podcast: https://a16z.com/podcasts/a16z-podcast/ • F1: The Movie: https://www.imdb.com/title/tt16311594/ • V03: https://v03ai.com/ • Careers at Scale: https://scale.com/careers — Recommended books: • The Selfish Gene: https://www.amazon.com/Selfish-Gene-Anniversary-Introduction/dp/0199291152 • The Road Less Traveled: A New Psychology of Love, Traditional Values, and Spiritual Growth: https://www.amazon.com/Road-Less-Traveled-Timeless-Traditional/dp/0743243153/ • Good to Great: Why Some Companies Make the Leap . . . And Others Don’t: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996 • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Albert Cheng has led growth at three of the world’s most successful consumer subscription companies: Duolingo, Grammarly, and Chess.com. A former Google product manager (and serious pianist!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 experiments a year, discovering counterintuitive insights that have driven tens of millions in revenue. What you’ll learn: 1. How to use the explore-exploit framework to find new growth opportunities 2. How showing premium features to free users doubled Grammarly’s upgrades to paid plans 3. What good retention looks like for a consumer subscription app 4. Why resurrected users drive 80% of mature product growth 5. Why “reverse trials” work better than time-based trials 6. The three pillars of successful gamification: core loop, metagame, and profile — Brought to you by: Vanta—Automate compliance. Simplify security. Jira Product Discovery—Confidence to build the right thing Miro—A collaborative visual platform where your best work comes to life — Where to find Albert Cheng: • X: https://x.com/albertc248 • LinkedIn: https://www.linkedin.com/in/albertcheng1/ • Chess.com: https://www.chess.com/member/Goniners — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — Referenced: • How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth • Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Explore vs. Exploit: https://brianbalfour.com/quick-takes/explore-vs-exploit • Grammarly: https://www.grammarly.com/ • Reforge: https://www.reforge.com/ • Chess.com: https://www.chess.com/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Figma: https://www.figma.com/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Claude Code: https://www.anthropic.com/claude-code • GitHub Copilot: https://github.com/features/copilot • Noam Lovinsky on LinkedIn: https://www.linkedin.com/in/noaml/ • The happiness and pain of product management | Noam Lovinsky (Grammarly, Facebook, YouTube, Thumbtack): https://www.lennysnewsletter.com/p/the-happiness-and-pain-of-product • Kyla Siedband on LinkedIn: https://www.linkedin.com/in/kylasiedband/ • The Duolingo handbook: https://blog.duolingo.com/handbook/ • Lenny’s post on X about the Duolingo handbook: https://x.com/lennysan/status/1889008405584683091 • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennysnewsletter.com/p/the-rituals-of-great-teams-shishir • Duolingo on TikTok: https://www.tiktok.com/@duolingo • Kasparov vs. Deep Blue | The Match That Changed History: https://www.chess.com/article/view/deep-blue-kasparov-chess • Magnus Carlsen: https://en.wikipedia.org/wiki/Magnus_Carlsen • Elo rating system: https://www.chess.com/terms/elo-rating-chess • Stockfish: https://en.wikipedia.org/wiki/Stockfish_(chess) • AlphaGo on Prime Video: https://www.primevideo.com/detail/AlphaGo/0KNQHKKDAOE8OCYKQS9WSSDYN0 • Statsig: https://www.statsig.com/ • The State of Product in 2026: Navigating Change, Challenge, and Opportunity: https://www.atlassian.com/blog/announcements/state-of-product-2026 • Erik Allebest on LinkedIn: https://www.linkedin.com/in/erikallebest/ • Daniel Rensch on X: https://x.com/danielrensch • Chariot: https://en.wikipedia.org/wiki/Chariot_(company) • San Francisco 49ers: https://www.49ers.com/ • Breville Barista Express: https://www.breville.com/en-us/product/bes870 — Recommended books: • Snuggle Puppy!: A Little Love Song: https://www.amazon.com/Snuggle-Puppy-Little-Boynton-Board/dp/1665924985 • Ogilvy on Advertising: https://www.amazon.com/Ogilvy-Advertising-David/dp/039472903X • Dark Squares: How Chess Saved My Life: https://www.amazon.com/Dark-Squares-Chess-Saved-Life/dp/1541703286 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provides a practical framework for creating products that serve both functional and emotional needs. Based in Paris, she now coaches founders and CPOs on implementing delight strategies in their organizations. What you’ll learn: 1. Why delight is a business strategy, not just “sprinkling confetti” on top of functionality 2. How to identify emotional motivators that drive product retention 3. The 50-40-10 rule for balancing delight in your roadmap 4. The 4-step delight model 5. The origin story of Spotify’s Discover Weekly 6. Why B2B products need delight just as much as B2C products 7. How to get buy-in from skeptical leaders who think delight is a luxury — Brought to you by: DX—The developer intelligence platform designed by leading researchers: https://getdx.com/lenny Jira Product Discovery—Confidence to build the right thing: https://atlassian.com/lenny LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny — Transcript: https://www.lennysnewsletter.com/p/a-4-step-framework-for-building-delightful-products — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/174199489/my-biggest-takeaways-from-this-conversation — Where to find Nesrine Changuel: • LinkedIn: https://www.linkedin.com/in/nesrinechanguel/ • Newsletter: https://nesrinechanguel.substack.com/ • Website: https://nesrine-changuel.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nesrine and product delight (04:56) Why delight matters (09:17) What makes a feature “delightful” (12:29) The three pillars of delight (13:03) Pillar 1: Removing friction (Uber refund example) (15:07) Pillar 2: Anticipating needs (Revolut eSIM example) (17:21) Pillar 3: Exceeding expectations (Edge coupon example) (18:35) The “confetti effect” and when it actually works (22:02) B2B vs. B2C: Why all products need emotional connection (29:52) The Delight Model: A 4-step framework (30:57) Step 1: Identifying user motivators (functional and emotional) (33:55) Step 2: Converting motivators into product opportunities (34:46) Step 3: Identifying solutions with the delight grid (36:46) Step 4: Validating ideas with the delight checklist (40:22) The Delight Model summarized (42:18) The importance of familiarity (Spotify Discover Weekly story) (45:21) Real examples: Chrome’s tab management solution (51:32) Google Meet’s solution for “Zoom fatigue” (55:02) Getting buy-in from skeptical leaders (59:39) Prioritizing delight: The 50-40-10 rule (1:02:41) Creating a culture of delight in your organization (1:06:45) The habituation effect (1:08:15) When delight goes wrong: Apple reactions example (1:10:21) How delight motivates product teams (1:12:24) Lightning round and final thoughts — Referenced: • Spotify: https://open.spotify.com/ • Linear: https://linear.app/ • How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product • Jira: https://www.atlassian.com/software/jira • Asana: https://asana.com/ • Monday: https://monday.com/ • The Product Delight Model: https://nesrinechanguel.substack.com/p/the-product-delight-model • Revolut: https://www.revolut.com/ • How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers • Microsoft Cashback: https://www.microsoft.com/en-us/edge/features/shopping-cashback • Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra • Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley • Workday: https://www.workday.com/ • SAP: https://www.sap.com/ • ServiceNow: https://www.servicenow.com/ • Salesforce: https://www.salesforce.com/ • GitHub: https://github.com/ • Atlassian: https://www.atlassian.com/ • Snowflake: https://www.snowflake.com/ • Data Superheroes: https://www.snowflake.com/en/data-superheroes/ • Google Meet: https://meet.google.com/ • Andy Nesling on LinkedIn: https://www.linkedin.com/in/andynesling/ • Matic: https://maticrobots.com/ • Diego Sanchez’s (Senior Product Manager at Buffer) post on LinkedIn: https://www.linkedin.com/feed/update/urn:li:activity:7365014292091346945/ • Miro: https://miro.com/ • Arc browser: https://arc.net/ • Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look • Migros Supermarket: https://www.migros.ch/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Suno: https://suno.com • Snapchat: https://www.snapchat.com/ • Use Reactions, Presenter Overlay, and other effects when videoconferencing on Mac: https://support.apple.com/en-us/105117 • Dr. Lipp: https://drlipp.com/ • How to be the best coach to product people | Petra Wille (Strong Product People): https://www.lennysnewsletter.com/p/how-to-be-the-best-coach-to-product • The Great American Baking Show: https://www.imdb.com/title/tt21822674/ • Le Meilleur Pâtissier: https://en.wikipedia.org/wiki/Le_Meilleur_P%C3%A2tissier • The Upside on Amazon Prime: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.3cb8500f-31af-9f4f-5dec-701e086d58e8 • The Intouchables: https://www.imdb.com/title/tt1675434/ • Yoyo stroller: https://www.stokke.com/USA/en-us/category/strollers/yoyo-strollers • UppaBaby strollers: https://uppababy.com/strollers/ — Recommended books: • Product Delight: How to Make Your Product Stand Out with Emotional Connection: https://www.amazon.com/Product-Delight-Stand-Emotional-Connection-ebook/dp/B0FGZ93D9Y/ • Factfulness: Ten Reasons We’re Wrong About the World—and Why Things Are Better Than You Think: https://www.amazon.com/Factfulness-Reasons-World-Things-Better/dp/1250107814 • STRONG Product Communities: The Essential Guide to Product Communities of Practice: https://www.amazon.com/STRONG-Product-Communities-Essential-Practice/dp/3982235189/r — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Hamel Husain and Shreya Shankar teach the world’s most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that’ll help you improve your AI product. What you’ll learn: 1. WTF evals are 2. Why they’ve become the most important new skill for AI product builders 3. A step-by-step walkthrough of how to create an effective eval 4. A deep dive into error analysis, open coding, and axial coding 5. Code-based evals vs. LLM-as-judge 6. The most common pitfalls and how to avoid them 7. Practical tips for implementing evals with minimal time investment (30 minutes per week after initial setup) 8. Insight into the debate between “vibes” and systematic evals — Brought to you by: Fin—The #1 AI agent for customer service Dscout—The UX platform to capture insights at every stage: from ideation to production Mercury—The art of simplified finances — Where to find Shreya Shankar • X: https://x.com/sh_reya • LinkedIn: https://www.linkedin.com/in/shrshnk/ • Website: https://www.sh-reya.com/ • Maven course: https://bit.ly/4myp27m — Where to find Hamel Husain • X: https://x.com/HamelHusain • LinkedIn: https://www.linkedin.com/in/hamelhusain/ • Website: https://hamel.dev/ • Maven course: https://bit.ly/4myp27m — In this episode, we cover: (00:00) Introduction to Hamel and Shreya (04:57) What are evals? (09:56) Demo: Examining real traces from a property management AI assistant (16:51) Writing notes on errors (23:54) Why LLMs can’t replace humans in the initial error analysis (25:16) The concept of a “benevolent dictator” in the eval process (28:07) Theoretical saturation: when to stop (31:39) Using axial codes to help categorize and synthesize error notes (44:39) The results (46:06) Building an LLM-as-judge to evaluate specific failure modes (48:31) The difference between code-based evals and LLM-as-judge (52:10) Example: LLM-as-judge (54:45) Testing your LLM judge against human judgment (01:00:51) Why evals are the new PRDs for AI products (01:05:09) How many evals you actually need (01:07:41) What comes after evals (01:09:57) The great evals debate (1:15:15) Why dogfooding isn’t enough for most AI products (01:18:23) OpenAI’s Statsig acquisition (1:23:02) The Claude Code controversy and the importance of context (01:24:13) Common misconceptions around evals (1:22:28) Tips and tricks for implementing evals effectively (1:30:37) The time investment (1:33:38) Overview of their comprehensive evals course (1:37:57) Lightning round and final thoughts — LLM Log Open Codes Analysis Prompt: Please analyze the following CSV file. There is a metadata field which has an nested field called z_note that contains open codes for analysis of LLM logs that we are conducting. Please extract all of the different open codes. From the _note field, propose 5-6 categories that we can create axial codes from. — Referenced: • Building eval systems that improve your AI product: https://www.lennysnewsletter.com/p/building-eval-systems-that-improve • Mercor: https://mercor.com/ • Brendan Foody on LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b • Nurture Boss: https://nurtureboss.io/ • Braintrust: https://www.braintrust.dev/ • Andrew Ng on X: https://x.com/andrewyng • Carrying Out Error Analysis: https://www.youtube.com/watch?v=JoAxZsdw_3w • Julius AI: https://julius.ai/ • Brendan Foody on X—“evals are the new PRDs”: https://x.com/BrendanFoody/status/1939764763485171948 • Who Validates the Validators? Aligning LLM-Assisted Evaluation of LLM Outputs with Human Preferences: https://dl.acm.org/doi/abs/10.1145/3654777.3676450 • Lenny’s post on X about evals: https://x.com/lennysan/status/1909636749103599729 • Statsig: https://statsig.com/ • Claude Code: https://www.anthropic.com/claude-code • Cursor: https://cursor.com/ • Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor • Frozen: https://www.imdb.com/title/tt2294629/ • The Wire on HBO: https://en.wikipedia.org/wiki/The_Wire — Recommended books: • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935 • Apple in China: The Capture of the World’s Greatest Company: https://www.amazon.com/Apple-China-Capture-Greatest-Company/dp/1668053373/ • Machine Learning: https://www.amazon.com/Machine-Learning-Tom-M-Mitchell/dp/1259096955 • Artificial Intelligence: A Modern Approach: https://www.amazon.com/Artificial-Intelligence-Modern-Approach-Global/dp/1292401133/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Julie Zhuo is the former VP and Head of Design at Facebook (now Meta), author of the bestselling book The Making of a Manager, and co-founder of Sundial, an AI-powered data analysis company. Also, my first-ever podcast guest over 3 years ago! In our conversation, we discuss: 1. The three core manager skills that translate directly to managing AI agents 2. How her team uses AI to learn new skills 10x faster 3. The “diagnose with data, treat with design” framework for balancing gut and data 4. Why hypergrowth AI companies have terrible data infrastructure (and why it doesn’t matter) 5. How to give feedback that actually lands—including Julie’s exact script for difficult conversations 6. What Julie’s teaching her kids about an AI future (hint: it’s not coding or STEM) — Brought to you by: Mercury — The art of simplified finances DX — The developer intelligence platform designed by leading researchers PostHog—How developers build successful products — Transcript: https://www.lennysnewsletter.com/p/from-managing-people-to-managing-ai-julie-zhuo — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/172723725/my-biggest-takeaways-from-this-conversation — Where to find Julie Zhuo: • X: https://x.com/joulee • LinkedIn: https://www.linkedin.com/in/julie-zhuo/ • Website: https://www.juliezhuo.com/ • Newsletter: https://lg.substack.com/ • Sundial: https://sundial.so/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Julie! (05:18) The success of The Making of a Manager (08:41) Why AI will make everyone a manager (11:38) The future of management roles (14:00) Empowering teams with AI (21:30) Specific roles being accelerated by AI (26:53) Data analysis in AI companies (32:02) The role of data in design (37:21) The evolving role of managers in the AI era (40:22) Embracing change and uncertainty (42:14) Timeless lessons for managers (49:03) Balancing strengths and weaknesses (57:49) Building a feedback culture (01:05:33) Creating win-win situations (01:09:27) Being aware of your own energy and conviction (01:12:12) Navigating disagreements with higher-ups (01:15:57) AI corner (01:20:08) Contrarian corner (01:23:14) Lightning round and final thoughts — Referenced: • Julie Zhuo on accelerating your career, impostor syndrome, writing, building product sense, using intuition vs. data, hiring designers, and moving into management: https://www.lennysnewsletter.com/p/episode-2-julie-zhuo • Waymo: https://waymo.com/ • How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO): https://www.lennysnewsletter.com/p/how-we-restructured-airtables-entire-org-for-ai • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop • Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect • Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/ • Methaphone: https://methaphone.com/ • Replit: https://replit.com/ • “Baby” by Justin Bieber on Spotify: https://open.spotify.com/track/6epn3r7S14KUqlReYr77hA • Kingdom Rush: https://www.kingdomrush.com/ • Dr. Becky on TikTok: https://www.tiktok.com/@drbeckyatgoodinside • Emily Oster on TikTok: https://www.tiktok.com/@profemilyoster • La La Land on Netflix: https://www.netflix.com/title/80095365 • Granola: https://www.granola.ai/ • Matic robots: https://maticrobots.com/ • Limitless pendant: https://www.limitless.ai/ • How I AI: https://www.youtube.com/@howiaipodcast — Recommended books: • The Making of a Manager: What to Do when Everyone Looks to You: https://www.amazon.com/Making-Manager-What-Everyone-Looks/dp/0525540423 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/ • Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0061673730 • Conscious Business: How to Build Value Through Values: https://www.amazon.com/Conscious-Business-Build-through-Values/dp/1622032020 • Good Inside: A Practical Guide to Resilient Parenting Prioritizing Connection Over Correction: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/0063159481/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brendan Foody is the CEO and co-founder of Mercor, the fastest-growing company in history to go from $1M to $500M in revenue (in just 17 months!). At 22, he is also the youngest American unicorn founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve their models. In this conversation, Brendan explains why evals have become the critical bottleneck for AI progress, how he discovered this massive opportunity, and what the future of work might look like in an AI-driven economy. What you’ll learn: 1. Why evals are becoming the primary bottleneck for AI progress and what this means for AI startups 2. How Mercor grew to $500M revenue in 17 months (fastest in history) 3. Brendan’s meeting with xAI that changed his company’s trajectory 4. Which skills and jobs will remain most valuable as AI continues to advance (hint: jobs with “elastic” demand) 5. Why Brendan believes AGI and superintelligence are not happening anytime soon 6. The three unique core values that drove Mercor’s success 7. How Harvard Lampoon writers are making Claude funnier — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams Enterpret—Transform customer feedback into product growth — Transcript: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/173303790/my-biggest-takeaways-from-this-conversation — Where to find Brendan Foody: • X: https://x.com/BrendanFoody • LinkedIn: https://www.linkedin.com/in/brendan-foody-2995ab10b/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Brendan Foody and Mercor (05:38) The “era of evals” (09:26) Understanding the AI training landscape (17:10) The future of work and AI (25:54) The evolution of labor markets (29:55) Understanding how AI models are trained (38:58) Building Mercor (53:27) Lessons from past ventures (56:55) The future of AI and model improvement (01:00:41) His personal use of AI and final thoughts — References: https://www.lennysnewsletter.com/p/experts-writing-ai-evals-brendan-foody — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffic converts six times better than Google search—and most companies are completely missing this opportunity. In our conversation, we discuss: 1. His 7-step playbook to rank #1 in ChatGPT 2. Why ChatGPT traffic converts 6x better than Google 3. How early-stage startups can win at AEO immediately (unlike with SEO, which takes years) 4. The three tactics that actually work: landing pages, YouTube videos, and Reddit comments 5. Why help-center content can suddenly be your highest-ROI investment 6. The specific Reddit strategy that works (spoiler: be authentic) 7. Why AI-generated content doesn’t work — Brought to you by: Orkes—The enterprise platform for reliable applications and agentic workflows Vanta—Automate compliance. Simplify security. Great Question—Empower everyone to run great research — Where to find Ethan Smith: • Twitter: https://twitter.com/ethan_l_s • LinkedIn: https://bit.ly/ethans-linkedin • Graphite: https://graphite.io/ • Graphite Research Papers: https://bit.ly/graphite-five-percent — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Ethan (04:34) The changing landscape of SEO (06:19) AEO (answer engine optimization) vs. GEO (generative engine optimization) (08:13) The impact of AEO (11:51) How early-stage startups can win at AEO (14:34) The quality of AEO leads (15:35) On-site vs. off-site traffic (16:32) Reddit’s role in AEO and avoiding spam (20:11) How AI models use citations (RAG) (21:41) Key principles for winning at AEO (25:00) Avoiding hyper-SEOed content, and the importance of originality (28:55) Actionable AEO playbook: steps and experiments (33:35) Tracking, measuring, and share of voice (38:34) Adapting AEO for B2B, commerce, and early-stage companies (41:11) Is letting AI index your content good? (43:06) Experimentation, control groups, and measuring results (46:15) The future of AEO, SEO, and search channels (51:35) AI-generated content: what works and what doesn’t (55:25) The dangers of infinite AI derivatives (58:44) The future: convergence of LLMs and search (01:00:40) Help-center optimization and the long tail (01:03:18) Lightning round and final thoughts — Resources and episode mentions: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-aeo-ethan-smith — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ben Horowitz is the co-founder of Andreessen Horowitz, Silicon Valley’s largest and most influential venture capital firm, with over $46B in committed capital across multiple funds. He took Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Airbnb to OpenAI to Databricks (now worth more than $100 billion). His management philosophy—forged through near-death experiences and refined through coaching hundreds of CEOs—contradicts most conventional startup wisdom. In our conversation, Ben shares: 1. Why “founder mode” is half right and half dangerously wrong 2. The story behind “Good Product Manager/Bad Product Manager” and why it went viral despite being written in anger 3. Where the biggest AI startup opportunities remain 4. Why you need to run toward fear, never away 5. The one trait that predicts that a founder will fail as CEO 6. Inside Paid in Full, Ben’s nonprofit awarding pensions to pioneering hip-hop artists — Brought to you by: DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny — Transcript: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/172439345/my-biggest-takeaways-from-this-conversation — Where to find Ben Horowitz: • X: https://x.com/bhorowitz • LinkedIn: https://www.linkedin.com/in/behorowitz/ • Website: https://benhorowitz.com/ • Andreessen Horowitz’s website: https://a16z.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Ben Horowitz (04:09) Important leadership lessons from Shaka Senghor (10:15) Running toward fear and why hesitation kills companies (19:35) Who shouldn’t start a company (22:36) The Databricks story: thinking bigger (24:54) Managerial leverage and CEO psychology (28:06) When founders should be replaced as CEOs (31:20) Normalizing failure for CEOs (37:57) Counterintuitive lessons about building companies (42:31) “Good Product Manager/Bad Product Manager” (48:21) Product managers as leaders (51:16) Why a16z invested in Adam Neumann after WeWork (56:23) Is AI in a bubble? (01:02:43) The biggest opportunities in AI (01:12:51) Why U.S. leadership in AI matters (01:18:53) The Paid in Full Foundation for hip-hop pioneers (01:23:18) Lightning round: book recommendations, products, and life mottos — References: https://www.lennysnewsletter.com/p/46b-of-hard-truths-from-ben-horowitz — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now than in the past decade—from Waterfall to Agile to AI. They are also the authors of Building Rocketships, a guide to building great products. In this conversation, the couple shares hard-won lessons they’ve learned from companies successfully adapting to AI, including their “shipyard” framework and their “sharp problem” methodology. What you’ll learn: 1. The “shipyard” framework: why the best AI teams embrace controlled chaos 2. Why Oji writes more code now than in the past 10 years—despite being a PM for more than 25 years 3. The three skills that matter most for PMs in 2025: curiosity, humility, and agency 4. How to identify “sharp problems” 5. AI at the core vs. AI at the edge: why companies that are building entirely new AI-centric codebases will beat those just “sprinkling AI” on existing products 6. The counterintuitive truth: engineers are moving so fast with AI that PMs are now the bottleneck 7. Their biggest product lesson from 50 combined years — Brought to you by: Mercury—The art of simplified finances Vanta—Automate compliance. Simplify security. Coda—The all-in-one collaborative workspace — Where to find Oji and Ezinne: • ProductMind on Substack: https://substack.com/@ojiudezue • ProductMind on LinkedIn: https://www.linkedin.com/company/productmindco • ProductMind on YouTube: https://www.youtube.com/@ProductMindX/videos • ProductMind on Spotify: https://open.spotify.com/show/07OVh5pdSv0szHPwWktzQQ • ProductMind website: https://www.productmind.co/ • Oji on LinkedIn: https://www.linkedin.com/in/ojiudezue/ • Ezinne on LinkedIn: https://www.linkedin.com/in/ezinne/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Oji and Ezinne (04:14) The evolving role of product managers (08:01) Challenges and opportunities in product management (10:34) Sharp problems (12:37) The shipyard model for product development (17:02) Hiring PMs in the AI era (24:55) The importance of staying humble (27:16) Hands-on learning and personal projects (39:10) Companies succeeding with AI adoption (46:25) Lessons from 50 years in product (49:22) Simplicity in design (51:24) The role of communication in strategy (55:17) Career intentions and personal growth (01:00:00) Ethics and responsibility in product management (01:03:09) Introducing Building Rocketships (01:06:42) Lightning round and final thoughts — Referenced: • How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft): https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma • Picking sharp problems, increasing virality, and unique product frameworks | Oji Udezue (Typeform, Twitter, Calendly, Atlassian): https://www.lennysnewsletter.com/p/picking-sharp-problems-increasing • Atlassian: https://www.atlassian.com/ • Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/ • Brownian motion: https://en.wikipedia.org/wiki/Brownian_motion • Calendly: https://calendly.com/ • Women in Product: https://womenpm.org/ • Brian Chesky’s secret mentor who died 9 times, started the Burning Man board, and built the world’s first midlife wisdom school | Chip Conley (founder of MEA): https://www.lennysnewsletter.com/p/chip-conley • Home Assistant: https://www.home-assistant.io/ • What people are vibe coding (and actually using): https://www.lennysnewsletter.com/p/what-people-are-vibe-coding-and-actually • How many layers should I wear today?: https://layers.today/ • Typeform: https://www.typeform.com/ • David Okuniev on X: https://x.com/okuiux • Clay: https://www.clay.com/ • Martin Eriksson on LinkedIn: https://www.linkedin.com/in/martineriksson/ • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead • Dave Mendlen on LinkedIn: https://www.linkedin.com/in/davemendlen/ • Deepfake: https://en.wikipedia.org/wiki/Deepfake • How to kickstart and scale a marketplace business: https://www.lennysnewsletter.com/p/how-to-kickstart-and-scale-a-marketplace • Forever on Netflix: https://www.netflix.com/title/81418639 • Paradise on Hulu: https://www.hulu.com/series/paradise-2b4b8988-50c9-4097-bf93-bc34a99a5b4f • Sinners: https://www.imdb.com/title/tt31193180/ • Claude: https://claude.ai/ • Nespresso Vertuo: https://www.nespresso.com/us/en/vertuo-coffee-machines • Gamma: https://gamma.app/ • Framer: https://www.framer.com/ • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Llama: https://www.llama.com/ — Recommended books: • Building Rocketships: Product Management for High-Growth Companies: https://www.amazon.com/Building-Rocketships-Management-High-Growth-Companies/dp/1962339068 • Coda version of Building Rocketships: https://www.productmind.co/brpro • Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 • The Let Them Theory: A Life-Changing Tool That Millions of People Can’t Stop Talking About: https://www.amazon.com/Let-Them-Theory-Life-Changing-Millions/dp/1401971369/ Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Howie Liu is the co-founder and CEO of Airtable, the no-code platform valued at around $12 billion. After a viral tweet declared “Airtable is dead” based on incorrect data, Howie led a radical transformation: reorganizing the entire company around AI, becoming an “IC CEO” who codes daily, and achieving over $100 million in free cash flow. What you’ll learn: 1. The “fast thinking” vs. “slow thinking” team structure that lets Airtable ship AI features weekly (inspired by Daniel Kahneman) 2. Why Howie uses AI hourly (not daily) and is Airtable’s #1 inference-cost user globally 3. Why CEOs must become ICs again in the AI era (and how to restructure your calendar to make it possible) 4. Why “playing” with AI tools should be mandatory—Howie tells employees to cancel all meetings for a week to experiment 5. The specific skills product managers, engineers, and designers need to develop to succeed in the AI era 6. Why evals can kill innovation (and when to use “vibes” instead) — Brought to you by: LucidLink—Real-time cloud storage for teams DX—The developer intelligence platform designed by leading researchers Claude.ai—The AI for problem solvers and enterprise — Where to find Howie Liu • X: https://x.com/howietl • LinkedIn: https://www.linkedin.com/in/howieliu/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Howie Liu and Airtable (04:05) The “Airtable is dead” viral tweet controversy (08:07) The rise of IC CEOs (10:57) AI’s paradigm shift in product development (16:27) Specific changes Airtable has made (21:38) Fast- and slow-thinking teams (32:57) The emergence of new form factors in AI models (34:48) Airtable’s vision and philosophy (40:20) Empowering teams with AI tools (46:50) Encouraging experimentation and play (50:55) Cross-functional skills in product teams (01:03:35) The importance of evals and open-ended testing (01:08:06) Key strategies for AI-driven success (01:12:43) Counterintuitive startup wisdom (01:22:21) Don't step away from the details that you love (01:25:50) Advice for aspiring engineers and designers (01:30:00) Lightning round and final thoughts — Referenced: • Airtable: https://www.airtable.com/ • All In podcast: https://allin.com/ • Nikita Bier on X: https://x.com/nikitabier • Figma: https://www.figma.com/ • The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder and CEO of Every): https://www.lennysnewsletter.com/p/inside-every-dan-shipper • Every: https://every.to/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Rippling: https://www.rippling.com/ • Omni: https://www.airtable.com/lp/ai-psu-plp • How ChatGPT accidentally became the fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • Palantir: https://www.palantir.com/ • Harvey: https://www.harvey.ai/ • v0: https://v0.dev/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Replit: https://replit.com/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Runway Game Worlds: https://play.runwayml.com/login • Sesame: https://www.sesame.com • NotebookLM: https://notebooklm.google • Salesforce: https://www.salesforce.com • Andrew Ofstad on LinkedIn: https://www.linkedin.com/in/aofstad/ • Stripe: https://stripe.com/ • Eames chair: https://en.wikipedia.org/wiki/Eames_Lounge_Chair • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • IDEO design thinking: https://designthinking.ideo.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • The Studio on AppleTV+: https://tv.apple.com/us/show/the-studio/umc.cmc.7518algxc4lsoobtsx30dqb52 • Silicon Valley on HBOMax: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d • Self Edge: https://www.selfedge.com/ • Studio D’Artisan: https://www.selfedge.com/studio-dartisan • Whitesville T-shirt: https://store.toyo-enterprise.co.jp/shopbrand/ct48/ • Guest Series | Dr. Paul Conti: How to Understand & Assess Your Mental Health: https://www.hubermanlab.com/episode/guest-series-dr-paul-conti-how-to-understand-and-assess-your-mental-health — Recommended books: • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555 • The Three-Body Problem: https://www.amazon.com/Three-Body-Problem-Cixin-Liu/dp/0765382032 • Trauma: The Invisible Epidemic: How Trauma Works and How We Can Heal From It: https://us.amazon.com/Trauma-Invisible-Epidemic-Works-Heal/dp/1683647351/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Asha Sharma leads AI product strategy at Microsoft, where she works with thousands of companies building AI products and has unique visibility into what’s working (and what’s not) across more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messenger. What you’ll learn: 1. Why we’re moving from “product as artifact” to “product as organism” and what this means for builders 2. Microsoft’s “seasons” planning framework that allows them to adapt quickly in the AI era 3. The death of the org chart: how agents are turning hierarchies into task networks and why “the loop, not the lane” is the new organizing principle 4. Why post-training will soon see more investment than pre-training—and how to build your own AI moat with fine-tuning 5. Her prediction for the “agentic society”—where org charts become work charts and agents outnumber humans in your company 6. The three-phase pattern every successful AI company follows (and why most fail at phase one) 7. The rise of code-native interfaces and why GUIs might be going the way of the desktop 8. What Asha learned from Satya Nadella about optimism — Brought to you by: Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny — Transcript: ⁠https://www.lennysnewsletter.com/p/how-80000-companies-build-with-ai-asha-sharma — My biggest takeaways (for paid newsletter subscribers): ⁠https://www.lennysnewsletter.com/i/171413445/my-biggest-takeaways-from-this-conversation⁠ — Where to find Asha Sharma: • LinkedIn: https://www.linkedin.com/in/aboutasha/ • Blog: https://azure.microsoft.com/en-us/blog/author/asha-sharma/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Asha Sharma (04:18) From “product as artifact” to “product as organism” (06:20) The rise of post-training and the future of AI product development (09:10) Successful AI companies: patterns and pitfalls (12:01) The evolution of full-stack builders (14:15) “The loop, not the lane”—the new organizing principle (16:24) The future of user interfaces: from GUI to code-native (19:34) The rise of the agentic society (22:58) The “work chart” vs. the “org chart” (26:24) How Microsoft is using agents (28:23) Planning and strategy in the AI landscape (35:38) The importance of platform fundamentals (39:31) Lessons from industry giants (42:10) What’s driving Asha (44:30) Reinforcement learning (RL) and optimization loops (49:19) Lightning round and final thoughts — Referenced: • Copilot: https://copilot.microsoft.com/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Inside ChatGPT: The fastest growing product in history | Nick Turley (Head of ChatGPT at OpenAI): https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley • GitHub: https://github.com • Dragon Medical One: https://www.microsoft.com/en-us/health-solutions/clinical-workflow/dragon-medical-one • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Lovable: https://lovable.dev/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Bolt: http://bolt.com • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Replit: https://replit.com/ •Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Sierra: https://sierra.ai/ • Spark: https://github.com/features/spark • Peter Yang on X: https://x.com/petergyang • How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management • Instacart: http://instacart.com/ • Terminator: https://en.wikipedia.org/wiki/Terminator_(franchise) • Porch Group: https://porchgroup.com/ • WhatsApp: https://www.whatsapp.com/ • Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html • Satya Nadella on X: https://x.com/satyanadella • Perfect Match 360°: Artificial intelligence to find the perfect donor match: https://ivi-fertility.com/blog/perfect-match-360-artificial-intelligence-to-find-the-perfect-donor-match/ • OpenAI’s GPT-5 shows potential in healthcare with early cancer detection capabilities: https://economictimes.indiatimes.com/news/international/us/openais-gpt-5-shows-potential-in-healthcare-with-early-cancer-detection-capabilities/articleshow/123173952.cms • F1: The Movie: https://www.imdb.com/title/tt16311594/ • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • The Home Depot: https://www.homedepot.com/ • Dewalt Powerstack: https://www.dewalt.com/powerstack • Regret Minimization Framework: https://s3.amazonaws.com/kajabi-storefronts-production/sites/2147500522/themes/2148012322/downloads/rLuObc2QuOwjLrinx5Yu_regret-minimization-framework.pdf — Recommended books: • The Thinking Machine: Jensen Huang, Nvidia, and the World’s Most Coveted Microchip: https://www.amazon.com/Thinking-Machine-Jensen-Coveted-Microchip/dp/0593832698 • Tomorrow, and Tomorrow, and Tomorrow: https://www.amazon.com/dp/0593466497 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. My biggest takeaways from this conversation: To hear more, visit www.lennysnewsletter.com

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating training data, in just eight months they’ve built a new business that hit $50 million in revenue in its first four months and is on track to blow past $100M in the first 12 months. What you’ll learn: 1. How Handshake found an opportunity to leverage their proprietary network of experts to launch a data-labeling business that’s on track to blow past $100 million ARR in 12 months 2. Why AI models need human experts (e.g. physics PhDs) to improve, and what this “data labeling” actually involves 3. Inside the actual work: what a biology PhD does for 8 hours that makes GPT-5 smarter 4. The playbook for building a startup inside a startup: separate teams, separate offices, separate everything 5. Why the shift from “generalist” to “expert” data labeling created a once-in-a-lifetime business opportunity 6. Why AI won’t eliminate entry-level jobs—it’s creating “Iron Man suits” that make junior employees 10x more productive — Brought to you by: CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ — Transcript: https://www.lennysnewsletter.com/p/inside-handshake-garrett-lord — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/171410958/my-biggest-takeaways-from-this-conversation — Where to find Garrett Lord: • X: https://x.com/garrettlord • LinkedIn: https://www.linkedin.com/in/garrettlord/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Garrett Lord (05:00) Understanding data labeling and its importance (13:08) The role of experts in AI model training (15:35) The future of AI and human collaboration (24:17) Why AI won’t eliminate entry-level jobs (27:58) The continuous improvement of AI models (33:05) The emergence of Handshake’s new business model (37:07) Incubating new ideas in established companies (40:42) Handshake's competitive advantage (45:43) Scaling up and meeting market demand (48:38) Overcoming challenges and adapting (53:08) The importance of separate teams and ownership (57:26) The future of job matching with AI (01:00:30) The biggest bottlenecks to advancing models further (01:02:37) Lightning round and final thoughts — Referenced: • GPQA: https://github.com/idavidrein/gpqa • Handshake: https://joinhandshake.com/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Goldman Sachs: https://www.goldmansachs.com/ • General Motors: https://www.gm.com/ • Google: https://about.google/ • Sahil Bhaiwala on LinkedIn: https://www.linkedin.com/in/sahil-bhaiwala-459b0354/ • Francisco “Paco” Guzman on LinkedIn: https://www.linkedin.com/in/guzmanhe/ • Avery Yip on LinkedIn: https://www.linkedin.com/in/averyyip/ • Game of Thrones on HBO: https://www.hbomax.com/shows/game-of-thrones/4f6b4985-2dc9-4ab6-ac79-d60f0860b0ac • SNOO: https://www.happiestbaby.com/products/snoo-smart-bassinet • Careers at Handshake: https://joinhandshake.com/careers/ — Recommended books: • Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296 • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and within six weeks, Intercom had a working prototype of what would become Fin. In this conversation, Eoghan shares the brutal reality of transforming a late-stage SaaS business valued at multiple billions into an AI-first company that’s now growing faster than most public software companies. We discuss: 1. Why Eoghan believes most late-stage companies won’t survive the AI transition 2. The “founder mode” transformation that required firing 40% of staff and resulted in 98% employee satisfaction 3. Why having “nothing to lose” is the ultimate advantage in AI transformation (and why comfortable companies will fail) 4. How Intercom transformed from a plateauing SaaS business to an AI-first company growing at 300%+ 5. How Intercom’s pricing evolved from “the most hated in SaaS” to a model that charges just $0.99 per resolved ticket 6. The cultural transformation required to compete with AI-native startups 7. How 12 years of therapy and a period of “ego death” shaped Eoghan’s leadership approach — Brought to you by: Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs: https://workos.com/lenny DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny — Transcript: ⁠https://www.lennysnewsletter.com/p/how-intercom-rose-from-the-ashes-eoghan-mccabe — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170710700/my-biggest-takeaways-from-this-conversation — Where to find Eoghan McCabe: • X: https://x.com/eoghan • LinkedIn: https://www.linkedin.com/in/eoghanmccabe/ • Website: https://eoghanmccabe.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Eoghan (05:00) The state of Intercom (09:53) The decision to pivot to AI (12:33) Why Eoghan is "anti-bot" in customer service (16:19) Pricing strategy evolution (19:26) Implementing the AI transformation (26:11) Cultural and organizational changes (31:18) Surviving a coup attempt (40:05) The future of AI and business (45:11) AI's impact on jobs (48:44) AI and human creativity (50:26) The importance of young AI talent (55:00) The cultural shift in AI adoption (58:00) Personal growth and leadership (01:04:34) Intercom’s success in producing product leaders (01:11:05) Intercom’s unique company culture (01:14:11) Lightning round and final thoughts — Referenced: • Intercom: https://www.intercom.com/ • Fin: https://fin.ai/ • Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/ • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann • Fergal Reid on LinkedIn: https://www.linkedin.com/in/fergalreid/ • How Perplexity builds product: https://www.lennysnewsletter.com/p/how-perplexity-builds-product • Yosi Amram’s website: https://yamram.com/ • (Nathaniel Russell) Ego Death Now: https://heythereprojects.shop/products/copy-of-nathaniel-russell-space-is-a-place • Daniel Kahneman: https://en.wikipedia.org/wiki/Daniel_Kahneman • Palantir: https://www.palantir.com/ • Stripe: https://stripe.com/ • Revolut: https://www.revolut.com/en-US/ • Paul Adams on LinkedIn: https://www.linkedin.com/in/pauladams • What AI means for your product strategy | Paul Adams (CPO of Intercom): https://www.lennysnewsletter.com/p/what-ai-means-for-your-product-strategy • Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm • N26: https://n26.com/en-eu • Notion: https://www.notion.so/ • Coinbase: https://www.coinbase.com/ • True Detective on Max: https://www.hbomax.com/shows/true-detective/9a4a3645-74e0-4e4d-9f35-31464b402357 • 28 Years Later: https://www.imdb.com/title/tt10548174/ • Trainspotting: https://www.imdb.com/title/tt0117951/ • 28 Days Later: https://www.imdb.com/title/tt0289043/ • Fellow: https://fellowproducts.com/ • Porsche 911: https://www.porsche.com/usa/models/911/ • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto — Recommended book: • Nuclear War: A Scenario: https://www.amazon.com/Nuclear-War-Scenario-Annie-Jacobsen/dp/0593476093 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Brian Balfour is the founder of Reforge, the former VP of Growth at HubSpot, and a student (and teacher) of product growth. Brian has studied every major platform shift—from Facebook to Apple to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT. In this conversation, you’ll learn: 1. The 4-step cycle every platform follows (and why ChatGPT just entered step 2) 2. Why ChatGPT’s platform launch could be bigger than Facebook’s early platform 3. The exact signals that ChatGPT will launch a third-party platform within six months 4. Why you have six months (not years) to make your platform bet 5. Why companies that don’t integrate with ChatGPT will lose to competitors that do 6. How Zynga grew to $1B by betting on Facebook’s platform early (before it was obvious) 7. Why so few companies are actually doing what they need to be doing right now — Brought to you by: DX—The developer intelligence platform designed by leading researchers: http://getdx.com/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Miro—A collaborative visual platform where your best work comes to life: https://miro.com/lenny — Transcript: https://www.lennysnewsletter.com/p/why-chatgpt-will-be-the-next-big-growth-channel-brian-balfour — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170294620/my-biggest-takeaways-from-this-conversation — Where to find Brian Balfour: • X: https://twitter.com/bbalfour • LinkedIn: https://www.linkedin.com/in/bbalfour/ • Website: https://brianbalfour.com/ • Substack: https://blog.brianbalfour.com/ • Podcast: https://www.reforge.com/podcast/unsolicited-feedback — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Brian! (04:13) The changing landscape of product growth (05:09) The importance of distribution (08:14) The role of new distribution platforms (09:45) The four-step cycle of distribution platforms (17:38) Examples of platform cycles (30:01) The rise of ChatGPT (44:47) The future of AI agents (46:01) Preferred partners and platform credibility (47:18) Monetization mechanisms and free tiers (48:14) Betting strategies for startups (01:04:34) Adopting AI tools: challenges and strategies (01:08:41) The importance of hard constraints (01:14:23) Effective AI adoption in companies (01:19:05) Lightning round and final thoughts — Referenced: • The Next Great Distribution Shift: https://blog.brianbalfour.com/p/the-next-great-distribution-shift • Brian Balfour: 10 lessons on career, growth, and life: https://www.lennysnewsletter.com/p/brian-balfour-10-lessons-on-career • This Week #9: Breaking into growth, leading with influence, and (not) stepping on toes: https://www.lennysnewsletter.com/p/this-week-9-breaking-into-growth • Distribution vs. Innovation: https://a16z.com/distribution-vs-innovation/ • On Platform Shifts and AI: https://caseyaccidental.com/on-platform-shifts-and-ai/ • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennysnewsletter.com/p/how-to-sell-your-ideas-and-rise-within • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey • ChatGPT: https://chatgpt.com/ • Claude: https://claude.ai/ • Gemini: https://gemini.google.com/ • Vine: https://en.wikipedia.org/wiki/Vine_(service) • Periscope: https://en.wikipedia.org/wiki/Periscope_(service) • Myspace: https://en.wikipedia.org/wiki/Myspace • Friendster: https://en.wikipedia.org/wiki/Friendster • AltaVista: https://en.wikipedia.org/wiki/AltaVista • Lycos: https://www.lycos.com/ • HubSpot: https://www.hubspot.com/ • Zynga: https://www.zynga.com/ • TBPN: https://www.tbpn.com/ • Deedy Das on LinkedIn: https://www.linkedin.com/in/debarghyadas/ • ChatGPT’s product retention curves are a product manager's wet dream: https://www.linkedin.com/posts/debarghyadas_chatgpts-product-retention-curves-are-a-activity-7338384752393035776-ice1/ • Windsurf: https://windsurf.com/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Udemy: https://www.udemy.com/ • Cursor: https://cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Notion: https://www.notion.com/ • Airtable: https://www.airtable.com/ • Monday: monday.com • Sierra: http://sierra.ai • He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor • Introducing ChatGPT agent: bridging research and action: https://openai.com/index/introducing-chatgpt-agent/ • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Marc Andreessen on Why Optimism Is the Safest Bet: https://nymag.com/marc-andressen-2014-10-20/ • Reforge: https://www.reforge.com • Reforge Insights: https://www.reforge.com/insights • Shopify: https://www.shopify.com/ • 25 proven tactics to accelerate AI adoption at your company: https://www.lennysnewsletter.com/p/25-proven-tactics-to-accelerate-ai • Clouded Judgement: https://cloudedjudgement.substack.com/ • NFX: https://www.nfx.com/news • James Currier: https://www.nfx.com/team/james-currier • Hallway Chat: https://www.hallwaychat.co/ • Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/ • Silicon Valley on HBO: https://www.hbomax.com/shows/silicon-valley/b4583939-e39f-4b5c-822d-5b6cc186172d • Stick: https://tv.apple.com/us/show/stick/umc.cmc.52w04zy67tiv11p8xvbc57wmc • Ergonofis standing desks: https://ergonofis.com/en-us/collections/standing-desks • Coping with the loss of a child and protecting your time | Brian Balfour (father of 2, CEO and founder Reforge, venture partner): https://www.startupdadpod.com/coping-with-the-loss-of-a-child-and-protecting-your-time-brian-balfour-father-of-2-ceo-and-found/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Matt LeMay spent 13 years as a music critic at Pitchfork before becoming one of product management’s most influential voices. He’s consulted with companies from startups to Fortune 500s and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he discovered a harsh truth: most PMs are optimizing for the wrong things. In this conversation, you’ll learn: 1. The one question that predicts if your team will survive the next layoffs (and why most teams can’t answer it) 2. Why following product “best practices” perfectly can actually accelerate your path to unemployment 3. The “low-impact PM death spiral”—how teams accidentally make themselves irrelevant 4. How to push back on executives without saying “no” (the options, plus a recommendation framework) 5. The counterintuitive reason why the happiest PMs are also the most commercially minded 6. The Liz Phair review that made Matt an internet villain for 22 years—and what it taught him about product management — Brought to you by: Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny Pragmatic Institute—Industry‑recognized product, marketing, and AI training & certifications: https://pragmaticinstitute.com/lenny Claude.ai—The AI for problem solvers and enterprise: http://claude.ai/ — Transcript: https://www.lennysnewsletter.com/p/the-one-question-that-saves-product-careers-matt-lemay — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109376/my-biggest-takeaways-from-this-conversation — Where to find Matt LeMay: • Instagram: https://www.instagram.com/mttlmy • LinkedIn: https://www.linkedin.com/in/mattlemay/ • Website: https://mattlemay.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt LeMay (04:23) Matt’s background and transition to product management (06:47) The goal of Matt's new book (12:00) How to stress test your thinking as a PM (15:32) Thinking like the CEO (17:33) The role of a product manager (23:36) The low-impact PM death spiral (27:47) Case study: Mailchimp’s transition to a platform company (32:53) Radical acceptance (41:24) Embracing constraints in product management (44:23) Steps to become an impact-first product team (49:38) Setting effective goals (01:02:15) Prioritization and impact estimation (01:07:58) Navigating stakeholder management (01:12:35) Summarizing the 3 steps (01:16:36) Lightning round and final thoughts — Referenced: • Pitchfork: https://pitchfork.com/ • Daniel Ek’s memo: https://newsroom.spotify.com/2023-12-04/an-update-on-december-2023-organizational-changes/ • How to create a winning product strategy | Melissa Perri: https://www.lennysnewsletter.com/p/how-to-create-a-winning-product-strategy • Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute): https://www.lennysnewsletter.com/p/product-owners-melissa-perri • Mailchimp: https://mailchimp.com/ • Intuit: https://www.intuit.com/ • Natalia Williams on LinkedIn: https://www.linkedin.com/in/nataliatwilliams/ • The ultimate guide to OKRs | Christina Wodtke (Stanford): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-okrs-christina • Miro: https://miro.com/ • Prioritizing: https://www.lennysnewsletter.com/p/prioritizing • Temptation Island on Netflix: https://www.netflix.com/title/81744518 • Mark L. Walberg’s website: https://markwalbergtv.com/about • Antiques Roadshow on PBS: https://www.pbs.org/wgbh/roadshow/ • Milkman amp: https://milkmansound.com/collections/amplifiers/products/the-amp • Matt’s review of Liz Phair’s self-titled album: https://pitchfork.com/reviews/albums/6255-liz-phair/ • Pitchfork Critic Apologizes for Bashing Liz Phair Album; Singer Graciously Accepts: https://variety.com/2019/music/news/pitchfork-critic-apologizes-liz-phair-album-review-zero-score-1203326897/ • RedMonk: https://redmonk.com/ — Recommended books: • Product Management in Practice: A Practical, Tactical Guide for Your First Day and Every Day After: https://www.amazon.com/Product-Management-Practice-Practical-Tactical/dp/1098119738/r • Impact-First Product Teams: Define Success. Do Work That Matters. Be Indispensable.: https://www.amazon.com/Impact-first-Product-Teams-Success-Indispensable/dp/B0DVH4R3QJ • Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/B08B46C8R1/ • Radical Focus: Achieving Your Most Important Goals with Objectives and Key Results: https://www.amazon.com/Radical-Focus-Achieving-Important-Objectives/dp/0996006028 • The Wisdom of Insecurity: A Message for an Age of Anxiety: https://www.amazon.com/Wisdom-Insecurity-Message-Age-Anxiety/dp/0307741206/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Nick Turley is Head of ChatGPT, the fastest-growing product in history, with 700 million weekly active users (10% of the world’s population). He was part of the original hackathon team that shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. We recorded this the day before GPT-5 launched. We discuss: 1. The 10-day sprint from deciding to ship ChatGPT to Sam Altman’s tweet (and why it was originally called “Chat with GPT-3.5”) 2. How they ran a willingness-to-pay Van Westendorp survey in their Discord to decide on the $20/month price point that everyone copied 3. The “Is it maximally accelerated?” philosophy that drives OpenAI’s insane shipping velocity 4. Why ChatGPT’s retention curve “smiles”—users leave, then come back months later using it more 5. The accidental decisions that changed history, including not having a waitlist 6. The impact ChatGPT will have on SEO and product growth 7. The counterintuitive reason why shipping unpolished AI features beats waiting for perfection 8. Why ChatGPT intentionally shipped with that “ugly” model-chooser dropdown 9. How TikTok comments became a primary user research channel early on — Brought to you by: Orkes—The enterprise platform for reliable applications and agentic workflows: https://www.orkes.io/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny — Transcript: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/170411252/my-biggest-takeaways-from-this-conversation — Where to find Nick Turley • X: https://x.com/nickaturley • LinkedIn: https://www.linkedin.com/in/nicholasturley/ • Website: https://nickturley.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nick Turley (04:52) GPT-5 launch (09:13) The vision for ChatGPT and AI assistants (13:52) The early days of ChatGPT (17:14) The success and impact of ChatGPT (20:44) Product development and iteration (23:11) Maximally accelerated: the OpenAI approach (26:17) Retention and user engagement (33:42) The future of chat interfaces (36:31) The evolution of ChatGPT (38:52) Subscription model and pricing strategies (42:10) Enterprise adoption and challenges (44:10) Balancing multiple product lines (52:13) Emergent use cases and user feedback (01:02:15) OpenAI’s unique product development approach (01:05:07) The importance of team composition (01:08:50) Balancing speed and quality in AI development (01:14:23) The role of evals in product development (01:16:13) The future of AI-driven content and GPTs (01:21:51) Philosophy and product leadership (01:23:47) Career journey and advice (01:27:49) Lightning round and final thoughts — References: https://www.lennysnewsletter.com/p/inside-chatgpt-nick-turley — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Chip Conley is the founder of Joie de Vivre hotels, the second-largest boutique hotel brand in the world. At age 52, he joined Airbnb as Head of Global Hospitality and Strategy, reporting to CEO Brian Chesky, who was 21 years younger. He earned the title of Airbnb’s “Modern Elder” by guiding the young founders on leadership and culture while learning Silicon Valley’s tech mindset himself. Today, Chip leads the Modern Elder Academy, the world’s first midlife wisdom school, and is the author of best-selling books like Wisdom@Work and Peak. He champions the idea that age and experience are assets—and that midlife can be a launchpad for renewed purpose and impact. In this conversation, we discuss: 1. The reality of Brian Chesky in “founder mode”—the good, bad, and stressful 2. How Chip went from running 52 boutique hotels to becoming Airbnb’s in-house mentor in his 50s 3. The “mentor and intern” mindset: how to simultaneously teach others and stay curious like a beginner 4. Why AI might actually favor older workers (hint: human wisdom vs. artificial intelligence) 5. His framework for navigating midlife transitions and finding meaning after 40 6. Specific tactics for older professionals to thrive in tech companies 7. Surprising data that midlife is often the happiest time of life—and how to leverage your 40s, 50s, and beyond 8. Chip’s formula for managing anxiety and fear (and how to regain control when worry strikes) — Brought to you by: Great Question—Empower everyone to run great research: https://www.greatquestion.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny — Transcript: https://www.lennysnewsletter.com/p/chip-conley — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168435278/my-biggest-takeaways-from-this-conversation — Where to find Chip Conley: • LinkedIn: https://www.linkedin.com/in/chipconleysf/ • Website: https://chipconley.com/ • Modern Elder Academy: https://www.meawisdom.com/ • Podcast: https://www.meawisdom.com/podcast/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Chip Conley (04:09) Chip’s journey with Airbnb (10:35) Insights on working with Brian Chesky (19:56) The value of intergenerational collaboration (25:57) Addressing ageism in tech (41:33) Chip’s early career and founding Joie de Vivre (43:54) A life-changing near-death experience (46:39) The importance of company culture (55:57) The Modern Elder Academy (59:21) The upside of aging (01:06:53) AI in daily life (01:09:14) Lightning round and final thoughts — Referenced: • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Natalie Tucci on LinkedIn: https://www.linkedin.com/in/natalietuccishoff/ • Laura Modi on LinkedIn: https://www.linkedin.com/in/laurahughes6/ • How to build a cult-like brand | Laura Modi (Bobbie): https://www.lennysnewsletter.com/p/from-growth-to-slowth-the-making • George Tenet: https://en.wikipedia.org/wiki/George_Tenet • Joie de Vivre Hospitality: https://www.hyatt.com/jdv-by-hyatt/en-US • Fest300: https://en.wikipedia.org/wiki/Fest300 • John Q. Smith on LinkedIn: https://www.linkedin.com/in/johnqsmith/ •Will A.I. Replace New Hires or Middle Managers?: https://www.nytimes.com/2025/07/07/business/ai-job-cuts.html • Burning Man: https://burningman.org/ • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Bill Graham: https://en.wikipedia.org/wiki/Bill_Graham_(promoter) • Maslow’s hierarchy: https://en.wikipedia.org/wiki/Maslow%27s_hierarchy_of_needs • Measuring what makes life worthwhile: https://www.ted.com/talks/chip_conley_measuring_what_makes_life_worthwhile • Jonathan Mildenhall on LinkedIn: https://www.linkedin.com/in/mildenhall/ • Becca Levy’s website: https://becca-levy.com/ • Kabuki Springs & Spa: https://kabukisprings.com/ • How positive age beliefs can support positive health outcomes with Becca Levy, PhD: https://www.ama-assn.org/delivering-care/population-care/how-positive-age-beliefs-can-support-positive-health-outcomes-becca • The U-shape of Happiness Across the Life Course: Expanding the Discussion: https://pmc.ncbi.nlm.nih.gov/articles/PMC7529452/ • The Midlife Unraveling: https://brenebrown.com/articles/2018/05/24/the-midlife-unraveling/ • Four Seasons: https://www.fourseasons.com/ • Blue Zones: https://www.bluezones.com/ • The Esalen Institute: https://www.esalen.org/ • Wisdom Well blog: https://www.meawisdom.com/wisdom-well/ • Elizabeth Gilbert TED Talk: Your elusive creative genius: https://www.ted.com/talks/elizabeth_gilbert_your_elusive_creative_genius • Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy • I’ll Push You: https://www.illpushyou.com/ • Vuori shorts: https://vuoriclothing.com/collections/shorts • Fly Ranch: https://flyranch.burningman.org/ — Recommended books: • Wisdom at Work: The Making of a Modern Elder: https://www.amazon.com/Wisdom-Work-Making-Modern-Elder/dp/0525572902 • Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484 • Peak: How Great Companies Get Their Mojo from Maslow: https://www.amazon.com/Peak-Great-Companies-Their-Maslow/dp/0787988618 • Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age: https://www.amazon.com/Learning-Love-Midlife-Reasons-Better/dp/0316567027 • Man’s Search for Meaning: https://www.amazon.com/Mans-Search-Meaning-Viktor-Frankl/dp/0807060100/ • Emotional Equations: Simple Steps for Creating Happiness + Success in Business + Life: https://www.amazon.com/Emotional-Equations-Creating-Happiness-Business/dp/1451607261/ • Big Magic: Creative Living Beyond Fear: https://www.amazon.com/Big-Magic-Creative-Living-Beyond/dp/1594634726 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Bret Taylor’s legendary career includes being CTO of Meta, co-CEO of Salesforce, chairman of the board at OpenAI (yes, during that drama), co-creating both Google Maps and the Like button, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met who’s been wildly successful at every level—from engineer to C-suite executive to founder—and across almost every discipline, including PM, engineer, CTO, COO, CPO, CEO, and board member. In this conversation, you’ll learn: 1. The brutal product review that nearly ended his Google career—and how that failure led to creating Google Maps 2. The question Sheryl Sandberg taught him to ask every morning (“What’s the most impactful thing I can do today?”) that transformed how he approached every role 3. The three AI market segments that matter 4. Why AI agents will replace SaaS products 5. His framework for knowing whose advice to actually listen to—and how that came in handy during the OpenAI board drama 6. The counterintuitive go-to-market strategy most AI startups get wrong 7. Sierra’s outcome-based pricing model that’s transforming how enterprise software is sold (and why every SaaS company should adopt it) 8. What he’s teaching his kids about AI that every parent should know — Brought to you by: CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny Basecamp—The famously straightforward project management system from 37signals: https://www.basecamp.com/lenny Vanta—Automate compliance. Simplify security: https://vanta.com/lenny — Transcript: https://www.lennysnewsletter.com/p/he-saved-openai-bret-taylor — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168905359/my-biggest-takeaways-from-this-conversation — Where to find Bret Taylor: • X: https://x.com/btaylor • LinkedIn: https://www.linkedin.com/in/brettaylor/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Bret Taylor (04:10) Bret’s early career and first major mistake (08:24) The birth of Google Maps (11:57) Lessons from FriendFeed and the importance of honest feedback (31:30) The future of coding and AI’s role (45:26) Preparing the next generation for an AI-driven world (48:46) AI in education (52:05) Business strategies in the AI market (01:04:38) Outcome-based pricing in AI (01:09:15) Productivity gains and AI (01:17:35) Go-to-market strategies for AI products (01:21:49) Lightning round and final thoughts — Referenced: • Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/ • “Lazy Sunday”—SNL: https://www.youtube.com/watch?v=sRhTeaa_B98 • Quip: https://quip.com/ • Sierra: https://sierra.ai/ • FriendFeed: https://en.wikipedia.org/wiki/FriendFeed • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Jim Norris on LinkedIn: https://www.linkedin.com/in/halfspin/ • Paul Buchheit on X: https://x.com/paultoo • Sanjeev Singh on LinkedIn: https://www.linkedin.com/in/sanjeev-singh-20a1b72/ • Barack Obama: https://www.obamalibrary.gov/obamas/president-barack-obama • Oprah Winfrey: https://en.wikipedia.org/wiki/Oprah_Winfrey • Ashton Kutcher: https://en.wikipedia.org/wiki/Ashton_Kutcher • PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia • Sam Altman on X: https://x.com/sama • Warren Buffett on X: https://x.com/warrenbuffett • Unix: https://en.wikipedia.org/wiki/Unix • Fortran: https://en.wikipedia.org/wiki/Fortran • C: https://en.wikipedia.org/wiki/C_(programming_language) • Python: https://www.python.org/ • Perl: https://www.perl.org/ • Rust: https://www.rust-lang.org/ • Eleven Labs: https://elevenlabs.io/ • The exact AI playbook (using MCPs, custom GPTs, Granola) that saved ElevenLabs $100k+ and helps them ship daily | Luke Harries (Head of Growth): https://www.lennysnewsletter.com/p/the-ai-marketing-stack • Confluent: https://www.confluent.io/ • Databricks: https://www.databricks.com/ • Snowflake: https://www.snowflake.com • Harvey: https://www.harvey.ai/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Larry Summers’s website: https://larrysummers.com/ • AutoCAD: https://www.autodesk.com/products/autocad/overview • Revit: https://www.autodesk.com/products/revit/ • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://lenny.substack.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Cursor: https://cursor.com/ • CodeX: https://openai.com/codex/ • Claude Code: https://www.anthropic.com/claude-code • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • DirecTV: https://www.directv.com/ • SiriusXM: https://www.siriusxm.com/ • Wayfair: https://www.wayfair.com/ • Akai: https://www.akaipro.com/ • Chubbies Shorts: https://www.chubbiesshorts.com/ • Weight Watchers: https://www.weightwatchers.com/ • CLEAR: https://www.clearme.com/ • Stripe: https://stripe.com/ • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Twilio: https://www.twilio.com/ • ServiceNow: https://www.servicenow.com/ • Adobe: https://www.adobe.com/ • Jobs to be done: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • Inception: https://www.imdb.com/title/tt1375666/ • Alan Kay’s quote: https://www.brainyquote.com/quotes/alan_kay_100831 • Jobs at Sierra: https://sierra.ai/careers — Recommended books: • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612 • Endurance: Shackleton’s Incredible Voyage: https://www.amazon.com/Endurance-Shackletons-Incredible-Alfred-Lansing/dp/0465062881 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Madhavan Ramanujam is the world’s foremost expert on pricing and monetization strategy. As managing partner at Simon-Kucher, he helped over 250 companies, including 30 unicorns, architect their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals how to build enduring businesses by dominating both market share and wallet share. He recently left Simon-Kucher to launch his own fund, 49 Palms, focused on helping early-stage AI companies. In this conversation, we discuss: 1. The 2x2 framework that identifies your optimal pricing model 2. Why AI companies can capture 25% to 50% of value created, vs. 10% to 20% for traditional SaaS products 3. Why popular AI coding tools may have already doomed themselves with underpricing 4. The “give-and-get” framework top negotiators use to extract maximum value from every deal 5. The negotiation strategy that helped one founder 4x their deal size overnight 6. How to frame POCs as “business case creation” instead of technical demos (and why this changes everything) 7. Why AI companies must get monetization right from day one—not “figure it out later” 8. How companies like Intercom’s Fin and Sierra pioneered outcome-based pricing (charging $0.99 per AI resolution) 9. The single question that reveals if your pricing is too complex — Brought to you by: Enterpret—Transform customer feedback into product growth: https://enterpret.com/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny — Transcript: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168109183/my-biggest-takeaways-from-this-conversation — Where to find Madhavan Ramanujam: • X: https://x.com/madhavansf • LinkedIn: https://www.linkedin.com/in/madhavansf/ • Promo email for Scaling Innovation: [email protected] — If you’re purchasing more than five copies, send a screenshot of your receipt to enter Madhavan’s exclusive bundle raffle. — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Madhavan and his work (04:30) The core thesis of Scaling Innovation (09:20) Common traps founders fall into (12:06) Beautifully simple pricing (15:00) Mastering negotiations (26:51) Other strategies for effective pricing and monetization (27:35) How AI pricing is different (31:33) Handling POCs (36:25) The importance of mastering monetization (38:58) Choosing the right AI pricing model (43:13) Current trends in AI pricing (44:48) Strategizing for outcome-based models (50:23) Packaging strategies for scaling (51:37) Adapting pricing strategies over time (53:40) Key axioms for pricing success (58:00) Takeaways for founders (01:01:33) Lightning round and final thoughts — Referenced: • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Cursor: https://www.cursor.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Sierra Finn: http://www.sierrafinn.com/ • Chargeflow: https://www.chargeflow.io/ • GitHub: https://github.com/ • Intercom: https://www.intercom.com/ • Warren Buffett’s quote: https://www.goodreads.com/quotes/11478913-if-you-ve-got-the-power-to-raise-prices-without-losing • Sierra: https://sierra.ai/ • Clay Bavor on LinkedIn: https://www.linkedin.com/in/claybavor/ • Mission: Impossible—The Final Reckoning: https://www.imdb.com/title/tt9603208/ • Delphi: https://www.delphi.ai/ • Dara Ladjevardian on LinkedIn: https://www.linkedin.com/in/dara-ladjevardian/ • Sam Spelsberg on LinkedIn: https://www.linkedin.com/in/samuel-spelsberg/ • Lennybot: https://www.lennybot.com/ • Granola: https://www.granola.ai/ • Simon-Kucher: https://www.simon-kucher.com/ • Josh Bloom on LinkedIn: https://www.linkedin.com/in/joshuabloompricingconsulting/ — Recommended books: • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 • Scaling Innovation: How Smart Companies Architect Profitable Growth: https://www.amazon.com/dp/1119633060 • Business Model Generation: A Handbook for Visionaries, Game Changers, and Challengers: https://www.amazon.com/Business-Model-Generation-Visionaries-Challengers/dp/0470876417 • Thinking Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555/ • Contagious: Why Things Catch On: https://www.amazon.com/Contagious-Things-Catch-Jonah-Berger/dp/1451686587/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to steer it responsibly. In this conversation, we discuss: 1. The inside story of leaving OpenAI with the entire safety team to start Anthropic 2. How Meta’s $100M offers reveal the true market price of top AI talent 3. Why AI progress is still accelerating (not plateauing), and how most people misjudge the exponential 4. Ben’s “economic Turing test” for knowing when we’ve achieved AGI—and why it’s likely coming by 2027-2028 5. Why he believes 20% unemployment is inevitable 6. The AI nightmare scenarios that concern him most—and how he believes we can still avoid them 7. How focusing on AI safety created Claude’s beloved personality 8. What three skills he’s teaching his kids instead of traditional academics — Brought to you by: Sauce—Turn customer pain into product revenue: https://sauce.app/lenny LucidLink—Real-time cloud storage for teams: https://www.lucidlink.com/lenny Fin—The #1 AI agent for customer service: https://fin.ai/lenny — Transcript: https://www.lennysnewsletter.com/p/anthropic-co-founder-benjamin-mann — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/168107911/my-biggest-takeaways-from-this-conversation — Where to find Ben Mann: • X: https://x.com/8enmann • LinkedIn: https://www.linkedin.com/in/benjamin-mann/ • Website: https://benjmann.net/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Benjamin (04:43) The AI talent war (06:28) AI progress and scaling laws (10:50) Defining AGI and the economic Turing test (12:26) The impact of AI on jobs (17:45) Preparing for an AI future (24:05) Founding Anthropic (27:06) Balancing AI safety and progress (29:10) Constitutional AI and model alignment (34:21) The importance of AI safety (43:40) The risks of autonomous agents (45:40) Forecasting superintelligence (48:36) How hard is it to align AI? (53:19) Reinforcement learning from AI feedback (RLAIF) (57:03) AI's biggest bottlenecks (01:00:11) Personal reflections on responsibilities (01:02:36) Anthropic’s growth and innovations (01:07:48) Lightning round and final thoughts — Referenced: • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Anthropic CEO: AI Could Wipe Out 50% of Entry-Level White Collar Jobs: https://www.marketingaiinstitute.com/blog/dario-amodei-ai-entry-level-jobs • Alexa+: https://www.amazon.com/dp/B0DCCNHWV5 • Azure: https://azure.microsoft.com/ • Sam Altman on X: https://x.com/sama • Opus 3: https://www.anthropic.com/news/claude-3-family • Claude’s Constitution: https://www.anthropic.com/news/claudes-constitution • Greg Brockman on X: https://x.com/gdb • Anthropic’s Responsible Scaling Policy: https://www.anthropic.com/news/anthropics-responsible-scaling-policy • Agentic Misalignment: How LLMs could be insider threats: https://www.anthropic.com/research/agentic-misalignment • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt): https://www.lennysnewsletter.com/p/ai-prompt-engineering-in-2025-sander-schulhoff • Unitree: https://www.unitree.com/ • Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke • How Reinforcement Learning from AI Feedback Works: https://www.assemblyai.com/blog/how-reinforcement-learning-from-ai-feedback-works • RLHF: https://en.wikipedia.org/wiki/Reinforcement_learning_from_human_feedback • Jared Kaplan on LinkedIn: https://www.linkedin.com/in/jared-kaplan-645843213/ • Moore’s law: https://en.wikipedia.org/wiki/Moore%27s_law • Machine Intelligence Research Institute: https://intelligence.org/ • Raph Lee on LinkedIn: https://www.linkedin.com/in/raphaeltlee/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Beth Barnes on LinkedIn: https://www.linkedin.com/in/elizabethmbarnes/ • “The Last Question”: https://en.wikipedia.org/wiki/The_Last_Question • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • Pantheon on Netflix: https://www.netflix.com/title/81937398 • Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy • Kurzgesagt—In a Nutshell: https://www.youtube.com/channel/UCsXVk37bltHxD1rDPwtNM8Q • 5 tips to poop like a champion: https://8enmann.medium.com/5-tips-to-poop-like-a-champion-3292481a9651 — Recommended books: • Superintelligence: Paths, Dangers, Strategies: https://www.amazon.com/Superintelligence-Dangers-Strategies-Nick-Bostrom/dp/0198739834 • The Hacker and the State: Cyber Attacks and the New Normal of Geopolitics: https://www.amazon.com/Hacker-State-Attacks-Normal-Geopolitics/dp/0674987551 • Replacing Guilt: Minding Our Way: https://www.amazon.com/Replacing-Guilt-Minding-Our-Way/dp/B086FTSB3Q • Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 • The Alignment Problem: Machine Learning and Human Values: https://www.amazon.com/Alignment-Problem-Machine-Learning-Values/dp/0393635821 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading voice on how AI is transforming the way we build and work. Learn: 1. Why Dan thinks AI won’t steal jobs en masse—and may actually reshore many jobs to the U.S. 2. The most underrated AI tool for non-programmers 3. An inside look at Every’s AI-first workflow 4. Why every company needs an “AI operations lead” 5. How Dan’s team uses an arsenal of AI agents (Claude, Codex, “Friday,” “Charlie”) in parallel, treating each AI like a specialist with unique strengths 6. Why generalists will thrive in an AI-first world, as rigid job titles blur and everyone becomes a “manager” of AI tools 7. Dan’s playbook for making any company AI-first—from the CEO setting the example, to hosting internal prompt-sharing sessions, to upskilling teams on AI tools — Brought to you by: CodeRabbit—Cut code review time and bugs in half. Instantly: https://coderabbit.link/lenny DX—A platform for measuring and improving developer productivity: https://getdx.com/lenny PostHog—How developers build successful products: https://posthog.com/lenny — Transcript: https://www.lennysnewsletter.com/p/inside-every-dan-shipper — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167681269/my-biggest-takeaways-from-this-conversation — Where to find Dan Shipper: • X: https://x.com/danshipper • LinkedIn: https://www.linkedin.com/in/danshipper/ • Podcast: https://every.to/podcast — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome and introduction (04:04) Hot takes on AI and job reshoring (07:06) The power of Claude Code for non-coders (14:35) The future of AI in business operations (18:45) AI’s role in enhancing human skills (22:26) The evolution of AI tools and their applications (25:40) Building an AI-first company (29:50) Innovative AI operations and team dynamics (35:35) Dan's AI stack (41:26) Compounding engineering (48:29) The impact of AI on learning and development (50:10) Accelerating career growth with AI (51:36) Revolutionizing code review and workflow (53:07) The importance of coding knowledge (57:26) Building AI-driven products (01:02:01) Innovative fundraising strategies (01:08:45) Consulting and AI adoption in companies (01:17:01) The allocation economy and future skills (01:20:12) The value of generalists in the AI age (01:24:07) Lightning round and final thoughts — Referenced: • Claude Code: https://www.anthropic.com/claude-code • Gemini CLI: https://blog.google/technology/developers/introducing-gemini-cli-open-source-ai-agent/ • Microsoft Copilot: https://copilot.microsoft.com/ • Cursor: https://www.cursor.com/ • Base44: https://base44.com/ • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Plato’s Argument Against Writing: https://fs.blog/an-old-argument-against-writing/ • From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng: https://www.lennysnewsletter.com/p/the-quiet-architect-peter-deng • Granola: https://www.granola.ai/ • Tobi Lutke’s post on X about context engineering: https://x.com/tobi/status/1935533422589399127 • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Every: https://every.to/ • Cora: https://www.cora.computer/ • Sparkle: https://makeitsparkle.co/ • Spiral: https://spiral.computer/ • Lex: https://lex.page/ • Nathan Baschez on LinkedIn: https://www.linkedin.com/in/nbashaw/ • Kate Lee on LinkedIn: https://www.linkedin.com/in/kate-lee-506768/ • Katie Parrott on LinkedIn: https://www.linkedin.com/in/katieparrott/ • Animalz: https://www.animalz.co/ • Rachel Woods on X: https://x.com/rachel_l_woods • Nityesh Agarwal on LinkedIn: https://www.linkedin.com/in/nityeshaga • Claude Opus 4: https://www.anthropic.com/claude/opus • Codex: https://openai.com/index/introducing-codex/ • Superwhisper: https://superwhisper.com/ • Wispr Flow: https://wisprflow.ai/ • Notion: https://www.notion.com/ • Kieran Klaassen on LinkedIn: https://www.linkedin.com/in/kieran-klaassen/ • Friday: https://www.friday.run/ • Charlie: https://www.gocharlie.ai/product/ai-agents/ • Avengers: https://en.wikipedia.org/wiki/Avengers_(Marvel_Cinematic_Universe) • Alex Duffy on LinkedIn: https://www.linkedin.com/in/alex-d/ • Danny Aziz on LinkedIn: https://www.linkedin.com/in/dannyaziz/ • Dia: https://www.diabrowser.com/ • Reid Hoffman’s website: https://www.reidhoffman.org/ • Starting Line VC: https://www.startingline.vc/ • Walleye Capital: https://walleyecapital.com/ • At This $10 Billion Hedge Fund, Using AI Just Became Mandatory: https://every.to/podcast/at-this-10-billion-hedge-fund-using-ai-just-became-mandatory • Reflexive AI usage is now a baseline expectation at Shopify: https://x.com/tobi/status/1909251946235437514 • Klarna CEO Sebastian Siemiatkowski on Getting AI to Do the Work of 700 Customer Service Reps: https://www.sequoiacap.com/podcast/training-data-sebastian-siemiatkowski/ • The Pin Factory: https://www.adamsmithworks.org/pin_factory.html • Deadwood on HBO: https://www.hbo.com/deadwood • Joel Spolsky on X: https://x.com/spolsky • Jason Fried’s website: https://world.hey.com/jason • Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking • Sam Harris’s website: https://www.samharris.org/ • Bill Simmons on X: https://x.com/billsimmons — Recommended books: • War and Peace: https://www.amazon.com/War-Peace-Vintage-Classics-Tolstoy/dp/1400079985 • Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002 • Playing and Reality: https://www.amazon.com/Playing-Reality-Routledge-Classics-86/dp/0415345464 • The Death of Ivan Ilyich: https://www.amazon.com/Death-Ivan-Ilyich-Leo-Tolstoy/dp/1468014315 • A Swim in a Pond in the Rain: https://www.amazon.com/Swim-Pond-Rain-Russians-Writing/dp/1984856022 • The Master and His Emissary: The Divided Brain and the Making of the Western World: https://www.amazon.com/Master-His-Emissary-Divided-Western/dp/0300245920/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The very beginning of a startup is your highest-leverage moment, and most teams waste months or years by skipping a few critical early questions. Jake and John developed the Foundation Sprint to help startups validate ideas and compress months of work into just two days. What you’ll learn: 1. The step-by-step Foundation Sprint process that compresses three or four months of validation into two days—including templates you can use immediately 2. Why differentiation is the #1 predictor of startup success (with the 2x2 framework that you can use with your team) 3. The three fundamental questions every founder should answer before writing a line of code 4. The “note and vote” technique that eliminates groupthink and gets honest answers from your colleagues 5. The seven “magic lenses” for choosing between multiple product ideas 6. The biggest mistake engineers make when building with AI tools 7. The paradox of speed: why “building nothing first” can get you to product-market fit faster — Brought to you by: Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs Paragon—Ship every SaaS integration your customers want: https://www.useparagon.com/lenny Coda—The all-in-one collaborative workspace: https://coda.io/lenny — Transcript: https://www.lennysnewsletter.com/p/the-foundation-sprint-jake-knapp-and-john-zeratsky — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167485876/my-biggest-takeaways-from-this-conversation — Where to find Jake Knapp: • X: https://twitter.com/jakek • LinkedIn: https://www.linkedin.com/in/jake-knapp/ • Website: https://jakeknapp.com/ — Where to find John Zeratsky: • X: https://twitter.com/jazer • LinkedIn: https://www.linkedin.com/in/johnzeratsky/ • Website: https://johnzeratsky.com/ — In this episode, we cover: (00:00) Introduction to Jake Knapp and John Zeratsky (04:41) Origins of the Design Sprint (11:06) The Foundation Sprint process (14:40) Phase one: The basics (16:57) Case study: Latchet (28:50) Phase two: Differentiation (36:24) The importance of differentiation (40:15) Thoughts on price differentiation (43:37) Case study: Mellow (46:04) Custom differentiators (49:30) The mini manifesto (52:02) Phase three: Approach to the project (54:50) Magic lenses activity (01:02:39) Prototyping and testing (01:10:00) Real-world examples and success stories (01:15:15) Motivation behind The Foundation Sprint (01:17:15) The outcome of the sprint: The founding hypothesis (01:19:28) The Design Sprint (01:28:19) The role of AI in prototyping (01:36:50) Final thoughts and resources — Referenced: • Introducing the Foundation Sprint: From the creators of the Design Sprint: https://www.lennysnewsletter.com/p/introducing-the-foundation-sprint • Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake • Eli Blee-Goldman on LinkedIn: https://www.linkedin.com/in/eli-blee-goldman/ • Character Capital: https://www.character.vc/ • Character Labs: https://www.character.vc/labs • Etsy: https://www.etsy.com/ • Shopify: https://www.shopify.com/ • Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding): https://www.lennysnewsletter.com/p/naming-expert-david-placek • Sonos: https://www.sonos.com/ • Vercel: https://vercel.com/ • Windsurf: https://windsurf.com/ • April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning • Positioning: https://www.lennysnewsletter.com/p/positioning • 10 things we know to be true: https://about.google/company-info/philosophy/ • Gandalf: https://en.wikipedia.org/wiki/Gandalf • Frodo: https://en.wikipedia.org/wiki/Frodo_Baggins • Mordor: https://en.wikipedia.org/wiki/Mordor • 35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley: https://www.lennysnewsletter.com/p/35-years-of-product-design-wisdom-bob-baxley • The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas • Base44: https://base44.com/ • Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo • Google Meet: https://meet.google.com/ • Blue Bottle Coffee: https://bluebottlecoffee.com • Reclaim: https://reclaim.ai/ • The official Foundation Sprint + Design Sprint template: https://www.character.vc/miro-template • Rippling: https://www.rippling.com/ • Latchet: https://latchet.com/ • Mellow: http://getmellow.com/ • AxionOrbital: https://axionorbital.space/ — Recommended books: • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY • Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422 • Click: How to Make What People Want: https://www.amazon.com/Click-Make-What-People-Want/dp/1668072114 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a dollar of outside funding. What you’ll learn: 1. The growth playbook that took Base44 from three friends to 400,000 users without spending any money on marketing 2. How he hasn’t written a single line of front-end code in three months—and how to structure your code repository to make it easier for AI to write your code 3. His AI productivity stack that allowed him to compete against heavily funded competitors 4. Why being a solo founder in AI might be the ultimate advantage (and the wedding story that almost killed the business) 5. The story of signing the $80M acquisition deal while war broke out with Iran 6. How to identify when to sell vs. stay independent (and why Maor chose acquisition despite being highly profitable) 7. The counterintuitive product decision that tripled activation by removing a “helpful” feature 8. How building in public on LinkedIn drove more growth than any paid channel — Brought to you by: Sauce—Turn customer pain into product revenue: https://sauce.app/lenny Dscout—The UX platform to capture insights at every stage: from ideation to production: https://www.dscout.com/ Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/ — Transcript: https://www.lennysnewsletter.com/p/the-base44-bootstrapped-startup-success-story-maor-shlomo — My biggest takeaways (for paid newsletter subscribers): https://www.lennysnewsletter.com/i/167384119/my-biggest-takeaways-from-this-conversation — Where to find Maor Shlomo: • X: https://x.com/ms_base44 • LinkedIn: https://www.linkedin.com/in/maor-shlomo-1088b4144/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Maor and Base44 (08:16) The origin story: how Base44 came to be (14:55) Bootstrapping and solo founding: challenges and insights (22:52) Productivity hacks and tech stack for solo founders (27:23) How to get started using Base44 (28:47) Thoughts on raising money (34:05) Distribution in the age of AI (36:09) Ambition and goals (40:05) Growth strategies: from first users to thousands (51:32) Building in public (57:42) The solo founder journey (01:00:23) Community support (01:03:23) Hackathons and partnerships (01:06:42) The importance of velocity in product development (01:08:20) Technical stack and infrastructure insights (01:15:24) Activation lessons (01:18:19) The acquisition journey with Wix (01:25:14) Final thoughts and advice for founders — Referenced: • Base44: https://base44.com/ • Retool: https://retool.com/ • Tzofim: https://www.israelscouts.org/ • Y Combinator: https://www.ycombinator.com/ • RescueTime: https://www.rescuetime.com/ • Cursor: https://www.cursor.com/ • Wix: https://www.wix.com/ • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Snowflake: https://www.snowflake.com • Yoav Orlev on LinkedIn: https://www.linkedin.com/in/yoav-orlev-4a044b72 • WhatsApp: https://www.whatsapp.com/ • Amazon: https://www.amazon.com/ • Google: https://about.google/ • MongoDB: https://www.mongodb.com/ • Deloitte: https://www.deloitte.com/ • Render: Render.com • Claude 4: https://www.anthropic.com/news/claude-4 • Gemini: https://gemini.google.com/app • Cloudflare: https://www.cloudflare.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital. In this conversation, you’ll learn: 1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices 2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant) 3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership” 4. Telltale signs you should shut down (or never start) that startup idea 5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication 6. His prediction that most knowledge work will be automated—and the skills to teach your kids now — Brought to you by: Sauce—Turn customer pain into product revenue Enterpret—Transform customer feedback into product growth Miro—A collaborative visual platform where your best work comes to life — Where to find Andrew Wilkinson: • X: https://x.com/awilkinson • LinkedIn: https://www.linkedin.com/in/awilkinson/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Andrew Wilkinson (04:07) Finding the right business idea (07:18) Avoiding common business pitfalls (11:58) Finding your unfair advantage (17:08) Fish where the fish are (20:08) Why boring is good (25:30) Bootstrapping vs. venture capital (31:20) Lessons from acquiring and managing businesses (36:47) Avoiding people problems (42:39) Leveraging AI in business and life (49:30) The Limitless device (53:13) Job displacement and AI’s future impact (58:20) Advice for new grads (01:02:50) Parenting in the age of AI (01:05:26) The pursuit of happiness beyond wealth (01:10:10) Mental health and medication (01:16:45) Lightning round and final thoughts — Referenced: • Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182 • Metalab: https://www.metalab.com/ • Letterboxd: https://letterboxd.com/ • AeroPress: https://aeropress.com/ • Brian Armstrong on X: https://x.com/brian_armstrong • Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman • Flow: https://www.getflow.com/ • Instacart: https://www.instacart.com/ • Things: https://culturedcode.com/things/ • Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/ • Salesforce: https://www.salesforce.com/ • Serato: https://serato.com/ • Chris Sparling on X: https://x.com/_sparling_ • Lindy: https://www.lindy.ai/ • Replit: https://replit.com/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman) • Malcolm Gladwell’s website: https://www.gladwellbooks.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Limitless: https://www.limitless.ai/ • Perplexity: https://www.perplexity.ai/ • Claude: https://claude.ai/ • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly • Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo • Sam Altman on X: https://x.com/sama • Dario Amodei on X: https://x.com/darioamodei • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc • Matic vacuum: https://maticrobots.com/ • Jerzy Gregorek’s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life • Tiny: https://www.tiny.com/ • Dribbble: https://dribbble.com/ — Recommended books: • The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143 • How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearly 4,000 brands and companies, employing over 250 linguists and pioneering naming innovation. What you’ll learn: 1. The three-step process that generated names like Windsurf and Vercel 2. How a name can give you the edge that no marketing budget can buy 3. Why you won’t “know it when you see it” 4. Why Microsoft called Azure “a dumb name” before it became their billion-dollar cloud platform 5. Why polarizing opinions are the strongest signal that you’ve found the right name 6. How every letter of the alphabet creates a specific psychological vibration 7. The diamond framework: a 4-step process any founder can use to find their perfect name 8. Why domain names don’t matter anymore in the age of AI — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Stripe—Helping companies of all sizes grow revenue OneSchema—Import CSV data 10x faster — Where to find David Placek: • LinkedIn: https://www.linkedin.com/in/david-placek-05a82/ • Website: https://www.lexiconbranding.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to David and Lexicon Branding (04:44) The story of Sonos (09:27) The psychology of naming (11:33) The initial resistance to Microsoft's Azure (14:35) The importance of a great brand name (18:11) The three steps of naming: create, invent, implement (28:23) Qualities of great brand name creators (31:24) How long the naming process takes (32:12) The Windsurf case study (36:10) Naming in the AI era (39:37) When to change your name (43:10) The role of linguists (45:54) The power of letters in branding (48:15) The Vercel case study (50:12) The implementation phase (52:52) Client management and market success (55:16) The diamond exercise (01:04:23) Suspending judgment (01:07:31) Polarization and boldness (01:11:01) Domain names (01:12:48) Final thoughts and lightning round — Referenced: • PowerBook: https://en.wikipedia.org/wiki/PowerBook • Pentium: https://en.wikipedia.org/wiki/Pentium • BlackBerry: https://en.wikipedia.org/wiki/BlackBerry • Swiffer: https://www.swiffer.com/ • Impossible Burger: https://impossiblefoods.com/ • Vercel: https://vercel.com/ • Windsurf: https://windsurf.com/ • CapCut: https://www.capcut.com/ • Azure: https://azure.microsoft.com/ • Sonos: https://www.sonos.com/ • John MacFarlane on LinkedIn: https://www.linkedin.com/in/john-macfarlane-08a8aa20/ • Harry Potter: https://en.wikipedia.org/wiki/Harry_Potter_(film_series) • The Call of the Wild: https://en.wikipedia.org/wiki/The_Call_of_the_Wild • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Sound symbolism: https://en.wikipedia.org/wiki/Sound_symbolism • Anduril: https://www.anduril.com/ • Anthropic: https://www.anthropic.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Y Combinator: https://www.ycombinator.com/ • Chevrolet Corvette: https://en.wikipedia.org/wiki/Chevrolet_Corvette • Viagra: https://www.viagra.com/ • In vino veritas: https://en.wikipedia.org/wiki/In_vino_veritas • Infoseek: https://en.wikipedia.org/wiki/Infoseek • Andy Grove: https://en.wikipedia.org/wiki/Andrew_Grove • Churchill at War on Netflix: https://www.netflix.com/title/81609374 • Yellowstone on Prime Video: https://www.amazon.com/Yellowstone-Season-1/dp/B07D7FBB8Z • 1883 on Prime Video: https://www.amazon.com/1883-Season-1/dp/B0B8JTS8QW • 1923 on Paramount+: https://www.paramountplus.com/shows/1923/ • Taylor Sheridan on X: https://x.com/taylorSheridan • Hardy fly rods: https://www.hardyfishing.com/collections/fly-rods • T.E. Lawrence quote: https://www.goodreads.com/quotes/11340-all-men-dream-but-not-equally-those-who-dream-by • Lawrence of Arabia: https://www.imdb.com/title/tt0056172/ • DreamWorks: https://www.dreamworks.com/ — Recommended books: • Thucydides’ Melian Dialogue: Commentary, Text, and Vocabulary: https://www.amazon.com/Thucydides-Melian-Dialogue-Commentary-Vocabulary/dp/0692772367 • Resilience: Hard-Won Wisdom for Living a Better Life: https://www.amazon.com/Resilience-Hard-Won-Wisdom-Living-Better/dp/054432398X/ • Churchill: Walking with Destiny: https://www.amazon.com/Churchill-Walking-Destiny-Andrew-Roberts/dp/1101980990 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his most valuable lessons from building and scaling some of tech’s most iconic products and companies. What you’ll learn: 1. Peter’s one‑sentence test for hiring superstars 2. Why your product (probably) doesn’t matter 3. Why you don’t need a tech breakthrough to build a huge business 4. The five PM archetypes, and how to build a team of Avengers 5. Counterintuitive lessons on growing products from 0 to 1, and 1 to 100 6. The importance of data flywheels and workflows — Brought to you by: Paragon—Ship every SaaS integration your customers want Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications Contentsquare—Create better digital experiences — Where to find Peter Deng: • X: https://x.com/pxd • LinkedIn: https://www.linkedin.com/in/peterxdeng/ — In this episode, we cover: (00:00) Introduction to Peter Deng (05:41) AI and AGI insights (11:35) The future of education with AI (16:53) The power of language in leadership (21:01) Building iconic products (36:44) Scaling from zero to 100 (41:56) Balancing short- and long-term goals (47:12) Creating a healthy tension in teams (50:02) The five archetypes of product managers (55:39) Primary and secondary archetypes (58:47) Hiring for growth mindset and autonomy (01:15:52) Effective management and communication strategies (01:19:23) Presentation advice and self-advocacy (01:25:50) Balancing craft and practicality in product management (01:30:40) The importance of empathy in design thinking (01:35:45) Career decisions and learning opportunities (01:42:05) Lessons from product failures (01:45:42) Lightning round and final thoughts — Referenced: • OpenAI: https://openai.com/ • Artificial general intelligence (AGI): https://en.wikipedia.org/wiki/Artificial_general_intelligence • Head of ChatGPT answers philosophical questions about AI at SXSW 2024 with SignalFire’s Josh Constine: https://www.youtube.com/watch?v=mgbgI0R6XCw • Professors Are Using A.I., Too. Now What?: https://www.npr.org/2025/05/21/1252663599/kashmir-hill-ai#:~:text=Now%20What • Herbert H. Clark: https://web.stanford.edu/~clark/ • Russian speakers get the blues: https://www.newscientist.com/article/dn11759-russian-speakers-get-the-blues/ • Ilya Sutskever (OpenAI Chief Scientist)—Building AGI, Alignment, Future Models, Spies, Microsoft, Taiwan, & Enlightenment: https://www.dwarkesh.com/p/ilya-sutskever • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/ • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Granola: https://www.granola.ai/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Fidji Simo on LinkedIn: https://www.linkedin.com/in/fidjisimo/ • Airtable: https://www.airtable.com/ • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/ • Andrew Chen on LinkedIn: https://www.linkedin.com/in/andrewchen/ • Lauryn Motamedi on LinkedIn: https://www.linkedin.com/in/laurynmotamedi/ • Twilio: https://www.twilio.com/ • Nick Turley on LinkedIn: https://www.linkedin.com/in/nicholasturley/ • Ian Silber on LinkedIn: https://www.linkedin.com/in/iansilber/ • Thomas Dimson on LinkedIn: https://www.linkedin.com/in/thomasdimson/ • Joey Flynn on LinkedIn: https://www.linkedin.com/in/joey-flynn-8291586b/ • Ryan O’Rourke’s website: https://www.rourkery.com/ • Joanne Jang on LinkedIn: https://www.linkedin.com/in/jangjoanne/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Jill Hazelbaker on LinkedIn: https://www.linkedin.com/in/jill-hazelbaker-3aa32422/ • Guy Kawasaki’s website: https://guykawasaki.com/ • Eric Antonow on LinkedIn: https://www.linkedin.com/in/antonow/ • Sachin Kansal on LinkedIn: https://www.linkedin.com/in/sachinkansal/ • IDEO design thinking: https://designthinking.ideo.com/ • The 7 Steps of the Design Thinking Process: https://www.ideou.com/blogs/inspiration/design-thinking-process • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Jeff Bezos’s quote: https://news.ycombinator.com/item?id=27778175 • Friendster: https://en.wikipedia.org/wiki/Friendster • Myspace: https://en.wikipedia.org/wiki/Myspace • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen • “Smile” by Jay-Z: https://www.youtube.com/watch?v=SSumXG5_rs8&list=RDSSumXG5_rs8&start_radio=1 • The Wire on HBO: https://www.hbo.com/the-wire • Felicis: https://www.felicis.com/ — Recommended books: • Sapiens: A Brief History of Humankind: https://www.amazon.com/Sapiens-Humankind-Yuval-Noah-Harari/dp/0062316095 • The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654 • The Silk Roads: A New History of the World: https://www.amazon.com/Silk-Roads-New-History-World/dp/1101912375 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and covering more than 200 prompting techniques. He also partners with OpenAI to run what was the first and is the largest AI red teaming competition, HackAPrompt, which helps discover the most state-of-the-art prompt injection techniques (i.e. ways to get LLMS to do things it shouldn’t). Sander teaches AI red teaming on Maven, advises AI companies on security, and has educated millions of people on the most state-of-the-art prompt engineering techniques. In this episode, you’ll learn: 1. The 5 most effective prompt engineering techniques 2. Why “role prompting” and threatening the AI no longer works—and what to do instead 3. The two types of prompt engineering: conversational and product/system prompts 4. A primer on prompt injection and AI red teaming—including real jailbreak tactics that are still fooling top models 5. Why AI agents and robots will be the next major security threat 6. How to get started in AI red teaming and prompt engineering 7. Practical defense to put in place for your AI products — Brought to you by: Eppo—Run reliable, impactful experiments Stripe—Helping companies of all sizes grow revenue Vanta—Automate compliance. Simplify security — Where to find Sander Schulhoff: • X: https://x.com/sanderschulhoff • LinkedIn: https://www.linkedin.com/in/sander-schulhoff/ • Website: https://sanderschulhoff.com/ • AI Red Teaming and AI Security Masterclass on Maven: https://bit.ly/44lLSbC • Free Lightning Lesson “How to Secure Your AI System” on 6/24: https://bit.ly/4ld9vZL — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sander Schulhoff (04:29) The importance of prompt engineering (06:30) Real-world applications and examples (10:54) Basic prompt engineering techniques (23:46) Advanced prompt engineering techniques (29:00) The role of context and additional information (39:24) Ensembling techniques and thought generation (49:48) Conversational techniques for better results (50:46) Introduction to prompt injection (52:27) AI red teaming and competitions (54:23) The growing importance of AI security (01:02:45) Techniques to bypass AI safeguards (01:05:21) Challenges in AI security and future outlook (01:18:33) Misalignment and AI's potential risks (01:25:03) Final thoughts and lightning round — Referenced: • Reid Hoffman’s tweet about using AI agents: https://x.com/reidhoffman/status/1930416063616884822 • AI Engineer World’s Fair: https://www.ai.engineer/ • What Is Artificial Social Intelligence?: https://learnprompting.org/blog/asi • Devin: https://devin.ai/ • Cursor: https://www.cursor.com/ • Inside Devin: The world’s first autonomous AI engineer that’s set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition): https://www.lennysnewsletter.com/p/inside-devin-scott-wu • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Granola: https://www.granola.ai/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Technique #3: Examples in Prompts: From Zero-Shot to Few-Shot: https://learnprompting.org/docs/basics/few_shot?srsltid=AfmBOor2owyGXtzJZ8n0fJVCctM7UPZgZmH-mBuxRW4t9-kkaMd3LJVv • The Prompt Report: Insights from the Most Comprehensive Study of Prompting Ever Done: https://learnprompting.org/blog/the_prompt_report?srsltid=AfmBOoo7CRNNCtavzhyLbCMxc0LDmkSUakJ4P8XBaITbE6GXL1i2SvA0 • State-of-the-Art Prompting for AI Agents | Y Combinator: https://www.youtube.com/watch?v=DL82mGde6wo • Use XML tags to structure your prompts: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags • Role Prompting: https://learnprompting.org/docs/basics/roles?srsltid=AfmBOor2jcxJQvWBZyFa030Qt0fIIov3hSiWvI9VFyjO-Qp478EPJIU7 • Is Role Prompting Effective?: https://learnprompting.org/blog/role_prompting?srsltid=AfmBOooiiyLD-0CsCYZ4m3SDhYOmtTyaTzeDo0FvK_i1x1gLM8MJS-Sn • Introduction to Decomposition Prompting Techniques: https://learnprompting.org/docs/advanced/decomposition/introduction?srsltid=AfmBOoojJmTQgBlmSlGYQ8kl-JPpVUlLKkL4YcFGS5u54JyeumUwlcBI • LLM Self-Evaluation: https://learnprompting.org/docs/reliability/lm_self_eval • Philip Resnik on X: https://x.com/psresnik • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Introduction to Ensembling Prompting: https://learnprompting.org/docs/advanced/ensembling/introduction?srsltid=AfmBOooGSyqsrjnEbXSYoKpG0ZlpT278NHQA6Fd8gMvNTJlWu7-qEYzh • Random forest: https://en.wikipedia.org/wiki/Random_forest • Chain-of-Thought Prompting: https://learnprompting.org/docs/intermediate/chain_of_thought?srsltid=AfmBOoqwE7SXlluy2sx_QY_VOKduyBplWtIWKEJaD6FkJW3TqeKPSJfx • Prompt Injecting: https://learnprompting.org/docs/prompt_hacking/injection?srsltid=AfmBOoqGgqbfXStrD6vlw5jy8HhEaESgGo2e57jyWL8lkZKktt_P6Zvn • Announcing HackAPrompt 2.0: The World’s Largest AI Red-Teaming Hackathon: https://learnprompting.org/blog/announce-hackaprompt-2?srsltid=AfmBOopXKsHxy4aUtsvPCUtEu7x74NCAEnlTIdNzo7nfMDVwZ9ilTlkp • Infant with rare, incurable disease is first to successfully receive personalized gene therapy treatment: https://www.nih.gov/news-events/news-releases/infant-rare-incurable-disease-first-successfully-receive-personalized-gene-therapy-treatment • Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO): https://www.lennysnewsletter.com/p/the-untold-story-of-windsurf-varun-mohan • Copilot: https://copilot.microsoft.com/chats/rcxhzvKgZvz8ajUrKdBtX • GitHub Copilot: https://github.com/features/copilot • Defensive Measures: https://learnprompting.org/docs/prompt_hacking/defensive_measures/introduction • Sam Altman on X: https://x.com/sama • Three Laws of Robotics: https://en.wikipedia.org/wiki/Three_Laws_of_Robotics • Anthropic’s new AI model turns to blackmail when engineers try to take it offline: https://techcrunch.com/2025/05/22/anthropics-new-ai-model-turns-to-blackmail-when-engineers-try-to-take-it-offline/ • Palisade Research: https://palisaderesearch.org/ • When AI Thinks It Will Lose, It Sometimes Cheats, Study Finds: https://time.com/7259395/ai-chess-cheating-palisade-research/ • A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html • 1883 on Paramount+: https://www.paramountplus.com/shows/1883/ • Black Mirror on Netflix: https://www.netflix.com/title/70264888 • Daylight Computer: https://daylightcomputer.com/ • Theodore Roosevelt’s quote: https://www.goodreads.com/quotes/622252-i-wish-to-preach-not-the-doctrine-of-ignoble-ease • HackAPrompt 2.0: https://www.hackaprompt.com/ — Recommended books: • Ender’s Game: https://www.amazon.com/Enders-Ender-Quintet-Orson-Scott/dp/0812550706 • The River of Doubt: Theodore Roosevelt’s Darkest Journey: https://www.amazon.com/River-Doubt-Theodore-Roosevelts-Darkest/dp/0767913736 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. Previously, she was a senior director of product at Big Health and a senior product marketing manager at Dropbox. In this episode, you’ll learn: • How to teach your team to be able to “take a punch” • Specific tactics to counter negative perceptions and reframe setbacks productively • Powerful behavioral strategies to form positive habits • Practical approaches for creating space in your workday to encourage creativity and deep thinking • The underestimated potential of AI in accelerating your personal and professional growth • Why you’re not the protagonist at your company (and why that’s liberating) • How WHOOP uses reward loops to drive real behavior change — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Persona—A global leader in digital identity verification Attio—The powerful, flexible CRM for fast-growing startups — Where to find Hilary Gridley: • X: https://x.com/yourgirlhils • LinkedIn: https://www.linkedin.com/in/hilarygridley/ • Newsletter: https://hils.substack.com/ • Maven course: https://maven.com/hilary-gridley/ai-powered-people-management — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Hilary’s background (04:31) Teaching teams to handle criticism and setbacks (17:57) Behavioral activation and mental health in the workplace (22:59) The importance of putting yourself out there (27:51) Transparency and communication in leadership (38:10) How to respectfully disagree with your manager (41:49) How to use “magic questions” to decode how people think (49:54) Why you’re not the protagonist at your company (52:48) Aligning with the CEO's vision (01:01:02) Building effective habits (01:11:14) Promoting team well-being (01:14:28) Creating space for creativity (01:20:45) AI’s role in accelerating learning (01:30:35) Pivotal career moments (01:37:21) Lessons from failure (01:39:49) Exciting new features of WHOOP 5.0 (01:44:19) Lightning round and final thoughts — Referenced: • How to become a supermanager with AI: https://www.lennysnewsletter.com/p/how-to-become-a-supermanager-with • How custom GPTs can make you a better manager | Hilary Gridley (Head of Core Product at Whoop): https://www.lennysnewsletter.com/p/how-custom-gpts-can-make-you-a-better-manager • WHOOP: https://www.whoop.com/ • Big Health: https://www.bighealth.com/ • What is behavioral activation?: https://www.medicalnewstoday.com/articles/behavioral-activation • Will Ahmed on LinkedIn: https://www.linkedin.com/in/willahmed/ • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams/ • Coinbase: https://www.coinbase.com/ • Bridge: https://www.bridge.xyz/ • Stripe: https://stripe.com/ • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer • Paths to Power course: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf • VO₂ max: https://en.wikipedia.org/wiki/VO2_max • Peter Attia on X: https://x.com/PeterAttiaMD • Hilary Gridley’s 30 days of GPT: https://docs.google.com/spreadsheets/d/1zJ4rbi9YcQuGqGxc6-AQD0-44oT9l4Eyono0AdpgJbA/edit?gid=0#gid=0 • The Handle Bar in Boston: https://www.thehandlebarstudios.com/ourstudios/charlestown • From chalkboards to chatbots: Transforming learning in Nigeria, one prompt at a time: https://blogs.worldbank.org/en/education/From-chalkboards-to-chatbots-Transforming-learning-in-Nigeria • Product Management Logic Coach GPT: https://chatgpt.com/g/g-673290301700819084afa36bdbcdfa3b-product-management-logic-coach • Dropbox: https://www.dropbox.com/ • WHOOP Advanced Labs: https://www.whoop.com/us/en/waitlist/?srsltid=AfmBOor2pP5qC3n7I23Z0ZIrYE99CjAKT9xSHQxbuyxmz_wFUBGH3e-n • Negative capability: https://en.wikipedia.org/wiki/Negative_capability • John Keats: https://en.wikipedia.org/wiki/John_Keats • The Rehearsal: https://www.hbo.com/the-rehearsal • Zwift: https://www.zwift.com/ • Beavis and Butthead Do ‘Creep’: https://www.youtube.com/watch?v=zv_gSmH0Ieg • “Sea Grapes” by Derek Walcott: https://www.poetryfoundation.org/poems/57111/sea-grapes • Free month of WHOOP: https://join.whoop.com/us/en/hilary/ — Recommended books: • 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/ • Outlive: The Science and Art of Longevity: https://www.amazon.com/Outlive-Longevity-Peter-Attia-MD/dp/0593236599 • East of Eden: https://www.amazon.com/East-Eden-John-Steinbeck-Centennial/dp/0142004235 • The Sun Also Rises: https://www.amazon.com/Sun-Also-Rises-Hemingway-Library/dp/1501121960/ • Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his calling after exploring photography, filmmaking, and music, ultimately recognizing software as the most powerful creative medium of our time. Bob champions the moral obligation designers have to reduce frustration in people’s daily digital interactions. What you’ll learn: • Why design should report to engineering, not product • The “Beatles principle”—why the best products come from teams of 4 to 6, not 40 to 60 • How to create design tenets vs. principles (with real examples) • The counterintuitive reason to delay drawing or prototyping as long as possible • Why software is fundamentally a medium, like film or music (not just a tool) • Why Bob “bounced off the culture” at Pinterest, and lessons from failure • The lunar landing story that teaches us about championing radical ideas • How to evaluate if a company truly values design before joining • The moral obligation of software makers to build great products — This entire episode is brought to you by Stripe—helping companies of all sizes grow revenue. — Where to find Bob Baxley: • Instagram: https://www.instagram.com/baxley/ • LinkedIn: https://www.linkedin.com/in/bbaxley/ • Website: http://www.bobbaxley.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Bob Baxley (03:52) Apple's lasting culture (06:15) Navigating unique company cultures (13:19) Finding a company that truly values your role (15:46) What is design? (17:17) How to help founders understand the value of design (23:08) How to align product managers and designers (26:31) Design reporting to engineering (30:54) Integrating engineers early in the design process (33:43) The maker mindset (35:14) Challenging the assumption that design is time-intensive (38:04) Design tenets vs. design principles (45:25) The moral obligation of great design (51:48) Understanding software as a medium (01:01:20) Reducing ambiguity for product teams (01:07:04) Giving designers space for creativity (01:08:48) The "primal mark" concept (01:12:05) AI prototyping tools: benefits and risks (01:17:00) AI as a life coach (01:21:22) Life lessons from the Apollo program (01:28:24) Lightning round and final thoughts — Referenced: • Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs • Walt Disney: https://en.wikipedia.org/wiki/Walt_Disney • Pinterest: https://www.pinterest.com/ • X: https://x.com/ • Uber: https://www.uber.com/ • Airbnb: https://www.airbnb.com/ • Slack: https://slack.com/ • Ed Catmull on X: https://x.com/edcatmull • John Lasseter on X: https://x.com/johnlasseter5 • Apple patented a pizza box, for pizzas: https://www.theverge.com/2017/5/16/15646154/apple-pizza-box-patent-come-on • Humane: https://en.wikipedia.org/wiki/Humane_Inc. • Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive • Tony Fadell on LinkedIn: https://www.linkedin.com/in/tonyfadell/ • Hiroki Asai on LinkedIn: https://www.linkedin.com/in/hiroki-asai-a44137110/ • Tim Cook on X: https://x.com/tim_cook • ThoughtSpot: https://www.thoughtspot.com/ • Ben Silbermann on LinkedIn: https://www.linkedin.com/in/silbermann/ • Ajeet Singh on LinkedIn: https://www.linkedin.com/in/ajeetsinghmann/ • Honeywell: https://www.honeywell.com • IDEO: https://www.ideo.com/ • Nutanix: https://www.nutanix.com/ • Lego: https://www.lego.com/ • Leica: https://leica-camera.com/ • Porsche: https://www.porsche.com/ • Patagonia: https://www.patagonia.com • Brian Eno’s website: https://www.brian-eno.net/ • Scenius: why creatives are stronger together: https://thecreativelife.net/scenius/ • The Beatles website: https://www.thebeatles.com/ • Disneyland: https://disneyland.disney.go.com/destinations/disneyland/ • Tomorrowland: https://disneyland.disney.go.com/destinations/disneyland/tomorrowland/ • Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product): https://www.lennysnewsletter.com/p/unorthodox-product-lessons-from-n26-and-more • Larry Page: https://en.wikipedia.org/wiki/Larry_Page • Sergey Brin: https://en.wikipedia.org/wiki/Sergey_Brin • Design Principles: https://principles.design/ • Tableau: https://www.tableau.com/ • Figma: https://www.figma.com/ • Target self-checkout: https://corporate.target.com/press/fact-sheet/2024/03/checkout-improvements • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • eBay: https://www.ebay.com/ • Williams Sonoma: https://www.williams-sonoma.com/ • Amazon: https://www.amazon.com/ • Monument to a Dead Child | Raw Data: https://podcasts.apple.com/ca/podcast/monument-to-a-dead-child/id1042137974 • Toast: https://pos.toasttab.com/ • The Primal Mark: How the Beginning Shapes the End in the Development of Creative Ideas: https://www.gsb.stanford.edu/faculty-research/publications/primal-mark-how-beginning-shapes-end-development-creative-ideas • The Plant: https://pixar.fandom.com/wiki/The_Plant • Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada: https://www.lennysnewsletter.com/p/microsoft-cpo-on-ai • How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna • Joff Redfern on LinkedIn: https://www.linkedin.com/in/mejoff/ • John C. Houbolt: https://www.nasa.gov/centers-and-facilities/langley/john-c-houbolt/ • The Apollo program: https://www.nasa.gov/the-apollo-program/ • Archive clip: JFK at Rice University, Sept. 12, 1962—“We choose to go to the moon”: https://www.youtube.com/watch?v=QXqlziZV63k • Alan Shepard: https://www.nasa.gov/former-astronaut-alan-shepard/\ • Blue Origin: https://www.blueorigin.com/ • Yuri Gagarin: https://en.wikipedia.org/wiki/Yuri_Gagarin • Wernher von Braun: https://en.wikipedia.org/wiki/Wernher_von_Braun • Yuri Kondratyuk: https://en.wikipedia.org/wiki/Yuri_Kondratyuk • John Houbolt’s memo: https://space.stackexchange.com/questions/2823/text-of-john-houbolts-letter-proposing-lunar-orbit-rendezvous-for-apollo • Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx • Lawrence of Arabia on Prime Video: https://www.amazon.com/Lawrence-Arabia-Peter-OToole/dp/B0088OINTU • Leica M6: https://leica-camera.com/en-US/photography/cameras/m/m6 • Habitica: https://habitica.com/static/home • Andor on Disney+: https://www.disneyplus.com/browse/entity-faba988a-a9f5-45f2-a074-0775a7d6f67a • Edward Tufte quote: https://quotefancy.com/quote/1449650/Edward-Tufte-Good-design-is-clear-thinking-made-visible-bad-design-is-stupidity-made • Ansel Adams quote: https://www.brainyquote.com/quotes/ansel_adams_106035 • It Takes a Village to Determine the Origins of an African Proverb: https://www.npr.org/sections/goatsandsoda/2016/07/30/487925796/it-takes-a-village-to-determine-the-origins-of-an-african-proverb • Henry Modisett on LinkedIn: https://www.linkedin.com/in/henrymodisett/ • Perplexity: https://www.perplexity.ai/ • Golden State Warriors: https://www.nba.com/warriors/ • Steph Curry: https://www.espn.com/nba/player/_/id/3975/stephen-curry — Recommended books: • From Counterculture to Cyberculture: Stewart Brand, the Whole Earth Network, and the Rise of Digital Utopianism: https://www.amazon.com/Counterculture-Cyberculture-Stewart-Network-Utopianism/dp/0226817423 • Hare Brain, Tortoise Mind: How Intelligence Increases When You Think Less: https://www.amazon.com/Hare-Brain-Tortoise-Mind-Intelligence/dp/0060955414 • The Elements of Typographic Style: https://www.amazon.com/Elements-Typographic-Style-Robert-Bringhurst/dp/0881791326 • Zen and the Art of Motorcycle Maintenance: An Inquiry into Values: https://www.amazon.com/Zen-Art-Motorcycle-Maintenance-Inquiry/dp/0060589469 • Time and the Art of Living: https://www.amazon.com/Time-Art-Living-Robert-Grudin/dp/0062503553/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he founded multiple startups, including a ridesharing company that competed directly with Uber in Latin America. And at just 17, he got a personal phone call from Steve Jobs asking him to take his app off the App Store. Today, Sebastian is the SVP of Engineering at Roblox. What you’ll learn: • Why Mercado Libre operates with 95% fewer PMs than typical tech companies (and how it actually works) • How to maintain product quality with 30,000 daily deployments and distributed ownership • The weekly email system Sebastian uses to maintain alignment with leadership • How to build a culture of radical candor and direct feedback in a traditionally hierarchical region • The counterintuitive approach to product reviews that keeps 18,000 engineers aligned • How to evaluate hype cycles (crypto, AI) pragmatically while staying innovative — Brought to you by: Merge—A single API to add hundreds of integrations into your app Vanta—Automate compliance. Simplify security LinkedIn Ads—Reach professionals and drive results for your business — Where to find Sebastian Barrios: • LinkedIn: https://www.linkedin.com/in/zebas/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Sebastian Barrios and Mercado Libre (05:03) Mercado Libre’s scale and unique ways of operating (14:48) AI’s impact on operations (19:19) Empowering teams and reducing fear of failure (34:20) The importance of radical candor (38:26) Weekly updates (41:03) Avoiding hype cycles (44:24) When Steve Jobs personally called 17-year-old Sebastian (49:00) Building successful app businesses (55:33) Unique personal habits (01:04:00) Raising independent children (01:07:15) Lightning round and final thoughts — Referenced: • Mercado Libre: https://www.mercadolibre.com/ • Claude: https://claude.ai/ • Salesforce: https://www.salesforce.com/ • Nvidia: https://www.nvidia.com/ • TikTok: https://www.tiktok.com/ • Adobe: https://www.adobe.com/ • Uber: https://www.uber.com/ • OpenAI: https://openai.com/ • Marcos Galperin on LinkedIn: https://www.linkedin.com/in/marcosgalperin/ • Cursor: https://www.cursor.com/ • Windsurf: https://windsurf.com/ • Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best • Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm • How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product): https://www.lennysnewsletter.com/p/how-revolut-trains-world-class-product-managers • Intercom: https://www.intercom.com/ • Atlassian: https://www.atlassian.com/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Managing up: https://www.lennysnewsletter.com/p/managing-up • Steve Jobs: https://en.wikipedia.org/wiki/Steve_Jobs • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Everything Everywhere All at Once: https://www.imdb.com/title/tt6710474/ • Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7 • Bluey on Disney+: https://www.disneyplus.com/browse/entity-fa6973b9-e7cf-49fb-81a2-d4908e4bf694 • Mentava: https://www.mentava.com/ • Matt Bateman’s website: https://mattbateman.xyz/ • Beast Academy: https://beastacademy.com/ • David protein bars: https://davidprotein.com/ • Marc Andreessen on X: https://x.com/pmarca • Tatami mats: https://en.wikipedia.org/wiki/Tatami — Recommended books: • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/ • The Odyssey: https://www.amazon.com/Odyssey-Homer/dp/0140268863 • The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119/ • Dune: https://www.amazon.com/Dune-Chronicles-Book-1/dp/0441013597/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mike Krieger is the chief product officer of Anthropic and the co-founder of Instagram. After leaving Meta, he co-founded Artifact, an AI-powered news app that I absolutely loved, and joined Anthropic to lead product in 2024. In this episode, you'll learn: • How Anthropic uses AI to write 90-95% of code for some products and the surprising new bottlenecks this creates • Why embedding product managers with AI researchers yields 10x the impact of traditional product development • The three areas where product teams can still add massive value as AI gets smarter • How Anthropic plans to compete with OpenAI long-term • How to use Claude as your product strategy partner (with specific prompting techniques) • Why Mike shut down Artifact despite loving the product, and what founders can learn from it • Where AI startups should build to avoid getting killed by OpenAI, Anthropic, and Google • Why MCP (Model Context Protocol) might reshape how all software works • The counterintuitive product metrics that matter for AI • How to evaluate whether your company is maximizing AI’s potential or just scratching the surface — Brought to you by: Productboard—Make products that matter Stripe—Helping companies of all sizes grow revenue OneSchema—Import CSV data 10x faster — Where to find Mike Krieger: • X: https://x.com/mikeyk • LinkedIn: https://www.linkedin.com/in/mikekrieger/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Mike Krieger (04:20) What Mike has changed his mind about regarding AI capabilities (07:38) How to avoid scary AI scenarios (08:55) Skills kids will need in an AI world (11:53) How product development changes when 90% of code is written by AI (17:07) Claude helping with product strategy (21:16) A new way of working (23:55) The future value of product teams in an AI world (27:18) Prompting tricks to get more out of Claude (29:52) The Rick Rubin collaboration on “vibe coding” (32:42) How Mike was recruited to Anthropic (35:55) Why Mike shut down Artifact (42:41) Anthropic vs. OpenAI (47:11) Where AI founders should play to avoid getting squashed (51:58) How companies can best leverage Anthropic’s models and APIs (54:29) The role of MCPs (Model Context Protocols) (58:25) Claude’s questions for Mike (01:03:15) Claude’s heartfelt message to Mike — Referenced: • Anthropic: https://www.anthropic.com/ • Claude Opus 4: https://www.anthropic.com/claude/opus • Dario Amodei on X: https://x.com/darioamodei • AI 2027: https://ai-2027.com/ • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Claude Shannon: https://en.wikipedia.org/wiki/Claude_Shannon • Information theory: https://en.wikipedia.org/wiki/Information_theory • TypeScript: https://www.typescriptlang.org/ • Python: https://www.python.org/ • Rust: https://www.rust-lang.org/ • Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor • Announcing a brand-new podcast: “How I AI” with Claire Vo: https://www.lennysnewsletter.com/p/announcing-a-brand-new-podcast-how • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k • Jack Clark on LinkedIn: https://www.linkedin.com/in/jack-clark-5a320317/ • Artifact: https://en.wikipedia.org/wiki/Artifact_(app) • Joel Lewenstein on LinkedIn: https://www.linkedin.com/in/joel-lewenstein/ • Daniela Amodei on LinkedIn: https://www.linkedin.com/in/daniela-amodei-790bb22a/ • Boris Cherny on LinkedIn: https://www.linkedin.com/in/bcherny/ • Gunnar Gray on LinkedIn: https://www.linkedin.com/in/gunnargray/ • The Model Context Protocol: https://www.anthropic.com/news/model-context-protocol • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Jimmy Kimmel Live: https://www.youtube.com/user/JimmyKimmelLive • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Windsurf: https://windsurf.com/ • Menlo Ventures: https://menlovc.com/ • Harvey: https://www.harvey.ai/ • Manus: https://manus.im/ • Bench: https://www.bench-ai.com/ • Strategy Letter V: https://www.joelonsoftware.com/2002/06/12/strategy-letter-v/ • Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/ — Recommended books: • The Goal: A Process of Ongoing Improvement: https://www.amazon.com/Goal-Process-Ongoing-Improvement/dp/0884271951 • The Way of the Code: The Timeless Art of Vibe Coding: https://www.thewayofcode.com/ • The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams. What you will learn: 1. Dogfooding at scale 2. “Ship, ship, ship” as a cultural mantra 3. Obsession with inputs over outputs 4. Uber’s hybrid marketplace vision for autonomy 5. How Uber changed its culture to focus on profitability 6. What to do when data says “no” but your gut says “yes” 7. Career advice: maximize cycles 8. AI as a research assistant, not an oracle 9. Uber rider etiquette tips — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Stripe—Financial infrastructure to grow your revenue • Coda—The all-in-one collaborative workspace — Where to find Sachin Kansal: • LinkedIn: https://www.linkedin.com/in/sachinkansal/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sachin’s background (05:00) Dogfooding in practice (11:24) Empathy and understanding drivers (20:18) Balancing metrics and user experience (22:04) Operationalizing dogfooding (24:26) Challenges and solutions in dogfooding (29:49) The motto: “ship, ship, ship” (36:37) Product announcements and live demos (40:49) Career advice for product managers (43:51) The evolution of product management with AI (46:55) Collaboration between engineers and product managers (49:36) Uber’s vision for self-driving cars (55:59) Uber’s path to profitability (01:01:58) Balancing data and gut decisions (01:07:21) AI tools in product management (01:10:14) Failure corner (01:13:48) Lightning round and final thoughts — Referenced: • Uber: https://www.uber.com/ • Oracle: https://www.oracle.com/ • Snowflake: https://www.snowflake.com/en/ • Fivetran: https://go.fivetran.com/ • Uber for Business: https://www.uber.com/us/en/business • McDonald’s: https://www.mcdonalds.com/ • Domino’s: https://www.dominos.com • PalmPilot: https://en.wikipedia.org/wiki/PalmPilot • Praveen Neppalli Naga on LinkedIn: https://www.linkedin.com/in/pneppalli/ • May Mobility: https://maymobility.com/ • Uber strikes deal with May Mobility to deploy ‘thousands’ of robotaxis: https://www.theverge.com/news/659563/uber-may-mobility-autonomous-ridehail-partnership • Waymo: https://waymo.com/ • WeRide: https://www.weride.ai/ • Uber and Avride Announce Autonomous Delivery and Mobility Partnership: https://investor.uber.com/news-events/news/press-release-details/2024/Uber-and-Avride-Announce-Autonomous-Delivery-and-Mobility-Partnership/default.aspx • Dara Khosrowshahi on X: https://x.com/dkhos • Uber Elevate: https://www.uber.com/us/en/elevate/vision/ • Uber AV: https://www.uber.com/us/en/autonomous/ • Uber Reserve: https://www.uber.com/us/en/ride/how-it-works/reserve/ • Uber for teens: https://www.uber.com/us/en/ride/teens/ • Flywheel: https://www.flywheel.com/ • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • NotebookLM: https://notebooklm.google/ • Behind the product: NotebookLM | Raiza Martin (Senior Product Manager, AI @ Google Labs): https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin • BlackBerry: https://en.wikipedia.org/wiki/BlackBerry • Peaky Blinders on Netflix: https://www.netflix.com/title/80002479 • Deep research: https://openai.com/index/introducing-deep-research/ — Recommended books: • Blitzscaling: The Lightning-Fast Path to Building Massively Valuable Companies: https://www.amazon.com/Blitzscaling-Lightning-Fast-Building-Massively-Companies/dp/1524761419 • Nobody Wants to Read Your Sh*t: Why That Is And What You Can Do About It: https://www.amazon.com/Nobody-Wants-Read-Your-Sh-ebook/dp/B01GZ1TJBI • Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1451648537 • Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281 • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing. What you will learn: 1. Why do most marketing playbooks often fail, and what’s a better way? 2. Which marketing lever should I pull first? 3. Why is trying to be better than competitors usually a losing strategy? 4. How do I craft positioning that actually converts? 5. What makes messaging stick with developers, enterprises, and consumers? 6. What pricing experiments actually move revenue? 7. What is working at OpenAI really like? 8. Why does consistency and quality matter more than speed? — Brought to you by: Eppo — Run reliable, impactful experiments Airtable ProductCentral—Launch to new heights with a unified system for product development LinkedIn Ads—Reach professionals and drive results for your business — Where to find Krithika Shankarraman: • X: https://x.com/krithix • LinkedIn: https://www.linkedin.com/in/krithix/ • Website: https://krithix.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Krithika (04:22) Early marketing lessons from OpenAI (11:17) Diagnosing marketing needs (15:06) The DATE framework and why being cheaper is a race to the bottom (17:11) Marketing strategies at Retool (22:29) Insights from marketing at Stripe (32:33) The importance of consistent marketing communication (39:55) Criteria for hiring a marketing expert (41:43) “Capital M” vs. “lowercase m” marketing (43:05) ChatGPT vs. Claude: market dominance (45:31) The future of AI and its societal impact (47:09) Work-life balance (48:41) Transitioning to Thrive (52:35) Career advice for marketers (55:00) The importance of taste and creativity in the AI era (01:00:04) AI product pricing (01:03:21) AI tools in marketing (01:05:17) Failure corner (01:08:46) Lightning round and final thoughts — Referenced: • OpenAI: https://openai.com/ • Stripe: https://stripe.com/ • Retool: https://retool.com/ • Dropbox: https://www.dropbox.com/ • Sam Altman talks about his business model: https://www.youtube.com/watch?v=pLnyjxgFxew • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy • Netflix: https://www.netflix.com/ • Stripe Connect: https://stripe.com/connect • John Collison on X: https://x.com/collision • Patrick Collison on X: https://x.com/patrickc • Cristina Cordova on LinkedIn: https://www.linkedin.com/in/cristinajcordova/ • Hackpad: https://en.wikipedia.org/wiki/Hackpad • Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg • Wiz: https://www.wiz.io/ • Thrive Capital: https://thrivecap.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Claude: https://claude.ai/new • ChatGPT: https://chatgpt.com/ • Lessons from scaling Stripe | Claire Hughes Johnson (former COO of Stripe): https://www.lennysnewsletter.com/p/lessons-from-scaling-stripe-tactics • Databricks: https://www.databricks.com/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • April Dunford on product positioning, segmentation, and optimizing your sales process: https://www.lennysnewsletter.com/p/april-dunford-on-product-positioning • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Severance on AppleTV+: https://tv.apple.com/us/show/severance/ • Granola: https://www.granola.ai/ • Some people think AI writing has a tell—the em dash. Writers disagree: https://www.washingtonpost.com/technology/2025/04/09/ai-em-dash-writing-punctuation-chatgpt/ — Recommended books: • Obviously Awesome: How to Nail Product Positioning So Customers Get It, Buy It, Love It: https://www.amazon.com/Obviously-Awesome-Product-Positioning-Customers/dp/1999023005 • Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda. Learn: 1. How to find and focus on the highest-leverage problems 2. Why you shouldn’t optimize for compensation early in your career 3. Why you should optimize for strengths, not weaknesses 4. Why you need to decide if you truly want the C-suite path 5. Why working at a fintech company creates exceptional PMs 6. Strategy = hypothesis × experimentation velocity 7. Small, fast wins compound faster than big, slow bets — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Paragon—Ship every SaaS integration your customers want • Vanta—Automate compliance. Simplify security. — Where to find Mayur Kamat: • X: https://x.com/5degreez • LinkedIn: https://www.linkedin.com/in/mayur/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction and Mayur’s background (04:49) Working at Binance: An inside look (18:18) Career advice for product managers (27:00) PM career paths (33:58) Understanding fintech customers (36:00) Understanding your strengths (44:46) Creating a culture of experimentation (51:14) Hiring and developing top talent (54:50) Building a diverse product portfolio (57:08) Working in high talent density areas (59:43) Personal and professional balance (01:06:32) High-leverage opportunities and decision making (01:14:28) AI tools in the workplace (01:19:14) Failure corner (01:25:11) Lightning round and final thoughts — Referenced: • Binance: https://www.binance.us/ • Google: https://about.google/ • Microsoft: https://www.microsoft.com/ • Agoda: https://www.agoda.com • N26: https://n26.com/ • Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm • Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best • Bezos Says Work-Life Balance is a “Debilitating” Phrase: https://www.investopedia.com/news/bezos-says-worklife-balance-debilitating-phrase/ • Maslow’s Hierarchy of Needs: https://www.simplypsychology.org/maslow.html • PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia • Changpeng Zhao on LinkedIn: https://www.linkedin.com/in/cpzhao/ • Ray Dalio on LinkedIn: https://www.linkedin.com/in/raydalio/ • Porter’s five forces: https://en.wikipedia.org/wiki/Porter%27s_five_forces_analysis • Jonathan Rosenberg on X: https://x.com/jjrosenberg • Aura: https://buy.aura.com/ • Intercom: https://www.intercom.com/ • Palantir: https://www.palantir.com/ • Revolut: https://www.revolut.com/ • Chime: https://www.chime.com/ • Stripe: https://stripe.com/ • Dropbox: https://www.dropbox.com/ • Alex Algard on LinkedIn: https://www.linkedin.com/in/alexalgard • Hiya: https://www.hiya.com/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Gemini: https://gemini.google.com/app • Writer: https://writer.com/ • Google Hangouts: https://en.wikipedia.org/wiki/Google_Hangouts • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/ • Google Meet: https://meet.google.com/landing • House on Hulu: https://www.hulu.com/series/ef39603f-eb90-4248-8237-f6168d7c1be1 • Big Bang Theory on Hulu: https://www.hulu.com/series/9bde5aeb-5297-4290-b173-19a4d59cc11d • Adolescence on Netflix: https://www.netflix.com/title/81756069 • The White Lotus on HBO: https://www.hbo.com/the-white-lotus • Robinhood: https://robinhood.com/us/en/ • Nikita Bier’s post on X about Bible Chat: https://x.com/nikitabier/status/1915252215507210349 • Bible Chat: https://apps.apple.com/us/app/bible-chat-daily-devotional/id6448849666?mt=8 • Suno: https://suno.com/home • Disfrutar: https://www.disfrutarbarcelona.com/ — Recommended books: • StrengthsFinder 2.0: https://www.amazon.com/StrengthsFinder-2-0-Tom-Rath/dp/159562015X • The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One. What you’ll learn: 1. How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product development 2. The three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat) 3. Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfaces 4. Why the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editing 5. How living “one year in the future” can be operationalized with programs like Microsoft’s Frontier 6. How even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approaches 7. Insights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems) 8. The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could alone 9. A practical framework for evaluating zero-to-one product opportunities — Brought to you by: Eppo—Run reliable, impactful experiments Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications Coda—The all-in-one collaborative workspace — Where to find Aparna Chennapragada: • X: https://x.com/aparnacd • LinkedIn: https://www.linkedin.com/in/aparnacd/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Aparna Chennapragada (04:28) Aparna’s stand-up comedy journey (07:29) Transition to Microsoft and enterprise insights (10:00) The Frontier program and AI integration (13:28) Understanding AI agents (17:59) NLX is the new UX (22:28) The future of product development (31:16) Building a custom Chrome extension (35:45) Leadership styles of Satya and Sundar (37:47) Counterintuitive lessons in product building (41:20) Inflection points for successful products (45:16) GitHub Copilot and code generation (48:34) Excel’s enduring success (50:27) Pivotal career moments (54:55) The future of human-agent collaboration (56:25) Lightning round and final thoughts — Referenced: • Google Lens: https://lens.google/ • Saturday Night Live: https://www.nbc.com/saturday-night-live • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ • Robinhood: https://robinhood.com/ • eBay: https://www.ebay.com/ • Capital One: https://www.capitalone.com/ • Microsoft: https://www.microsoft.com/ • Aparna’s LinkedIn post about enterprise vs. consumer: https://www.linkedin.com/posts/aparnacd_every-enterprise-user-feature-has-a-shadow-activity-7321176091610542080-8X-E/ • The Epic Split: https://en.wikipedia.org/wiki/The_Epic_Split • AI Frontiers: https://www.microsoft.com/en-us/research/lab/ai-frontiers/ • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Deepseek: https://www.deepseek.com/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Tobi Lütke’s post on X about reflexive AI: https://x.com/tobi/status/1909251946235437514 • GitHub Copilot: https://github.com/features/copilot • Sundar Pichai on LinkedIn: https://www.linkedin.com/in/sundarpichai/ • South Park “Underwear Gnomes” episode: https://southpark.cc.com/episodes/13y790/south-park-gnomes-season-2-ep-17 • Google Home: https://home.google.com/welcome/ • Cursor: https://www.cursor.com/ • v0: https://v0.dev/ • Bolt: https://bolt.new/ • Lovable: https://lovable.dev/ • Replit: https://replit.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO): https://www.lennysnewsletter.com/p/the-rise-of-cursor-michael-truell • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Microsoft Excel World Championship: https://fmworldcup.com/microsoft-excel-world-championship/ • Google Now: https://en.wikipedia.org/wiki/Google_Now • Hacks on Max: https://www.max.com/shows/hacks/67e940b7-aab2-46ce-a62b-c7308cde9de7 • Granola: https://www.granola.ai/ • Alan Kay quote: https://www.brainyquote.com/quotes/alan_kay_100831 • Sindhu Vee’s website: https://sindhuvee.com/ • Nate Bargatze’s website: https://natebargatze.com/ — Recommended book: • A Brief History of Intelligence: Evolution, AI, and the Five Breakthroughs That Made Our Brains: https://www.amazon.com/Brief-History-Intelligence-Evolution-Breakthroughs/dp/0063286351 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world’s top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut’s relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience. What you’ll learn: 1. Revolut’s unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing power 2. How a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launches 3. How Revolut maintains quality while shipping hundreds of features across over 50 countries 4. Why Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company’s most successful product leaders 5. How Revolut’s founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovation 6. Their framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countries 7. The importance of treating products that are 99% done as closer to 0% done, vs. 100% done — This entire episode is brought to you by Stripe—Helping companies of all sizes grow revenue. — Where to find Dmitry Zlokazov: • X: https://x.com/Dzlokazov • LinkedIn: https://www.linkedin.com/in/zlokazov/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Dmitry and Revolut (03:41) Revolut’s unique approach to product management (06:58) The role and responsibilities of product owners (09:28) Types of product owners at Revolut (15:50) Building “wow” products (25:00) Hiring practices (31:33) Managing teams and projects (41:07) Revolut’s diverse product offerings (44:40) Scaling new products successfully (52:10) Attracting top talent (58:43) Failure corner (01:02:49) Lightning round and final thoughts — Referenced: • Revolut: https://www.revolut.com/ • Intercom: https://www.intercom.com/ • Palantir: https://www.palantir.com/ • Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best • Which companies accelerate PM careers most: https://www.lennysnewsletter.com/p/which-companies-accelerate-your-pm • Deliver WOW to our customers: https://www.revolut.com/blog/post/deliver-wow/ • Nik Storonsky on LinkedIn: https://www.linkedin.com/in/nstoronsky • Vlad Yatsenko on LinkedIn: https://www.linkedin.com/in/yatsenko/ • How Palantir built the ultimate founder factory | Nabeel S. Qureshi (entrepreneur and writer, ex-Palantir): https://www.lennysnewsletter.com/p/inside-palantir-nabeel-qureshi • Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product • Gokul Rajaram on X: https://x.com/gokulr • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Schlep blindness: https://www.paulgraham.com/schlep.html • Revolut Launches RevPoints Loyalty Programme, Turning Daily Expenses into Exclusive Rewards: https://www.revolut.com/news/revolut_launches_revpoints_loyalty_programme_turning_daily_expenses_into_exclusive_rewards/ • Gemini: https://gemini.google.com/ • ChatGPT: https://chatgpt.com/ • Figma: https://www.figma.com/ • Oppenheimer: https://www.imdb.com/title/tt15398776/ • Manus: https://manus.im/ • Eisenhower quote: https://quoteinvestigator.com/2017/11/18/planning/ • Wealth protection: https://help.revolut.com/help/security-logging-in/wealth-protection/what-is-wealth-protection/ — Recommended books: • The Hard Thing About Hard Things: Building a Business when There Are No Easy Answers―Straight Talk on the Challenges of Entrepreneurship: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 • Build: An Unorthodox Guide to Making Things Worth Making―Personal Journey from Product Designer to Mentor: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn. What you’ll learn: • Why almost a third of all Palantir’s PMs go on to start companies • How the “forward-deployed engineer” model works and why it creates exceptional product leaders • How Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% margins • The unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive people • Why the company intentionally avoids traditional titles and career ladders—and what they do instead • Why they built an ontology-first data platform that LLMs love • How Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent types • The moral case for working at a company like Palantir — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Attio—The powerful, flexible CRM for fast-growing startups • OneSchema—Import CSV data 10x faster — Where to find Nabeel S. Qureshi: • X: https://x.com/nabeelqu • LinkedIn: https://www.linkedin.com/in/nabeelqu/ • Website: https://nabeelqu.co/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nabeel S. Qureshi (05:10) Palantir’s unique culture and hiring (13:29) What Palantir looks for in people (16:14) Why they don't have titles (19:11) Forward-deployed engineers at Palantir (25:23) Key principles of Palantir's success (30:00) Gotham and Foundry (36:58) The ontology concept (38:02) Life as a forward-deployed engineer (41:36) Balancing custom solutions and product vision (46:36) Advice on how to implement forward-deployed engineers (50:41) The current state of forward-deployed engineers at Palantir (53:15) The power of ingesting, cleaning and analyzing data (59:25) Hiring for mission-driven startups (01:05:30) What makes Palantir PMs different (01:10:00) The moral question of Palantir (01:16:03) Advice for new startups (01:21:12) AI corner (01:24:00) Contrarian corner (01:25:42) Lightning round and final thoughts — Referenced: • Reflections on Palantir: https://nabeelqu.co/reflections-on-palantir • Palantir: https://www.palantir.com/ • Intercom: https://www.intercom.com/ • Which companies produce the best product managers: https://www.lennysnewsletter.com/p/which-companies-produce-the-best • Gotham: https://www.palantir.com/platforms/gotham/ • Foundry: https://www.palantir.com/platforms/foundry/ • Peter Thiel on X: https://x.com/peterthiel • Alex Karp: https://en.wikipedia.org/wiki/Alex_Karp • Stephen Cohen: https://en.wikipedia.org/wiki/Stephen_Cohen_(entrepreneur) • Joe Lonsdale on LinkedIn: https://www.linkedin.com/in/jtlonsdale/ • Tyler Cowen’s website: https://tylercowen.com/ • This Scandinavian City Just Won the Internet With Its Hilarious New Tourism Ad: https://www.afar.com/magazine/oslos-new-tourism-ad-becomes-viral-hit • Safe Superintelligence: https://ssi.inc/ • Mira Murati on X: https://x.com/miramurati • Stripe: https://stripe.com/ • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Airbus: https://www.airbus.com/en • NIH: https://www.nih.gov/ • Jupyter Notebooks: https://jupyter.org/ • Shyam Sankar on LinkedIn: https://www.linkedin.com/in/shyamsankar/ • Palantir Gotham for Defense Decision Making: https://www.youtube.com/watch?v=rxKghrZU5w8 • Foundry 2022 Operating System Demo: https://www.youtube.com/watch?v=uF-GSj-Exms • SQL: https://en.wikipedia.org/wiki/SQL • Airbus A350: https://en.wikipedia.org/wiki/Airbus_A350 • SAP: https://www.sap.com/index.html • Barry McCardel on LinkedIn: https://www.linkedin.com/in/barrymccardel/ • Understanding ‘Forward Deployed Engineering’ and Why Your Company Probably Shouldn’t Do It: https://www.barry.ooo/posts/fde-culture • David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/ • Retool’s Path to Product-Market Fit—Lessons for Getting to 100 Happy Customers, Faster: https://review.firstround.com/retools-path-to-product-market-fit-lessons-for-getting-to-100-happy-customers-faster/ • How to foster innovation and big thinking | Eeke de Milliano (Retool, Stripe): https://www.lennysnewsletter.com/p/how-to-foster-innovation-and-big • Looker: https://cloud.google.com/looker • Sorry, that isn’t an FDE: https://tedmabrey.substack.com/p/sorry-that-isnt-an-fde • Glean: https://www.glean.com/ • Limited Engagement: Is Tech Becoming More Diverse?: https://www.bkmag.com/2017/01/31/limited-engagement-creating-diversity-in-the-tech-industry/ • Operation Warp Speed: https://en.wikipedia.org/wiki/Operation_Warp_Speed • Mark Zuckerberg testifies: https://www.businessinsider.com/facebook-ceo-mark-zuckerberg-testifies-congress-libra-cryptocurrency-2019-10 • Anduril: https://www.anduril.com/ • SpaceX: https://www.spacex.com/ • Principles: https://nabeelqu.co/principles • Wispr Flow: https://wisprflow.ai/ • Claude code: https://docs.anthropic.com/en/docs/agents-and-tools/claude-code/overview • Gemini Pro 2.5: https://deepmind.google/technologies/gemini/pro/ • DeepMind: https://deepmind.google/ • Latent Space newsletter: https://www.latent.space/ • Swyx on x: https://x.com/swyx • Neural networks in chess programs: https://www.chessprogramming.org/Neural_Networks • AlphaZero: https://en.wikipedia.org/wiki/AlphaZero • The top chess players in the world: https://www.chess.com/players • Decision to Leave: https://www.imdb.com/title/tt12477480/ • Oldboy: https://www.imdb.com/title/tt0364569/ • Christopher Alexander: https://en.wikipedia.org/wiki/Christopher_Alexander — Recommended books: • The Technological Republic: Hard Power, Soft Belief, and the Future of the West: https://www.amazon.com/Technological-Republic-Power-Belief-Future/dp/0593798694 • Zero to One: Notes on Startups, or How to Build the Future: https://www.amazon.com/Zero-One-Notes-Startups-Future/dp/0804139296 • Impro: Improvisation and the Theatre: https://www.amazon.com/Impro-Improvisation-Theatre-Keith-Johnstone/dp/0878301178/ • William Shakespeare: Histories: https://www.amazon.com/Histories-Everymans-Library-William-Shakespeare/dp/0679433120/ • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Anna Karenina: https://www.amazon.com/Anna-Karenina-Leo-Tolstoy/dp/0143035002 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity. In our conversation, we cover: 1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?” 2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience 3. Why teams most often fail (hint: it’s not lack of talent or strategy) 4. How busyness often masks deeper issues of self-worth 5. Why a “growth mindset” can be problematic 6. The importance of legacy and what it means to live a meaningful life 7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots 8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity — Brought to you by: Eppo—Run reliable, impactful experiments Contentsquare—Create better digital experiences OneSchema—Import CSV data 10x faster — Where to find Jerry Colonna: • X: https://x.com/jerrycolonna • LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/ • Website: https://reunion.reboot.io/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Jerry Colonna (04:12) Jerry’s key question (06:55) The equation for great leadership (09:37) The big lie of success and happiness (12:12) The consciousness hack (15:56) Getting over the fear of consequences (20:23) The problem with bypassing our childhood baggage (23:22) Radical self-inquiry: asking the tough questions (27:05) Shared experiences: the power of community (30:25) The trap of busyness and attachment (40:45) Understanding our own intentions (46:58) Legacy and purpose (55:43) Writing for self-discovery (57:12) The impact of AI on humanity (01:05:00) Turning a growth mindset into a fixed mindset (01:11:30) The role of radical self-inquiry in leadership (01:19:24) Final thoughts and reflections — Referenced: • Naropa University: https://www.naropa.edu/ • Fitler Club: https://fitlerclub.com • Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/ • Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830 • Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products • The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism • 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821 • Simon Sinek’s website: https://simonsinek.com/ • Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/ • Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318 • Evernote: https://evernote.com/ • Claude: https://claude.ai • Peter Senge on X: https://x.com/petersenge • Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your • Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/ • The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living — Recommended books: • Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536 • Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139 • Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511 • 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431 • Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586 • The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott’s background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you’ll learn: 1. How a team of “Devins” are already producing 25% of Cognition’s pull requests, and they are on track to hit 50% by year’s end 2. How each engineer on Cognition’s 15-person engineering team works with about five Devins each 3. How Devin has evolved from a “high school CS student” to a “junior engineer” over the past year 4. Why engineering will shift from “bricklayers” to “architects” 5. Why AI tools will lead to more engineering jobs rather than fewer 6. How Devin creates its own wiki to understand and document complex codebases 7. The eight pivots Cognition went through before landing on their current approach 8. The cultural shifts required to successfully adopt AI engineers — Brought to you by: Enterpret—Transform customer feedback into product growth Paragon—Ship every SaaS integration your customers want Attio—The powerful, flexible CRM for fast-growing startups — Where to find Scott Wu: • X: https://x.com/scottwu46 • LinkedIn: https://www.linkedin.com/in/scott-wu-8b94ab96/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Scott Wu and Devin (09:13) Scaling and future prospects (10:23) Devin's origin story (17:26) The idea of Devin as a person (22:19) How a team of “Devins” are already producing 25% of Cognition’s pull requests (25:17) Important skills in the AI era (30:21) How Cognition’s engineering team works with Devin's (34:37) Live demo (42:20) Devin’s codebase integration (44:50) Automation with Linear (46:53) What Devin does best (52:56) The future of AI in software engineering (57:13) Moats and stickiness in AI (01:01:57) The tech that enables Devin (01:04:14) AI will be the biggest technology shift of our lives (01:07:25) Adopting Devin in your company (01:15:13) Startup wisdom and hiring practices (01:22:32) Lightning round and final thoughts — Referenced: • Devin: https://devin.ai/ • GitHub: https://github.com/ • Linear: https://linear.app/ • Waymo: https://waymo.com/ • GitHub Copilot: https://github.com/features/copilot • Cursor: https://www.cursor.com/ • Anysphere: https://anysphere.inc/ • Bolt: https://bolt.new/ • StackBlitz: https://stackblitz.com/ • Cognition: https://cognition.ai/ • v0: https://v0.dev/ • Vercel: https://vercel.com/ • Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js): https://www.lennysnewsletter.com/p/everyones-an-engineer-now-guillermo-rauch • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Assembly: https://en.wikipedia.org/wiki/Assembly_language • Pascal: https://en.wikipedia.org/wiki/Pascal_(programming_language) • Python: https://www.python.org/ • Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox • Datadog: https://www.datadoghq.com/ • Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Windsurf: https://windsurf.com/ • COBOL: https://en.wikipedia.org/wiki/COBOL • Fortran: https://en.wikipedia.org/wiki/Fortran • Magic the Gathering: https://magic.wizards.com/en • Aura frames: https://auraframes.com/ • AirPods: https://www.apple.com/airpods/ • Steven Hao on LinkedIn: https://www.linkedin.com/in/steven-hao-160b9638/ • Walden Yan on LinkedIn: https://www.linkedin.com/in/waldenyan/ — Recommended books: • How to Win Friends & Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 • The Power Law: Venture Capital and the Making of the New Future: https://www.amazon.com/Power-Law-Venture-Capital-Making/dp/052555999X • The Great Gatsby: https://www.amazon.com/Great-Gatsby-F-Scott-Fitzgerald/dp/0743273567 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future. What you’ll learn: • Cursor's early pivot from automating CAD to automating code • Michael’s vision for “what comes after code” and how programming will evolve • Why Cursor built their own custom AI models despite not starting there • Key lessons from Cursor’s rapid growth • Why “taste” and logic design will become more valuable engineering skills than technical coding ability • Why the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winner • Michael’s advice for engineers and product teams preparing for the AI future — Brought to you by: Eppo—Run reliable, impactful experiments Vanta—Automate compliance. Simplify security OneSchema—Import CSV data 10x faster — Where to find Michael Truell: • X: https://x.com/mntruell • LinkedIn: https://www.linkedin.com/in/michael-t-5b1bbb122/ • Website: https://mntruell.com/ — In this episode, we cover: (00:00) Introduction to Michael Truell and Cursor (04:20) What comes after code (08:32) The importance of taste (12:39) Cursor’s origin story (18:31) Why they chose to build an IDE (22:39) Will everyone become engineering managers? (24:31) How they decided it was time to ship (26:45) Reflecting on Cursor's success (32:03) Counterintuitive lessons on building AI products (34:02) Inside Cursor's stack (38:42) Defensibility and market dynamics in AI (46:13) Tips for using Cursor (51:25) Hiring and building a strong team (59:10) Staying focused amid rapid AI advancements (01:02:31) Final thoughts and advice for aspiring AI innovators — Referenced: • Cursor: https://www.cursor.com/ • Microsoft Copilot: https://copilot.microsoft.com/ • Scaling laws for neural language models: https://openai.com/index/scaling-laws-for-neural-language-models/ • MIT: https://www.mit.edu/ • Telegram: https://telegram.org/ • Signal: https://signal.org/ • WhatsApp: https://www.whatsapp.com/ • Devin: https://devin.ai/ • Visual Studio Code: https://code.visualstudio.com/ • Chromium: https://chromium.googlesource.com/chromium/src/base/ • Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: https://learnprompting.org/blog/gpt_wrappers • OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter): https://www.lennysnewsletter.com/p/kevin-weil-open-ai • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • DALL-E 3: https://openai.com/index/dall-e-3/ • Stable Diffusion 3: https://stability.ai/news/stable-diffusion-3 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide. What you’ll learn: 1. How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their team 2. How sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignment 3. How focusing on impact, rather than just shipping features, has transformed the company’s culture 4. The story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioning 5. How they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver faster 6. Daniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective — Brought to you by: • Enterpret—Transform customer feedback into product growth • Airtable ProductCentral—Launch to new heights with a unified system for product development • Vanta—Automate compliance. Simplify security — Where to find Daniel Lereya: • LinkedIn: https://www.linkedin.com/in/daniel-lereya-aa487646/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Daniel and monday.com (04:20) The pivotal moment: competitors shipping faster (08:50) Setting ambitious goals (17:44) Focusing on impact rather than features (27:07) Transforming your product quarterly (32:07) Scaling monday.com: challenges and strategies (39:14) How monday.com maintains transparency as a public company (45:40) The importance of taking risks (51:02) Counterintuitive lessons in product development (54:33) The value of timeboxing and deadlines (57:28) Embracing user feedback (59:54) Adapting leadership styles (01:04:43) Personal reflections on leadership (01:10:41) Handling crises and strategic planning (01:17:28) The role of AI in work and personal life (01:22:13) Final thoughts and lightning round — Referenced: • Monday.com: https://monday.com/ • The basics of a monday.com board: https://support.monday.com/hc/en-us/articles/115005317249-The-basics-of-a-board • Eran Zinman on LinkedIn: https://www.linkedin.com/in/eranzinman/ • Roy Mann on LinkedIn: https://www.linkedin.com/in/manroy/ • Tal Harari on LinkedIn: https://www.linkedin.com/in/tal-harari-a2515215/ • Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile • A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals): https://www.lennysnewsletter.com/p/shape-up-ryan-singer • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • AI blocks: https://support.monday.com/hc/en-us/articles/18433811274386-AI-Automation-blocks • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of • Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox • SpaceX: https://www.spacex.com/ • Why and how to lead with transparency: https://monday.com/blog/monday-insights/may-30th/ • How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can’t copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra • This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your data scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Bryan Johnson on LinkedIn: https://www.linkedin.com/in/bryanrjohnson/ • ChatGPT: https://chatgpt.com/ • Cursor: https://www.cursor.com/ • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • FIFA 22: https://store.playstation.com/en-us/concept/10002538/ • Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890 • Google Photos: https://photos.google.com/ — Recommended books: • Shape Up: Stop Running in Circles and Ship Work that Matters: https://basecamp.com/shapeup • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860 • Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

AI is rapidly changing how we live and work. It’s exciting, but also overwhelming. If you’re struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I’m thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny’s Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they’ve learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just looking to level up your AI skills, How I AI is for you. — SUBSCRIBE TO THE SHOW → YouTube: ⁠https://www.youtube.com/channel/UCRYY7IEbkHLH_ScJCu9eWDQ⁠ → Spotify: ⁠https://open.spotify.com/show/4aRP2XSavdtrLG5FZoonOK → Apple: https://podcasts.apple.com/us/podcast/how-i-ai/id1809663079 This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE. In this conversation, you'll learn: 1. Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers code 2. The surprising UI discovery that tripled adoption rates overnight. 3. The secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdom. 4. How non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costs 5. Why Varun believes 90% of code will be AI-generated, but engineering jobs will actually increase 6. How training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-term 7. Why agency is the most undervalued and important skill in the AI era — Brought to you by: • Brex—The banking solution for startups • Productboard—Make products that matter • Coda—The all-in-one collaborative workspace — Where to find Varun Mohan: • X: https://x.com/_mohansolo • LinkedIn: https://www.linkedin.com/in/varunkmohan/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Varun’s background (03:57) Building and scaling Windsurf (12:58) Windsurf: The new purpose-built IDE to harness magic (17:11) The future of engineering and AI (21:30) Skills worth investing in (23:07) Hiring philosophy and company culture (35:22) Sales strategy and market position (39:37) JetBrains vs. VS Code: extensibility and enterprise adoption (41:20) Live demo: building an Airbnb for dogs with Windsurf (42:46) Tips for using Windsurf effectively (46:38) AI’s role in code modification and review (48:56) Empowering non-developers to build custom software (54:03) Training Windsurf (01:00:43) Windsurf’s unique team structure and product strategy (01:06:40) The importance of continuous innovation (01:08:57) Final thoughts and advice for aspiring developers — Referenced: • Windsurf: https://windsurf.com/ • VS Code: https://code.visualstudio.com/ • JetBrains: https://www.jetbrains.com/ • Eclipse: https://eclipseide.org/ • Visual Studio: https://visualstudio.microsoft.com/ • Vim: https://www.vim.org/ • Emacs: https://www.gnu.org/software/emacs/ • Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze): https://www.lennysnewsletter.com/p/lessons-from-uri-levine • IntelliJ: https://www.jetbrains.com/idea/ • Julia: https://julialang.org/ • Parallel computing: https://en.wikipedia.org/wiki/Parallel_computing • Douglas Chen on LinkedIn: https://www.linkedin.com/in/douglaspchen/ • Carlos Delatorre on LinkedIn: https://www.linkedin.com/in/cadelatorre/ • MongoDB: https://www.mongodb.com/ • Cursor: https://www.cursor.com/ • GitHub Copilot: https://github.com/features/copilot • Llama: https://www.llama.com/ • Mistral: https://mistral.ai/ • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • React: https://react.dev/ • Sonnet: https://www.anthropic.com/claude/sonnet • OpenAI: https://openai.com/ • FedRamp: https://www.fedramp.gov/ • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Amdahl’s law: https://en.wikipedia.org/wiki/Amdahl%27s_law • How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions): https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra — Recommended book: • Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide. In this episode, you’ll learn: 1. How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay ahead 2. Why the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teams 3. Specific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved products 4. How Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering time 5. The exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever before 6. Guillermo’s actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta — Automate compliance. Simplify security • LinkedIn Ads—Reach professionals and drive results for your business — Where to find Guillermo Rauch: • X: https://x.com/rauchg • LinkedIn: https://www.linkedin.com/in/rauchg/ • Website: https://rauchg.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Guillermo Rauch (04:43) v0's mission (07:03) The impact and growth of v0 (15:54) The future of product development with AI (19:05) Empowering engineers and product builders (24:01) Skills for the future: coding, math, and eloquence (35:05) v0 in action: real-world applications (36:40) Tips for using v0 effectively (45:46) Core skills for building AI apps (49:44) Live demo (59:45) Understanding how AI thinks (01:04:35) AI integration and future prospects (01:07:22) Building taste (01:13:43) Limitations of v0 (01:16:54) Improving the design of your product (01:20:09) The secret to product quality (01:22:35) Vercel’s AI-driven development (01:25:43) Guillermo's vision for the future — Referenced: • v0: https://v0.dev/ • Vercel: https://vercel.com/ • GitHub: https://github.com/ • Cursor: https://www.cursor.com/ • Next.js Framework: https://nextjs.org/ • Claude: https://claude.ai/new • Grok: https://x.ai/ • Midjourney: https://www.midjourney.com • SocketIO: https://socket.io/ • Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder): https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao • Notion: https://www.notion.com/ • Automattic: https://automattic.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • v0 Community: https://v0.dev/chat/community • Figma: https://www.figma.com/ • Git Commit: https://www.atlassian.com/git/tutorials/saving-changes/git-commit • What are Artifacts and how do I use them?: https://support.anthropic.com/en/articles/9487310-what-are-artifacts-and-how-do-i-use-them • Design Engineering at Vercel: https://vercel.com/blog/design-engineering-at-vercel • CSS: https://en.wikipedia.org/wiki/CSS • Tailwind: https://tailwindcss.com/ • Wordcel / Shape Rotator / Mathcel: https://knowyourmeme.com/memes/wordcel-shape-rotator-mathcel • Steve Jobs’s Ultimate Lesson for Companies: https://hbr.org/2011/08/steve-jobss-ultimate-lesson-fo • Bloom Hackathon: https://bloom.build/ • Expenses Should Do Themselves | Saquon Barkley x Ramp (Super Bowl Ad): https://www.youtube.com/watch?v=p1Tgsy7D0Jg • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp • JavaScript: https://www.javascript.com/ • React: https://react.dev/ • Mapbox: https://www.mapbox.com/ • Leaflet: https://leafletjs.com/ • Escape hatches: https://react.dev/learn/escape-hatches • Supreme: https://supreme.com/ • Shadcn: https://ui.shadcn.com/ • Charles Schwab: https://www.schwab.com/ • Fortune: https://fortune.com/ • Semafor: https://www.semafor.com/ • AI SDK: https://sdk.vercel.ai/ • DeepSeek: https://www.deepseek.com/ • Stripe: https://stripe.com/ • Vercel templates: https://vercel.com/templates • GC AI: https://getgc.ai/ • OpenEvidence: https://www.openevidence.com/ • Paris Fashion Week: https://www.fhcm.paris/en/paris-fashion-week • Guillermo’s post on X about making great products: https://x.com/rauchg/status/1887314115066274254 • Everybody Can Cook billboard: https://www.linkedin.com/posts/evilrabbit_activity-7242975574242037760-uRW9/ • Ratatouille: https://www.imdb.com/title/tt0382932/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook. In this episode, you’ll learn: 1. How OpenAI structures its product teams and maintains agility while developing cutting-edge AI 2. The power of model ensembles—using multiple specialized models together like a company of humans with different skills 3. Why writing effective evals (AI evaluation tests) is becoming a critical skill for product managers 4. The surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescence 5. How “vibe coding” is changing how companies operate 6. What OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity) 7. “Model maximalism” and why today’s AI is the worst you’ll ever use again 8. Practical prompting techniques that improve AI interactions, including example-based prompting — Brought to you by: • Eppo—Run reliable, impactful experiments • Persona—A global leader in digital identity verification • OneSchema—Import CSV data 10x faster — Where to find Kevin Weil: • X: https://x.com/kevinweil • LinkedIn: https://www.linkedin.com/in/kevinweil/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kevin’s background (04:06) OpenAI’s new image model (06:52) The role of chief product officer at OpenAI (10:18) His recruitment story and joining OpenAI (17:20) The importance of evals in AI (24:59) Shipping quickly and consistently (28:34) Product reviews and iterative deployment (39:35) Chat as an interface for AI (43:59) Collaboration between researchers and product teams (46:41) Hiring product managers at OpenAI (48:45) Embracing ambiguity in product management (51:41) The role of AI in product teams (53:21) Vibe coding and AI prototyping (55:55) The future of product teams and fine-tuned models (01:04:36) AI in education (01:06:42) Optimism and concerns about AI’s future (01:16:37) Reflections on the Libra project (01:20:37) Lightning round and final thoughts — Referenced: • OpenAI: https://openai.com/ • The AI-Generated Studio Ghibli Trend, Explained: https://www.forbes.com/sites/danidiplacido/2025/03/27/the-ai-generated-studio-ghibli-trend-explained/ • Introducing 4o Image Generation: https://openai.com/index/introducing-4o-image-generation/ • Waymo: https://waymo.com/ • X: https://x.com • Facebook: https://www.facebook.com/ • Instagram: https://www.instagram.com/ • Planet: https://www.planet.com/ • Sam Altman on X: https://x.com/sama • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k • OpenAI evals: https://github.com/openai/evals • Deep Research: https://openai.com/index/introducing-deep-research/ • Ev Williams on X: https://x.com/ev • OpenAI API: https://platform.openai.com/docs/overview • Dwight Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720 • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • StackBlitz: https://stackblitz.com/ • Claude 3.5 Sonnet: https://www.anthropic.com/news/claude-3-5-sonnet • Anthropic: https://www.anthropic.com/ • Four-minute mile: https://en.wikipedia.org/wiki/Four-minute_mile • Chad: https://chatgpt.com/g/g-3F100ZiIe-chad-open-a-i • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Figma: https://www.figma.com/ • Julia Villagra on LinkedIn: https://www.linkedin.com/in/juliavillagra/ • Andrej Karpathy on X: https://x.com/karpathy • Silicon Valley CEO says ‘vibe coding’ lets 10 engineers do the work of 100—here’s how to use it: https://fortune.com/2025/03/26/silicon-valley-ceo-says-vibe-coding-lets-10-engineers-do-the-work-of-100-heres-how-to-use-it/ • Cursor: https://www.cursor.com/ • Windsurf: https://codeium.com/windsurf • GitHub Copilot: https://github.com/features/copilot • Patrick Srail on X: https://x.com/patricksrail • Khan Academy: https://www.khanacademy.org/ • CK-12 Education: https://www.ck12.org/ • Sora: https://openai.com/sora/ • Sam Altman’s post on X about creative writing: https://x.com/sama/status/1899535387435086115 • Diem (formerly known as Libra): https://en.wikipedia.org/wiki/Diem_(digital_currency) • Novi: https://about.fb.com/news/2020/05/welcome-to-novi/ • David Marcus on LinkedIn: https://www.linkedin.com/in/dmarcus/ • Peter Zeihan on X: https://x.com/PeterZeihan • The Wheel of Time on Prime Video: https://www.amazon.com/Wheel-Time-Season-1/dp/B09F59CZ7R • Top Gun: Maverick on Prime Video: https://www.amazon.com/Top-Gun-Maverick-Joseph-Kosinski/dp/B0DM2LYL8G • Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google): https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske • MySQL: https://www.mysql.com/ — Recommended books: • Co-Intelligence: Living and Working with AI: https://www.amazon.com/Co-Intelligence-Living-Working-Ethan-Mollick/dp/059371671X • The Accidental Superpower: Ten Years On: https://www.amazon.com/Accidental-Superpower-Ten-Years/dp/1538767341 • Cable Cowboy: https://www.amazon.com/Cable-Cowboy-Malone-Modern-Business/dp/047170637X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career. What you’ll learn: 1. The #1 communication mistake leaders make—and Wes’s proven fix to instantly gain buy-in 2. Wes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetings 3. How to master concise communication—including Wes’s tactical approach for brevity without losing meaning 4. The art of executive presence: actionable strategies for conveying confidence and clarity, even under pressure 5. The “sales, then logistics” framework—and why your ideas keep getting ignored without it 6. The power of “signposting”—and why executives skim your docs without it 7. Exactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without friction 8. Practical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executives 9. Managing up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leaders 10. Career accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing out 11. Real-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Where to find Wes Kao: • LinkedIn: https://www.linkedin.com/in/weskao/ • Website: https://www.weskao.com/ • Maven course: https://maven.com/wes-kao/executive-communication-influence — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Wes Kao (05:34) Working with Wes (06:58) The importance of communication (10:44) Sales before logistics (18:20) Being concise (24:31) Books to help you become a better writer (27:30) Signposting and formatting (32:05) How to develop and practice your communication skills (40:41) Slack communication (42:23) Confidence in communication (50:17) The MOO framework (54:00) Staying calm in high-stakes conversations (57:36) Which tactic to start with (58:53) Effective tactics for managing up (01:04:53) Giving constructive feedback: strategy, not self-expression (01:09:39) Delegating effectively while maintaining high standards (01:16:36) The swipe file: collecting inspiration for better communication (01:19:59) Leveraging AI for better communication (01:22:01) Lightning round — Referenced: • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto • Communication is the job: https://boz.com/articles/communication-is-the-job • Maven: https://maven.com/ • Sales, not logistics: https://newsletter.weskao.com/p/sales-not-logistics • How to be more concise: https://newsletter.weskao.com/p/how-to-be-concise • Signposting: How to reduce cognitive load for your reader: https://newsletter.weskao.com/p/sign-posting-how-to-reduce-cognitive • Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev • Tone and words: Use accurate language: https://newsletter.weskao.com/p/tone-and-words-use-accurate-language • Quote by Joan Didion: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it • Strategy, not self-expression: How to decide what to say when giving feedback: https://newsletter.weskao.com/p/strategy-not-self-expression • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • The CEDAF framework: Delegating gets easier when you get better at explaining your ideas: https://newsletter.weskao.com/p/delegating-and-explaining • Swipe file: https://en.wikipedia.org/wiki/Swipe_file • Apple Notes: https://apps.apple.com/us/app/notes/id1110145109 • Claude: https://claude.ai/new • ChatGPT: https://chatgpt.com/ • Arianna Huffington’s phone bed charging station (Oak): https://www.amazon.com/Arianna-Huffingtons-Phone-Charging-Station/dp/B079C5DBF4?th=1 • The Harlan Coben Collection on Netflix: https://www.netflix.com/browse/genre/81180221 • Oral-B Pro 1000 rechargeable electric toothbrush: https://www.amazon.com/dp/B003UKM9CO/ • The Best Electric Toothbrush: https://www.nytimes.com/wirecutter/reviews/best-electric-toothbrush/ • Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A • 1,000,000: https://www.lennysnewsletter.com/p/1000000 — Recommended books: • On Writing Well: The Classic Guide to Writing Nonfiction: https://www.amazon.com/Writing-Well-Classic-Guide-Nonfiction/dp/0060891548/ • Stein on Writing: A Master Editor of Some of the Most Successful Writers of Our Century Shares His Craft Techniques and Strategies: https://www.amazon.com/Stein-Writing-Successful-Techniques-Strategies/dp/0312254210/ • On Writing: A Memoir of the Craft: https://www.amazon.com/Writing-Memoir-Craft-Stephen-King/dp/1982159375 • Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413/ • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long: https://www.amazon.com/Your-Brain-Work-Revised-Updated/dp/0063003155/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to them them escape the cycle of endless sprints, missed deadlines, and dragging projects. What you’ll learn: 1. Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones. 2. The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines. 3. The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources. 4. Why most teams struggle with too little detail in their planning, not too much. 5. Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes. 6. Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process. 7. The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details. 8. The clear warning signs that your current development process is failing before it’s too late to change course. 9. Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment. 10. A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation. 11. Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management. 12. How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp. — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Merge—A single API to add hundreds of integrations into your app • Airtable ProductCentral—Launch to new heights with a unified system for product development — Where to find Ryan Singer: • X: https://x.com/rjs • LinkedIn: https://www.linkedin.com/in/feltpresence/ • Website: https://www.ryansinger.co/ • Course: https://www.ryansinger.co/srl/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Ryan’s background (04:38) The origins of Shape Up (07:40) Implementing Shape Up in different companies (09:56) How Shape Up is different (19:02) The core elements of Shape Up (26:29) Shaping sessions and timeboxing (37:23) Flexible sprint planning (38:56) The output of a shaping session (46:57) Balancing detail and flexibility (53:50) A deep dive into shaping sessions (01:01:32) Fat marker sketches (01:02:48) Getting started using Shape Up (01:13:20) Signs it's time to try the Shape Up method (01:18:25) Feature factories (01:25:59) The role of the PM in Shape Up (01:28:26) What makes Basecamp unique (01:35:55) The second edition of the book (01:38:30) Linking product strategy and shaping (01:41:53) Conclusion and final thoughts — Referenced: • Basecamp: https://basecamp.com/ • David Heinemeier Hansson on LinkedIn: https://www.linkedin.com/in/david-heinemeier-hansson-374b18221/ • Jason Fried on LinkedIn: https://www.linkedin.com/in/jason-fried/ • Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking • Des Traynor on LinkedIn: https://www.linkedin.com/in/destraynor/ • Intercom: https://www.intercom.com/ • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of “Job Moves”): https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta • Scrum: https://www.scrum.org/ • 37signals: https://37signals.com/ • Jobs to Be Done Theory: https://www.christenseninstitute.org/theory/jobs-to-be-done/ — Recommended books: • Shape Up: Stop Running in Circles and Ship Work That Matters: https://basecamp.com/shapeup • Demand-Side Sales 101: Stop Selling and Help Your Customers Make Progress: https://www.amazon.com/Demand-Side-Sales-101-Customers-Progress/dp/1544509987/ • Competing Against Luck: The Story of Innovation and Customer Choice: https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612/ • Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Gaurav Misra is the co-founder and CEO of Captions, an AI-powered video creation company and one of the most successful consumer AI products in the world today. Previously he was a product leader at Snap, where he created the design engineering function and spent years helping develop features used by hundreds of millions of users worldwide. With a background in both engineering and design, Gaurav brings a unique cross-functional perspective to product development. What you’ll learn: 1. Why the “ship a marketable feature every week” approach helps his team stay focused and the product stay top of mind for users amid constant AI breakthroughs 2. How to balance rapid shipping with maintaining quality by cutting scope rather than compromising on timelines 3. The “secret roadmap” strategy that helps Captions develop breakthrough features competitors never see coming 4. Why taking on strategic technical debt is essential for startups to outpace larger companies 5. How Captions accidentally ignored their most successful product for 1.5 years (and why it still grew to 500K users with no updates or support) 6. How Snap’s unique product development approach—with designers functioning as PMs—enabled their success as the last major social network to break through 7. Why AI video will transform marketing before other industries — Brought to you by: • Brex — The banking solution for startups • Paragon—Ship every SaaS integration your customers want • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-win-in-the-ai-era-gaurav-misra — Where to find Gaurav Misra: • X: https://x.com/gmharhar • LinkedIn: https://www.linkedin.com/in/gamisra1/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Gaurav’s background (04:47) The exciting era of AI and startups (09:30) Staying top of mind (11:26) Tips for staying focused (13:14) Shipping marketable features weekly (19:03) Managing technical debt in startups (25:31) Snap’s unique product development approach (32:09) Brainstorming with AI (35:09) What Snap got right (41:06) Scaling with a small, agile team (49:33) The shift toward prototyping in product management (51:47) The product manager role (55:40) Snap’s mission and product decisions (01:02:13) The future of AI-generated video (01:10:20) Leveraging AI for marketing (01:14:37) Failure corner (01:20:21) Lightning round and closing thoughts — Referenced: • Snap: https://www.snap.com/ • Captions: https://www.captions.ai/ • Iron Man on Disney+: https://www.disneyplus.com/movies/iron-man/6aM2a8mZATiu • J.A.R.V.I.S.: https://en.wikipedia.org/wiki/J.A.R.V.I.S. • Cursor: https://www.cursor.com/ • Devin: https://devin.ai/ • Eye contact: https://www.captions.ai/eye-contact • Nvidia: https://www.nvidia.com • Descript: https://www.descript.com • Evan Spiegel on LinkedIn: https://www.linkedin.com/in/evan-spiegel-8ab74034a/ • TikTok: https://www.tiktok.com/ • Spotlight: https://www.snapchat.com/spotlight/ • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • Patrick Collison on X: https://x.com/patrickc • DeepSeek: https://www.deepseek.com/ • ByteDance Goku: New video generation AI model, better than OpenAI Sora: https://medium.com/data-science-in-your-pocket/bytedance-goku-new-video-generation-ai-model-better-than-openai-sora-56c017a320a5 • Will Smith eating spaghetti and other weird AI benchmarks that took off in 2024: https://techcrunch.com/2024/12/31/will-smith-eating-spaghetti-and-other-weird-ai-benchmarks-that-took-off-in-2024/ • Silo on AppleTV+: https://tv.apple.com/us/show/silo/umc.cmc.3yksgc857px0k0rqe5zd4jice • Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx • Linear: https://linear.app/ • Superhuman: https://superhuman.com/ • Notion: https://www.notion.com • Perplexity: https://www.perplexity.ai/ • OmniHuman-1 AI Video Generation Looks Too Real: https://www.youtube.com/watch?v=fY0KB516m-E — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer. What you’ll learn: • The unexpected insight about virality Rahul gained from LinkedIn’s head of growth. • Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities. • The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap. • How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows. • The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications. • How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep. — Brought to you by: • Eppo—Run reliable, impactful experiments • Fundrise Flagship Fund—Invest in $1.1 billion of real estate • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra — Where to find Rahul Vohra: • X: https://x.com/rahulvohra • LinkedIn: https://www.linkedin.com/in/rahulvohra/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Rahul and Superhuman (05:00) The most pivotal moment in Rahul's career (07:01) The secret to virality (11:02) Superhuman’s product evolution and core values (13:32) Overcoming slowdowns at scale (18:06) Time management and meditation (27:35) The role of a president (30:56) Attention to detail (43:00) Finding your unique position (47:32) The power of manual onboarding (52:37) Mastering product-market fit (59:33) Game design in business software (01:05:35) Contrarian pricing strategies (01:09:29) Leveraging AI (01:15:40) Transitioning to enterprise solutions (01:19:08) The Single Decisive Reason framework (01:22:32) Conclusion and final thoughts — Referenced: • Superhuman: https://superhuman.com/ • Rapportive: https://techcrunch.com/2012/02/22/rapportive-linkedin-acquisition/ • Elliot Shmukler on LinkedIn: https://www.linkedin.com/in/eshmu/ • What Are ‘Whales’ in Video Games: https://gamerant.com/video-games-whales-concept-term-explained/ • Figma: https://www.figma.com/ • Notion: https://www.notion.com/ • Loom: https://www.loom.com/ • How to use Team Comments to reimagine email collaboration: https://blog.superhuman.com/how-to-use-team-comments-to-reimagine-email-collaboration/ • Rajiv Ayyangar’s post on X about Superhuman: https://x.com/rajivayyangar/status/1816176308130570385 • Transcendental Meditation: https://www.tm.org/ • Laurent Valosek on LinkedIn: https://www.linkedin.com/in/laurent-valosek-18708b5a/ • Peak Leadership Institute: https://www.peakleadershipinstitute.com/ • Ed Sim’s website: https://edsim.net/ • Adelle Sans: https://fonts.adobe.com/fonts/adelle-sans • Comic Sans: https://en.wikipedia.org/wiki/Comic_Sans • Greenfield project: https://en.wikipedia.org/wiki/Greenfield_project • Why Mailbox died: https://www.theverge.com/2015/12/8/9873268/why-dropbox-mailbox-shutdown • Bill Trenchard on X: https://x.com/btrenchard • How Superhuman Built an Engine to Find Product-Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ • Using the Sean Ellis Test for Measuring Your Product-Market Fit: https://medium.productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c • Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/ • The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”): https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis • The Trouble with Rewards: https://www.kornferry.com/insights/briefings-magazine/issue-13/519-the-trouble-with-rewards • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan •  Van Westendorp Price Sensitivity Meter: https://en.wikipedia.org/wiki/Van_Westendorp%27s_Price_Sensitivity_Meter • AI-powered email for high-performing teams: https://superhuman.com/ai • Linear’s secret to building beloved B2B products | Nan Yu (Head of Product): https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu • Single Decisive Reason: decision-making for fast-scaling startups: https://blog.superhuman.com/single-decisive-reason-decision-making-for-fast-scaling-startups/ • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ — Recommended books: • Positioning: The Battle for Your Mind: https://www.amazon.com/Positioning-Battle-Your-Al-Ries/dp/0071373586 • Monetizing Innovation: How Smart Companies Design the Product Around the Price: https://www.amazon.com/Monetizing-Innovation-Companies-Design-Product/dp/1119240867 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Susan Cain, author of the groundbreaking bestseller Quiet: The Power of Introverts in a World That Can’t Stop Talking, shares a guide for how introverts can thrive in the workplace without sacrificing their authentic selves. Drawing from her extensive research and personal experience, Cain offers a powerful reframing: success doesn’t require becoming more extroverted—it demands becoming more fully yourself. — What you’ll learn: 1. A simple definition of introversion and how it differs from shyness—plus a simple two-question test to determine where you fall on the spectrum 2. Five practical tactics introverts can use to be more successful in business while staying true to their natural temperament 3. How to handle challenging workplace scenarios like meetings dominated by loud voices and networking events that drain your energy 4. Specific strategies for managers and founders to create environments where introverted team members can contribute their best work 5. Practical techniques for saying no to energy-draining commitments 6. Strategies for managers to better support and leverage introverted team members 7. Practical advice for raising introverted children to help them develop confidence while honoring their natural temperament 8. Why seeking to become “more extroverted” is the wrong goal—and what to focus on instead to achieve professional success — Brought to you by: • Enterpret—Transform customer feedback into product growth • Vanta—Automate compliance. Simplify security • Fundrise Flagship Fund—Invest in $1.1 billion of real estate — Find the transcript at: https://www.lennysnewsletter.com/p/the-hidden-power-of-introverts-susan-cain — Where to find Susan Cain: • X: https://x.com/susancain • LinkedIn: https://www.linkedin.com/in/susancain/ • Website: https://susancain.net/ • Instagram: https://www.instagram.com/susancainauthor/# • Facebook: https://www.facebook.com/authorsusancain • Substack: https://thequietlife.net/ — In this episode, we cover: (00:00) Introduction to Susan Cain (05:07) Understanding introversion (08:55) The spectrum of introversion and extroversion (13:27) Overcoming public speaking anxiety (17:13) Learning to embrace your introverted self (23:16) The power of leaning into your strengths (24:36) Strategies for introverts to thrive in their career (34:06) The importance of saying no (38:35) What to do instead of networking (41:59) Effective meeting participation for introverts (47:31) Creating a productive work environment (51:14) Raising an introverted child (57:58) Finding the right career fit (01:08:09) Lightning round and final thoughts — Referenced: • The power of introverts: https://www.ted.com/talks/susan_cain_the_power_of_introverts • The hidden power of sad songs and rainy days: https://www.ted.com/talks/susan_cain_and_min_kym_the_hidden_power_of_sad_songs_and_rainy_days • Why bittersweet emotions underscore life’s beauty: https://www.ted.com/talks/susan_cain_why_bittersweet_emotions_underscore_life_s_beauty • Desensitization: https://en.wikipedia.org/wiki/Desensitization_(psychology) • Malcolm Gladwell’s website: https://www.gladwellbooks.com/ • Warren Buffett on X: https://x.com/warrenbuffett • Dale Carnegie speaking courses: https://www.dalecarnegie.com/en/presentation-skills-public-speaking-training • Bill Gates on X: https://x.com/billgates • Kathy Fish on LinkedIn: https://www.linkedin.com/in/kathy-fish-23b5777/ • Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello • Ultraspeaking: https://ultraspeaking.com/lenny/ • Rethinking the Extraverted Sales Ideal: The Ambivert Advantage: https://faculty.wharton.upenn.edu/wp-content/uploads/2013/06/Grant_PsychScience2013.pdf • Cutco: https://www.cutco.com/ • Tim Ferriss’s post about his new book: https://x.com/tferriss/status/1878936085033791817 •  Mihaly Csikszentmihalyi: https://en.wikipedia.org/wiki/Mihaly_Csikszentmihalyi • Naval on X: https://x.com/naval • On saying no: https://www.lennysnewsletter.com/p/how-to-say-no • Susan Cain—How to Overcome Fear and Embrace Creativity: https://tim.blog/2019/01/24/susan-cain/ • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Renee Wood on LinkedIn: https://www.linkedin.com/in/recoale/ • The Sopranos on Max: https://play.max.com/show/818c3d9d-1831-48a6-9583-0364a7f98453 • The Talented Mr. Ripley on Prime Video: https://www.primevideo.com/detail/The-Talented-Mr-Ripley/0HA0GNFQ4ZXYPDNJHQEENK2Q6Q • Tugboat Institute: https://www.tugboatinstitute.com/ • Leonard Cohen quote: https://www.goodreads.com/quotes/4484-there-is-a-crack-in-everything-that-s-how-the-light — Recommended books: • Quiet: The Power of Introverts in a World That Can’t Stop Talking: https://www.amazon.com/Quiet-Power-Introverts-World-Talking/dp/0307352153 • Creativity: Flow and the Psychology of Discovery and Invention: https://www.amazon.com/Creativity-Flow-Psychology-Discovery-Invention/dp/0062283251 • Quiet Power: The Secret Strengths of Introverted Kids: https://www.amazon.com/Quiet-Power-Secret-Strengths-Introverted/dp/0147509920 • Gandhi: An Autobiography—The Story of My Experiments with Truth: https://www.amazon.com/Gandhi-Autobiography-Story-Experiments-Truth/dp/0807059099 • Flow: The Psychology of Optimal Experience: https://www.amazon.com/Flow-Psychology-Experience-Perennial-Classics/dp/0061339202 • The Power of Myth: https://www.amazon.com/Power-Myth-Joseph-Campbell/dp/0385418868/ • Bittersweet: How Sorrow and Longing Make Us Whole: https://www.amazon.com/Bittersweet-Oprahs-Book-Club-Longing/dp/0451499794 • Good Energy: The Surprising Connection Between Metabolism and Limitless Health: https://www.amazon.com/Good-Energy-Surprising-Connection-Metabolism/dp/0593712641 • The 5 Types of Wealth: A Transformative Guide to Design Your Dream Life: https://www.amazon.com/Types-Wealth-Transformative-Guide-Design/dp/059372318X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Eric Simons is the founder and CEO of StackBlitz, the company behind Bolt—the #1 web-based AI coding agent and one of the fastest-growing products in history. After nearly shutting down, StackBlitz launched Bolt on Twitter and exploded from zero to $40 million ARR and 1 million monthly active users in about five months. What you’ll learn: 1. How Bolt reached nearly $40M ARR and 3 million registered users in just five months with a team of only 15 to 20 people 2. How Bolt leverages WebContainer technology—a browser-based operating system developed over seven years—to create a dramatically faster, more reliable AI coding experience than competitors 3. Why Anthropic’s 3.5 Sonnet model was the critical breakthrough that made AI-generated code production-ready and unlocked the entire text-to-app market 4. Why PMs may be better positioned than engineers in the AI era 5. How AI will dramatically reshape company org charts 6. Eric’s wild founder story (including squatting at AOL’s HQ) and how scrappiness fueled his innovation — Brought to you by: • Eppo—Run reliable, impactful experiments • Fundrise Flagship Fund—Invest in $1.1 billion of real estate • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/inside-bolt-eric-simons — Where to find Eric Simons: • X: https://x.com/ericsimons40 • LinkedIn: https://www.linkedin.com/in/eric-simons-a464a664/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Eric Simons and StackBlitz (04:46) Unprecedented growth and user adoption (10:40) Demo: Building a Spotify clone with Bolt (15:28) Expanding to native mobile apps with Expo (19:09) The journey and technology behind WebContainer (25:03) Lessons learned and future outlook (29:15) Post-launch analysis (34:15) Growing fast with a small team (41:00) Prioritization at Bolt (45:51) Tooling and PRD's (48:42) Integration and use cases of Bolt (52:24) Limitations of Bolt (54:24) The role of PMs and developers in the AI era (59:56) Skills for the future (01:14:18) Upcoming features of Bolt (01:20:17) How to get the most out of Bolt (01:23:00) Eric’s journey and final thoughts — Referenced: • Bolt: https://bolt.new/ • Cursor: https://www.cursor.com/ • Wix: https://www.wix.com/ • Squarespace: https://www.squarespace.com/ • Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/ • Evan Wallace’s website: https://madebyevan.com/ • WebGL: https://en.wikipedia.org/wiki/WebGL • WebAssembly: https://webassembly.org/ • CloudNine: https://cloudnine.com/ • Canva: https://www.canva.com/ • StackBlitz: https://stackblitz.com/ • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups • Y Combinator: https://www.ycombinator.com/ • Anthropic: https://www.anthropic.com/ • Dario Amodei on LinkedIn: https://www.linkedin.com/in/dario-amodei-3934934/ • Linear: https://linear.app/ • Notion: https://www.notion.com/ • Salesforce: https://www.salesforce.com/ • Atlassian: https://www.atlassian.com/ • Photoshop: https://www.adobe.com/products/photoshop/ • Figma: https://www.figma.com/ • Greenfield projects: https://en.wikipedia.org/wiki/Greenfield_project • Gartner: https://www.gartner.com/ • OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic): https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen • Albert Pai on LinkedIn: https://www.linkedin.com/in/albertpai/ • Bolt’s post on X about “Bolt Builders”: https://x.com/boltdotnew/status/1887546089294995943 • Sonnet: https://www.anthropic.com/claude/sonnet • ChatGPT: https://chatgpt.com/ • Breaking the Rules: The Young Entrepreneur Who Squatted at AOL: https://www.inc.com/john-mcdermott/eric-simons-interview-young-entrepreneur-squatted-at-aol.html • Imagine K12: http://www.imaginek12.com/ • Geoff Ralston on LinkedIn: https://www.linkedin.com/in/geoffralston/ • AOL: https://www.aol.com/ • Bolt on X: https://x.com/boltdotnew — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Anton Osika is the co-founder and CEO of Lovable, which is building what they call “the last piece of software”—an AI-powered tool that turns descriptions into working products without requiring any coding knowledge. Since launching three months ago, Lovable hit $4 million ARR in the first four weeks and $10 million ARR in two months with a team of just 15 people, making it Europe’s fastest-growing startup ever. — What you’ll learn: 1. Why you need to be in the top 1% of AI tool users 2. Watch Lovable build a functional Airbnb clone in 30 seconds—complete with working features and modern design 3. The unconventional hiring approach that helped build a 15-person team capable of extraordinary execution 4. How traditional product development will look with AI 5. What skills will matter most to product teams going forward 6. How Anton’s team discovered a breakthrough in AI “unsticking itself” — Brought to you by: • Sinch—Build messaging, email, and calling into your product • Persona—A global leader in digital identity verification • Fundrise Flagship Fund—Invest in $1.1 billion of real estate — Find the transcript at: https://www.lennysnewsletter.com/p/building-lovable-anton-osika — Where to find Anton Osika: • X: https://x.com/antonosika • LinkedIn: https://www.linkedin.com/in/antonosika/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Anton and Lovable (05:12) Lovable’s rapid growth (09:39) Live demo: Building an Airbnb clone (18:34) Tips for mastering Lovable (21:42) The origin story (26:50) Scaling laws and getting AI unstuck (33:20) Reliability and unique features (36:25) The vision and future of Lovable (38:14) Skills and job market evolution in the age of AI (40:30) Hiring philosophy and team dynamics (46:21) Building in Europe (48:02) Prioritization and product roadmap (51:38) Tools and work environment (53:17) Tactics for moving fast (54:37) Advice for building product teams (57:11) Empowering non-technical founders (58:31) Future developments and user support (01:01:23) Failure corner (01:05:20) Final thoughts and advice — Referenced: • Lovable: https://lovable.dev/ • Lovable Launched: https://launched.lovable.app/ • Cloudflare: https://www.cloudflare.com/ • Supabase: https://supabase.com/ • GPT engineer: https://github.com/gpt-engineer-org/gptengineer.app • Microsoft Copilot: https://copilot.microsoft.com/chats/cmFw8dTsGU8D6b9siqQ6U • Fabian Hedin on LinkedIn: https://www.linkedin.com/in/fabian-hedin-2377b0144/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • Replit: https://replit.com/ • Cursor: https://www.cursor.com • Bolt: https://bolt.new/ • GitHub: https://github.com/ • Lane Shackleton on LinkedIn: https://www.linkedin.com/in/laneshackleton/ • FigJam: https://www.figma.com/figjam/ • Linear: https://linear.app/ • Sana Labs: https://sanalabs.com/ • Duolingo: https://www.duolingo.com/ • Claude: https://claude.ai/ • ChatGPT: https://chatgpt.com/ • Lovable on X: https://x.com/Lovable_dev — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ivan Zhao is the co-founder and CEO of Notion. Ivan shares the untold story of Notion, from nearly running out of database space during Covid to finding product-market fit after several “lost years,” and the hard-won lessons along the way. — What you’ll learn: 1. Why you sometimes need to “hide your vision” behind something people actually want—what Ivan calls “sugar-coating the broccoli” 2. How Ivan and his co-founder persevered through multiple product resets and complete code rewrites 3. Why Notion prioritized systems over headcount, keeping the team small and focused even at scale 4. Why Ivan believes in craft and values as the foundation for product development, balancing technical excellence with aesthetic sensibility 5. The surprising story of how Notion nearly collapsed during Covid when their single database almost ran out of space with only weeks to spare 6. Community-led growth tactics 7. Ivan’s unique journey from a small town in China 8. Much more — Brought to you by: • Eppo—Run reliable, impactful experiments • Airtable ProductCentral—Launch to new heights with a unified system for product development • Sinch—Build messaging, email, and calling into your product — Find the transcript at: https://www.lennysnewsletter.com/p/inside-notion-ivan-zhao — Where to find Ivan Zhao: • X: https://x.com/ivanhzhao • LinkedIn: https://www.linkedin.com/in/ivanhzhao/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Ivan Zhao (04:41) Ivan’s early life and education (07:46) Discovering the vision for Notion (10:49) The lost years of Notion (13:56) Rebuilding and perseverance (17:14) Layoffs and company morale (18:53) Advice for startup founders (25:08) Product-market fit (29:56) Staying lean and efficient (34:27) Creating a unique office culture (37:20) Craft and values: the foundation of Notion’s philosophy (38:44) Navigating tradeoffs in product and business building (41:24) Leadership and personal growth (49:11) Challenges and crises: lessons from Notion’s journey (51:08) Building horizontal software: joys and pains (01:02:40) Philosophy of tools and human potential (01:06:17) Lightning round and final thoughts — Referenced: • Ürümqi: https://en.wikipedia.org/wiki/%C3%9Cr%C3%BCmqi • Notion: https://www.notion.com/ • SpongeBob SquarePants: https://en.wikipedia.org/wiki/SpongeBob_SquarePants • Augmenting Human Intellect: https://web.stanford.edu/class/history34q/readings/Engelbart/Engelbart_AugmentIntellect.html • Alan Kay: https://en.wikipedia.org/wiki/Alan_Kay • Ted Nelson: https://en.wikipedia.org/wiki/Ted_Nelson • Steve Jobs on Why Computers Are Like a Bicycle for the Mind (1990): https://www.themarginalian.org/2011/12/21/steve-jobs-bicycle-for-the-mind-1990/ • Xerox Alto: https://en.wikipedia.org/wiki/Xerox_Alto • React: https://react.dev/ • Simon Last on LinkedIn: https://www.linkedin.com/in/simon-last-41404140/ • Magna-Tiles: https://www.magnatiles.com/ • Design on a deadline: How Notion pulled itself back from the brink of failure: https://www.figma.com/blog/design-on-a-deadline-how-notion-pulled-itself-back-from-the-brink-of-failure/ • Bryan Johnson on X: https://x.com/bryan_johnson • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Smalltalk: https://en.wikipedia.org/wiki/Smalltalk#: • Lisp: https://en.wikipedia.org/wiki/Lisp_(programming_language) • DeepSeek: https://www.deepseek.com/ • Shana Fisher: https://www.crunchbase.com/person/shana-fisher • LAMY 2000 fountain pens: https://www.jetpens.com/LAMY-2000-Fountain-Pens/ • Macintosh 128K: https://en.wikipedia.org/wiki/Macintosh_128K • Toshiba rice cooker: https://www.toshiba-lifestyle.com/us/cooking-appliances/rice-cooker • Transistor radio: https://en.wikipedia.org/wiki/Transistor_radio • Jira: https://www.atlassian.com/software/jira • Salesforce: https://www.salesforce.com/ • HubSpot: https://www.hubspot.com/ • Zendesk: https://www.zendesk.com/ • Misattributed McLuhan quote: https://mcluhangalaxy.wordpress.com/2013/04/01/we-shape-our-tools-and-thereafter-our-tools-shape-us/ • Phin Barnes on LinkedIn: https://www.linkedin.com/in/phineasbarnes/ • Hacker News: https://news.ycombinator.com/ • Pablo Picasso quote: https://www.goodreads.com/quotes/629531-good-artists-copy-great-artists-steal#:~ • Connections with James Burke on Prime Video: https://www.amazon.com/gp/video/detail/amzn1.dv.gti.484e32c5-60bd-4493-a800-e44fd0940312 • The Enneagram Institute: https://www.enneagraminstitute.com/ — Recommended book: • The Romance of the Three Kingdoms: https://www.amazon.com/Romance-Three-Kingdoms-Luo-Guanzhong/dp/024133277X — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matt Mullenweg is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with over 1,700 employees across 90 countries. In this episode, he discusses some of the most controversial topics surrounding WordPress, Automattic, and the broader open source community. — What you’ll learn: • Matt’s response to public criticism • Why products like Meta’s Llama are “fake open source” • How his team is turning around Tumblr after acquiring it for just $3 million (after Yahoo bought it for $1.1 billion) • Why he mortgaged his home to fund San Francisco’s iconic Bay Lights project • Matt’s philosophy: “Don’t just build a product; build a movement” • Why open source matters: “If the Founding Fathers were around today, they’d be open source advocates” — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security. • Loom—The easiest screen recorder you’ll ever use — Find the transcript at: https://www.lennysnewsletter.com/p/the-creator-of-wordpress-opens-up-matt-mullenweg — Where to find Matt Mullenweg: • X: https://x.com/photomatt • LinkedIn: https://www.linkedin.com/in/mattm/ • Instagram: https://www.instagram.com/photomatt/ • Website: https://ma.tt/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Matt Mullenweg (05:10) Matt’s career journey (11:15) Bay Lights project and philanthropy (17:28) How Matt got involved with open source (23:25) Why products like Meta’s Llama are “fake open source” (27:14) The future of open source and how to get involved (35:25) Building a successful online community (39:12) The WP Engine controversy (50:24) Facing criticism and controversy (55:29) Addressing community concerns (01:08:29) Forking Advanced Custom Fields (01:11:15) The role of social media and public perception (01:16:43) Acquiring and reviving Tumblr (01:24:25) Automattic’s acquisition strategy (01:28:51) Final thoughts and future plans — Referenced: • WordPress: https://wordpress.com/ • Automattic: https://automattic.com/ • CNET: https://www.cnet.com/ • Akismet: https://akismet.com/wordpress/ • Jetpack: https://jetpack.com/ • Toni Schneider on LinkedIn: https://www.linkedin.com/in/tonischneider/ • WooCommerce: https://woocommerce.com/ • Beeper: https://www.beeper.com/ • Day One: https://dayoneapp.com/ • Simplenote: https://simplenote.com/ • Pocket Casts: https://pocketcasts.com/ • Creative Commons: https://creativecommons.org/ • Audrey Capital: https://audrey.co/ • Stripe: https://stripe.com/ • SpaceX: https://www.spacex.com/ • Calm: https://www.calm.com/ • August: https://august.com/ • Daylight Computer: https://daylightcomputer.com/ • Keys Jazz Bistro: https://keysjazzbistro.com/ • Joomla: https://www.joomla.org/ • Drupal: https://new.drupal.org/ • Shopify: https://www.shopify.com/ • Wix: https://www.wix.com/ • Squarespace: https://www.squarespace.com/ • Tumblr: https://www.tumblr.com/ • Gravatar: https://gravatar.com/ • The Bay Lights: https://illuminate.org/projects/thebaylights/ • The Bay Lights 360: https://illuminate.org/the-bay-lights-360/ • Ben Davis on LinkedIn: https://www.linkedin.com/in/ben-davis-sf/ • Kinder High School for the Performing and Visual Arts: https://www.houstonisd.org/hspva • Jack Dorsey: We’re Losing our Free Will to Algorithms: https://www.youtube.com/watch?v=9_8NganZSFI • Marc Andreessen: https://a16z.com/author/marc-andreessen/ • Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/ • An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead): https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet • Llama: https://www.llama.com/ • WordCamp US & Ecosystem Thinking: https://ma.tt/2024/09/ecosystem-thinking/ • As Wall Street Chases Profits, Fire Departments Have Paid the Price: https://www.nytimes.com/2025/02/17/us/fire-engines-shortage-private-equity.html • WordCamp Asia: https://asia.wordcamp.org/2025/ • Justin Baldoni Hit with Defamation Suit as PR Teams Turn on Each Other over Blake Lively’s ‘It Ends with Us’ Smear Campaign Allegations: https://deadline.com/2024/12/justin-baldoni-defamation-lawsuit-publicist-blake-lively-1236241784/ • How WordPress Hot Nacho Scandal Shapes WP Engine Dispute: https://www.searchenginejournal.com/how-wordpress-hot-nacho-scandal-shapes-wp-engine-dispute/539069/ • Gutenberg: https://wordpress.org/gutenberg/ • ClassicPress: https://www.classicpress.net/ • Behind the founder: Marc Benioff: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff • Mary Hubbard on LinkedIn: https://www.linkedin.com/in/maryfhubbard/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Founder mode: https://paulgraham.com/foundermode.html • Cow.com: https://www.cow.com/ • David Karp on X: https://x.com/davidkarp • Marissa Mayer on LinkedIn: https://www.linkedin.com/in/marissamayer/ • Alibaba: https://www.alibaba.com/ • WP Engine Tracker: https://wordpressenginetracker.com/ • Kumbh Mela: https://en.wikipedia.org/wiki/Kumbh_Mela — Recommended book: • Maintenance: Of Everything (in progress): https://books.worksinprogress.co/book/maintenance-of-everything/addenda/page/introduction — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Keith Coleman (VP of product) and Jay Baxter (founding ML engineer), the minds behind Community Notes, reveal how a small, scrappy team inside Twitter/X built the most trusted crowdsourced information system on the internet—one that’s changing the way we understand truth online. What you’ll learn: 1. How Community Notes actually works—a deep dive into the groundbreaking algorithm that rewards “bridging agreement” instead of majority rule 2. The seemingly crazy yet brilliant way this idea survived multiple CEO changes—from Jack to Parag to Elon 3. How this project started with a dumpster fire GIF (literally)—the untold backstory of its early launch 4. The secret to running ultra-fast, high-impact product teams—no OKRs, no Jira; just one Google Doc 5. What Meta’s adoption of Community Notes means for the future of online (mis)information—why this open source system is becoming the industry standard — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Productboard—Make products that matter • Wix Studio—The web creation platform built for agencies — Find the transcript at: https://www.lennysnewsletter.com/p/how-x-built-the-best-fact-checking-system-on-the-internet — Where to find Keith Coleman: • X: https://x.com/kcoleman • LinkedIn: https://www.linkedin.com/in/keith-coleman-19b12b46/ — Where to find Jay Baxter: • X: https://x.com/_jaybaxter_ • LinkedIn: https://www.linkedin.com/in/jaybaxter/ • Website: http://jaybaxter.net/ — In this episode, we cover: (00:00) Introduction to Community Notes (06:56) How the “bridging-based” algorithm works (13:33) The impact and scale of Community Notes (17:24) Understanding the note publishing threshold (21:32) Challenges and philosophies (26:26) The effect of notes on re-sharing content (29:41) Origin story (35:46) Embracing small teams for big impact (40:23) The thermal project approach (47:47) Algorithm development and internal competitions (50:34) An inside look at how the team operates (58:56) Working with Elon (01:05:30) Launching Birdwatch (01:10:48) The core principles behind Community Notes (01:26:15) Anonymity and pseudonymity in contributions (01:32:17) Sustaining the project through leadership changes (01:37:57) Future directions for Community Notes (01:42:12) Final thoughts and optimism for the future — Referenced: • Community Notes on X: https://x.com/CommunityNotes • Sign up to be a Community Notes contributor: https://communitynotes.x.com/guide/en/contributing/signing-up • The Making of Community Notes: https://asteriskmag.com/issues/08/the-making-of-community-notes • “Readers added a Community Note to this Tweet”: https://x.com/HelpfulNotes/status/1718103364792205704 • Note-ranking algorithm: https://communitynotes.x.com/guide/en/under-the-hood/ranking-notes#matrix-factorization • Study: Community Notes on X could be key to curbing misinformation: https://giesbusiness.illinois.edu/news/2024/11/18/study--community-notes-on-x-could-be-key-to-curbing-misinformation • Study Finds X’s (Formerly Twitter’s) Community Notes Provide Accurate, Credible Answers to Vaccine Misinformation: https://qi.ucsd.edu/study-finds-xs-formerly-twitters-community-notes-provide-accurate-credible-answers-to-vaccine-misinformation/ • Did the Roll-Out of Community Notes Reduce Engagement with Misinformation on X/Twitter?: https://dl.acm.org/doi/10.1145/3686967 • Kayvon Beykpour on LinkedIn: https://www.linkedin.com/in/kayvz/ • Jack Dorsey on X: https://x.com/jack • “Birdwatch gives me the creeps” tweet: https://x.com/elonmusk/status/1589454464611540992 • Blake Scholl on LinkedIn: https://www.linkedin.com/in/blakescholl/ • Creating Truthtelling Incentives with the Bayesian Truth Serum: https://www.eecs.harvard.edu/cs286r/courses/fall12/papers/DW08.pdf • Asana: https://asana.com/ • Spaces: https://blog.x.com/en_us/topics/product/2021/spaces-is-here • Amazon MTurk: https://www.mturk.com/ • Community notes on GitHub: https://github.com/twitter/communitynotes • What do I think about Community Notes?: https://vitalik.eth.limo/general/2023/08/16/communitynotes.html • X’s community-led approach: tackling inaccurate and misleading information: https://blog.x.com/en_us/topics/company/2023/xs-community-led-approach-tackling-inaccurate-and-misleading-information • Linda Yaccarino on LinkedIn: https://www.linkedin.com/in/lindayaccarino/ • Messi-Ronaldo rivalry: https://en.wikipedia.org/wiki/Messi%E2%80%93Ronaldo_rivalry • Supernotes paper: https://arxiv.org/pdf/2411.06116v1 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Bob Moesta, co-creator of the Jobs to Be Done framework, recently published a new book, Job Moves. Drawing from interviews with over 1,000 people about their career transitions, it offers a practical playbook for career development. In our conversation, we discuss: • The four different “quests” that drive career changes • Why job features (salary, title) matter less than experiences • How to identify what gives you energy vs. drains you • The power of taking a “jobcation” • A template for crafting your career story • Tips for hiring and retaining great talent • The importance of prototyping potential careers • Much more — Brought to you by: • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-work-you-love-bob-moesta — Where to find Bob Moesta: • X: https://x.com/bmoesta • LinkedIn: https://www.linkedin.com/in/bobmoesta/ • Website: https://www.jobmoves.com/ • Podcast: https://pca.st/gg6goo1n • The Re-Wired Group: https://therewiredgroup.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Bob's background (05:10) Bob’s new book, Job Moves (09:31) Job features vs. job experiences (11:16) Four reasons people leave jobs (17:20) Energy drivers and energy drains (31:05) Prototyping your next job (34:32) Pushes and pulls (40:01) Understanding that no job is perfect (43:18) Taking a jobcation (51:22) Finding the right next step (55:18) Navigating job applications and interviews (58:28) How to craft your career story (01:04:04) Strengths and weaknesses: leveraging your superpowers (01:06:21) Hiring and writing job descriptions (01:11:20) Self-awareness and founding a startup (01:21:24) Conclusion and final thoughts — Referenced: • The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-jtbd-bob-moesta • Ethan S. Bernstein on LinkedIn: https://www.linkedin.com/in/ethanbernstein/ • National Geographic: https://www.nationalgeographic.com/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career • The Story Spine (also known as Pixar’s Story Structure): https://www.storyprompt.com/blog/the-story-spine-also-known-as-pixars-story-structure • Tobi Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke • Job Moves resources: https://www.jobmoves.com/resources • Why Employees Quit: https://hbr.org/2024/11/why-employees-quit — Recommended book: • Job Moves: 9 Steps for Making Progress in Your Career: https://www.amazon.com/Job-Moves-Making-Progress-Career/dp/0063283581 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover: • The two types of startup crisis and how to handle them • Why speed of action is the most important thing • How to keep your team motivated when things look dire • A framework for deciding whether or not to pivot • What to do when product-market fit disappears • How to approach raising money during a crisis • More — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Rippling—Automate HR, IT, and finance so you can scale faster • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/a-founders-guide-to-crisis-management-uri-levine — Where to find Uri Levine: • X: https://twitter.com/urilevine1 • LinkedIn: https://www.linkedin.com/in/uri-levine • Website: https://urilevine.com • Book: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637746601/ref=tmm_pap_swatch_0?_encoding=UTF8&qid=&sr= — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Uri! (05:10) The new chapter: navigating crises (08:15) Types of crises founders face (29:10) Navigating cash crises (38:31) The importance of never giving up (46:26) How to keep people engaged through a crises (47:59) Transparency in crisis management (56:58) Navigating product-market-fit challenges (59:27) Deciding when to pivot or shut down (01:13:34) Real-life startup survival stories (01:17:06) Avoiding and preparing for crises (01:21:21) Final thoughts and book promotion — Referenced: • Waze: https://www.waze.com/ • Moovit: https://en.wikipedia.org/wiki/Moovit • Order Chat: https://www.crunchbase.com/organization/order-chat • Fibo: https://finder.startupnationcentral.org/company_page/fibo • Behind the founder: Drew Houston (Dropbox): https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox • TomTom: https://www.tomtom.com/ • Khosla Ventures: https://www.khoslaventures.com/ • WeSki: https://www.weski.com/ • Larry Silverstein: https://en.wikipedia.org/wiki/Larry_Silverstein • Oversee: https://oversee.biz/ • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups • Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify): https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook • Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/ • Zip: https://zip.co/us • Qualcomm: https://www.qualcomm.com/ • Einstein quote: https://www.brainyquote.com/quotes/albert_einstein_148788 — Recommended book: • Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs (updated 2025 version): https://urilevine.com/book/#Pre-order — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspective on the cutting edge of AI and large language models. In our conversation, we discuss: • How OpenAI builds product • What people misunderstand about AI model training • Differences between how OpenAI and Anthropic operate • The role of synthetic data in model development • How to build trust between users and AI models • Why she moved from engineering to research • Much more — Brought to you by: • Enterpret—Transform customer feedback into product growth • Vanta—Automate compliance. Simplify security • Loom—The easiest screen recorder you’ll ever use — Find the transcript at: https://www.lennysnewsletter.com/p/why-soft-skills-are-the-future-of-work-karina-nguyen — Where to find Karina Nguyen: • X: https://x.com/karinanguyen_ • LinkedIn: https://www.linkedin.com/in/karinanguyen28 • Website: https://karinanguyen.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Karina Nguyen (04:42) Challenges in model training (08:21) Synthetic data and its importance (12:38) Creating Canvas (18:33) Day-to-day operations at OpenAI (20:28) Writing evaluations (23:22) Prototyping and product development (26:57) Building Canvas and Tasks (33:34) Understanding the job of a researcher (35:36) The future of AI and its impact on work and education (42:15) Soft skills in the age of AI (47:50) AI’s role in creativity and strategy development (53:34) Comparing Anthropic and OpenAI (57:11) Innovations and future visions (01:07:13) The potential of AI agents (01:11:36) Final thoughts and career advice — Referenced: • What’s in your stack: The state of tech tools in 2025: https://www.lennysnewsletter.com/p/whats-in-your-stack-the-state-of • Anthropic: https://www.anthropic.com/ • OpenAI: https://openai.com/ • What is synthetic data—and how can it help you competitively?: https://mitsloan.mit.edu/ideas-made-to-matter/what-synthetic-data-and-how-can-it-help-you-competitively • GPQA: https://datatunnel.io/glossary/gpqa/ • Canvas: https://openai.com/index/introducing-canvas/ • Barret Zoph on LinkedIn: https://www.linkedin.com/in/barret-zoph-65990543/ • Mira Murati on LinkedIn: https://www.linkedin.com/in/mira-murati-4b39a066/ • JSON Schema: https://json-schema.org/ • Anthropic—100K Context Windows: https://www.anthropic.com/news/100k-context-windows • Claude 3 Haiku: https://www.anthropic.com/news/claude-3-haiku • A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html • Cursor: https://www.cursor.com/ • How AI will impact product management: https://www.lennysnewsletter.com/p/how-ai-will-impact-product-management • Lee Byron on LinkedIn: https://www.linkedin.com/in/lee-byron/ • GraphQL: https://graphql.org/ • Claude in Slack: https://www.anthropic.com/claude-in-slack • Sam Altman on X: https://x.com/sama • Jakub Pachocki on LinkedIn: https://www.linkedin.com/in/jakub-pachocki/ • Lennybot: https://www.lennybot.com/ • ElevenLabs: https://elevenlabs.io/ • Westworld on Prime Video: https://www.amazon.com/Westworld-Season-1/dp/B01N05UD06 • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k • Tuple: https://tuple.app/ • How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss: • Why complexity kills entrepreneurship • How to develop and leverage your unique talent stack • How specifically Tobi approaches thinking from first principles • The importance of focusing on unquantifiable qualities like joy and delight • Why Tobi works backward from a 100-year vision • Why metrics should support decisions, not make them • The power of following your curiosity • What Tobi believes it takes to be a great product leader • Much more — Brought to you by: • Sinch—Build messaging, email, and calling into your product • Liveblocks—Ready-made collaborative features to drop into your product • Loom—The easiest screen recorder you’ll ever use — Find the transcript at: https://www.lennysnewsletter.com/p/tobi-lutkes-leadership-playbook — Where to find Tobi Lütke: • X: https://x.com/tobi • LinkedIn: https://www.linkedin.com/in/tobiaslutke/ • Website: https://tobi.lutke.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome and introduction (04:17) The Tobi tornado (07:10) Maximizing human potential (11:05) Education and personal growth (16:47) Operating without KPIs (25:00) First-principles thinking (40:04) Remote work (45:59) Why Tobi never stopped coding (54:46) Embracing disagreement (01:01:27) The 100-year vision (01:09:29) Balancing tactics and positioning (01:17:15) Encouraging entrepreneurship (01:19:34) The power of good UX (01:28:42) The talent stack and unique opportunities (01:34:30) The role of passion in product development (01:36:39) Final thoughts and farewell — Referenced: • How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawar • Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams • The ultimate guide to performance marketing | Timothy Davis (Shopify): https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis • Brandon Chu on building product at Shopify, how writing changed the trajectory of his career, the habits that make you a great PM, pros and cons of being a platform PM, how Shopify got through Covid: https://www.lennysnewsletter.com/p/brandon-chu-on-what-its-like-to-build • IRC: https://en.wikipedia.org/wiki/IRC • Goodhart’s law: https://en.wikipedia.org/wiki/Goodhart%27s_law • Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates/ • How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product • The Last Dance on Netflix: https://www.netflix.com/title/80203144 • Autoregressive Models for Natural Language Processing: https://medium.com/@zaiinn440/autoregressive-models-for-natural-language-processing-b95e5f933e1f • Archimedean property: https://en.wikipedia.org/wiki/Archimedean_property • Tabula rasa: https://en.wikipedia.org/wiki/Tabula_rasa • Daniel Weinand on LinkedIn: https://www.linkedin.com/in/danielweinand/ • World of Warcraft: https://worldofwarcraft.blizzard.com • Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf/ • Monorepo: https://en.wikipedia.org/wiki/Monorepo • The Sarbanes Oxley Act: https://sarbanes-oxley-act.com/ • Shopify builds Shopify Balance with Stripe to give small businesses an easier way to manage money: https://stripe.com/customers/shopify • Stanford marshmallow experiment: https://en.wikipedia.org/wiki/Stanford_marshmallow_experiment • Brian Armstrong on LinkedIn: https://www.linkedin.com/in/barmstrong/ • We are the Web: https://link.wired.com/public/32945405 — Recommended books: • Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713 • The Infinite Game: https://www.amazon.com/Infinite-Game-Simon-Sinek/dp/073521350X/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss: • Why speed and quality aren’t actually at odds • Linear’s unique approach to product development • Nan’s systematic approach to creativity • Linear’s philosophy on deadlines • The “double triangle” framework for product management • Nan’s approach to landing his dream product roles • Much more — Brought to you by: • Sinch—Build messaging, email, and calling into your product • Paragon—Ship every SaaS integration your customers want • Wix Studio—The web creation platform built for agencies — Find the transcript at: https://www.lennysnewsletter.com/p/linears-secret-to-building-beloved-b2b-products-nan-yu — Where to find Nan Yu: • X: https://x.com/thenanyu • LinkedIn: https://www.linkedin.com/in/thenanyu/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Nan Yu and Linear (04:54) Survey insights: Linear vs. Jira (07:51) The speed vs. quality myth (09:24) Building and iterating quickly (15:31) Avoiding bloat in enterprise software (23:57) Understanding user needs deeply (30:09) How to approach customer calls (34:10) Creating strong emotional hooks (40:31) Managing the product backlog (44:46) Systemizing creativity (48:16) Demo: Saving drafts in Linear (51:38) Breaking constraints and building at extremes (54:15) Adopting new tools (58:22) The “double triangle” framework for product management (01:04:23) Effective job-hunting strategies for PMs (01:09:15) Thoughts on deadlines (01:14:15) Lightning round — Referenced: • Jira: https://www.atlassian.com/software/jira • Linear: https://linear.app/ • Patrick Collison’s post on X: https://x.com/patrickc/status/1869422495985750459 • Magnus Carlsen on X: https://x.com/magnuscarlsen • Hikaru Nakamura on X: https://x.com/gmhikaru • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead • Customer Request feature on Linear: https://linear.app/customer-requests • Everlane: https://www.everlane.com/ • Schlep Blindness: https://paulgraham.com/schlep.html • Linear’s triage tool: https://linear.app/docs/triage • Patrick Collison’s post about mental models on X: https://x.com/patrickc/status/1443215022029619200 • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of • Mode: https://mode.com/ • The Diplomat on Netflix: https://www.netflix.com/title/81288983 • Sakura Micron pens: https://www.amazon.com/SAKURA-PIGMA-MICRON-ESSENTIAL-COLORS/dp/B07VJFXT3C/ — Recommended books: • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • The Design of Everyday Things: https://www.amazon.com/Design-Everyday-Things-Revised-Expanded/dp/0465050654/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares: • His playbook for developing a product strategy • The difference between “small s” and “big S” strategy • How to run strategy sprints • Who should be involved in strategy work • Common pitfalls in strategy development • The role of AI in future strategy development • More — Brought to you by: • Eppo—Run reliable, impactful experiments • Airtable ProductCentral—Launch to new heights with a unified system for product development • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/an-operators-guide-to-product-strategy-chandra-janakiraman — Where to find Chandra Janakiraman: • LinkedIn: https://www.linkedin.com/in/chandramohanj/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Chandra’s background (04:47) The importance of strategy (12:40) Defining product strategy (15:42) Developing a winning strategy: an overview (18:51) The preparation phase (30:46) The strategy sprint process (45:51) The design sprint (51:19) Document writing (57:39) Rolling out your strategy (01:01:28) Resourcing and roadmapping (01:04:42) Strategy lessons from Zynga (01:11:34) Strategy lessons from Meta (01:15:55) Big S strategy (01:26:58) AI in strategy formulation (01:38:12) Final thoughts and lightning round — Referenced: • Headspace: https://www.headspace.com/ • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin • VRChat: https://hello.vrchat.com/ • Andrew Chen on LinkedIn: https://www.linkedin.com/in/pmandrewchen/ • Template: Working Backwards PR FAQ: https://www.workingbackwards.com/resources/working-backwards-pr-faq • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen • Making time for what matters | Jake Knapp and John Zeratsky (authors of Sprint and Make Time, co-founders of Character Capital): https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake • Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures): https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis • Chandra’s flow chart: https://docs.google.com/document/d/1SLmQ0oRFadzJnNM3MJetnLUvB18U4W4GXU4KtJ2ujEQ/edit?tab=t.0 • Chandra’s strategy template: https://docs.google.com/document/d/1iNeYUaMnpicvkpVZO-gj9cCxLeHfWN0xtGm_QoxgemE/edit?tab=t.0#heading=h.5d3jz6v86yrs • Zynga: https://www.zynga.com/ • David Foster Wallace’s quote about water: https://www.goodreads.com/quotes/97082-there-are-these-two-young-fish-swimming-along-and-they • Oculus: https://en.wikipedia.org/wiki/Oculus • Elon Musk’s quote: https://www.youtube.com/shorts/wf8TadbGYok • Concept car: https://en.wikipedia.org/wiki/Concept_car • Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview • Armand Ruiz on LinkedIn: https://www.linkedin.com/in/armand-ruiz/ • What is a multi-armed bandit? Full explanation: https://amplitude.com/explore/experiment/multi-armed-bandit • IF on Prime Video: https://www.amazon.com/IF-John-Krasinski/dp/B0CW19SCVW • Dune: Part 2 on AppleTV+: https://tv.apple.com/us/movie/dune-part-two/umc.cmc.363aycnv6vy9qgekvew6fveb9 • Dune Prophecy on Max: https://www.max.com/shows/dune-prophecy-2024/57660b16-a32a-476f-89da-3302ac379e91 • Capybara Go on the App Store: https://apps.apple.com/ph/app/capybara-go/id6596787726 • Bluesky: https://bsky.app/ • Steve Jobs: The Lost Interview on Prime Video: https://www.amazon.com/Steve-Jobs-Lost-Interview/dp/B01IJD1BES — Recommended books: • The Art of War: https://www.amazon.com/Art-War-Sun-Tzu/dp/1599869772 • Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487/ • Good Strategy Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239/ • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422 • Sprint: https://www.amazon.com/SPRINT-Jake-Zeratsky-Knapp/dp/0593076117 • Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473 • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649/ • The Ten Faces of Innovation: Strategies for Heightening Creativity: https://www.amazon.com/dp/0385512074 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss: • 10 growth tactics that never work • Her 3 favorite growth frameworks • How to increase your career optionality — Brought to you by: • Sinch—Build messaging, email, and calling into your product • Vanta—Automate compliance. Simplify security • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/10-growth-tactics-that-never-work-elena-verna — Where to find Elena Verna: • Newsletter: https://www.elenaverna.com/ • X: https://x.com/elenaverna • LinkedIn: https://www.linkedin.com/in/elenaverna — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Welcome back, Elena! (06:02) Common mistakes growth teams make (08:31) #1: Hiring for growth roles too soon (15:09) #2: Hiring a head of growth to fix your problems (19:20) #3: Doing a rebrand to drive growth (25:11) #4: Obsessing over your competition (34:00) #5: Believing that your problems are unique (42:32) #6: Prioritizing other growth channels above earned channels (50:55) #7: Failing to evolve your growth model (01:01:06) #8: Not hiring advisors (01:05:55) #9: Over-experimenting (01:10:44) #10: Color optimizations, third-party signups, one-email wonders, and removing friction (01:15:00) Elena’s favorite growth frameworks (01:18:50) Contrarian corner: full-time jobs (01:26:05) Lightning round and final thoughts — Referenced: • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • Six rules of hiring for growth: https://www.lennysnewsletter.com/p/hiring-growth • Figma: https://www.figma.com/ • Miro: https://www.figma.com/ • Notion: https://www.figma.com/ • Carol Wong on LinkedIn: https://www.linkedin.com/in/carol-wong-14133927/ • Dropbox: https://www.dropbox.com/ • The Law of S****y Clickthroughs: https://andrewchen.com/the-law-of-s****y-clickthroughs/ • Miroverse: https://miro.com/miroverse/ • GitHub: https://github.com/ • My 9 Favorite Growth Frameworks: https://www.elenaverna.com/p/my-9-favorite-growth-frameworks • Growth Loops are the New Funnels: https://www.reforge.com/blog/growth-loops • Racecar Growth Framework: https://www.reforge.com/blog/racecar-growth-framework • The Adjacent User: https://andrewchen.com/the-adjacent-user-theory/ • Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YouTube, Instagram, Facebook, Instacart): https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba • Why I’m Unquitting Full-Time Roles: https://www.elenaverna.com/p/why-im-unquitting-full-time-roles • Noah Smith’s newsletter: https://www.noahpinion.blog/ • Beef on Netflix: https://www.netflix.com/title/81447461 • Veep on Max: https://www.max.com/shows/veep/37cb4217-c710-4166-8e9f-352a61f2cd3a • The Last of Us on Max: https://www.max.com/shows/last-of-us/93ba22b1-833e-47ba-ae94-8ee7b9eefa9a • Heated boots: https://www.amazon.com/heated-boots/s?k=heated+boots • Airpods Max: https://www.apple.com/airpods-max/ • Memes by Elena: https://www.elenaverna.com/p/ten-funniest-growth-memes — Recommended books: • Project Hail Mary: https://www.amazon.com/Project-Hail-Mary-Andy-Weir/dp/0593135229/ • The Martian: https://www.amazon.com/Martian-Andy-Weir/dp/0553418025 • We Are Legion (Bobiverse #1): https://www.amazon.com/We-Are-Legion-Bob-Bobiverse/dp/1680680587 • Fire Upon the Deep: https://www.amazon.com/Fire-Upon-Deep-Zones-Thought/dp/0812515285 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss: • Why everything worthwhile requires suffering • Why most people operate on autopilot, and how to break free • The “genie methodology” for discovering your true path • The Nine Lives exercise for exploring different life possibilities • How to overcome limiting beliefs that hold you back • Why “not now” is often just another way of saying “never” • More — Brought to you by: • Merge—A single API to add hundreds of integrations into your app • Persona—A global leader in digital identity verification • Liveblocks—Ready-made collaborative features to drop into your product — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver — Where to find Graham Weaver: • LinkedIn: https://www.linkedin.com/in/graham-weaver-2b79 • Instagram: https://www.instagram.com/grahamcweaver • YouTube: https://www.youtube.com/@grahamcweaver • Website: https://www.grahamweaver.com • TikTok: https://www.tiktok.com/@grahamcweaver — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Graham’s background (05:30) Helping students find their true path (07:40) The genie methodology (12:36) Breaking free from autopilot mode (17:54) Identifying and overcoming limiting beliefs (20:33) Teaching entrepreneurship and personal fulfillment (22:53) The reality of long-term success (35:14) The role of accountability and executive coaching (40:22) Daily goal setting for success (43:11) The Nine Lives framework (48:01) The dangers of the “not now” mentality (55:27) Navigating life’s transitions (57:19) Failure corner (01:00:24) When to quit and when to persevere (01:02:18) Final thoughts and lightning round — Referenced: • Setting Goals: Demystified: https://www.grahamweaver.com/blog/goals • Tony Robbins’s website: https://www.tonyrobbins.com • Alpine Investors: https://alpineinvestors.com • Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: https://www.grahamweaver.com/blog/stanford-graduate-business-school-last-lecture-2024 • I turned 50 today. Here is the most important thing I learned in my first half century: https://www.grahamweaver.com/blog/turning-50 • Where the Crawdads Sing on Prime Video: https://www.amazon.com/Where-Crawdads-Sing-Daisy-Edgar-Jones/dp/B0B5KBKDNL • Chilipad Cube Bed Cooling System: https://www.amazon.com/Chilipad-Cube-Bed-Cooling-System/dp/B07GT9MYRW • Sleepme OOLER Sleep System: https://www.amazon.com/OOLER-Sleep-System-Temperature-Integration/dp/B07RX8LT9G • Eightsleep: https://www.eightsleep.com • Howard Thurman’s quote: https://www.goodreads.com/quotes/6273-don-t-ask-what-the-world-needs-ask-what-makes-you — Recommended books: • Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752 • The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379 • Don’t Believe Everything You Think: Why Your Thinking Is the Beginning and End of Suffering: https://www.amazon.com/Dont-Believe-Everything-Think-Expanded/dp/B0D47VYQMY • How to Win Friends and Influence People: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss: • Key indicators that it’s time to hire PMs • How to build your early PM team • Why founders should initially take on the product manager role themselves • How to attract top PM talent • What she’s learned about going multi-product • A case for investing in quality • More — Skip the Mercury Personal waitlist: https://mercurytechnologies.typeform.com/lenny — Brought to you by: • Cloudinary—The foundational technology for all images and video on the internet • OneSchema—Import CSV data 10x faster • Airtable ProductCentral—Launch to new heights with a unified system for product development — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-build-your-product-team-from-scratch-rohini-pandhi — Where to find Rohini Pandhi: • X: https://x.com/rohinip • LinkedIn: https://www.linkedin.com/in/rohinipandhi — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Rohini’s background (05:00) The role of product managers at Mercury (09:51) Key indicators that it’s time to hire PMs (13:18) Building the product team at Mercury (19:53) Why you should avoid hiring PMs too early (22:26) The different flavors of product management (26:15) How to attract top talent (35:59) Advocating for quality in product development (44:10) Going multi-product (46:37) Organizational structure for multi-product success (50:57) Organizational culture for multi-product success (52:07) Customer obsession and product development (57:36) More lessons from going multi-product (01:05:57) Transparent Collective: supporting underrepresented founders (01:09:54) Lightning round — Referenced: • Immad Akhund on X: https://x.com/immad • Mercury: https://mercury.com • Square: https://squareup.com • Product management career ladders: https://www.lennysnewsletter.com/p/product-management-career-ladders • Pioneers, Settlers, Town Planners [Wardley]: https://orghacking.com/pioneers-settlers-town-planners-wardley-9dcd3709cde7 • Jason Zhang on LinkedIn: https://www.linkedin.com/in/jason-zhang-5645a860 • What is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html • Mercury Bill Pay: https://mercury.com/bill-pay • Zip: https://zip.co • Jira: https://www.atlassian.com/software/jira • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Gokul Rajaram on designing your product development process, when and how to hire your first PM, a playbook for hiring leaders, getting ahead in you career, how to get started angel investing, more: https://www.lennysnewsletter.com/p/gokul-rajaram-on-designing-your-product • Gokul Rajaram on X: https://x.com/gokulr • Transparent Collective: https://www.transparentcollective.com • 16 Reading Tips from Naval Ravikant: https://alexandbooks.com/archive/16-reading-tips-from-naval-ravikant • Shrinking on AppleTV+: https://tv.apple.com/us/show/shrinking • Bad Sisters on AppleTV+: https://tv.apple.com/us/show/bad-sisters • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses • Severance on AppleTV+: https://tv.apple.com/us/show/severance • Presumed Innocent on AppleTV+: https://tv.apple.com/us/show/presumed-innocent • Waymo: https://waymo.com • Adam Robinson on X: https://x.com/IAmAdamRobinson • Cyan Banister—From Homeless and Broke to Top Angel Investor (Uber, SpaceX, and 100+ More): https://tim.blog/2024/11/28/cyan-banister • Bobby Matson on LinkedIn: https://www.linkedin.com/in/bobbymatson • Jobs at Mercury: https://mercury.com/jobs — Recommended books: • Vectors: Aphorisms & Ten-Second Essays: https://www.amazon.com/Vectors-Aphorisms-Ten-Second-James-Richardson/dp/0967266890 • The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance: https://www.amazon.com/Inner-Game-Tennis-Classic-Performance/dp/0679778314 • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927 • Cutting for Stone: https://www.amazon.com/Cutting-Stone-Abraham-Verghese/dp/0375714367 • The Song of Achilles: https://www.amazon.com/Song-Achilles-Novel-Madeline-Miller/dp/0062060627 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about: • The three eras of Dropbox’s growth and evolution • The challenges he’s faced over the past 18 years • What he learned about himself • How he’s been able to manage his psychology as a founder • The importance of maintaining your learning curve • Finding purpose beyond metrics and growth • The micro, macro, and meta aspects of building companies • Much more — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Explo—Embed customer-facing analytics in your product • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-drew-houston-dropbox — Where to find Drew Houston: • X: https://x.com/drewhouston • LinkedIn: https://www.linkedin.com/in/drewhouston/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Drew and Dropbox (04:44) The three eras of Dropbox (07:53) The first era: Viral growth and early success (14:19) The second era: Challenges and competition (20:49) Strategic shifts and refocusing (29:36) Personal reflections and leadership lessons (40:19) Unlocking mindfulness and building support systems (43:14) The Enneagram test (50:35) The challenges of being a founder CEO (58:11) The third era: Rebooting the team and core business (01:22:41) Lessons and advice for aspiring founders (01:27:46) Balancing personal and professional growth (01:42:38) Final reflections and future outlook — Referenced: • Dropbox: https://www.dropbox.com/ • Y Combinator: https://www.ycombinator.com/ • Paul Graham’s website: https://www.paulgraham.com/ • Hacker News: https://news.ycombinator.com/ • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/ • Sequoia Capital: https://www.sequoiacap.com/ • Pejman Nozad on LinkedIn: https://www.linkedin.com/in/pejman/ • Mike Moritz on LinkedIn: https://www.linkedin.com/in/michaelmoritz/ • TechCrunch Disrupt: https://techcrunch.com/events/tc-disrupt-2024/ • Dropbox viral demo: https://youtu.be/7QmCUDHpNzE • Digg: https://digg.com/ • Reddit: https://www.reddit.com/ • Hadi and Ali Partovi: https://www.partovi.org/ • Zynga: https://www.zynga.com/ • Steve Jobs announces Apple’s iCloud: https://www.youtube.com/watch?v=ilnfUa_-Rbc • Dropbox Carousel: https://en.wikipedia.org/wiki/Dropbox_Carousel • Dropbox Is Buying Mega-Hyped Email Startup Mailbox: https://www.businessinsider.com/dropbox-is-buying-mega-hyped-email-startup-mailbox-2013-3 • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin • Intel: https://www.intel.com/ • Gordon Moore: https://en.wikipedia.org/wiki/Gordon_Moore • Netscape: https://en.wikipedia.org/wiki/Netscape • Myspace: https://en.wikipedia.org/wiki/Myspace • Bill Campbell: https://en.wikipedia.org/wiki/Bill_Campbell_(business_executive) • Enneagram type descriptions: https://www.enneagraminstitute.com/type-descriptions/ • The Myers-Briggs Type Indicator: https://www.themyersbriggs.com/en-US/Products-and-Services/Myers-Briggs • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Ben Horowitz on X: https://x.com/bhorowitz • Why Read Peter Drucker?: https://hbr.org/2009/11/why-read-peter-drucker • GitLab: https://about.gitlab.com/ • Automattic: https://automattic.com/ • Dropbox Dash: https://www.dash.dropbox.com/ • Welcome Command E to Dropbox: https://blog.dropbox.com/topics/company/welcome-command-e-to-dropbox- • StarCraft: https://en.wikipedia.org/wiki/StarCraft_(video_game) • Procter & Gamble and the Beauty of Small Wins: https://hbr.org/2009/10/the-beauty-of-small-wins • Teaching Smart People How to Learn: https://hbr.org/1991/05/teaching-smart-people-how-to-learn — Recommended books: • Guerrilla Marketing: Easy and Inexpensive Strategies for Making Big Profits from Your Small Business: https://www.amazon.com/Guerilla-Marketing-Inexpensive-Strategies-Business/dp/0618785914 • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884/ • Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821 • Zone to Win: Organizing to Compete in an Age of Disruption: https://www.amazon.com/Zone-Win-Organizing-Compete-Disruption/dp/1682302113 • Warren Buffett’s books: https://www.amazon.com/warren-buffett-Books/s?k=warren+buffett&rh=n%3A283155 • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239 • Invent and Wander: The Collected Writings of Jeff Bezos: https://www.amazon.com/Invent-Wander-Collected-Writings-Introduction/dp/1647820715/ • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up, which won the 2022 Independent Press Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss: • The psychology behind why we avoid difficult conversations • Specific scripts for having five common difficult conversations • How to handle defensive reactions in the moment • The three questions you should end every meeting with • “The founder prenup” that every founding team should work through • Common leadership myths • Stories of failure from Alisa’s career — Brought to you by: • Eppo—Run reliable, impactful experiments • Rippling—Automate HR, IT, and finance so you can scale faster • Liveblocks—Ready-made collaborative features to drop into your product — Find the transcript at: https://www.lennysnewsletter.com/p/scripts-for-difficult-conversations-alisa-cohn — Where to find Alisa Cohn: • X: https://x.com/AlisaCohn • LinkedIn: https://www.linkedin.com/in/alisacohn • Website: https://www.alisacohn.com • Podcast: https://www.alisacohn.com/podcast — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Alisa’s background (04:48) Having difficult conversations (12:48) Scripts for performance feedback (20:20) How to respond when someone is defensive or upset (25:07) Scripts for handling promotion disappointments (31:00) Scripts for handling terminations (35:44) The importance of positive feedback (38:49) Understanding your job as a leader (44:55) Recognizing your own blind spots (49:38) Three vital questions to ask in every meeting (55:57) The founder prenup (01:08:24) Failure corner (01:13:00) Final thoughts and lightning round — Referenced: • Alisa’s free PDF downloads for Lenny’s listeners: https://www.alisacohn.com/Lenny/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Non-Violent Communication (NVC) Model: https://www.ucop.edu/ombuds/_files/nvc-model-requesting-change-remove.pdf • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652 • How embracing emotions will accelerate your career | Joe Hudson (executive coach, Art of Accomplishment): https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson • Joe Gebbia on X: https://x.com/jgebbia • Noam Wasserman on LinkedIn: https://www.linkedin.com/in/noam-wasserman-462425 • Core Values List: https://jamesclear.com/core-values • How Cofounders Can Prevent Their Relationship from Derailing: https://hbr.org/2022/04/how-cofounders-can-prevent-their-relationship-from-derailing • Inside Out 2 on Disney+: https://www.disneyplus.com/movies/inside-out-2/6MeZYf9JkFii • Ninja CREAMi: https://www.amazon.com/Ninja-NC299AMZ-Milkshakes-One-Touch-Container/dp/B09QV24FFZ • Joseph Campbell quote: https://www.goodreads.com/quotes/136819-if-the-path-before-you-is-clear-you-re-probably-on — Recommended books: • From Start-Up to Grown-Up: Grow Your Leadership to Grow Your Business: https://www.amazon.com/Start-Up-Grown-Up-Grow-Leadership-Business/dp/1398601403 • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Revised-Kick-Ass-Humanity/dp/1250235375 • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of • Walt Disney: The Triumph of the American Imagination: https://www.amazon.com/Walt-Disney-Triumph-American-Imagination/dp/0679757473 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss: • Gong’s unique approach to working with design partners • Their unique pod model • Why Eilon makes big decisions quickly • Lessons learned from being early in AI • The power of extreme focus • His “spiral method” for learning complex topics quickly • How to maintain quality while optimizing for speed — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Think Fast Talk Smart—Tools and techniques to help you communicate more effectively • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/inside-gong-eilon-reshef — Where to find Eilon Reshef:• LinkedIn: https://www.linkedin.com/in/eilonreshef — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Eilon’s background (04:20) The pod model (06:33) Working with design partners (09:13) Finding and coordinating design partners (13:12) Balancing customer feedback and vision (15:10) Gong's 95% feature adoption (17:05) The importance of autonomy and trust (23:30) How to implement this unique way of working (27:15) Speed and decision-making (31:47) Early AI adoption and lessons learned (35:50) Building effective AI teams (38:16) The spiral method for learning (41:36) Narrowing down the initial customer profile (44:24) Failure corner (46:35) Lightning round — Referenced: • Gong: https://www.gong.io • Cisco: https://www.cisco.com/ • How Gong builds product: https://www.lennysnewsletter.com/p/how-gong-builds-product • What is Montessori education?: https://amshq.org/About-Montessori/What-Is-Montessori • Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov • Amit Bendov on LinkedIn: https://www.linkedin.com/in/amitbendov/ • Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): https://www.lennysnewsletter.com/p/lessons-from-scaling-spotify-the • Nvidia: https://www.nvidia.com • Figma: https://www.figma.com • The Spiral Method: https://www.gong.io/blog/using-the-spiral-method/ • Webex: https://www.webex.com/ • L’Oréal: https://www.lorealparisusa.com/ • American Express: https://www.americanexpress.com/ • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Dishwasher basket: https://www.amazon.com/Munchkin-High-Capacity-Dishwasher-Basket/dp/B07ZPMYKKS/ • What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing • Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor • Hanlon’s razor: https://en.wikipedia.org/wiki/Hanlon%27s_razor • Sabich: https://en.wikipedia.org/wiki/Sabich#Ingredients_and_description • Careers at Gong: https://www.gong.io/careers — Recommended books: • Marty Cagan’s books: https://www.amazon.com/stores/Marty-Cagan/author/B00J21JTNM • “The Machine That Won the War”: https://www.goodreads.com/book/show/18402398-the-machine-that-won-the-war • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • The Ideal Executive: https://www.amazon.com/Ideal-Executive-Ichak-Kalderon-Adizes/dp/0937120030/ • Crucial Conversations: Tools for Talking when Stakes Are High: https://www.amazon.com/Crucial-Conversations-Tools-Talking-Stakes/dp/1260474186/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Shaun Clowes is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversation, we discuss: • Why most PMs are bad, and how to fix this • Why great AI products are all about the data • Why he changed his mind about being data-driven • How to build your B2B growth team • How to choose your next career stop • Much more — Brought to you by: • Enterpret—Transform customer feedback into product growth • BuildBetter—AI for product teams • Wix Studio—The web creation platform built for agencies — Find the transcript at: https://www.lennysnewsletter.com/p/why-great-ai-products-are-all-about-the-data-shaun-clowes — Where to find Shaun Clowes: • X: https://x.com/ShaunMClowes • LinkedIn: https://www.linkedin.com/in/shaun-clowes-80795014/ • Website: https://shaunclowes.com/about-shaun • Reforge: https://www.reforge.com/profiles/shaun-clowes — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Shaun’s background (05:08) The state of product management (09:33) Becoming a 10x product manager (13:23) Specific ways to leverage AI in product management (17:15) Feedback rivers (19:20) AI's impact on data management (24:35) The future of enterprise businesses with AI (35:41) Data-driven decision-making (45:50) Building effective growth teams (50:18) The evolution of product-led growth (56:16) Career insights and decision-making (01:07:45) Failure corner (01:12:32) Final thoughts and lightning round — Referenced: • Steve Blank’s website: https://steveblank.com/ • Getting Out of the Building. 2 Minutes to See Why: https://www.youtube.com/watch?v=TbMgWr1YVfs • OpenAI: https://openai.com/ • Claude: https://claude.ai/ • Sachin Rekhi on LinkedIn: https://www.linkedin.com/in/sachinrekhi/ • Video: Building Your Product Intuition with Feedback Rivers: https://www.sachinrekhi.com/video-building-your-product-intuition-with-feedback-rivers • Confluent: https://www.confluent.io • Workday: https://www.workday.com/ • Lenny and Friends Summit: https://lennyssummit.com/ • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: https://www.youtube.com/watch?v=IxkvVZua28k • Anthropic: https://www.anthropic.com/ • Salesforce: https://www.salesforce.com/ • Atlassian: https://www.atlassian.com/ • Jira: https://www.atlassian.com/software/jira • Ashby: https://www.ashbyhq.com/ • Occam’s razor: https://en.wikipedia.org/wiki/Occam%27s_razor • Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams • Charlie Munger quote: https://www.goodreads.com/quotes/11903426-show-me-the-incentive-and-i-ll-show-you-the-outcome • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • The ultimate guide to product-led sales | Elena Verna: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-product-led • Metromile: https://www.metromile.com/ • Tom Kennedy on LinkedIn: https://www.linkedin.com/in/tom-kennedy-37356b2b/ • Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy): https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg • Wiz: https://www.wiz.io • Colin Powell’s 40-70 rule: https://www.42courses.com/blog/home/2019/12/10/colin-powells-40-70-rule • Detroiters on Netflix: https://www.netflix.com/title/80165019 • Glean: https://www.glean.com/ • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • Listen: Five Simple Tools to Meet Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301 • Empress Falls Canyon and abseiling: https://bmac.com.au/blue-mountains-canyoning/empress-falls-canyon-and-abseiling — Recommended books: • The Lean Startup: How Today’s Entrepreneurs Use Continuous Innovation to Create Radically Successful Businesses: https://www.amazon.com/Lean-Startup-Entrepreneurs-Continuous-Innovation/dp/0307887898 • Inspired: How to Create Products Customers Love: https://www.amazon.com/Inspired-Create-Products-Customers-Love/dp/0981690408 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Marc Benioff is the co-founder and CEO of Salesforce, the second-largest software company in the world. He started programming at age 15, selling his first program for $75, and went on to build Salesforce into a company worth more than $300 billion that also owns Slack, Tableau, Quip, and MuleSoft. Marc is known as a marketing legend, and is now leading Salesforce into the era of AI agents. In our conversation, we discuss: • The importance of maintaining a beginner’s mind • His approach to product launches and marketing • Managing through tough times and layoffs • His relationship with Steve Jobs and lessons learned • Why Salesforce is betting big on AI agents • Many stories from his entrepreneurial roller coaster • Much more — Brought to you by: • Cloudinary—The foundational technology for all images and video on the internet • Enterpret—Transform customer feedback into product growth • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-founder-marc-benioff — Where to find Marc Benioff: • X: https://x.com/benioff • LinkedIn: https://www.linkedin.com/in/marcbenioff — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Marc Benioff and Salesforce (03:54) Marc’s early career and domain names (05:59) The App Store story and lessons from Steve Jobs (15:18) Lessons from launching Salesforce (22:03) The importance of keeping a beginner’s mindset (29:53) Why Marc calls Salesforce the “25-year startup” (31:47) Agentforce (36:09) Why Marc says AI is the defining technology of our lifetime (40:12) AI’s impact on the workforce (42:31) Entrepreneurs need to be like conductors (46:02) Failure corner (50:32) The future of AI agents (56:34) Final thoughts and farewell — Referenced: • Bill.com: https://www.bill.com • App Store: https://www.apple.com/app-store/ • Salesforce: https://www.salesforce.com • Oracle: https://www.oracle.com • Larry Ellison on X: https://x.com/larryellison • Siebel Systems: https://en.wikipedia.org/wiki/Siebel_Systems • Saba Software: https://talentedlearning.com/lms-vendor-directory/saba-software • Tom Siebel on LinkedIn: https://www.linkedin.com/in/thomassiebel • Avon: https://www.avon.com • Salesforce Chief Has Pulled Some Crazy Stunts: https://www.businessinsider.com/marc-benioff-salesforcecom-chief-has-pulled-some-crazy-stunts-2012-3 •  Matthew McConaughey on Instagram: https://www.instagram.com/officiallymcconaughey • Woody Harrelson on Instagram: https://www.instagram.com/woodyharrelson • “Ask More of AI” with Matthew McConaughey: https://www.youtube.com/playlist?list=PLnobS_RgN7JaxOsLD8WH0I9E6osK3UrfI • Marc’s tweet about the ad with McConaughey and Harrelson: https://x.com/Benioff/status/1866175950062239784 • Chris Rock on Instagram: https://www.instagram.com/chrisrock • Sushi Iwa: http://www.sushiiwa.jp/en/ • Ryoanji Temple Rock Garden: https://www.japan.travel/en/spot/1145/ • Neil Young Archives on Instagram: https://www.instagram.com/neilyoungarchives • Mount Tam: https://en.wikipedia.org/wiki/Mount_Tamalpais • Spirit Rock: https://www.spiritrock.org • Jack Kornfield: https://www.spiritrock.org/teachers/jack-kornfield • Agentforce: https://www.salesforce.com/form/agentforce/demo • Minority Report on Prime: https://www.amazon.com/Minority-Report-Tom-Cruise/dp/B00A2FSSHK • Peter Schwartz on X: https://x.com/peterschwartz2 • UCSF Health: https://www.ucsfhealth.org • A.I. Chatbots Defeated Doctors at Diagnosing Illness: https://www.nytimes.com/2024/11/17/health/chatgpt-ai-doctors-diagnosis.html • Does AI improve doctors’ diagnoses? Study puts it to the test: https://www.sciencedaily.com/releases/2024/11/241113123419.htm • A.I. Will Transform the Global Economy—if Humans Let It: https://www.nytimes.com/2024/12/07/special-series/ai-transform-global-economy.html • Wargames on Prime: https://www.amazon.com/Wargames-Dabney-Coleman/dp/B0011EQBOS • Her on Prime: https://www.amazon.com/Her-Joaquin-Phoenix/dp/B00KATY250 • AI (Einstein) at Salesforce: https://www.salesforce.com/in/artificial-intelligence • Salesforce Signs Definitive Agreement to Acquire Airkit.ai: https://www.salesforce.com/news/stories/salesforce-signs-definitive-agreement-to-acquire-airkit-ai • Salesforce Buys Big Data Startup RelateIQ for Up to $390M: https://techcrunch.com/2014/07/11/salesforce-buys-big-data-startup-relateiq-for-up-to-390m • Salesforce to cut workforce by 10% after hiring ‘too many people’ during the pandemic: https://techcrunch.com/2023/01/04/salesforce-to-cut-workforce-by-10-after-hiring-too-many-people-during-the-pandemic • Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell • Bret Taylor on LinkedIn: https://www.linkedin.com/in/brettaylor • Akio Toyoda: https://en.wikipedia.org/wiki/Akio_Toyoda • Kaizen: https://en.wikipedia.org/wiki/Kaizen • TRS-80: https://en.wikipedia.org/wiki/TRS-80 • CLOAD Magazine: https://archive.org/details/cload_newsletter — Recommended books: • Ghost Fleet: A Novel of the Next World War: https://www.amazon.com/Ghost-Fleet-Novel-Next-World/dp/054470505X • Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company—and Revolutionized an Industry: https://www.amazon.com/Behind-Cloud-Salesforce-com-Billion-Dollar-Company/dp/0470521163 • Trailblazer: The Power of Business as the Greatest Platform for Change: https://www.amazon.com/Trailblazer-Business-Greatest-Platform-Change/dp/1984825194 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Farhan Thawar is the head of engineering at Shopify, where he oversees more than 1,000 engineers and a platform that powers over 10% of all U.S. e-commerce. Before Shopify, he was VP of engineering at Pivotal Labs and Xtreme Labs, and co-founder of Helpful.com. In our conversation, Farhan shares: • Why choosing the harder path leads to better outcomes • How to create intensity within your org (without burnout) • Why every company should be embracing pair programming • How he hires without interviewing • How he built the world’s largest internship program • His mission to create a “crafter’s paradise” for engineers • Much more — Brought to you by: • DX—A platform for measuring and improving developer productivity • Persona—A global leader in digital identity verification • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/how-shopify-builds-a-high-intensity-culture-farhan-thawer — Where to find Farhan Thawar: • X: https://x.com/fnthawar • LinkedIn: https://www.linkedin.com/in/fnthawar — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Farhan’s background (05:38) Choosing the hard path (09:37) Getting comfortable with looking dumb (13:20) Lessons from working with visionaries (19:19) Creating intensity in organizations (22:06) The power of pair programming (29:18) Shopify’s culture of intensity (37:18) Meeting Armageddon: revolutionizing company meetings (39:46) Reducing distractions (41:10) Deleting 1M+ lines of code (49:05) Three buckets of building (57:45) Remote work and trust battery (01:00:29) Finding stability in uncomfortable times (01:03:14) Hiring philosophy (01:11:41) Internship programs and co-op systems (01:15:32) Lessons from managing 120 direct reports (01:20:40) Failure corner (01:27:46) Lightning round and closing thoughts — Referenced: • The Steve Jobs quote about connecting dots: https://www.goodreads.com/quotes/463176-you-can-t-connect-the-dots-looking-forward-you-can-only • Shopify: https://www.shopify.com/ • GitHub: https://github.com/ • Farhan’s “questions to ask” framework: https://x.com/fnthawar/status/1514193402828574721 • Palantir: https://www.palantir.com/ • Joe Liemandt: https://www.linkedin.com/in/liemandt • Chamath Palihapitya: https://en.wikipedia.org/wiki/Chamath_Palihapitiya • Xtreme Labs: https://www.xtremelabs.io • Parkinson’s law: https://www.verywellmind.com/what-is-parkinsons-law-6674423 • Pair programming: https://dev.to/documatic/pair-programming-best-practices-and-tools-154j • Cody Fauser on LinkedIn: https://www.linkedin.com/in/codyfauser • How Shopify builds product: https://www.lennysnewsletter.com/p/how-shopify-builds-product • Chaos Monkey: We look at Shopify’s new ‘culture of focus’: https://www.siliconrepublic.com/careers/shopify-chaos-monkey-meetings-culture-deann-evans • Empowering devs with AI: How Shopify made GitHub Copilot core to its culture: https://www.youtube.com/watch?v=wVKBwcm5dbw&t=2318s • Tobi Lütke of Shopify: Powering a Team with a ‘Trust Battery’: https://www.nytimes.com/2016/04/24/business/tobi-lutke-of-shopify-powering-a-team-with-a-trust-battery.html • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Stop Being Deceived by Interviews When You’re Hiring: https://www.forbes.com/sites/forbesleadershipforum/2012/02/07/stop-being-deceived-by-interviews-when-youre-hiring/ • Shopify’s made the Life Story a major part of their interview: https://news.ycombinator.com/item?id=39294140 • Internships at Shopify: https://internships.shopify.com • Nick Adams on LinkedIn: https://www.linkedin.com/in/nick-adams-32b28139 • React Native: https://reactnative.dev • Swift: https://www.swift.org • Acquired podcast: The Mark Zuckerberg interview: https://www.acquired.fm/episodes/the-mark-zuckerberg-interview • The Power of Performance Reviews: Use This System to Become a Better Manager: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager • Airbnb’s Vlad Loktev on embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” (Partner at Index Ventures, Airbnb GM/VP Product): https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev • The Secret to a Great Planning Process—Lessons from Airbnb and Eventbrite: https://review.firstround.com/the-secret-to-a-great-planning-process-lessons-from-airbnb-and-eventbrite • How to do great work: https://www.paulgraham.com/greatwork.html • Challengers on Prime: https://www.amazon.com/Challengers-Luca-Guadagnino/dp/B0CX5MZ9M4 • Halt and Catch Fire on Prime: https://www.amazon.com/Halt-Catch-Fire-Season-1/dp/B0CKXZNT96 • Meta Ray-Bans: https://www.meta.com/smart-glasses/shop-all • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto — Recommended books: • The Undoing Project: A Friendship That Changed Our Minds: https://www.amazon.com/Undoing-Project-Friendship-Changed-Minds/dp/0393254593 • Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484 • Manna: Two Visions of Humanity’s Future: https://www.amazon.com/Manna-Two-Visions-Humanitys-Future-ebook/dp/B007HQH67U • Business Adventures: Twelve Classic Tales from the World of Wall Street: https://www.amazon.com/Business-Adventures-Twelve-Classic-Street/dp/1504000021 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jackson Shuttleworth is a Group PM at Duolingo, where he leads the retention team and the powerful streak feature. The streak feature, which gamifies consecutive days of learning, has been Duolingo’s most important and innovative growth lever and a key driver of their growth to a $14 billion business with almost 600 million users. In our conversation, we dive deep into the history and lessons of this feature: • The evolution of the streak feature • Biggest insights from over 600 streak-related experiments • Biggest specific wins and misses along the way • Key principles for building effective streak mechanics • How to operate a high-velocity product team • Tips for building engaging notification systems • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-duolingo-streaks — Where to find Jackson Shuttleworth:• LinkedIn: https://www.linkedin.com/in/jackson-shuttleworth/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jackson’s background and an overview of Duolingo’s streak feature (06:00) The impact of streaks on Duolingo’s success (09:58) The origin and evolution of streaks (14:50) Key experiments and insights (24:38) User psychology and engagement strategies (28:36) Duolingo’s product review structure (33:07) Designing for clarity and adaptability (46:59) Developing the Streak Freeze feature (50:47) Balancing monetization and retention (54:08) Notification strategies (58:15) The Perfect Streak feature (01:00:40) Enhancing the user experience  (01:04:47) Team operations and experimentation (01:18:57) Who can benefit from streaks (01:21:00) Lightning round — Referenced: • Duolingo streaks: https://duolingo.fandom.com/wiki/Streak • How to make learning as addictive as social media: https://www.ted.com/talks/luis_von_ahn_how_to_make_learning_as_addictive_as_social_media?subtitle=en • Luis von Ahn on LinkedIn: https://www.linkedin.com/in/luis-von-ahn-duolingo/ • FarmVille: https://en.wikipedia.org/wiki/FarmVille • Royal Match: https://www.dreamgames.com/games/royal-match • How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth • You’re on fire! Or, how we brought the streak milestone to life: https://blog.duolingo.com/streak-milestone-design-animation/ • Duolingo Doubles Down on Design and Animation with Acquisition of Hobbes: https://investors.duolingo.com/news-releases/news-release-details/duolingo-doubles-down-design-and-animation-acquisition-hobbes • Hobbes: https://www.hobbes.work/ • Jira: https://www.atlassian.com/software/jira • Atlassian: https://www.atlassian.com/ • Bing Gordon on LinkedIn: https://www.linkedin.com/in/binggordon/ • Peloton: https://www.onepeloton.com/ • Bluey on Disney+: https://www.disneyplus.com/series/bluey/1xy9TAOQ0M3r • Emily in Paris on Netflix: https://www.netflix.com/title/81037371 • Multi-position ladders at Home Depot: https://www.homedepot.com/b/Building-Materials-Ladders-Multi-Position-Ladders/N-5yc1vZasew — Recommended books: • A Guide to Midwestern Conversation: https://www.amazon.com/Guide-Midwestern-Conversation-Taylor-Phillips/dp/1984861336 • Fate Is the Hunter: A Pilot’s Memoir: https://www.amazon.com/Fate-Hunter-Ernest-K-Gann/dp/0671636030 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Seth Godin is a legend. He’s a marketer, teacher, entrepreneur, and author of more than 20 books, including Purple Cow, Permission Marketing, and Linchpin. He also writes one of the most popular and longest-running blogs in the world (approaching publishing 10,000 in a row!) and continues to shape how we think about marketing, brand, product, and creating lasting change in the world. In our conversation, we discuss: • How to build remarkable products that spread • The four critical strategic choices that determine your future • How to develop good taste and high standards • The role of tension in great strategy • How Seth used Claude to write his newest book • Much more — Brought to you by: • DX—A platform for measuring and improving developer productivity • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products — Where to find Seth Godin: • Blog: http://seths.blog/ • LinkedIn: https://www.linkedin.com/in/sethgodin • Website: https://www.sethgodin.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Seth’s background (05:17) Understanding good taste and upholding high standards (08:09) Become the best at whatever you do (09:48) Seth’s journey as a product manager (14:09) What people often get wrong when building products (16:00) Building a brand in the age of AI (19:04) Using AI to enhance writing (22:40) Four critical elements for an effective strategy (27:38) The role of tension in strategy (29:15) The concept of the purple cow (33:11) "Safe is risky" (34:56) The power of systems (37:07) Better waves make better surfers (38:10) Rebranding vs. re-logoing (43:07) Empathetic leadership (44:14) Conclusion and farewell — Referenced: • Seth Godin on the Tim Ferriss Show: https://tim.blog/2024/03/20/seth-godin-3/ • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennysnewsletter.com/p/persuasive-communication-wes-kao • Spinnaker: https://spinnaker.io • Ray Bradbury: https://en.wikipedia.org/wiki/Ray_Bradbury • Arthur C. Clarke: https://en.wikipedia.org/wiki/Arthur_C._Clarke • Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov • Roger Zelazny: https://en.wikipedia.org/wiki/Roger_Zelazny • Herbie Hancock: https://en.wikipedia.org/wiki/Herbie_Hancock • Fahrenheit 451 (game): https://www.filfre.net/2013/09/fahrenheit-451-the-game/ • RTFM: https://en.wikipedia.org/wiki/RTFM# • Intercom: https://www.intercom.com • Claude: https://claude.ai • ChatGPT: https://chatgpt.com • Anthropic: https://www.anthropic.com • Steam: https://store.steampowered.com • P.F. Flyers: https://pfflyers.com • Steve Blank’s website: https://steveblank.com • Marissa Mayer on X: https://x.com/marissamayer • Jaguar unveils new logo ahead of electric relaunch: https://www.bbc.com/news/articles/cgr0pw00n7qo • IHOP Becomes IHOb, the International House of ... Burgers: https://www.npr.org/2018/06/11/618844977/ihop-becomes-ihob-the-international-house-of-burgers • Oreo’s Super Bowl Power-Outage Tweet Was 18 Months in the Making: https://www.businessinsider.com/oreos-super-bowl-power-outage-tweet-was-18-months-in-the-making-2013-3 • Tesla’s New ‘Ludicrous Mode’ Makes the Model S a Supercar: https://www.wired.com/2015/07/teslas-new-ludicrous-mode-makes-model-s-supercar — Recommended books: • This Is Strategy: Make Better Plans (Create a Strategy to Elevate Your Career, Community & Life): https://www.amazon.com/This-Strategy-Better-Elevate-Community/dp/B0D47T8S7N• Purple Cow: Transform Your Business by Being Remarkable: https://www.amazon.com/Purple-Cow-New-Transform-Remarkable/dp/1591843170 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders. In our conversation, we discuss: • The difference between being a founder and being a CEO • Common failure modes for startup CEOs and how to avoid them • The four key elements of an effective go-to-market strategy • A framework for evaluating potential acquisitions: the magic box paradigm • How to find and hire the best people • How to build a repeatable GTM machine • Why founders need to trust their intuition • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • OneSchema—Import CSV data 10x faster • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/how-a-great-founder-becomes-a-great-ceo-jonathan-lowenhar — Where to find Jonathan Lowenhar: • X: https://x.com/jlowenhar • LinkedIn: https://www.linkedin.com/in/jlowenhar/ • Enjoy the Work: https://etw.live/lenny — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jonathan’s background (02:56) Understanding the rhythm of well-run companies (09:20) The founder mode vs. manager mode debate (12:05) Common company failure modes (13:36) Common CEO failure modes (25:25) The magic box paradigm for selling your startup (43:07) Advice for founders on building relationships (49:28) Hiring and building an amazing team (57:11) Types of executives: architect, optimizer, scaler (59:45) Working backward in hiring (01:02:54) Four key components of a go-to-market strategy (01:15:01) Trusting founder intuition (01:19:12) Founder vs. CEO: different roles, different skills (01:20:52) Closing thoughts and lightning round — Referenced: • Founder mode memes: https://techcrunch.com/2024/09/04/those-founder-mode-memes-keep-coming/ • Founder mode: https://paulgraham.com/foundermode.html • “Founder Mode” Is a Dangerous Red Herring: https://enjoythework.com/founder-mode-is-a-dangerous-red-herring/ • Magic Box Paradigm: A Framework for Startup Acquisitions: https://www.amazon.com/Magic-Box-Paradigm-Framework-Acquisitions/dp/0692778047 • Facebook Buys Instagram for $1 Billion: https://archive.nytimes.com/dealbook.nytimes.com/2012/04/09/facebook-buys-instagram-for-1-billion/ • Chris Voss on X: https://x.com/fbinegotiator • Who: https://www.amazon.com/Who-Geoff-Smart/dp/0345504194 • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Nathan Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/ • 4 questions Shreyas Doshi wishes he’d asked himself sooner | Former PM leader at Stripe, Twitter, Google: https://www.lennysnewsletter.com/p/shreyas-doshi-live • Traction: How Any Startup Can Achieve Explosive Customer Growth: https://www.amazon.com/Traction-Startup-Achieve-Explosive-Customer/dp/1591848369 • Adam Grant on LinkedIn: https://www.linkedin.com/in/adammgrant/ • This will make you a better decision maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player): https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke • How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer • How to get your marketing team to drive more impact: https://www.lennysnewsletter.com/p/how-to-get-your-marketing-team-to • The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756 • The Untethered Soul: The Journey Beyond Yourself: https://www.amazon.com/Untethered-Soul-Journey-Beyond-Yourself/dp/1572245379 • Will & Harper on Netflix: https://www.netflix.com/title/81760197 • Slow Horses on AppleTV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Aura frames: https://auraframes.com/ • Augie studio: https://augie.studio/ • Harrah’s Entertainment: https://en.wikipedia.org/wiki/Harrah%27s_Entertainment — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Michael Margolis has been a UX research partner at Google Ventures (GV) for nearly 15 years. He has developed a unique approach to helping startups identify their “bullseye customer”—the specific subset of their target market who initially is most likely to adopt their product. Michael has conducted over 300 hands-on research sprints with GV portfolio companies across various industries and helped develop the “design sprint” process made famous by the book Sprint. In our conversation, we discuss: • The step-by-step process of running a bullseye customer sprint • The most common mistakes founders make when picking their first customers • Practical tips for conducting effective customer interviews • How to create simple but effective prototypes for user research • The power of “watch parties” in aligning teams around customer insights • How to apply these methods beyond typical tech startups — Brought to you by: • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want • Enterpret—Transform customer feedback into product growth — Find the transcript at: https://www.lennysnewsletter.com/p/finding-your-bullseye-customer-michael-margolis — Where to find Michael Margolis: • X: https://x.com/mmargolis • LinkedIn: https://www.linkedin.com/in/mmargolis/ • Website: https://www.learnmorefaster.com/ • Medium: https://medium.com/@mmargolis — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Michael’s background (09:11) Bullseye customers vs. ideal customer profiles (ICPs) (12:32) An overview of the bullseye customer sprint (20:56) When to use the bullseye customer sprint (22:19) Step one: Agree on goals and key questions (23:48) Step two: Define your bullseye customer (25:52) The importance of a narrow target audience (29:00) An example of step two in action (38:24) Narrowing attributes and exclusion criteria (43:28) Step three: Recruiting and compensating participants (56:11) Step four: Creating effective prototypes (01:01:10) Step five: Drafting your interview guide (01:08:49) Step six: The watch party method (01:19:40) Common pitfalls and final thoughts (01:24:43) Closing thoughts and where to find Michael — Referenced: • Learn More Faster: How to Find Your Bullseye Customer and Their Perfect Product: https://www.learnmorefaster.com • Alcoa: https://www.alcoa.com • Dupont: https://www.dupont.com • Ericsson: https://www.ericsson.com • Google Ventures: https://www.gv.com/ • Kate Aronowitz on LinkedIn: https://www.linkedin.com/in/katearonowitz/ • Vanessa Cho on LinkedIn: https://www.linkedin.com/in/veecho/ • How to kickstart and scale a consumer business—Step 2: Identify your super-specific who: https://www.lennysnewsletter.com/p/consumer-business-super-specific-who • When enough is enough | Andy Johns (ex-FB, Twitter, Quora): https://www.lennysnewsletter.com/p/when-enough-is-enough-andy-johns • Zipline for health care: https://www.flyzipline.com/solutions/healthcare • Jobs to Be Done framework: https://www.christenseninstitute.org/theory/jobs-to-be-done • User Interviews: https://www.userinterviews.com/ • Respondent: https://www.respondent.io/ • Flatiron Health: https://flatiron.com/ • How to identify your ideal customer profile (ICP): https://www.lennysnewsletter.com/p/how-to-identify-your-ideal-customer • Gong: https://www.gong.io • Linear: https://linear.app • Gusto: https://gusto.com/ • Humble Inquiry: The Gentle Art of Asking Instead of Telling: https://bookshop.org/p/books/humble-inquiry-second-edition-the-gentle-art-of-asking-instead-of-telling-edgar-h-schein/14739375 • Figma: https://www.figma.com — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jen Abel is the co-founder of JJELLYFISH, where she and her team have worked with over 300 early-stage founders to learn how to sell, do early customer discovery, and set up a repeatable sales motion on the way to their first $1M ARR. In our conversation, Jen shares: • Why founder-led sales is so crucial early on • The sales process, step by step • How to craft effective outreach messages • Where to find leads • What three channels work best for outreach • What to say on your first call • How to maintain momentum • Strategies for navigating procurement and closing deals • Common pitfalls in the sales process and how to avoid them — Brought to you by: • Brave Search—A smarter way to search • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/master-founder-led-sales-jen-abel — Where to find Jen Abel: • X: https://x.com/jjen_abel • LinkedIn: https://www.linkedin.com/in/earlystagesale — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jen’s background (02:20) The importance of founder-led sales (08:24) The steps of a sales cycle (12:01) Tactics for effective cold outreach (16:47) Conversion rate vs. win rate (20:20) The time it takes to find product-market fit (23:06) Identifying and engaging prospects (30:58) Nailing the first phone call (34:14) Buying vs. selling (38:08) Testing the questions to ask (41:57) Avoiding common sales questions and securing the second call (43:08) Co-authoring with customers (45:06) Time-boxing service contracts (49:20) Why you should avoid demos on the first call (51:05) Dealing with procurement (54:22) The power of enterprise sales (58:14) Getting a signature (01:00:15) Choosing a focus and overcoming sales challenges (01:02:19) General timelines (01:04:27) Final thoughts and advice (01:13:32) Working with Jen — Referenced: • Wiz: https://www.wiz.io/ • JJELLYFISH: https://www.jjellyfish.com/ • Clay: https://www.clay.com/ • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit • Airtable: https://www.airtable.com/ • Figma: https://www.figma.com/ • GitHub: https://github.com/ • Vanta: https://www.vanta.com/ • Christine Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/ • Glengarry Glen Ross: https://www.imdb.com/title/tt0104348/ • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand-ebook/dp/B0CHY6BNDN • Sprig: https://sprig.com/ • Zip: https://zip.co/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Amjad Masad is the co-founder and CEO of Replit, a browser-based coding environment that allows anyone to write and deploy code. Replit has 34 million users globally and is one of the fastest-growing developer communities in the world. Prior to Replit, Amjad worked at Facebook, where he led the JavaScript infrastructure team and contributed to popular open-source developer tools. Additionally, he played a key role as a founding engineer at the online coding school Codecademy. In our conversation, Amjad shares: • A live demo of Replit in action • How Replit’s AI agent can build full-stack web applications from a simple text prompt • The implications of AI-powered development for product managers, designers, and engineers • How this might reshape companies and careers • Why being “generative” will become an increasingly valuable skill • “Amjad’s law” and how learning to debug AI-generated code is becoming ever more valuable • Much more — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Persona—A global leader in digital identity verification • LinkedIn Ads—Reach professionals and drive results for your business — Find the transcript at: https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad — Where to find Amjad Masad: • X: https://x.com/amasad • LinkedIn: https://www.linkedin.com/in/amjadmasad/ • Website: https://amasad.me/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Amjad Masad and Replit (02:41) The vision and challenges of Replit (06:50) Replit’s growth and user stories (10:49) Demo of Replit’s capabilities (16:51) Building and iterating with Replit (25:04) Real-world applications and use cases (30:13) The technology stack (33:48) The evolution of Replit and its capabilities (39:36) The future of AI in software development (44:04) Skills for the future: generative thinking and coding (47:26) Amjad’s law (50:36) Replit’s new developments and future plans — Referenced: • Replit: https://replit.com/ • Cursor: https://www.cursor.com • Aman Mathur on LinkedIn: https://www.linkedin.com/in/aman-mathur/ • Node: https://nodejs.org/en • Claude: https://claude.ai/ • Salesforce: https://www.salesforce.com/ • Wasm: https://webassembly.org/ • Figma: https://www.figma.com/ • Codecademy: https://www.codecademy.com/ • Hacker News: https://news.ycombinator.com/news • Paul Graham’s website: https://www.paulgraham.com/ • Jevons paradox: https://en.wikipedia.org/wiki/Jevons_paradox • Anthropic: https://www.anthropic.com/ • Open AI: https://openai.com/ • Amjad’s tweet about “society of models”: https://x.com/amasad/status/1568941103709290496 • About HCI: https://www.designdisciplin.com/p/hci-profession • Taylor Swift’s website: https://www.taylorswift.com/ • Andrew Wilkinson on LinkedIn: https://www.linkedin.com/in/awilkinson/ • Haya Odeh on LinkedIn: https://www.linkedin.com/in/haya-odeh-b0725928/ • Amjad’s law: https://x.com/snowmaker/status/1847377464705896544 • Ray Kurzweil’s website: https://www.thekurzweillibrary.com/ • God of the gaps: https://en.wikipedia.org/wiki/God_of_the_gaps — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Raaz Herzberg is the chief marketing officer and VP of product strategy at Wiz. Wiz hit $100 million ARR within 18 months (the fastest growth in startup history) and, five years in, is generating over $500 million ARR. It also serves over 45% of the Fortune 100. Raaz was one of the first five employees at Wiz, joining as the first product manager, and helped the team pivot to what may be the most intense PMF in history. Before Wiz, Raaz led security products at Microsoft, including Azure Sentinel. In our conversation, we discuss: • How Wiz pivoted from their initial idea and found deep product-market fit • What Raaz learned about listening to customers • Why she moved from product to marketing, despite no prior experience • How she thinks differently as a marketer with a product background • Lessons learned from scaling a hypergrowth startup like Wiz • Much more — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Rippling—Automate HR, IT, and finance so you can scale faster • Cloudinary—The foundational technology for all images and video on the internet — Find the transcript at: https://www.lennysnewsletter.com/p/building-wiz-raaz-herzberg — Where to find Raaz Herzberg: • X: https://x.com/raazherzberg • LinkedIn: https://www.linkedin.com/in/raazh — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Raaz’s background (02:54) Early challenges and Wiz’s essential pivot (06:41) Finding product-market fit (11:31) Lessons from early customer interactions (14:54) The power in speaking up when you don’t understand something (17:46) How Wiz pivoted from their initial idea (23:52) Marketing and leadership insights (34:12) The challenges of being a marketing leader (28:05) Following the “heat” in your organization (30:22) How Raaz found success as CMO (34:01) Common CMO mistakes (36:23) Creating noise and standing out (40:28) Embracing failure and taking risks (44:53) The importance of clear communication (48:32) The “dummy” explanation (51:00) Building trust and company culture (53:45) Contrarian corner (56:34) Lightning round — Referenced: • Wiz: https://www.wiz.io/ • An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth): https://www.lennysnewsletter.com/p/an-inside-look-at-deels-unprecedented • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp • Assaf Rappaport on LinkedIn: https://www.linkedin.com/in/assafrappaport/ • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen • Shardul Shah on LinkedIn: https://www.linkedin.com/in/shardul-shah-3589062/ • Doug Leone on LinkedIn: https://www.linkedin.com/in/douglas-leone-a2714/ • Jeff Horing on LinkedIn: https://www.linkedin.com/in/jeffhoring2009/ • RSA Conference: https://www.rsaconference.com/ • Microsoft acquires Adallom to advance identity and security in the cloud: https://blogs.microsoft.com/blog/2015/09/08/microsoft-acquires-adallom-to-advance-identity-and-security-in-the-cloud/ • Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome • Careers at Wiz: https://www.wiz.io/careers • Setting the Table: The Transforming Power of Hospitality in Business: https://www.amazon.com/Setting-Table-Transforming-Hospitality-Business/dp/0060742763 • No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860/ • Gong: https://www.gong.io/ • The Wire on HBO: https://www.hbo.com/the-wire • Raaz’s pen holder recommendation: https://www.paper-republic.com/products/le-loop-penholder — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Aman Khan is Director of Product at Arize AI, an observability company for AI engineers at companies like Uber, Instacart, and Discord. Previously he was an AI Product Manager at Spotify on the ML Platform team, enabling hundreds of engineers to build and ship products across the company. He has also led and worked on products at Cruise, Zipline, and Apple. In our conversation, we discuss: • What is an “AI product manager”? • How to break into AI PM • What separates top 5% AI PMs • How to thrive as an individual-contributor PM • Common pitfalls to avoid when building AI products • The importance of energy and curiosity in product roles • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/becoming-an-ai-pm-aman-khan — Where to find Aman Khan: • X: https://x.com/_amankhan • LinkedIn: https://www.linkedin.com/in/amanberkeley/ • Website: https://amanalikhan.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Aman’s background (06:16) Understanding AI product management roles (13:29) Getting started as an AI product manager (18:14) Building a portfolio and standing out (22:31) Why product management is not dead (28:56) How to thrive as an AI product manager (35:42) Finding good ideas that are AI-oriented (39:27) Be careful not to automate away every customer experience (42:53) What separates top 5% AI PMs (46:55) Key habits for long-term IC success (52:48) The importance of energy in meetings (57:00) Wandering vs. waiting (01:01:41) Amplifying signal through AI tools (01:03:18) Just have fun (01:05:36) Lightning round — Referenced: • AI Resources and Tools for PMs (Updated Oct 2024): https://open.substack.com/pub/amankhan1/p/ai-resources-and-tools-for-pms-updated • Unlocking the AI PM Dream: Your Roadmap to Success: https://amankhan1.substack.com/p/unlocking-the-ai-pm-dream-your-roadmap • Arize: https://arize.com/ • Ryzen: https://www.amd.com/en/products/processors/business-systems/ryzen-ai.html • NotebookLM: https://notebooklm.google/ • Figma: https://www.figma.com/ • Cursor: https://www.cursor.com/ • Replit: https://replit.com/ • Excalidraw: https://excalidraw.com/ • Vercel: https://vercel.com/ • v0: https://v0.dev/ • How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Midjourney: https://www.midjourney.com/ • Dall-E: https://openai.com/index/dall-e-3/ • Introducing the Realtime API: https://openai.com/index/introducing-the-realtime-api/ • Intro to Large Language Models | Andrej Karpathy: https://www.youtube.com/watch?v=zjkBMFhNj_g • Watch Me Build an App in 60 Minutes With o1 and Cursor: https://www.youtube.com/watch?v=9Zmhe6_T-xU • Greg Isenberg on LinkedIn: https://www.linkedin.com/in/gisenberg/ • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Spotify: https://open.spotify.com/ • Instacart: https://www.instacart.com/ • How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennysnewsletter.com/p/transform-your-subscription-growth • When Identifying the Problem Isn’t Enough: Lessons from Boxed Cake Mix by Ann M. Aly, TechFlow Director of Human Centered Design: https://www.techflow.com/when-identifying-the-problem-isnt-enough-lessons-from-boxed-cake-mix/ • Waymo: https://waymo.com/ • The Ikea effect: https://thedecisionlab.com/biases/ikea-effect • Blue Apron: https://www.blueapron.com/ • Unorthodox PM wisdom: Automating user insights, unselling job candidates, logging every decision, more | Kevin Yien (Stripe, Square, Mutiny): https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien • LeBron James: https://en.wikipedia.org/wiki/LeBron_James • The Secrets Behind Lyft’s Dynamic Culture: https://www.forbes.com/sites/marissaperetz/2018/05/16/the-secrets-behind-lyfts-dynamic-culture/ • Aparna Dhinakaran on LinkedIn: https://www.linkedin.com/in/aparnadhinakaran/ • Why most public speaking advice is wrong—and how to finally overcome your speaking anxiety | Tristan de Montebello (CEO & co-founder of Ultraspeaking): https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello • Ultraspeaking: https://ultraspeaking.com/lenny/ • A Short History of Nearly Everything: https://www.amazon.com/Short-History-Nearly-Everything/dp/076790818X • Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321 • Tour de France: Unchained on Netflix: https://www.netflix.com/title/81153133 • Formula 1: Drive to Survive on Netflix: https://www.netflix.com/title/80204890 • Websim: https://websim.ai/ • Appeel Books: https://appeel.brandeditems.com/ • Steve Jobs quote: https://www.goodreads.com/quotes/374630-your-time-is-limited-so-don-t-waste-it-living-someone# • Becoming a conscious leader: Leading without fear, finding your life’s objective function, and getting better at vision and strategy | John Mark Nickels (Uber, Waymo, DoorDash): https://www.lennysnewsletter.com/p/becoming-a-conscious-leader-john-mark-nickels • Aman Khan (cricket player): https://en.wikipedia.org/wiki/Aman_Hakim_Khan — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Melissa Perri is the founder of Product Institute, author of Escaping the Build Trap, and host of the Product Thinking Podcast. She has worked with startups, Fortune 50 companies, and everything in between to help them build better products and level up their product teams. In our conversation, we discuss: • The history of the product owner role • The differences between product owners and product managers • How to transition from product owner to product manager • The evolution of and problems with the SAFe framework • How large non-tech companies can improve their product practices • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • OneSchema—Import CSV data 10x faster • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/product-owners-melissa-perri — Where to find Melissa Perri: • X: https://twitter.com/lissijean • LinkedIn: https://www.linkedin.com/in/melissajeanperri/ • Website: https://melissaperri.com/ • Product Institute: https://productinstitute.com/ • Podcast: https://www.produxlabs.com/product-thinking — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Melissa’s background (02:12) The rise of the product owner role (06:37) Understanding Agile and Scrum (08:27) Challenges in Agile transformations (10:41) The history of the product owner role (13:58) The Scrum Guide (15:43) Product owner responsibilities (21:01) Adopting Scrum in organizations (26:21) The origins and implementation of SAFe (35:20) Why Melissa doesn’t recommend SAFe (40:33) Advice for implementing a digital transformation (49:12) An example of SAFe adoption (51:27) The value of experienced product leaders (56:53) Career paths for product owners (01:04:14) Transitioning from product owner to product manager (01:06:41) Be careful relying on certifications (01:11:43) Evaluating existing product owners (01:16:55) Final thoughts on Agile and product management — Referenced: • Escaping the Build Trap: How Effective Product Management Creates Real Value: https://www.amazon.com/Escaping-Build-Trap-Effective-Management/dp/149197379X • Lean UX: https://leanuxnyc.co/ • Scrum: https://www.scrum.org/ • What is Extreme Programming? https://www.agilealliance.org/glossary/xp/ • Capital One: https://www.capitalone.com/ • The Agile Manifesto: https://www.atlassian.com/agile/manifesto • Ken Schwaber on X: https://x.com/kschwaber • Jeff Sutherland on X: https://x.com/jeffsutherland • Kanban: https://www.atlassian.com/agile/kanban • What is a kanban board?: https://www.atlassian.com/agile/kanban/boards • Ron Jeffries’s website: https://www.ronjeffries.com/ • Jeff Patton on X: https://x.com/jeffpatton • The Scrum Guide: https://www.scrum.org/resources/scrum-guide • OpenSky: https://www.openskycc.com/ • SAFe: https://scaledagileframework.com/ • Dean Leffingwell on LinkedIn: https://www.linkedin.com/in/deanleffingwell/ • Capital One scraps 1,100 tech positions: https://www.reuters.com/technology/capital-one-scraps-1100-tech-positions-source-2023-01-19/ • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennysnewsletter.com/p/product-management-theater-marty • Marty Cagan on LinkedIn: https://www.linkedin.com/in/cagan/ • Jeff Gothelf on X: https://x.com/jboogie • Shruti Patel on LinkedIn: https://www.linkedin.com/in/shruti-patel-32bb573a/ • Product Thinking Podcast: Mastering Product Focus: Balancing Legacy and Innovation with Shruti Patel: https://www.produxlabs.com/product-thinking-blog/2024/9/25/episode-190-mastering-product-focus-balancing-legacy-and-innovation-with-shruti-patel • Melissa Douros on LinkedIn: https://www.linkedin.com/in/melissadouros/ • Mind the Product: https://www.mindtheproduct.com/ • Athenahealth: https://www.athenahealth.com/ • McKinsey: https://www.mckinsey.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Archie Abrams is the VP of Product and Head of Growth at Shopify, where he leads a 600+ person growth org across product, design, engineering, data, ops, and growth marketing. Shopify powers over 10% of e-commerce in the United States, with $235 billion in GMV in 2023 (roughly the size of Finland’s economy). He previously led Consumer product and growth at Lyft and was at Udemy for 8 years as SVP of Product having joined the company when it was 10 people. In our conversation, we discuss: • Why Shopify optimizes for churn • Why the core product team doesn’t use metrics-based goals • Why they keep multi-year experiment holdouts • How they structure their growth team • The benefits of not having a CMO • Lessons learned about integrating sales into a product-led growth model • The power of discounting as a growth lever • Much more — Brought to you by: • Explo—Embed customer-facing analytics in your product • Dovetail—The customer insights hub for product teams — Find the transcript at: https://www.lennysnewsletter.com/p/shopifys-growth-archie-abrams — Where to find Archie Abrams: • X: https://x.com/archieabrams • LinkedIn: https://www.linkedin.com/in/archie-abrams-b6aa8b6/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Archie’s background  (02:30) Shopify’s impressive growth (06:17) Shopify’s unique approach to churn and retention (08:43) Monetization model and success metrics (11:08) Long-term experimentation and metrics (23:00) Examples of big wins that Archie’s team has shipped (26:42) Monetary friction (27:14) Metrics (29:47) Shopify’s growth team structure (33:03) Goal setting and forecasting (37:10) Examples of long-term results within Shopify (41:36) Shipping neutral experiments (42:05) Building a hundred-year company (48:04) Why Shopify doesn’t use KPIs (51:30) Shopify’s “Get s**t done” framework (54:30) Cross-team collaboration  (58:48) The importance of an opinionated founder  (01:01:12) Growth and sales integration (01:06:42) Shopify’s marketing structure (01:08:49) Insights on discounting from Udemy (01:11:09) Lightning round — Referenced: • Shopify: https://www.shopify.com/ • Tobias Lütke on LinkedIn: https://www.linkedin.com/in/tobiaslutke • Gross Merchandise Value: Calculation and Best Practices: https://www.shopify.com/retail/gross-merchandise-value • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Glen Coates on LinkedIn: https://www.linkedin.com/in/glcoates • Harley Finkelstein on LinkedIn: https://www.linkedin.com/in/harleyf • Udemy: https://www.udemy.com/ • Scientific Advertising: https://www.amazon.com/Scientific-Advertising-Original-Claude-Hopkins/dp/1640954252 • Four-Minute Mile: https://www.amazon.com/Four-Minute-Mile-Roger-Bannister/dp/1493038753/ • The Sopranos on HBO: https://www.hbo.com/the-sopranos • Suno: https://suno.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Alistair Croll is the co-author of the best-selling book Lean Analytics and a longtime product manager, entrepreneur, and startup advisor. He was also instrumental in my starting a company, funding it, and helping us exit to Airbnb as part of his Year One Labs incubator. He’s chaired notable events such as O’Reilly’s Strata and UBM’s Cloud Connect and founded FWD50. In our conversation, we focus on lessons from an upcoming book by Alistair and his co-author, Emily Ross, Just Evil Enough, which is set for release in late 2024. We cover: • The importance of subversive marketing strategies in most startups’ growth • 11 specific subversive tactics that successful companies have used • Examples of companies like Netflix, Airbnb, and Tesla that used clever tactics early on • A framework for scanning your market for opportunities • The importance of finding your “zero-day marketing exploit” • How to apply these tactics ethically without actually being evil • Much more — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Hex—Helping teams ask and answer data questions by working together • Vanta—Automate compliance. Simplify security — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/just-evil-enough-alistair-croll — Where to find Alistair Croll: • X: https://x.com/acroll • Threads: https://www.threads.net/@alistairish • LinkedIn: https://www.linkedin.com/in/alistaircroll/ • Website: https://justevilenough.com/ • Substack: https://acroll.substack.com/ • Just Evil Enough on X: https://x.com/evilenough • Just Evil Enough on LinkedIn: https://www.linkedin.com/company/just-evil-enough/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Alistair’s background  (02:00) The story behind Alistair and Emily’s book Just Evil Enough (06:17) Examples of subversive tactics (07:43) The importance of unfair advantage (10:36) The origin of the title “Just Evil Enough” (14:24) System awareness and novelty (19:16) How to use this thinking successfully  (22:37) Normalizing disagreeable thinking  (25:49) Recon canvas and market scanning (32:43) 11 tactics for subversive marketing (57:01) Implementing subversive strategies (01:05:01) Ethical considerations in marketing (01:08:19) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Shreyas Doshi is a former product leader at Stripe, Twitter, Google, and Yahoo. He’s now a full-time advisor and coach to founders and executives. Shreyas is known for his incredibly insightful writing on products, which has garnered him a passionate following in the PM and startup community. Last week, we sat down together at the very first Lenny and Friends Summit in San Francisco for a special live episode. We covered: • Why product leaders often feel overwhelmed with work, and how to combat it • The importance of developing good taste, and how to do it • How to reduce frustration in your product leadership role • The critical skill of truly listening as a leader • Common pitfalls in annual planning and decision-making • Lots of laughs — To learn more from Shreyas, check out these courses: • Improving Your Product Sense: https://bit.ly/product-sense • Managing Your PM Career: https://bit.ly/pm-career-course — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Paragon—Ship every SaaS integration your customers want • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/shreyas-doshi-live — Where to find Shreyas Doshi: • X: https://x.com/shreyas • LinkedIn: https://www.linkedin.com/in/shreyasdoshi/ • Threads: https://www.threads.net/@shreyas.threads • Linktree: https://linktr.ee/shreyasdoshi • YouTube: https://www.youtube.com/@ShreyasDoshiVideos — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (05:35) Question one: Why am I so busy? (10:08) Annual planning as an example (16:48) Tactical tips for staying less busy (25:20) Question two: Do I actually have good taste? (38:09) Question three: Why does my job feel so frustrating? (43:29) Question four: Am I really listening? (44:35) Closing remarks — Referenced: • Shreyas Doshi on pre-mortems, the LNO framework, the three levels of product work, why most execution problems are strategy problems, and ROI vs. opportunity cost thinking: https://www.lennysnewsletter.com/p/episode-3-shreyas-doshi • LNO framework: https://twitter.com/shreyas/status/1492345184171945984 • Time management techniques that actually work: https://www.lennysnewsletter.com/p/time-management-techniques-that-actually • Part 2: Time management techniques that actually work: https://www.lennysnewsletter.com/p/part-2-time-management-techniques • Eisenhower quote: https://www.brainyquote.com/quotes/dwight_d_eisenhower_164720 • Stripe Connect: https://stripe.com/connect • Jeff Bezos explains one-way door decisions and two-way door decisions: https://www.youtube.com/watch?v=rxsdOQa_QkM • Spotify Is America’s Most Loved Workplace: https://www.newsweek.com/2021/10/29/spotify-americas-most-loved-workplace-1639982.html • Shreyas on “thinking is cheap”: https://www.linkedin.com/posts/shreyasdoshi_thinking-is-very-cheap-doing-is-very-expensive-activity-7225237421813116929-Qzi3/ • Good Product Strategy, Bad Product Strategy from Shreyas: https://x.com/shreyas/status/1244810075908128768 • Shreyas on annual planning and metrics: https://x.com/shreyas/status/1302423854095036421 https://x.com/shreyas/status/1304628719374544896 • Jensen Huang on LinkedIn: https://www.linkedin.com/in/jenhsunhuang/ • Patrick Mahomes’s website: https://www.adidas.com/us/patrick_mahomes • Virat Kohli: https://en.wikipedia.org/wiki/Virat_Kohli • Reversible and Irreversible Decisions: https://fs.blog/reversible-irreversible-decisions/ • Fail fast: https://en.wikipedia.org/wiki/Fail_fast • 3 levels of product work: https://twitter.com/shreyas/status/1370248637842812936 • Shakespeare quote: https://nosweatshakespeare.com/quotes/famous/to-thine-own-self-be-true/ • Rick Rubin: Legendary Music Producer | Lex Fridman Podcast #275: https://Dwww.youtube.com/watch?v=H_szemxPcTI • Blake Burge on Rick Ruben: https://x.com/blakeaburge/status/1794470295828341222 • Rick Rubin on X: https://x.com/RickRubin • Dee Hock on X: https://x.com/deewhock • Dee Hock quote on listening: https://x.com/shreyas/status/1351279398423465984 • Peter Drucker: https://en.wikipedia.org/wiki/Peter_Drucker • Peter Drucker quotes on listening: https://www.azquotes.com/author/4147-Peter_Drucker/tag/listening • Lenny’s first podcast recording: https://www.youtube.com/watch?v=YP_QghPLG-8 • A Recipe to Become a Great Listener: https://www.youtube.com/watch?v=gUQJkiDy2Ko — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Naomi Gleit is head of product at Meta, joined as employee #29, and is the longest-serving executive at Meta other than Mark Zuckerberg. She’s been at the center of some of the company’s most foundational products, including Facebook’s early growth team. In our conversation, we discuss: • How she originally landed at Facebook • The evolution of Facebook’s growth team and key metrics • Lessons from working with Mark Zuckerberg • Insights from Facebook’s activation metric and retention strategies • Leadership lessons and “Naomiisms” for effective product management • Tactics for creating extreme clarity in team communication • Advice for running effective meetings • More — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Vanta—Automate compliance. Simplify security • Eppo—Run reliable, impactful experiments — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/metas-head-of-product-naomi-gleit — Where to find Naomi Gleit: • Instagram: https://www.instagram.com/naomigleit • LinkedIn: https://www.linkedin.com/in/naomi-gleit/ • Website: https://naomi.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Naomi Gleit (01:53) Naomi’s journey at Meta (06:18) Landing a job at Facebook (10:40) Becoming a product manager (13:40) Working as Head of Product at Meta (14:55) Insights on working with Mark Zuckerberg (20:04) Small Groups and “disagreeable givers” (24:28) The legendary growth team (33:45) Activation metrics and onboarding (43:44) Naomi’s leadership and PM philosophy (53:00) Canonical documents (55:55) Simplifying complex projects (01:00:33) Teen accounts: a case study (01:06:37) Running effective meetings (01:12:10) The importance of exercise (01:16:36) The role of a product manager (01:25:49) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jessica Hische is a lettering artist and New York Times bestselling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books, and her work has been featured in design and illustration annuals both in the U.S. and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under 30 in Art and Design, an ADC Young Gun, a “Person to Watch” by GD USA, and an Adweek “Creative 100.” In our conversation, we discuss: • My new logo and brand! • Jessica’s process for refreshing my logo/brand • Why most startups shouldn’t worry about their logo/brand • The psychology behind different typography choices • Balancing creativity with business needs in logo design • Jessica’s unique approach to pricing logo work • How AI is (and isn’t) impacting the design world • Jessica’s other creative pursuits, including children’s books and art supply stores — Brought to you by: • The Enterprise Ready Conference — For B2B leaders building enterprise SaaS • OneSchema — Import CSV data 10x faster • Merge — A single API to add hundreds of integrations into your app — Find the transcript at: https://www.lennysnewsletter.com/p/seeing-like-a-designer-jessica-hische — Where to find Jessica Hische: • Threads: https://www.threads.net/@jessicahische • Instagram: https://www.instagram.com/jessicahische • Website: https://jessicahische.is — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jessica’s background (01:32) The logo refresh process (09:45) When to refresh your logo (11:45) High-level overview (18:04) Approaching Lenny’s brand refresh (24:25) How to see like a designer (37:53) Lenny’s new logo: where we landed (44:07) Brand’s role in company success (50:04) Jessica’s flexible pricing strategies and collaborative design process (57:14) Balancing multiple creative projects (01:01:48) Using AI in creative work (01:05:50) Upcoming projects and final thoughts (01:08:24) Lightning round — Referenced: • Jeni’s: https://jenis.com • James Edmondson on LinkedIn: https://www.linkedin.com/in/jamestedmondson/ • Figma Config: https://config.figma.com/ • Helvetica: https://en.wikipedia.org/wiki/Helvetica • MyFonts: https://www.myfonts.com/ • Geometric sans serif fonts: https://www.myfonts.com/pages/tags/geometric%20sans%20serif-fonts • The Rise of Fractional Executives: https://www.reforge.com/blog/leveraging-fractional-executives • JH&F: https://jessicahische.shop/pages/my-oakland-store • Drawling: https://drawling.shop/ • Jessica Hische’s books on Amazon: https://www.amazon.com/stores/Jessica-Hische/author/B082XDN54V • Dreamforce: https://www.salesforce.com/dreamforce • Bezier handles: https://www.tella.tv/definition/bezier-handles • My First Book of Fancy Letters: https://www.amazon.com/My-First-Book-Fancy-Letters/dp/0593385012/r • The Creative Act: A Way of Being: https://www.amazon.com/Creative-Act-Way-Being/dp/0593652886/ • Inside Paragraphs: Typographic Fundamentals: https://www.amazon.com/Inside-Paragraphs-Fundamentals-Cyrus-Highsmith/dp/1616899417 • Just Kids: https://www.amazon.com/Just-Kids-Patti-Smith/dp/0060936223 • Robert Mapplethorpe: https://en.wikipedia.org/wiki/Robert_Mapplethorpe • The Emperor of All Maladies: A Biography of Cancer: https://www.amazon.com/Emperor-All-Maladies-Biography-Cancer/dp/1439170916/r • Severance on Prime Video: https://www.amazon.com/Severance-Toby-Stephens/dp/B001ARYGCU • Penco brown bag stand: https://penco.jp/en/products/db079/ • XOXO: https://xoxofest.com/ • Mariame Kaba quotes: https://www.goodreads.com/author/quotes/8156101.Mariame_Kaba — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Anneka Gupta is the Chief Product Officer at Rubrik, a leading B2B cybersecurity company. She previously spent 11 years at LiveRamp, where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti and teaches product management at Stanford University. In our conversation, we discuss: • Navigating “founder mode” dynamics in organizations • Navigating difficult personalities and aligning teams • The PM skill of summarization • Giving and receiving hard feedback effectively • The value of a positive mindset • Tips for breaking into product management • Much more — Brought to you by: • The Enterprise Ready Conference — For B2B leaders building enterprise SaaS • Command AI — AI-powered user assistance for modern products and impatient users • Eppo — Run reliable, impactful experiments — Find the transcript at: https://www.lennysnewsletter.com/p/becoming-more-strategic-anneka-gupta — Where to find Anneka Gupta: • X: https://x.com/annekagupta • LinkedIn: https://www.linkedin.com/in/annekagupta — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Anneka Gupta (01:43) Key mindsets for success (05:30) Managing energy for optimal performance (09:05) Founder mode (18:26) Becoming more strategic (27:54) The importance of decision-making (37:18) Navigating difficult personalities (41:38) Techniques for giving and receiving feedback (51:01) Transitioning into product management (54:56) Advice for aspiring product managers (59:39) Leveraging AI tools in product management (01:01:27) The power of a positive mindset (01:04:30) Lightning round — Referenced: • Founder Mode: https://paulgraham.com/foundermode.html • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career • The Skip community: https://www.linkedin.com/company/skip-community/ • Rubrik: https://www.rubrik.com/ • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske: https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske • Acquired podcast interviews Zuckerberg in San Francisco: https://transistor.fm/acquired-live/ • Hema Mohan on LinkedIn: https://www.linkedin.com/in/hemamohan/ • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • LiveRamp: https://liveramp.com/ • Product Management class at Stanford: https://www.gsb.stanford.edu/experience/learning/experiential-learning/action-learning-program/product-management • Figma: https://www.figma.com/ • Dovetail: https://try.dovetail.com/ • The Remarkable Advantage of Abundant Thinking: https://review.firstround.com/the-remarkable-advantage-of-abundant-thinking/ • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 • Brandon Sanderson’s books: https://www.amazon.com/stores/Brandon-Sanderson/author/B001IGFHW6 • Fallout on Prime Video: https://www.amazon.com/dp/B0CN4HV16N • Thunderbolt 4 ( 3-meter cable): https://www.apple.com/shop/product/MW5H3AM/A/thunderbolt-4-usb%E2%80%91c-pro-cable-3-m • Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov • The complete Foundation series: https://www.amazon.com/Complete-Asimovs-Foundation-Foundations-Prelude/dp/B01EFDEMS8 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tristan de Montebello is the co-creator of Ultraspeaking, the most effective method I’ve come across for rapidly improving communication and presentation skills. In 2017, Tristan became the fastest person ever to reach the finals of the World Championship of Public Speaking, achieving this feat in just seven months with no prior experience. In our conversation, we discuss: • Why public speaking is a meta skill that can transform your life • Practical games and exercises to improve your speaking skills • The “Accordion Method” for preparing talks without memorization • The “Bow and Arrow Technique” for crafting memorable presentations • Tristan’s journey to the World Championship of Public Speaking finals • Lenny doing some of the exercises live on-screen Tristan is offering a limited-time discount to Ultraspeaking. Both codes are valid until November 14, 2024: → $500 off an Unlimited Membership with code UNLIMITEDLENNY500 → $200 off a Rapid Tier pass for a single cohort with code RAPIDLENNY200 — Brought to you by: • Eppo—Run reliable, impactful experiments • Command AI—AI-powered user assistance for modern products and impatient users • Brave Search—A smarter way to search — Find the transcript at: https://www.lennysnewsletter.com/p/master-public-speaking-tristan-de-montebello — Where to find Tristan de Montebello: • X: https://x.com/Montebello • LinkedIn: https://www.linkedin.com/in/tristandemontebello/ • Website: https://ultraspeaking.com • Free email course: https://ultraspeaking.com/lenny/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Tristan de Montebello and Ultraspeaking (01:42) Personal experiences with public speaking (05:35) Misconceptions and meta skills in public speaking (08:56) Enjoyment as a barometer for effective speaking (15:30) Tactical tips for public speaking (29:15) The importance of practice and games (34:50) Game 1: The Conductor (Accessing different emotional states) (45:54) Mindset shift: playing the game (51:07) Game 2: Triple Step (Staying focused amid distractions) (01:07:51) Quieting the noise (01:09:46) Game 3: Conviction Prompts (Building executive presence) (01:17:27) The Accordion Method explained (01:37:57) The Bow and Arrow technique (01:43:43) Final thoughts and encouragement (01:44:55) Lightning round — Referenced: • Michael Gendler on LinkedIn: https://www.linkedin.com/in/michaelgendler • Alienor playing Conductor: https://www.youtube.com/watch?v=nmholFWwHro • Triple Step: https://ultraspeaking.com/triple-step-game/ • Rapid Fire Analogies: https://ultraspeaking.com/rapid-fire-game/ • Joe Rogan Experience #1309 — Naval Ravikant: https://www.youtube.com/watch?v=3qHkcs3kG44 • The Big Leap: Conquer Your Hidden Fear and Take Life to the Next Level: https://www.amazon.com/Big-Leap-Conquer-Hidden-Level/dp/0061735361 • Tall poppy syndrome: https://en.wikipedia.org/wiki/Tall_poppy_syndrome • Peaky Blinders on Netflix: https://www.netflix.com/title/80002479 • The Nice Guys on Prime Video: https://www.amazon.com/Nice-Guys-Russell-Crowe/dp/B01FV1GLR8 • Ember temperature control smart mug: https://www.amazon.com/Ember-Temperature-Control-1-5-hr-Battery/dp/B07NQRM6ML • How I got to the World Championships of Public Speaking in 7 months: https://medium.com/the-mission/3000-people-staring-c2cbd14c6d6c — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Raiza Martin is a senior product manager for AI at Google Labs, where she leads the team behind NotebookLM, an AI-powered research tool that includes a delightful podcast-on-demand feature called “Audio Overviews.” NotebookLM started as a 20% project and has grown into a product that’s spreading across social media and has a Discord server with over 60,000 users. Raiza previously worked on AI Test Kitchen and has a background in startups, payments, and ads. In our conversation, we discuss: • The origin story of NotebookLM • The future road map for NotebookLM • How Google Labs operates differently from the rest of Google • The development of the “Audio Overviews” feature • Key metrics and growth of NotebookLM • Stories about collaborating with author Steven Johnson • Navigating potential misuse of AI technology — Brought to you by: • Explo — Embed customer-facing analytics in your product • Sprig⁠⁠ — Build products for people, not data points • Sidebar — Accelerate your career by surrounding yourself with extraordinary peers — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/googles-notebooklm-raiza-martin — Where to find Raiza Martin: • X: https://x.com/raiza_abubakar • LinkedIn: https://www.linkedin.com/in/whatsaraiza/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to NotebookLM (05:43) The genesis of NotebookLM (08:08) Innovative features and use cases (18:52) Building a startup culture within Google (24:28) Expanding user demographics (27:30) The product roadmap (32:18) Other use cases (36:11) Collaborating with Steven Johnson (42:49) Ensuring ethical AI (46:06) Future directions and user engagement — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

JM Nickels is a Senior Director of Product Management at Uber. Previously, he was Head of Product for Commercialization at Waymo and led product teams at DoorDash. JM is also a coach and advisor focused on conscious leadership. In our conversation, we discuss: • How to sharpen your vision and strategy skills • What “conscious leadership” means and how to practice it • Practical techniques for managing stress • The power of soft skills and emotional intelligence in product leadership • Lessons from working at Uber, Waymo, and DoorDash • Keys to living a successful and fulfilling life • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • The Enterprise Ready Conference — For B2B leaders building enterprise SaaS • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/becoming-a-conscious-leader-john-mark-nickels — Where to find John Mark Nickels: • X: https://x.com/nickelsjm • LinkedIn: https://www.linkedin.com/in/jmnickels/ • Website: https://www.rhythmofbeing.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to JM (02:02) Conscious leadership explained (03:41) The power of soft skills (07:34) Navigating Uber’s evolution (12:41) Embracing emotions and inner work (21:46) Crafting strategy and vision (41:16) Balancing vision and execution (46:13) Lessons from DoorDash, Uber, and Waymo (52:32) The future of autonomous ride-hailing (55:18) Contrarian corner: Embracing emotions in the workplace (59:47) Keys to a fulfilling life (01:04:45) Taking responsibility and agency (01:07:29) Lightning round and final thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Alex Komoroske is a strategic leader who merges the practice, theory, and mindset necessary to tackle complex problems. He spent 13 years at Google, where he worked on Search and DoubleClick and led Chrome’s Open Web Platform. He also spearheaded Augmented Reality in Google Maps and developed toolkits to align companywide strategy from the ground up. After serving as Head of Corporate Strategy at Stripe, he is now co-founding a startup aimed at reimagining the web for the AI era. Alex created the popular “Slime Molds” deck, which offers fresh insights into organizational dynamics. He is also the author of the widely read “Bits and Bobs,” a collection of thought-provoking reflections.In our conversation, we delve into: • “Organizational kayfabe” • “Gardening” vs. “building” • How AI will soon change how we build product • How and why to embrace the adjacent possible • The power of reflection and how to build it into your workflow • How to create emergent properties in organizations • How to run effective “strategy salons” or “nerd clubs” • Much more — Brought to you by: • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske — Where to find Alex Komoroske: • X: https://x.com/komorama • LinkedIn: https://www.linkedin.com/in/alex-komoroske-6597336/ • Website: https://www.komoroske.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Alex (01:53) Alex’s Bits and Bobs document (06:20) The Compendium and note-taking process (10:10) The impact of AI and LLMs on product development (14:24) Skills to lean into as a product manager (19:02) How AI makes us better as individuals (23:04) Organizational kayfabe (31:48) Gardening vs. building (34:46) Emergence-oriented thinking (41:55) Slime molds and organizational structure (45:15) Identifying resonant ideas (47:05) The power of metaphors (48:02) Strategy salons and nerd clubs (52:30) Building and sustaining communities (55:59) Productivity hacks and self-control (01:01:04) Life philosophy and personal insights (01:07:52) The adjacent possible (01:15:56) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Benjamin Lauzier has been building and scaling marketplaces for almost 15 years. He was the VP of product and growth at Thumbtack, where he rebuilt the product team and Thumbtack’s growth levers, re-architected their revenue model, and helped double the company’s growth within three years. Prior to Thumbtack, Ben was at Lyft for six years, where he led the supply side of the product organization to a point where 1% of U.S. workers were driving for Lyft every month. Currently, he advises marketplace teams and founders, teaches a Reforge course on marketplace growth, and has recently launched a health tech company called Nurra, which connects users with care advocates to navigate the health-care system. In our conversation, we cover: • What defines a marketplace business • Strategies for growing supply and demand in the early stages • How to measure liquidity and other marketplace health metrics • How to evaluate if a marketplace model is right for your idea • Lessons from Lyft, Thumbtack, and other successful marketplaces • The differences between product management in the U.S. and Europe — Brought to you by: • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want • Vanta—Automate compliance. Simplify security — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-marketplaces-win-benjamin-lauzier — Where to find Benjamin Lauzier: • LinkedIn: https://www.linkedin.com/in/benjaminlauzier/ • Ben’s Reforge course: https://www.reforge.com/courses/marketplace-growth/details — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Ben’s background (02:24) Defining a marketplace (07:52) Challenges in building a marketplace (13:28) Methods for growing supply (15:57) Understanding marketplace liquidity (21:36) Identifying product-market fit in marketplaces (24:10) Evaluating marketplace business models (27:20) Common pitfalls and failures in marketplaces (36:23) Managed marketplaces and quality control (42:26) Lyft’s rental car initiative (46:35) Mentorship and ambassador programs (51:21) Driver recruitment strategies (54:12) Lyft vs. Uber: a strategic analysis (59:24) Cultural differences in tech: Europe vs. U.S. (01:10:30) Building a health advocacy platform (01:16:52) Lightning round and final thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tamar Yehoshua is the president of product and technology at Glean. Prior to joining Glean, Tamar was chief product officer at Slack, where she led product, design, and research as the company scaled, including a 10x increase in revenue, its public listing, and an acquisition by Salesforce. She also led product and engineering teams at Google, working on search, identity, and privacy, and at A9.com, an Amazon company. Tamar has served on the board of directors for RetailMeNot, ServiceNow, Snyk, and Yext. In our conversation, we discuss: • Why you don’t need to be a well-run company to win • The impact of AI on product management and the future of work • How to build strong cross-functional relationships, especially with engineers • Lessons learned from working with leaders like Jeff Bezos and Stewart Butterfield • Strategies for staying ahead in a rapidly evolving tech landscape • Much more — Brought to you by: • Explo—Embed customer-facing analytics in your product • Sprig⁠⁠—Build products for people, not data points • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua — Where to find Tamar Yehoshua: • X: https://x.com/TYehoshua • LinkedIn: https://www.linkedin.com/in/tamar-yehoshua-886217/ • Newsletter: https://tamaryehoshua.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Tamar’s background (02:09) Key advice for career success (06:54) Understanding people and motivations (09:33) The importance of impact (11:20) Navigating company chaos (18:40) Career planning: a different perspective (26:22) Lessons from industry leaders (37:59) Building stronger cross-functional relationships (42:00) Streamlining OKR reviews with async methods (45:26) Why you shouldn’t worry so much about making users unhappy (47:50) The power of listening in leadership (52:34) How to leverage AI so you don’t fall behind (01:06:39) Closing thoughts and lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tal Raviv is a product manager at Riverside, where he joined as its first PM. Over his 12-year career as an individual contributor, Tal has been an early PM at Patreon, AppsFlyer, and Wix, working in consumer growth, developer API platforms, and pricing. He started his career by co-founding a profitable SaaS company and also volunteers as a surf instructor for people with disabilities. In our conversation, Tal shares: • Why he has chosen to stay an individual contributor rather than moving into management • The rise of “super ICs” and how companies can support this career path • Advice for succeeding as a long-term IC product manager • How he uses AI to enhance his productivity • How to build self-reliant teams and make yourself redundant • Lessons from failures • Much more — Brought to you by: • Gamma—A new way to present, powered by AI • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Eppo—Run reliable, impactful experiments — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-super-ic-pm-tal-raviv — Where to find Tal Raviv: • X: https://x.com/talraviv • LinkedIn: https://www.linkedin.com/in/talsraviv/ • Maven course: https://maven.com/tal-raviv/product-manager-productivity-system/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Tal’s background (02:24) Choosing to stay an IC product manager (07:05) The value of IC roles (08:31) Compensation and career path (12:37) Advice for companies on creating space for ICs (14:33) Leveraging AI for productivity (22:44) Build your personal PM productivity system (37:39) Contrarian opinions and insights (44:32) Book smart vs. street smart decision-making (51:51) There’s no one right way to get things done (57:03) Failure corner (01:19:04) Lightning round (01:26:50) Living through conflict — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Eli Schwartz is a leading SEO consultant and the author of Product-Led SEO. He has worked with industry giants like Zapier, Tinder, Coinbase, Quora, LinkedIn, and WordPress to build and execute global SEO strategies that significantly enhanced their organic visibility at scale. In our conversation, Eli shares: • How AI and LLMs are reshaping the SEO landscape • Why you should be focused on mid-funnel SEO strategies • How to determine if SEO is the right approach for your business • Why SEO should be treated as a product rather than just a marketing tactic • SEO myths • The future of search in light of recent legal challenges faced by Google • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Brave Search—A smarter way to search • OneSchema—Import CSV data 10x faster — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/rethinking-seo-in-the-age-of-ai-eli-schwartz — Where to find Eli Schwartz: • X: https://x.com/5le • LinkedIn: https://www.linkedin.com/in/schwartze/ • Website: https://www.elischwartz.co/ • Newsletter: https://www.productledseo.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Eli’s background (02:10) The impact of AI on SEO strategies (11:34) Understanding search intent (15:30) Real-world impact and structured vs. unstructured data (20:19) Top-of-funnel vs mid-funnel SEO strategies (22:57) Case studies (31:29) Steps for getting started with SEO (35:20) Examples of when not to focus on SEO (39:17) Evaluating SEO investment (44:00) Understanding the tradeoffs in marketing channels (46:23) SEO conversion metrics and expectations (52:09) Understanding the time horizon of SEO (59:37) The role of AI in content creation (01:05:26) AI overviews  (01:07:40) Brand building and SEO (01:09:51) Programmatic vs. editorial SEO strategies (01:16:06) Insights from the Google antitrust verdict (01:20:36) Google’s dominance in search (01:23:52) The future of SEO and user choice (01:26:28) SEO myths debunked (01:36:58) Forecasting SEO success (01:44:18) The need for SEO expertise (01:46:26) Lightning round and closing thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Camille Fournier is the author of The Manager’s Path, which many consider the definitive guide for navigating one’s career path in tech. Camille was previously the CTO of Rent the Runway, VP of Technology at Goldman Sachs, Head of Platform Engineering at Two Sigma, and Global Head of Engineering and Architecture at JPMorgan Chase. She is about to release new newest book, Platform Engineering: A Guide for Technical, Product, and People Leaders. In our conversation, we discuss: • What product managers do that annoys engineers • Why major rewrites are a trap • Why you should have fewer one-on-ones • Strategies for organizing and working with platform teams • Tips for new managers • Advice for transitioning from individual contributor to manager • Much more — Brought to you by: • DX—A platform for measuring and improving developer productivity • CommandBar—AI-powered user assistance for modern products and impatient users • Coda—The all-in-one collaborative workspace — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/engineering-leadership-camille-fournier — Where to find Camille Fournier: • LinkedIn: https://www.linkedin.com/in/camille-fournier-9011812/ • Website: https://skamille.medium.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Camille’s background (02:17) Common annoyances between PMs and engineers (07:09) Avoiding the telephone game (08:05) Hoarding ideas and over-engineering (09:55) The importance of involving engineers in ideation (11:37) The middle-person dilemma (14:21) Rewriting systems: a big trap? (20:40) Engineering leadership lessons (36:02) Moving from IC to management (40:32) One-on-one meetings (45:10) Pushing beyond comfort zones (45:27) Building a balanced work culture (48:01) Effective time management strategies (54:15) Advice for platform team success (01:02:42) Platform team responsibilities (01:04:43) When to form a platform team (01:07:02) Thriving on a platform team (01:12:48) AI corner (01:17:03) Lightning round and final thoughts — Referenced: • Platform Engineering: A Guide for Technical, Product, and People Leaders: https://www.amazon.com/Platform-Engineering-Technical-Product-Leaders/dp/1098153642/ • The Manager’s Path: A Guide for Tech Leaders Navigating Growth and Change: https://www.amazon.com/Managers-Path-Leaders-Navigating-Growth/dp/1491973897 • 97 Things Every Engineering Manager Should Know: Collective Wisdom from the Experts: https://www.amazon.com/Things-Every-Engineering-Manager-Should/dp/1492050903 • Avoiding the Rewrite Trap: https://skamille.medium.com/avoiding-the-rewrite-trap-b1283b8dd39e • Levelsio on X: https://x.com/levelsio • Pieter Levels on the Lex Fridman Podcast: https://www.youtube.com/watch?v=oFtjKbXKqbg • GraphQL: https://graphql.org/ • New Blue Sun by André 3000 on Spotify: https://open.spotify.com/album/33Ek6daAL3oXyQIV1uoItD • Musk’s 5 Steps to Cut Internal Bureaucracy at Tesla and SpaceX: https://icecreates.com/insight/musk-s-5-steps-to-cut-internal-bureaucracy-at-tesla-and-spacex-you-may-say-it-s-his-algorithm/ • Ian Nowland on LinkedIn: https://www.linkedin.com/in/inowland/ • Studio Pulls ‘Megalopolis’ Trailer Using Fake Quotes from Famed Movie Critics: https://www.huffpost.com/entry/studio-pulls-megalopolis-trailer-using-fake-quotes-from-famed-movie-critics_n_66c74046e4b0f1ca469413c7 • Claude 2: https://www.anthropic.com/news/claude-2 • What Got You Here Won’t Get You There: How Successful People Become Even More Successful: https://www.amazon.com/What-Got-Here-Wont-There/dp/1401301304 • When Things Fall Apart: Heart Advice for Difficult Times: https://www.amazon.com/When-Things-Fall-Apart-Difficult/dp/1611803438 • Alien: Romulus: https://www.imdb.com/title/tt18412256/ • Whoop: https://www.whoop.com — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Phyl Terry is the author of Never Search Alone, which I’ve seen so many people reference as the most impactful guide they read for finding a job. Phyl was on the founding team of the first company Amazon acquired back in the ’90s and then was CEO of pioneering product consulting firm Creative Good, with companies like Apple, Facebook, and Microsoft as customers. Today, Phyl is the founder and CEO of Collaborative Gain, which 20 years ago pioneered bringing councils to senior product leaders and GMs in Silicon Valley. That’s their day job—in addition to that, Phyl runs a free global community for job seekers based on their latest book. In our conversation, we discuss: • Why you should never search for a job alone • How job search councils work • How to determine your “candidate-market fit” • How to conduct a listening tour • Creating your job mission and OKRs • How to negotiate job offers • The art of asking for help • Tactics for effective networking and interviewing • Much more — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers • Sprig—Build products for people, not data points • Dovetail—The customer insights hub for product teams — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/land-your-dream-phyl-terry — Where to find Phyl Terry: • X: https://x.com/phylterry • LinkedIn: https://www.linkedin.com/in/phylterry/ • Website: https://www.phyl.org/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Phyl’s background (01:58) The concept of job search councils (04:27) The power of community in job searching (08:55) The scale and structure of job search councils (12:27) The impact of job search councils (20:19) The concept of candidate-market fit (22:50) Writing a Mnookin two-pager (24:37) Conducting listening tours (30:12) Creating a focused candidate-market fit (36:20) Advice on finding the right stage of company for you (40:37) Identifying your unique path (45:30) Navigating tough job markets (49:07) Playing to win (53:36) Negotiation tactics for job offers (01:05:12) The gratitude house exercise (01:10:48) The power of asking for help (01:19:18) How to ask for help (01:28:40) Final thoughts and advice (01:38:21) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tomer Cohen is the chief product officer at LinkedIn, responsible for setting the company’s product strategy, leading product development, user experience design, business development, content creation, and customer operations. He also hosts the Building One podcast, where he interviews exceptional builders across various disciplines. In our conversation, we discuss: • How LinkedIn transformed its feed into an engaging content and social platform • Tomer’s famous “We might be wrong, but we are not confused” mantra • The importance of conviction and passion in product leadership • LinkedIn’s approach to experimenting with and implementing AI features • Lessons from Tomer’s rapid career progression at LinkedIn • Strategies for embracing AI in product development — Brought to you by: • Gamma—A new way to present, powered by AI • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Merge—A single API to add hundreds of integrations into your app — Find the transcript at: https://www.lennysnewsletter.com/p/how-linkedin-became-interesting-tomer-cohen — Where to find Tomer Cohen: • LinkedIn: https://www.linkedin.com/in/tomercohen/ • Podcast: https://podcasts.apple.com/us/podcast/building-one-with-tomer-cohen/id1726672498 — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Tomer Cohen and his role at LinkedIn (02:28) The mantra “We might be wrong, but we are not confused” (06:45) Clarity of thought and focus (13:03) Setting ambitious goals and overdelivering (16:18) Transforming LinkedIn’s feed: strategy and execution (22:03) Running experiments at scale (26:24) Goal setting and identifying opportunities  (30:58) AI’s role in LinkedIn’s evolution (35:38) The AI-first mindset at LinkedIn (35:38) Developing an AI-first mindset (44:49) Letting go of your roadmaps and allowing room for exploration (49:12) Career growth and personal insights (55:01) Takeaways (56:39) Lightning round and final thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sean Ellis is one of the earliest and most influential thinkers and operators in growth. He coined the term “growth hacking,” invented the ICE prioritization framework, was one of the earliest people to use freemium as a growth lever, and, most famously, developed the Sean Ellis Test for product-market fit (which a large percentage of founders use today to track if they’ve found PMF). Over the course of his career, Sean was head of growth at Dropbox and Eventbrite; helped companies like Microsoft and Nubank refine their growth strategy; was on the founding team of LogMeIn, which sold for over $4 billion; and is the author of one of the most popular growth books of all time, Hacking Growth, which has sold over 750,000 copies. In our conversation, he shares: • The proper use of the Sean Ellis Test for measuring product-market fit • How to increase your activation and retention rates • How to select the right North Star metric for your business • Case studies from his work growing Dropbox and other products • How growth strategy has changed over the past decade • How AI is impacting growth efforts • Much more — Brought to you by: • Gamma—A new way to present, powered by AI • CommandBar—AI-powered user assistance for modern products and impatient users • Merge—A single API to add hundreds of integrations into your app — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/the-original-growth-hacker-sean-ellis — Where to find Sean Ellis: • X: https://x.com/seanellis • LinkedIn: https://www.linkedin.com/in/seanellis/ • Website: https://www.seanellis.me/ • Substack: https://substack.com/@seanellis — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sean’s background (02:18) The Sean Ellis test explained (06:28) The 40% rule (08:06) Case study: improving product-market fit (12:34) Understanding and leveraging customer feedback (16:50) Challenges and nuances of product-market fit (22:22) When to use the Sean Ellis Test (23:46) When not to use the Sean Ellis Test and other caveats (27:13) Defining your own threshold and how the Sean Ellis Test came about (36:13) Tools for implementing the survey  (37:30) Transitioning from surveys to retention cohorts (39:13) Nubank’s approach (40:18) Case study: Superhuman’s strategy for increasing product-market fit (45:18) Coining the term “growth hacking” (48:24) How to approach growth (57:25) Improving activation and onboarding (01:05:17) Identifying effective growth channels (01:10:28) The power of customer conversations (01:12:43) Developing the Dropbox referral program (01:14:47) The importance of word of mouth (01:15:23) Freemium models and engagement (01:19:21) Picking a North Star metric (01:24:30) The evolution of growth strategies (01:27:12) The ICE and RICE frameworks (01:30:11) AI’s role in growth and experimentation (01:32:52) Final thoughts and lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Vlad Loktev spent 10 years at Airbnb, where he started as an IC PM and quickly advanced to lead the core Airbnb marketplace business and then GM the entire homes business, managing over 1,000 people and reporting directly to CEO Brian Chesky. He recently left Airbnb and joined Index Ventures as their newest partner. Vlad was my manager at Airbnb for many years, and is the person I credit most for teaching me how to be a great product manager. Prior to Airbnb, Vlad spent a year at Zynga, where he helped grow Words with Friends to over 14 million daily active users. In our conversation, Vlad shares: • Insight into Brian Chesky’s leadership style • Why success as a PM is all about impact, impact, impact • Why chaos can be good • Why as a leader it’s OK to let some fires burn • Why you should learn to “poke the bear” • Balancing product release speed with quality • Lessons on prioritization, decision-making, and organizational design • Advice for founders on building company culture • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Vanta—Automate compliance. Simplify security • Eppo—Run reliable, impactful experiments — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/impact-impact-impact-vlad-loktev — Where to find Vlad Loktev: • X: https://x.com/vladimirloktev • LinkedIn: https://www.linkedin.com/in/vladimirloktev/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Vlad’s background (02:54) Reflecting on transformative years at Airbnb (04:28) Skills and mindsets for success (11:03) Impact-driven mindset (13:16) Saying no and inquiry before advocacy  (17:54) “Poking the bear” (22:46) Psychological tools for leadership (30:08) Building and scaling teams (36:12) Letting fires burn (47:34) Embracing chaos (54:40) The unsell email strategy (01:02:01) Finding your place in an organization (01:05:38) The importance of company culture (01:13:16) Airbnb’s unique approach to product management (01:26:41) Failure corner (01:31:32) Lightning round and final thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Nikita Bier is one of the most in-demand consumer, social, and growth experts in the world. He’s the co-founder of TBH (sold to Meta for more than $30 million) and Gas (sold to Discord for millions more) and has helped more consumer apps that have hit #1 in the app stores than any other person I’ve come across. He currently spends his time advising founders on growth, product, and design and is an investor and advisor to some of the best consumer tech companies, including Flo, Locket, Eight Sleep, Citizen, BeReal, Captions, and more. In our conversation, we discuss: • The inside story of how TBH and Gas achieved explosive growth • Strategies for building viral consumer apps • Why teens are such a great audience • Fighting the human trafficking hoax at Gas • The challenge of creating durable social products • His experience working as a PM at Facebook • Advice for founders on building consumer apps • Much more — Brought to you by: • Webflow—The web experience platform • Vanta—Automate compliance. Simplify security • Explo—Embed customer-facing analytics in your product — Book Nikita for 1:1 consultation/mentoring: https://intro.co/NikitaBier — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier — Where to find Nikita Bier: • X: https://x.com/nikitabier  • Threads: https://www.threads.net/@nikitabier • Website: https://intro.co/NikitaBier — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Nikita’s background  (06:08) Nikita’s early ventures: Politify and Outline (08:42) Transition to consumer apps (13:45) The birth of TBH (16:43) Building for teens vs. adults (20:00) TBH’s viral success (32:18) Leveraging live chat (34:08) Lasting lessons from TBH (37:00) Selling TBH to Facebook (42:19) Big-tech product management (48:46) Nikita on why “product management is not real” (51:49) The Tim Cook painting story (53:53) Leaving Facebook and starting a new venture (58:02) Rebuilding TBH and overcoming challenges (59:46) Addressing criticism (01:04:24) The human trafficking hoax (01:09:51) Selling to Discord and lessons learned (01:11:36) Lasting lessons from Gas (01:13:14) Building durable consumer apps (01:22:35) The VC route (01:23:27) Contact permissions in iOS 18 (01:26:53) The success of Dupe (01:31:53) Advice for startup founders (01:34:14) Work with Nikita — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Deb Liu is the CEO of Ancestry and former longtime VP of Product at Facebook. At Facebook, Deb led the creation of Facebook Marketplace, developed the first mobile ad product for apps, built the company’s games business, and launched Facebook Pay. She’s also held leadership roles at PayPal and eBay, serves on the board of Intuit, and is the author of Take Back Your Power. In our conversation, we discuss: • Why you should PM your career like you PM your product • Strategies for incubating new products within large companies • Creating a successful 30-60-90-day plan when starting a new job • The pitfalls of perfectionism • The challenges introverts face in the workplace and how to overcome them • The value of resilience and turning failures into stepping stones • How to leverage coaching in your career development — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Webflow—The web experience platform — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/succeeding-as-an-introvert-deb-liu — Where to find Deb Liu: • Threads: https://www.threads.net/@debliu • LinkedIn: https://www.linkedin.com/in/deborahliu • Substack: https://debliu.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Deb Liu (02:18) Deb’s career journey and key advice (09:45) Navigating new roles and challenges (11:27) Overcoming adversity and failure (15:07) Building billion-dollar businesses at Facebook (19:33) Strategies for zero-to-one innovation (23:40) PM your career like a product (33:53) Challenges and strategies for introverts in business (39:19) Reframing self-promotion (42:25) The power of accountability (46:15) Growth: a game of inches (50:52) The 30-60-90-day plan (56:52) Contrarian corner: career and marriage (58:57) Final nuggets of wisdom (01:03:09) How to find a coach (01:04:47) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kevin Yien leads product for merchant experiences at Stripe. Before that, he meandered his way from being a technical designer to a product manager, built the restaurants business and ecosystem team at Square, and most recently was head of product and design at Mutiny. He also makes ice cream and teaches for fun. In our conversation, we discuss: • Why aspiring PMs should start in engineering, design, or sales • The importance of writing skills, and how to become a better writer • How to automate user research • Kevin’s “unsell email” technique for hiring • The value of keeping a decision log • Insights on AI and its impact on future generations • Lessons from failure — Brought to you by: • BuildBetter—AI for product teams • OneSchema—Import CSV data 10x faster • Eppo—Run reliable, impactful experiments — Find the transcript and show notes at: https://www.lennysnewsletter.com/p/unorthodox-pm-wisdom-kevin-yien — Where to find Kevin Yien: • X: https://x.com/kevinyien • LinkedIn: https://www.linkedin.com/in/kevinyien/ • Website: https://kevinyien.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kevin’s background  (02:00) The story behind Kevin’s profile picture (08:41) The role of a product manager (10:48) Getting started in product management (12:47) The importance of writing skills (15:06) Becoming a better writer (19:10) The PM’s role with engineering and design (28:41) Drawing the perimeter for your team (31:37) Feedback tips (35:13) Decision logs and product sense (45:36) Unorthodox hiring strategies (47:01) The unsell email strategy (54:01) Automating user research (01:02:27) AI in everyday life (01:06:05) Lessons from failure (01:14:34) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Evan LaPointe is the founder of CORE Sciences, which teaches companies and individuals how our brains work and how that translates to improved collaboration, better products, faster decision-making, and more growth. Previously, Evan was the co-founder of Satellite, the fourth-largest analytics product on the internet today (it mostly runs behind the scenes, and pretty much everyone listening will have used it today without knowing it), which was acquired by Adobe, where he later ran product strategy, innovation, and long-range thinking for Adobe’s digital experiences business. In our conversation, we discuss: • The three different systems of the brain • How knowing this can help you become more influential • How understanding different brain states will help you increase productivity and creativity • How to improve your vision and strategy skills • How to design a work environment that fosters innovation • How to build better relationships at work • Much more — Use discount code “LENNY” for $5 off the CORE Sciences personality profile: https://www.core-sciences.com/new-core-identity — Brought to you by: • Webflow—The web experience platform • Explo—Embed customer-facing analytics in your product • Eppo—Run reliable, impactful experiments — Find the transcript and references at: https://www.lennysnewsletter.com/p/understanding-your-brain-evan-lapointe — Where to find Evan LaPointe: • X: https://x.com/evanlapointe • LinkedIn: https://www.linkedin.com/in/evanlapointe/ • Website: https://www.core-sciences.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Evan’s background (02:37) Understanding the brain’s complex systems (07:17) The three core brain systems: safety, reward, and purpose (11:03) Applying brain science to team dynamics (14:27) The role of personality in team performance (17:27) Creating effective work environments (23:16) The science of meetings and decision-making (29:35) Enhancing strategy and vision (54:46) Understanding personality traits in strategy and vision (58:58) Tactical tips for increasing openness (01:05:46) Building influence and effective relationships (01:21:17) The importance of trust and appeal in relationships (01:36:47) Creating a positive organizational habitat (01:50:35) Enhancing focus and productivity (02:00:58) Practical tips for deep work and gamma time (02:07:11) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Joe Hudson is one of the most sought-after executive coaches in Silicon Valley. He is the founder of Art of Accomplishment, a transformational coaching program that has helped tens of thousands of people, including many tech executives and founders from companies like Apple, OpenAI, and Google. His unique method of transformation comes from over 25 years of exploring neurological, psychological, and spiritual traditions, tested against real-world challenges. In our conversation, Joe shares: • Why the critical voice in your head is always wrong, and how to change your relationship with that voice • Why authenticity trumps self-improvement • The importance of embracing all of your emotions • How to create more enjoyable and effective meetings • The power of gratitude in transforming your life • Practical experiments for personal growth • Much more — Apply for Joe’s Connection Course: Thousands of students have taken Joe’s most popular experience, the Connection Course. Unlike most online courses, there is no reading, lectures, or written homework. It is a three-week experiential deep dive where you will apply your learnings to real-life problems—how to make your team more productive, communicate more effectively, and resolve conflicts with ease. Apply here and use the code LENNY for $300 off your enrollment: view.life/lenny. — Brought to you by: • BuildBetter—AI for product teams • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Coda—The all-in-one collaborative workspace — Find the transcript and references at: https://www.lennysnewsletter.com/p/embracing-your-emotions-joe-hudson — Where to find Joe Hudson: • X: https://x.com/FU_joehudson • LinkedIn: https://www.linkedin.com/in/joe-hudson/ • Website: https://www.artofaccomplishment.com/ • Podcast: https://www.artofaccomplishment.com/podcast • Linktree: https://linktr.ee/theartofaccomplishment — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Joe’s background (02:31) The critical voice in your head (06:39) Changing your relationship with the critical voice (13:19) Understanding and embracing emotions (19:52) The importance of emotional fluidity (24:40) Questioning assumptions and self-perception (30:25) The consequences of avoiding emotions (36:57) Experimenting with self-improvement (39:42) Understanding efficiency and enjoyment (43:17) The power of enjoyment in daily tasks (45:03) Innate enjoyment vs. learned enjoyment (46:31) Authenticity vs. self-improvement (50:01) Embracing emotional experiences (55:49) How understanding your emotions helps you make better decisions (01:02:53) Creating effective teams and meetings (01:10:40) Gratitude practice for personal growth (01:15:36) Conclusion and final thoughts — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Brian Tolkin is the Head of Product at Opendoor. Previously, he was one of the early employees at Uber, where he was instrumental in launching and growing UberPool, UberHop, and UberExpress and started one of the first product operations teams in tech. In our conversation, we dive into: • How to enable product and ops to work well together • How to run great product reviews • How to make good decisions with limited data • How he uses the jobs-to-be-done framework at Opendoor • How to stay calm under pressure as a leader • Wild stories from his time at Uber • Challenges faced at Opendoor during the pandemic • Much more — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Explo—Embed customer-facing analytics in your product • Attio—The powerful, flexible CRM for fast-growing startups — Find the transcript and references at: https://www.lennysnewsletter.com/p/scaling-uber-and-opendoor-brian-tolkin — Where to find Brian Tolkin: • X: https://x.com/briantolkin • LinkedIn: https://www.linkedin.com/in/briantolkin/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Brian’s background (02:14) Career beginnings at Uber (02:49) Transitioning from product operations to product management (06:47) Product and operations synergy (10:00) Surge pricing at Uber (12:18) Scaling challenges, and stories (15:47) Opendoor and Covid adaptations (25:38) Product reviews and Jobs to Be Done (40:30) The challenges of A/B testing (42:23) Increasing conviction in solutions (44:33) Leveraging intuition in product decisions (47:07) Partnering with Zillow (52:55) Staying calm under pressure (56:25) Finding the “kernel of truth” in product management (01:00:21) Failure corner: Early days of Uber Pool (01:06:11) Lightning round and final thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Timothy Davis has led performance marketing for all of Shopify for the past 2.5 years, and as a consultant has helped companies like Pinterest, LinkedIn, Redfin, and Eventbrite kickstart and scale their performance marketing teams. In every one of those cases, he got them so performant at paid growth that they significantly scale spend and investment in these channels. In our conversation, we cover: • When and how to start investing in performance marketing • Common mistakes companies make with paid ads • How to build and structure a performance marketing team • How to get your creatives performing better • Strategies for optimizing workflows and team efficiency • How AI will change performance marketing • Much more — Brought to you by: • BuildBetter—AI for product teams • OneSchema—Import CSV data 10x faster • Eppo—Run reliable, impactful experiments — Find the transcript and references at: https://www.lennysnewsletter.com/p/performance-marketing-timothy-davis — Where to find Timothy Davis: • LinkedIn: https://www.linkedin.com/in/timothypatrickdavis/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Timothy’s background  (02:31) Understanding performance marketing  (06:31) The importance of paid search  (08:39) Identifying growth potential  (09:54) Case studies: Hairstory and Ipsy  (12:22) Experimenting with new platforms  (18:57) Choosing the right platforms  (20:23) LinkedIn for B2B marketing  (27:56) When to start investing in paid growth  (33:33) Common mistakes in performance marketing  (37:41) Working with agencies and consultants  (40:36) Hiring for performance marketing  (47:33) Metrics that matter  (54:43) Competitor analysis and CPC insights  (56:15) Custom reports and data visualization (56:38) Understanding impression and click share  (59:10) True competition metrics  (01:02:14) Attribution and incrementality  (01:08:52) Building a performance marketing team  (01:10:53) Creative and ad copy collaboration  (01:15:48) Managing workload and hiring strategy  (01:20:52) Training and onboarding new hires  (01:24:41) Impact of ATT on performance marketing  (01:25:56) The power of creative in ads  (01:29:47) Using AI in performance marketing  (01:37:16) Lightning round  — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Roger Martin is one of the world’s leading experts on strategy and the author of Playing to Win, one of the most beloved books on strategy. He’s written extensively for the Harvard Business Review; consulted for dozens of Fortune 500 companies, including P&G, Lego, and Ford; and written 11 other books. In our conversation, we discuss: • The five key questions you need to answer to develop an effective strategy • Why most companies get strategy wrong • How to avoid “playing to play” instead of playing to win • Real-world strategy examples from Procter & Gamble, Southwest Airlines, Lego, and Figma • How to think about differentiation vs. low cost • Shortcomings of current strategy education • Much more — Correction: Roger pointed out that he made an error during our chat. When I asked him about Richard Rumelt (~16 mins), he thought I said Richard D'Aveni. — Brought to you by: • Webflow—The web experience platform • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Cycle—Your feedback hub, on autopilot — Find the transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin — Where to find Roger Martin: • X: https://x.com/RogerLMartin • LinkedIn: https://www.linkedin.com/in/roger-martin-9916911a9/ • Website: https://rogerlmartin.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Roger’s background (02:20) The importance of strategy (07:00) Challenges in developing strategy (08:30) Critique of modern strategy education (14:00) Hamilton Helmer and Richard Rumelt (17:40) Defining strategy (19:12) The Strategy Choice Cascade (23:20) Playing to win vs. playing to play (24:57) Examples of strategic success (30:49) Differentiation and moats (40:23) Applying strategy to real-world scenarios (43:47) Customer-centric strategy (44:45) Defining the market and product (45:59) Value chain and distribution (48:28) Cost leadership vs. differentiation (53:16) Capabilities and management systems (57:14) Competitive advantage and market positioning (01:02:41) Counterpositioning and fault lines (01:05:53) Adapting to AI and market changes (01:14:11) Betterment over perfection (01:18:42) Final thoughts on strategy — Referenced: • Nearly 10% of S&P 500 CEOs are alumni of Procter & Gamble: https://www.bizjournals.com/cincinnati/news/2023/02/06/10-of-s-p-500-ceos-pg.html • FigJam: https://www.figma.com/figjam/ • Figma: https://www.figma.com/ • What Is Resource-Based Theory?: https://www.igi-global.com/dictionary/the-impact-of-technological-governance-and-political-capabilities-on-firms-performances-under-economic-turbulence/67915 • Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/ • Competitive Strategy: Techniques for Analyzing Industries and Competitors: https://www.amazon.com/Competitive-Strategy-Techniques-Industries-Competitors/dp/0684841487 • VRIO Framework Explained: https://strategicmanagementinsight.com/tools/vrio/ • Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • Boston Consulting Group: https://www.bcg.com/ • Bruce Henderson: https://en.wikipedia.org/wiki/Bruce_Henderson • Lego: https://www.lego.com • Vanguard: https://investor.vanguard.com/ • Southwest Airlines: https://www.southwest.com/ • How Amazon Managed to Dethrone Walmart: https://www.nytimes.com/interactive/2021/08/20/technology/how-amazon-beat-walmart.html • GM Lost a 10-Year Battle with Tesla, Pulling the Plug on a Long Line of EVs: https://www.forbes.com/sites/brookecrothers/2023/07/09/gm-killed-its-electric-cars-and-lost-a-10-year-battle-with-tesla/ • Westlaw: https://www.westlawinternational.com/ • What Is an Economic Moat? Why Warren Buffett Says It Matters for Investors: https://finance.yahoo.com/news/economic-moat-why-warren-buffett-160046125.html • Salomon Brothers: https://en.wikipedia.org/wiki/Salomon_Brothers • US Airways: https://en.wikipedia.org/wiki/US_Airways • Four Seasons: https://www.fourseasons.com/ • Michael Dell on LinkedIn: https://www.linkedin.com/in/mdell/ • Bill Gates on LinkedIn: https://www.linkedin.com/in/williamhgates/ • Mandarin Oriental: https://www.mandarinoriental.com/en/ • Continental Lite: https://en.wikipedia.org/wiki/Continental_Lite • Ted (airline): https://en.wikipedia.org/wiki/Ted_(airline) • Case Study: Oil of Olay: https://www.studocu.com/es/document/universidad-de-murcia/estrategia-de-marketing/case-study-old-of-olay/95079369 • AG Lafley on LinkedIn: https://www.linkedin.com/in/ag-lafley-2381b3201/ • Jack Bogle: https://en.wikipedia.org/wiki/John_C._Bogle • Seven Ways Windows 95 Changed the World: https://www.forbes.com/sites/ianmorris/2015/08/24/windows-95-changed-the-world/ • Where to Start with Strategy? Focus on Betterment: https://rogermartin.medium.com/where-to-start-with-strategy-bae40506304c • Brick by brick: The man who rebuilt the house of Lego shares his leadership secrets: https://www.washingtonpost.com/news/on-leadership/wp/2016/12/08/brick-by-brick-the-man-who-rebuilt-the-house-of-lego-shares-his-leadership-secrets/ • A New Way to Think: Your Guide to Superior Management Effectiveness: https://www.amazon.com/New-Way-Think-Management-Effectiveness/dp/164782351X/ • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • The Design of Business: Why Design Thinking Is the Next Competitive Advantage: https://www.amazon.com/Design-Business-Thinking-Competitive-Advantage/dp/1422177807 • The Opposable Mind: How Successful Leaders Win Through Integrative Thinking: https://www.amazon.com/Opposable-Mind-Successful-Integrative-Thinking/dp/1422118924 • When More Is Not Better: Overcoming America’s Obsession with Economic Efficiency: https://www.amazon.com/When-More-Not-Better-Overcoming/dp/1647820065 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Rory Sutherland is widely regarded as one of the most influential (and most entertaining) thinkers in marketing and behavioral science. He’s the vice chairman of Ogilvy UK, the author of Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life, and the founder of Nudgestock, the world’s biggest festival of behavioral science and creativity. He champions thinking from first principles and using human psychology—what he calls “thinking psycho-logically”—over mere logic. In our conversation, we cover: • Why good products don’t always succeed, and bad ones don’t necessarily fail • Why less functionality can sometimes be more valuable • The importance of fame in building successful brands • The importance of timing in product success • The concept of “most advanced, yet acceptable” • Why metrics-driven workplaces can be demotivating • Lots of real-world case studies • Much more Note: We encountered some technical difficulties that led to less than ideal video quality for this episode, but the lessons from this conversation made it impossible for me to not publish it anyway. Thanks for your understanding and for bearing with the less-than-ideal video quality.  — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Cycle—Your feedback hub, on autopilot • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/what-most-people-miss-about-marketing — Where to find Rory Sutherland: • X: https://x.com/rorysutherland • LinkedIn: https://www.linkedin.com/in/rorysutherland • Book: Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Rory’s background (02:37) The success and failure of products (04:08) Why the urge to appear serious can be a disaster in marketing (08:05) The role of distinctiveness in product design (12:29) The MAYA principle (15:50) How thinking irrationally can be advantageous (17:40) The fault of multiple-choice tests (21:31) Companies that have successfully implemented out-of-the-box thinking (30:31) “Psycho-logical” thinking (31:45) The hare and the dog metaphor (38:51) Marketing’s crucial role in product adoption (49:21) The quirks of Google Glass (55:44) Survivorship bias (56:09) Balancing rational ideas with irrational ideas (01:06:19) The rise and fall of tech innovations (01:09:54) Consistency, distinctiveness, and clarity (01:21:12) Considering psychological, technological, and economic factors in parallel (01:23:35) Where to find Rory — Referenced: • Google Glass: https://en.wikipedia.org/wiki/Google_Glass • Meta Portal TV: https://www.meta.com/portal/products/portal-tv/ • Rory’s quote in a LinkedIn post: https://www.linkedin.com/posts/brad-jackson-04766642_the-urge-to-appear-serious-is-a-disaster-activity-7093497742710210560-1LYN/ • The MAYA Principle: Design for the Future, but Balance It with Your Users’ Present: https://www.interaction-design.org/literature/article/design-for-the-future-but-balance-it-with-your-users-present • Ogilvy: https://www.ogilvy.com/ • MCI: https://www.mci.world/ • Veuve Clicquot: https://en.wikipedia.org/wiki/Veuve_Clicquot • Why do the French call the British ‘the roast beefs’?: http://news.bbc.co.uk/2/hi/2913151.stm • The Killing on Hulu: https://www.hulu.com/series/the-killing-f5da5c2d-4626-4ba9-bcf3-ff5f891771fb • Original The Killing on BBC: https://www.bbc.co.uk/programmes/b017h7m1 • The Mandarin Oriental, Hong Kong: https://www.mandarinoriental.com/en/hong-kong/victoria-harbour • SAT: https://satsuite.collegeboard.org/sat • The Widening Racial Scoring Gap on the SAT College Admissions Test: https://www.jbhe.com/features/49_college_admissions-test.html • What is the age of the captain?: https://www.icopilots.com/what-is-the-age-of-the-captain/ • Octopus Energy: https://octopus.energy/ • Kraken: https://octopusenergy.group/kraken-technologies • Toby Shannan: https://theorg.com/org/shopify/org-chart/toby-shannan • Dunbar’s number: Why we can only maintain 150 relationships: https://www.bbc.com/future/article/20191001-dunbars-number-why-we-can-only-maintain-150-relationships • AO: https://ao.com/ • Zappos: https://www.zappos.com/ • Joe Cano on LinkedIn: https://www.linkedin.com/in/joeycano/ • John Ralston Saul’s website: https://www.johnralstonsaul.com/ • Voltaire’s Bastards: The Dictatorship of Reason in the West: https://www.amazon.com/Voltaires-Bastards-Dictatorship-Reason-West/dp/0679748199 • Psycho-Logic: Why Too Much Logic Deters Magic: https://coffeeandjunk.com/psycho-logic/ • Herbert Simon’s Decision-Making Approach: https://bura.brunel.ac.uk/bitstream/2438/4995/1/Fulltext.pdf • Robert Trivers’s website: https://roberttrivers.com/Welcome.html • Crazy Ivan: https://jollycontrarian.com/index.php?title=Crazy_Ivan • The Joys of Being a Late Tech Adopter: https://www.nytimes.com/2019/08/28/technology/personaltech/joys-late-tech-adopter.html • Jean-Claude Van Damme: https://en.wikipedia.org/wiki/Jean-Claude_Van_Damme • Tim Berners-Lee: https://en.wikipedia.org/wiki/Tim_Berners-Lee • Edward Jenner and the history of smallpox and vaccination: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1200696/ • The real story behind penicillin: https://www.pbs.org/newshour/health/the-real-story-behind-the-worlds-first-antibiotic • What Are Japanese Toilets?: https://www.bigbathroomshop.co.uk/info/blog/japanese-toilets/ • reMarkable: https://remarkable.com/ • Chumby: https://en.wikipedia.org/wiki/Chumby • Survivorship bias: https://en.wikipedia.org/wiki/Survivorship_bias • Jony Ive: https://en.wikipedia.org/wiki/Jony_Ive • Marc Newson’s website: https://marc-newson.com/ • Designing Men: https://www.vanityfair.com/news/business/2013/11/jony-ive-marc-newson-design-auction • Qantas A330: https://marc-newson.com/qantas-a330/ • Herodotus: https://en.wikipedia.org/wiki/Herodotus • Big Decision? Consider It Both Drunk and Sober: https://www.forbes.com/sites/chunkamui/2016/03/22/wine-and-sleep-make-for-better-decisions/?sh=5c97fdc524b1 • How Henry Ford and Thomas Edison killed the electric car: https://www.speakev.com/threads/how-henry-ford-and-thomas-edison-killed-the-electric-car.4270/ • Watch Jay Leno get nostalgic and swoon over this 1909 EV: https://thenextweb.com/news/jay-leno-talk-about-electric-car-1909-baker • Jay Leno’s Garage: https://www.youtube.com/@jaylenosgarage • Nudgestock: https://nudgestock.com/ • Akio Morita: https://en.wikipedia.org/wiki/Akio_Morita • Don Norman on LinkedIn: https://www.linkedin.com/in/donnorman/ • What Makes Tesla’s Business Model Different: https://www.investopedia.com/articles/active-trading/072115/what-makes-teslas-business-model-different.asp • Monica Lewinsky on X: https://x.com/MonicaLewinsky • Blindsight: The (Mostly) Hidden Ways Marketing Reshapes Our Brains: azon.com/Blindsight-Mostly-Hidden-Marketing-Reshapes-ebook/dp/B07ZKZ5DWF • Branding That Means Business: https://www.amazon.com/Branding-that-Means-Business-Economist-ebook/dp/B09QBCCH9N • PwC: https://www.pwc.com • Ryanair: https://www.ryanair.com • British Airways: https://www.britishairways.com/ • Wrigley’s began as a soap business: know when to pivot: https://theamericangenius.com/entrepreneur/wrigleys-began-as-soap-know-when-to-pivot/ • Transport for Humans: https://www.amazon.com/Transport-Humans-Perspectives-Pete-Dyson/dp/1913019357 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jessica Lachs is the global head of analytics and data science at DoorDash, where she’s built one of the largest and most respected data organizations in tech. In her more than 10 years at DoorDash, she has served as the first general manager, responsible for launching new markets; the head of business ops and analytics; and the VP of analytics and data science. Previously, Jessica founded GiftSimple, a social gifting startup, and started her career at Lehman Brothers as an investment banking analyst. In our conversation, she shares: • How to structure and scale a high-impact analytics organization • Centralized vs. decentralized data teams • How to pick the right metric and aligning incentives • Advice for data people on how and when to push back • Lessons learned from building a global data team • How to foster a culture of extreme ownership • The role of AI in improving analytics team productivity • Advice for aspiring data leaders without formal training — Brought to you by: • Webflow—The web experience platform • Anvil—The fastest way to build software for documents • Attio—The powerful, flexible CRM for fast-growing startups — Find the transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-data-org-jessica-lachs — Where to find Jessica Lachs: • X: https://x.com/jesslachs • LinkedIn: https://www.linkedin.com/in/jessica-lachs/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jessica’s background (04:59) Centralized vs. embedded analytics teams (10:52) The benefits of a centralized analytics team (15:10) Balancing proactive and reactive work (20:45) Advice on how to push back effectively (24:20) Hiring for curiosity and problem solving (28:57) Coming from a non-traditional background (34:40) The early days and culture at DoorDash (40:39) Encouraging cross-functional roles (44:39) Defining effective metrics (46:30) Simplifying metrics for better outcomes (55:28) Focusing on edge cases and fail states (01:00:12) Managing a global data organization (01:02:31) Leveraging AI for productivity (01:05:25) Building diverse and skilled data teams (01:08:40) Lightning round — Referenced: • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • Riley Newman on LinkedIn: https://www.linkedin.com/in/rileynewman/ • Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/ • Imposter Syndrome: Why You May Feel Like a Fraud: https://www.verywellmind.com/imposter-syndrome-and-social-anxiety-disorder-4156469 • Stanley Tang on LinkedIn: https://www.linkedin.com/in/stanleytang/ • Andy Fang on LinkedIn: https://www.linkedin.com/in/fangsterr/ • Evan Moore on LinkedIn: https://www.linkedin.com/in/evanmoore/ • How WeDash became the flagship employee program for DoorDash: https://careers.doordash.com/blog/wedash-doordash-employee-program-how-does-it-work • Leading with empathy | Keith Yandell (DoorDash, Uber): https://www.lennysnewsletter.com/p/leading-with-empathy-keith-yandell • The Rose Code: https://www.amazon.com/Rose-Code-Novel-Kate-Quinn/dp/006305941X • Libby app: https://libbyapp.com/ • The West Wing on Prime: https://www.amazon.com/West-Wing-Complete-First-Season/dp/B000KZPG04 • Alias on Prime: https://www.amazon.com/Alias-Season-1/dp/B00748O13S • Joseon sunscreens: https://beautyofjoseon.com/ • Innisfree sunscreens: https://us.innisfree.com/ • John Steinbeck quote: https://www.brainyquote.com/quotes/john_steinbeck_103825 • Vanessa Roberts on LinkedIn: https://www.linkedin.com/in/vanessa-roberts-b8a509a/ • Tia Sherringham on LinkedIn: https://www.linkedin.com/in/tiasherringham/ • Elizabeth Jarvis-Shean on LinkedIn: https://www.linkedin.com/in/elizabeth-jarvis-shean-141a7966/ • Regina (Gina) Tarone on LinkedIn: https://www.linkedin.com/in/regina-tarone-a565a2/overlay/about-this-profile/ • My Journey (Part 1): I have a job that I would never be hired for: https://www.linkedin.com/posts/jessica-lachs_anniversary-datascience-finance-activity-7216912300056727553-mEv6/?utm_source=share&utm_medium=member_desktop • Starting an Analytics Org From Scratch — Lessons From a Decade at DoorDash: https://review.firstround.com/starting-an-analytics-org-from-scratch-lessons-from-a-decade-at-doordash/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jeff Weinstein is a product lead at Stripe, where he helped grow their payment APIs to hundreds of billions in volume and transformed the way founders start companies into a few simple clicks with Atlas. Prior to Stripe, Jeff led several startups and sold companies to Groupon and Box. He’s known for his customer obsession, craft, quality, and building beloved products businesses rely on. In our conversation, we discuss: • The power of customer obsession and how to operationalize it in the product development process • How to pick the right metrics and use them to drive impact • Techniques for getting things done at big companies • A group practice Jeff started to uplevel product craft, called Study Group • The story behind Stripe Atlas and its mission to increase entrepreneurship globally • Lessons from working with the founders of Stripe — Brought to you by: • Pendo—The only all-in-one product experience platform for any type of application • Cycle—Your feedback hub, on autopilot • Anvil—The fastest way to build software for documents — Find the transcript at: https://www.lennysnewsletter.com/p/creating-a-culture-of-excellence — Where to find Jeff Weinstein: • X: https://x.com/jeff_weinstein • LinkedIn: https://www.linkedin.com/in/jeffwweinstein/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jeff’s background  (10:16)  The “go, go, go ASAP + optimistic, long-term compounding” approach (15:38) The importance of craft and quality (24:15) Effective customer communication strategies (28:57) The importance of speed in customer interactions  (33:19) Narrowing your focus (36:53) Why you should pay attention only to paying-customer feedback (40:24) Practicing silence when communicating  (45:33) The role of metrics in product success (54:08) Empowering teams with a single metric (58:23) Picking the right metric for your audience (01:05:10) The importance of metric hygiene (01:11:33) How Stripe uses “study groups” for product improvement (01:37:20) Stripe’s Atlas: simplifying company formation (01:50:38) Automation and operational efficiency (01:55:13) Diversity and team building (02:03:09) Building new products within a large company (02:21:10) Lightning round — Referenced: • Atlas: https://stripe.com/atlas • Stripe: https://stripe.com/ • SQL: https://en.wikipedia.org/wiki/SQL • GitHub: https://github.com/ • Linear: https://linear.app/ • Figma: https://www.figma.com/ • Jeff’s tweet about Stripe’s bug-finder program: https://x.com/jeff_weinstein/status/1777487507934040300 • The “Collison installation”: https://news.ycombinator.com/item?id=18400504 • How we use friction logs to improve products at Stripe: https://dev.to/stripe/how-we-use-friction-logs-to-improve-products-at-stripe-i6p • Fidelity: https://www.fidelity.com/ • 83(b) election: https://docs.stripe.com/atlas/83b-election • Jeff’s tweet about Atlas’s NPS score: https://x.com/jeff_weinstein/status/1788644576330469638 • What is a Delaware corporation? Here’s what makes this state so attractive to businesses: https://stripe.com/resources/more/what-is-a-delaware-corporation • Incorporating in Delaware explained: Why it’s such a popular option for businesses: https://stripe.com/resources/more/incorporating-in-delaware-explained • 7 of Pixar’s Best Storyboard Examples and the Stories Behind Them: https://boords.com/blog/7-of-pixars-best-storyboard-examples-and-the-stories-behind-them • Alex Kehayias on LinkedIn: https://www.linkedin.com/in/alexkehayias/ • Patrick McKenzie on LinkedIn: https://www.linkedin.com/in/patrickmckenzie/ • AngelList: https://www.angellist.com/ • Dan Hightower on LinkedIn: https://www.linkedin.com/in/danhighto/ • Stripe Atlas perks partners: https://support.stripe.com/questions/stripe-atlas-perks-partners • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • High Output Management: https://www.amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884 • Orbiting the Giant Hairball: A Corporate Fool’s Guide to Surviving with Grace: https://www.amazon.com/Orbiting-Giant-Hairball-Corporate-Surviving/dp/0670879835 • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer • Box: https://www.box.com/ • Patrick Collison on X: https://x.com/patrickc • How to with John Wilson on HBO: https://www.hbo.com/how-to-with-john-wilson • The Quiet Girl on Hulu: https://www.hulu.com/movie/the-quiet-girl-b50a4b8e-d3ff-4635-b806-5e7dbd292ca4 • Raycast: https://www.raycast.com/ • Quicksilver: https://qsapp.com/ • Alfred: https://www.alfredapp.com/help/workflows/automations/ • CleanShot: https://cleanshot.com/ • John Collison on X: https://x.com/collision — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mike Maples, Jr. is a legendary early-stage startup investor and a co-founder and partner at Floodgate. He’s made early bets on transformative companies like Twitter, Lyft, Twitch, Okta, Rappi, and Applied Intuition and is one of the pioneers of seed-stage investing as a category. He’s been on the Forbes Midas List eight times and enjoys sharing the lessons he’s learned from his years studying iconic companies. In his new book, Pattern Breakers: Why Some Start-Ups Change the Future, co-authored with Peter Ziebelman, he discusses what he’s found separates startups and founders that break through and change the world from those that don’t. After spending years reviewing the notes and decks from the thousands of startups he’s known over the past two decades, he’s uncovered three ways that breakthrough founders think and act differently. In our conversation, Mike talks about: • The three elements of breakthrough startup ideas • Why you need to both think and act differently • How to avoid the “comparison trap” and “conformity trap” • The importance of movements, storytelling, and healthy disagreeableness in startup success • How to apply pattern-breaking principles within large companies • Mike’s one piece of advice for founders • Much more Pre-order Mike’s book here and get a second signed copy for free. Limited copies are available, so order ASAP: patternbreakers.com/lenny. — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Webflow—The web experience platform — Find the transcript at: https://www.lennysnewsletter.com/p/how-to-find-a-great-startup-idea-mike-maples-jr — Where to find Mike Maples, Jr.: • X: https://x.com/m2jr • LinkedIn: https://www.linkedin.com/in/maples/ • Substack: https://greatness.substack.com/ • Website: https://www.floodgate.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Mike’s background (03:10) The inspiration behind Pattern Breakers (08:09) Uncovering startup insights (11:37) A quick summary of Pattern Breakers (13:52) Coming up with an idea (15:30) Inflections (17:09) Examples of inflections (28:10) Insights (36:58) The power of surprises (47:36) Founder-future fit (55:33) Advice for aspiring founders (56:41) Living in the future: valid opinions (55:34) Case study: Maddie Hall and Living Carbon (58:40) Identifying lighthouse customers (01:00:53) The importance of desperation in customer needs (01:03:57) Creating movements and storytelling (01:24:22) The role of disagreeableness in startups (01:34:42) Applying these principles within a company (01:40:43) Lightning round — Referenced: • Pattern Breakers: Why Some Start-Ups Change the Future: https://www.amazon.com/Pattern-Breakers-Start-Ups-Change-Future/dp/1541704355 • Justin.tv: https://en.wikipedia.org/wiki/Justin.tv • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • The Unconventional Exit: How Justin Kan Sold His First Startup on eBay: https://medium.datadriveninvestor.com/the-unconventional-exit-how-justin-kan-sold-his-first-startup-on-ebay-4d705afe1354 • Kyle Vogt on LinkedIn: https://www.linkedin.com/in/kylevogt/ • The State of Telehealth Before and After the COVID-19 Pandemic: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9035352/ • The Craigslist Killers: https://www.gq.com/story/craigslist-killers • The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host): https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston • Michael Seibel on LinkedIn: https://www.linkedin.com/in/mwseibel/ • The Airbnb Story: How Three Ordinary Guys Disrupted an Industry, Made Billions ... and Created Plenty of Controversy: https://www.amazon.com/Airbnb-Story-Ordinary-Disrupted-Controversy/dp/0544952669 • Scott Cook: https://www.forbes.com/profile/scott-cook/ • Chegg: https://www.chegg.com/ • Aayush Phumbhra on LinkedIn: https://www.linkedin.com/in/aayush/ • Osman Rashid on LinkedIn: https://www.linkedin.com/in/osmanrashid/ • Okta: https://www.okta.com/ • The Man Who Makes the Future: Wired Icon Marc Andreessen: https://www.wired.com/2012/04/ff-andreessen/ • Peter Ludwig on LinkedIn: https://www.linkedin.com/in/peterwludwig/ • Qasar Younis on LinkedIn: https://www.linkedin.com/in/qasar/ • Paul Allen’s website: https://paulallen.com/ • Louis Pasteur quote: https://www.forbes.com/quotes/6145/ • What was Atrium and why did it fail? https://www.failory.com/cemetery/atrium • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/ • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/ • William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly • Maddie Hall on LinkedIn: https://www.linkedin.com/in/maddie-hall-76293135/ • Living Carbon: https://www.livingcarbon.com • Zenefits (now Trinet): https://connect.trinet.com/ • Sam Altman on X: https://x.com/sama • Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/ • Horsley Bridge Partners: https://www.horsleybridge.com/ • David Swensen: https://en.wikipedia.org/wiki/David_F._Swensen • Judith Elsea on LinkedIn: https://www.linkedin.com/in/judithelsea/ • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • Business strategy with Hamilton Helmer (author of 7 Powers): https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer • Lyft’s Focus on Community and the Story Behind the Pink Mustache: https://techcrunch.com/2012/09/17/lyfts-focus-on-community-and-the-story-behind-the-pink-mustache/ • Logan Green on LinkedIn: https://www.linkedin.com/in/logangreen/ • John Zimmer on LinkedIn: https://www.linkedin.com/in/johnzimmer11/ • Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks: https://www.lennysnewsletter.com/p/storytelling-with-nancy-duarte-how • Steve Jobs Introducing the iPhone at MacWorld 2007: https://www.youtube.com/watch?v=x7qPAY9JqE4 • Jonathan Livingston Seagull: https://www.amazon.com/Jonathan-Livingston-Seagull-Richard-Bach/dp/0743278909 • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer • Robin Roberts on LinkedIn: https://www.linkedin.com/in/robin-roberts-393a934b/ • Skunkworks: https://www.lockheedmartin.com/en-us/who-we-are/business-areas/aeronautics/skunkworks.html • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery): https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson • Figma: https://www.figma.com/ • Atlassian: https://www.atlassian.com/ • Vinod Khosla: https://www.khoslaventures.com/team/vinod-khosla/ • Top Five Regrets of the Dying: A Life Transformed by the Dearly Departing: https://www.amazon.com/Top-Five-Regrets-Dying-Transformed-ebook/dp/B07KNRLY1L • Chase, Chance, and Creativity: The Lucky Art of Novelty: https://www.amazon.com/Chase-Chance-Creativity-Lucky-Novelty/dp/0262511355 • Clay Christensen’s books: https://www.amazon.com/stores/Clayton-M.-Christensen/author/B000APPD3Y • Resonate: Present Visual Stories That Transform: https://www.amazon.com/Resonate-Present-Stories-Transform-Audiences/dp/0470632011 • Ferrari on Prime: https://www.amazon.com/Ferrari-Adam-Driver/dp/B0CNDBN672 • Montblanc fountain pens: https://www.montblanc.com/en-us — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dylan Field is the co-founder and CEO of Figma, the collaborative design platform that has revolutionized how product teams work. In my first-ever live podcast, recorded at Figma Config, Dylan and I dig into: • How intuition and product taste drive Dylan’s decision-making • The challenge of keeping things simple • Dylan’s thoughts on the future of product management • Lessons from Figma’s early days • How Figma built their initial user base • Dylan’s journey from intern to CEO of a 1,000+-person company • The future of design tools and AI — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Anvil—The fastest way to build software for documents • User Testing—Human understanding. Human experiences. — Find the transcript at: https://www.lennysnewsletter.com/p/dylan-field-live-at-config — Where to find Dylan Field: • X: https://x.com/zoink?lang=en • LinkedIn: https://www.linkedin.com/in/dylanfield/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction (01:11) Welcoming Dylan Field (02:36) Highlights and surprises from Config (06:58) The philosophy of design (08:01) Raccoon feet and muffin hands (09:57) Building and refining intuition and product taste (12:50) How to influence leadership (16:14) The role of product managers (21:12) The future of product management (22:20) The importance of simplicity in design (26:10) The long road to Figma’s launch (27:44) Advice for aspiring entrepreneurs (29:07) Knowing when it’s time to ship (30:39) Early user acquisition strategies (35:50) Spotting trends and future innovations (39:20) Reflections on leadership and growth (43:16) Lightning round — Referenced: • Mihika Kapoor on LinkedIn: https://www.linkedin.com/in/mihikakapoor/ • Rick Rubin on the Creative Act—60 Minutes: https://www.youtube.com/watch?v=sE1teB5bN-w • Figma pages: https://help.figma.com/hc/en-us/articles/360038511293-Create-and-manage-pages • Leading through uncertainty: A design-led company—Brian Chesky (Config 2023): https://www.youtube.com/watch?v=Dkfijg7s76o • An inside look at how Figma builds product | Yuhki Yamashita (CPO of Figma): https://www.lennysnewsletter.com/p/an-inside-look-at-how-figma-builds • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • An inside look at Figma’s unique GTM motion | Claire Butler (first GTM hire): https://www.lennysnewsletter.com/p/an-inside-look-at-figmas-unique-bottom • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Nadia Singer on LinkedIn: https://www.linkedin.com/in/nadiasinger/ • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/ • FigJam: https://www.figma.com/figjam/ • Tim Van Damme on LinkedIn: https://www.linkedin.com/in/tim-van-damme-maxvoltar/ • Coda: https://coda.io/ • Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/ • Websim: https://websim.ai/ • eToys.com commercial (from Dylan’s childhood acting career): https://www.youtube.com/watch?v=k3Y92aCmmbU — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jessica Livingston is a co-founder of Y Combinator, the first and most successful startup accelerator. Y Combinator has funded over 5,000 companies, 200 of which are now unicorns, including Airbnb, Dropbox, DoorDash, Stripe, Coinbase, and Reddit. Jessica played a crucial role in YC’s early success, when she was nicknamed the “social radar” because of her uncanny ability to quickly evaluate people—an essential skill when investing in early-stage startups. She’s also the host of the popular podcast The Social Radars, where she interviews billion-dollar-startup founders, and the author of the acclaimed book Founders at Work, which captures the origin stories of some of today’s most interesting companies. In our conversation, we discuss: • How Jessica gained the affectionate title of the “social radar” • Why defensive founders are a red flag • How to develop your social radar • What she looks for in founders during YC interviews • How YC’s early inexperience in angel investing led to the batch model • Her favorite stories from interviews with Airbnb, Rippling, and more • Lessons learned from hosting her own podcast • Much more — Brought to you by: • Enterpret—Transform customer feedback into product growth • Anvil—The fastest way to build software for documents • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/the-social-radar-jessica-livingston — Where to find Jessica Livingston: • X: https://x.com/jesslivingston • LinkedIn: https://www.linkedin.com/in/jessicalivingston1/ • Podcast: https://www.thesocialradars.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jessica’s background (02:42) Thoughts on being under-recognized (07:52) Jessica’s superpower: the social radar (15:11) Evaluating founders: key traits and red flags (21:00) The Airbnb story: a lesson in hustle and determination (25:57) A YC success story (28:26) The importance of earnestness (32:45) Confidence vs. defensiveness (34:43) Commitment and co-founder disputes (37:46) Relentless resourcefulness (40:00) Jessica’s social radar: origins and insights (43:24) Honing her social radar skills (45:44) Conviction and scams: a Y Combinator story (46:50) The interview process: challenges and insights (48:20) Operationalizing founder evaluation (49:38) Advice for building social radar skills (52:08) The “Reading the Mind in the Eyes” quiz (55:19) Jessica’s podcast: The Social Radars (01:00:34) Lessons from podcasting and interviewing (01:09:58) Lightning round — Referenced: • Paul Graham’s post about Jessica: https://paulgraham.com/jessica.html • Paul Graham on X: https://x.com/paulg • Robert Tappan Morris: https://en.wikipedia.org/wiki/Robert_Tappan_Morris • Trevor Blackwell on X: https://x.com/tlbtlbtlb • Y Combinator: https://www.ycombinator.com/ • “The Founders” examines the rise and legend of PayPal: https://www.economist.com/culture/2022/02/19/the-founders-examines-the-rise-and-legend-of-paypal • Patrick Collison on X: https://x.com/patrickc • John Collison on X: https://x.com/collision • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Nate Blecharczyk on LinkedIn: https://www.linkedin.com/in/blecharczyk/ • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/ • Zenefits: https://connect.trinet.com/hr-platform • Goat: https://www.goat.com/ • Eddy Lu on LinkedIn: https://www.linkedin.com/in/eddylu/ • Drew Houston on LinkedIn: https://www.linkedin.com/in/drewhouston/ • Arash Ferdowsi on LinkedIn: https://www.linkedin.com/in/arashferdowsi/ • Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups •Bitcoin launderer pleads guilty, admits to massive Bitfinex hack: https://www.cnbc.com/2023/08/03/new-york-man-admits-being-original-bitfinex-hacker-during-guilty-plea-in-dc-to-bitcoin-money-laundering.html • Paul Graham’s tweet with the facial recognition test: https://x.com/paulg/status/1782875262855663691 • SmartLess podcast: https://www.smartless.com • Jason Bateman on X: https://x.com/batemanjason • Will Arnett on X: https://x.com/arnettwill • Sean Hayes on X: https://x.com/seanhayes • The Social Radars with Tony Xu, Co-Founder & CEO of DoorDash: https://www.ycombinator.com/library/Ja-tony-xu-co-founder-ceo-of-doordash • The Social Radars with Brian Chesky: https://www.ycombinator.com/library/JW-brian-chesky-co-founder-ceo-of-airbnb • The Social Radars with Patrick and John Collison: https://www.ycombinator.com/library/Kx-patrick-john-collison-co-founders-of-stripe • The Social Radars with Brian Armstrong: https://www.ycombinator.com/library/K3-brian-armstrong-co-founder-and-ceo-of-coinbase • The Social Radars with Emmett Shear: https://www.ycombinator.com/library/KM-emmett-shear-co-founder-of-twitch • The Social Radars with Paul Graham: https://www.ycombinator.com/library/JV-paul-graham-co-founder-of-y-combinator-and-viaweb • The Social Radars with Adora Cheung: https://www.ycombinator.com/library/L0-adora-cheung-co-founder-of-homejoy-instalab • Founders at Work: Stories of Startups’ Early Days: https://www.amazon.com/Founders-Work-Stories-Startups-Early/dp/1430210788 • Startup School: https://www.startupschool.org/ • The Social Radars with Parker Conrad: https://www.ycombinator.com/library/Ky-parker-conrad-founder-of-zenefits-rippling • Rippling: https://www.rippling.com/ • Carry on, Jeeves: https://www.amazon.com/Carry-Jeeves-Dover-Thrift-Editions/dp/0486848957 • Very Good, Jeeves: https://www.amazon.com/Very-Good-Jeeves-Wooster-Book-ebook/dp/B0051GST06 • Right Ho, Jeeves: https://www.amazon.com/Right-Ho-Jeeves-P-Wodehouse-ebook/dp/B083FFDNHN/ • Life: https://www.amazon.com/Life-Keith-Richards-ebook/dp/B003UBTX72/ • My Name Is Barbra: https://www.amazon.com/My-Name-Barbra-Streisand/dp/0525429522 • Clarkson’s Farm on Prime: https://www.amazon.com/Clarksons-Farm-Season-1/dp/B095RHJ52R • Schitt’s Creek on Hulu: https://www.hulu.com/series/schitts-creek-a2e7a946-9652-48a8-884b-3ea7ea4de273 • Yellowstone on Peacock: https://www.peacocktv.com/stream-tv/yellowstone • Sam Altman on X: https://x.com/sama • Justin Kan on LinkedIn: https://www.linkedin.com/in/justinkan/ • Alexis Ohanian on X: https://x.com/alexisohanian • Steve Huffman on LinkedIn: https://www.linkedin.com/in/shuffman56/ • Breaking News: Condé Nast/Wired Acquires Reddit: https://techcrunch.com/2006/10/31/breaking-news-conde-nastwired-acquires-reddit/ • Charles River Venture: https://www.crv.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ami Vora is the Chief Product Officer of Faire, which connects independent retailers and brands around the world. Before Faire, Ami spent over 15 years at Meta, including as VP of Product and Design for WhatsApp (2B+ users), VP of Product for Facebook’s ads system (now $130B of annual revenue), and director at Instagram. She began her career working on developer tools at Microsoft. In our conversation, we discuss: • Why execution eats strategy for breakfast • Using metaphor to rally teams around one shared goal • How to build cross-functional relationships • “Dinosaur brain,” “Toddler soccer,” and the “hill climbing” metaphors • A tactic for handling disagreement • Tips for working well with product-minded founders as a product leader • The story of Ami’s incredible 15-year journey from temp to VP at Meta • Much more — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers. • Anvil—The fastest way to build software for documents. • User Testing—Human understanding. Human experiences. — Find the transcript at: https://www.lennysnewsletter.com/p/authenticity-and-curiosity-ami-vora — Where to find Ami Vora: • LinkedIn: https://www.linkedin.com/in/amvora/ • Substack: https://amivora.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Ami’s background (02:00) The myth of perfection in success (07:55) Emotionally connecting with the job (09:55) Embracing curiosity in moments of challenge (13:16) Thinking in feedback loops (17:17) The “dinosaur brain” metaphor in product reviews (20:20) Strategies for conducting effective product reviews (26:33) Using metaphors and imagery to communicate your vision (29:35) The power of having a shared narrative (31:55) WhatsApp: an example of metaphor in action (34:44) Emulating people that inspire you (36:19) WhatsApp video calling (37:35) Why execution is greater than strategy (41:36) Time allotment for strategy vs. execution (45:10) How to become a better strategic thinker (47:59) The intricacies of implementing feedback (51:53) Being a female leader in tech (55:13) Advice for young women in tech (56:07) Setting goals and aligning incentives (01:01:40) Acknowledging hard truths (01:05:46) Lessons from transitioning to Faire (01:08:40) The importance of a good CPO/CEO relationship (01:11:17) Vetting heads of product and maintaining customer focus (01:12:40) How Ami went from intern to leading major products at Meta (01:14:53) The one thing you should do to be successful in product (01:17:25) Lightning round — Referenced: • Faire: https://www.faire.com/ • Making Meta | Andrew “Boz” Bosworth (CTO): https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto •  Community Wisdom: AMA with Dan Hockenmaier + Facilitating a roadmap session, structuring product teams, navigating an acquisition, companies not needing PMs anymore, and much more: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto • Developing a growth model + marketplace growth strategy | Dan Hockenmaier (Faire, Thumbtack, Reforge): https://www.lennysnewsletter.com/p/developing-a-growth-model-marketplace • Dan Hockenmaier’s website: https://www.danhock.com/ • On Reviews: https://boz.com/articles/reviews • Finding a global optimum always feels like a hill climb: https://www.linkedin.com/posts/amvora_finding-a-global-optimum-always-feels-like-activity-7074776143882588161-jhyy/ • Dolores Park: https://sfrecpark.org/892/Mission-Dolores-Park • Rob Goldman on LinkedIn: https://www.linkedin.com/in/robgoldman/ • Execution eats strategy for breakfast, but execution without strategy leads to burnout: https://rationalpm.substack.com/p/execution-eats-strategy-for-breakfast • The goal of a “strategy” is to change our own team’s behavior: https://amivora.substack.com/p/the-goal-of-a-strategy-is-to-change • The paths to power: How to grow your influence and advance your career | Jeffrey Pfeffer (author of 7 Rules of Power, professor at Stanford GSB): https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer • Path to Power course outline: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Max Rhodes on LinkedIn: https://www.linkedin.com/in/max-rhodes/ • Coupa Coffee: https://www.coupacafe.com/ • Brandee Barker on LinkedIn: https://www.linkedin.com/in/brandeedbarker/ • Year of Yes: How to Dance It Out, Stand In the Sun and Be Your Own Person: https://www.amazon.com/Year-Yes-Dance-Stand-Person/dp/1476777128  • How to tell better stories | Matthew Dicks (Storyworthy): https://www.lennyspodcast.com/how-to-tell-better-stories-matthew-dicks-storyworthy/ • A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4 • The Office on Peacock: https://www.peacocktv.com/stream-tv/the-office • 30 Rock on Peacock: https://www.peacocktv.com/watch-online/tv/30-rock/6240863759978157112 • Dall-E-2: https://openai.com/index/dall-e-2/ • ChatGPT: https://chatgpt.com • Fellow kettles: https://fellowproducts.com/products/stagg-ekg-electric-pour-over-kettle • TikTok’s “Roman Empire” Meme, Explained: https://www.forbes.com/sites/danidiplacido/2023/09/21/tiktoks-roman-empire-meme-explained/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Tanguy Crusson is the product lead for Jira Product Discovery at Atlassian. In his more than 10 years at the company, he has been instrumental in taking several new products from zero to one, including HipChat, Statuspage, and Jira Product Discovery. In this episode, we dive deep into the struggles of innovating and building new products inside a large company. Tanguy shares candid stories about what worked, what didn’t, and his many hard-won lessons learned about how to successfully build 0 to 1. We cover: • Why large companies with so many advantages still fail at creating new products • Lessons learned from building HipChat • How to avoid common pitfalls like competitive myopia and premature scaling • Lessons learned from the acquisition and integration of Statuspage • Insights from the success of Jira Product Discovery • Tactics for protecting your “ugly babies” • The power of “lighthouse users” • The importance of having a “why now” • Much more — Brought to you by: • Vanta—Automate compliance. Simplify security • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/building-0-to-1-inside-atlassian-tanguy-crusson — Where to find Tanguy Crusson: • X: https://x.com/tanguycrusson • LinkedIn: https://www.linkedin.com/in/tanguy-crusson-99832a — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Tanguy’s background (02:30) Tanguy’s journey at Atlassian (07:03) The challenges of innovating in large companies (10:42) Atlassian's high bar for excellence  (12:58) The HipChat story: successes, failures, and lessons learned (20:47) Lessons learned from building HipChat (33:49) Statuspage: a journey of perseverance (39:48) Acquisition challenges and lessons (47:22) Strategic decisions: build, buy, or partner? (48:17) Learning to articulate "why now" (54:08) A quick summary of lessons in this episode (55:40) The success and pain of launching Jira Product Discovery  (58:10) Incubating new products: the Point A program (01:00:13) Failure is the most likely outcome (01:04:15) Atlassian's four-phase approach to launching new products (01:09:20) Breaking rules without breaking trust (01:16:16) Early success and team autonomy (01:17:22) Innovating without disrupting existing customers (01:23:17) The Lighthouse Users program (01:30:00) Protecting and nurturing new ideas (01:36:14) Balancing innovation with personal well-being (01:38:17) A reminder to look after yourself (01:42:06) Lightning round — Referenced: • Atlassian: https://www.atlassian.com/ • HipChat: https://community.atlassian.com/t5/Hipchat/ct-p/hipchat • Stride: https://community.atlassian.com/t5/Stride/ct-p/stride • Statuspage: https://www.atlassian.com/software/statuspage • Opsgenie: https://www.atlassian.com/software/opsgenie • Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery • HipChat billboard: https://x.com/HubSpot/status/654696998126272512 • Announcing our new partnership with Slack: https://www.atlassian.com/blog/announcements/new-atlassian-slack-partnership • Slack shows it’s worried about Microsoft Teams with a full-page newspaper ad: https://www.theverge.com/2016/11/2/13497766/slack-microsoft-teams-new-york-times-ad • What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html • Jira: https://www.atlassian.com/software/jira • Confluence: https://www.atlassian.com/software/confluence • PagerDuty: https://www.pagerduty.com/ • New Relic: https://newrelic.com/ • BigPanda: https://www.bigpanda.io/ • Transparent Uptime: http://www.transparentuptime.com/ • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Figma: https://www.figma.com/ • Lessons from Atlassian: Launching new products, getting buy-in, and staying ahead of the competition | Megan Cook (head of product, Jira): https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching • Noah Weiss on LinkedIn: https://www.linkedin.com/in/noahw/ • Tanguy’s LinkedIn post about “lighthouse users”: https://www.linkedin.com/posts/tanguy-crusson-99832a_lighthouse-users-one-of-the-pm-techniques-activity-7176654510801502210-hWNi/ • Pixar Chief: Protect Your ‘Ugly Babies’ (Your Unsightly Ideas): https://www.forbes.com/sites/andyboynton/2014/03/17/pixar-chief-protect-your-ugly-babies-your-unsightly-ideas/ • Atlas: https://www.atlassian.com/software/atlas • Point A: https://www.atlassian.com/point-a • Scott Farquhar on LinkedIn: https://www.linkedin.com/in/scottfarquhar • Who: A Method for Hiring: https://www.amazon.com/Who-Method-Hiring-HC-2008/dp/B004C79SRS/ • Hakim’s Odyssey: Book 1: From Syria to Turkey: https://www.amazon.com/Hakims-Odyssey-Book-Syria-Turkey/dp/1637790007 • Living with the Earth, Volume 1: Permaculture, Ecoculture: Inspired by Nature: https://www.amazon.com/Living-Earth-Gardeners-Permaculture-Ecoculture/dp/1856232603/ • INRIA: https://en.wikipedia.org/wiki/French_Institute_for_Research_in_Computer_Science_and_Automation • How a Hydrofoil Works: https://web.mit.edu/2.972/www/reports/hydrofoil/hydrofoil.html • What Is Kitefoil or Foilboarding?: https://www.whenitswindy.com/wp/?page_id=534 • Freediving: https://en.wikipedia.org/wiki/Freediving • Tanguy’s freediving stats: https://www.aidainternational.org/Athletes/Profile-00000000-0000-0000-0000-000000000a45 • Perplexity: https://www.perplexity.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jeffrey Pfeffer teaches the single most popular (and somewhat controversial) class at Stanford’s Graduate School of Business: The Paths to Power. He’s also the author of 16 books, including 7 Rules of Power: Surprising—But True—Advice on How to Get Things Done and Advance Your Career. He has taught at Harvard, the London Business School, and IESE and has written for publications like Fortune and the Washington Post. Recognized by the Academy of Management and listed in the Thinkers50 Hall of Fame, Jeffrey also serves on several corporate and nonprofit boards, bringing his expertise to global audiences through seminars and executive education. In our conversation, we discuss: • Jeffrey’s seven rules of power • How individuals can acquire and use power in business • Networking, and how to do it effectively • How to build a non-cringe personal brand • How to increase your influence to amplify your impact • Examples and stories of people building power • Tradeoffs and challenges that come with power — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Webflow—The web experience platform • Heap—Cross-platform product analytics that converts, engages, and retains customers — Find the transcript at: https://www.lennysnewsletter.com/p/the-paths-to-power-jeffrey-pfeffer — Where to find Jeffrey Pfeffer: • X: https://x.com/JeffreyPfeffer • LinkedIn: https://www.linkedin.com/in/jeffrey-pfeffer-57a01b6/ • Website: https://jeffreypfeffer.com/ • Podcast: https://jeffreypfeffer.com/pfeffer-on-power/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jeffrey’s background  (02:54) Understanding discomfort with power (04:56) Power skills for underrepresented groups (07:51) The popularity and challenges of Jeffrey’s class at Stanford (12:21) The seven rules of power (13:03) Success stories from his course (15:43) Building a personal brand (21:11) Getting out of your own way (26:04) Breaking the rules to gain power (30:34) Networking relentlessly (40:10) Why Jeffrey says to “pursue weak ties” (42:00) Using your power to build more power (44:34) The importance of appearance and body language (47:15) Mastering the art of presentation (55:12) Examples of homework assignments that Jeffrey gives students (59:11) People will forget how you acquired power (01:03:58) More good people need to have power (01:10:49) The price of power and autonomy (01:17:13) A homework assignment for you — Referenced: • Gerald Ferris on LinkedIn: https://www.linkedin.com/in/gerald-r-ferris-5816b1b5/ • Political Skill at Work: https://tarjomefa.com/wp-content/uploads/2015/10/4173-engilish.pdf • Laura Esserman, MD: https://cancer.ucsf.edu/people/esserman.laura • Taylor Swift’s website: https://www.taylorswift.com/ • Matthew 7: https://www.biblegateway.com/passage/?search=Matthew%207&version=NIV • Mother Teresa quote: https://www.goodreads.com/quotes/2887-if-you-judge-people-you-have-no-time-to-love • Paths to Power course description: https://jeffreypfeffer.com/wp-content/uploads/2019/10/Pfeffer-OB377-Course-Outline-2018.pdf • 7 Rules of Power: https://jeffreypfeffer.com/books/7-rules-of-power/ • The Knowing-Doing Gap: https://jeffreypfeffer.com/books/the-knowing-doing-gap/ • Derek Kan on LinkedIn: https://www.linkedin.com/in/derekkan/ • Mitt Romney on X: https://x.com/mittromney • Elaine Chao’s website: https://www.elainechao.com/ • Tony Hsieh: https://en.wikipedia.org/wiki/Tony_Hsieh • Zappos: https://www.zappos.com/ • How I Did It: Zappos’s CEO on Going to Extremes for Customers: https://hbr.org/2010/07/how-i-did-it-zapposs-ceo-on-going-to-extremes-for-customers • McKinsey & Company: https://www.mckinsey.com/ • Bain & Company: https://www.bain.com/ • BCG: https://www.bcg.com/ • Keith Ferrazzi’s website: https://www.keithferrazzi.com/ • Deloitte: https://www2.deloitte.com/ • Tristan Walker: https://www.linkedin.com/in/tristanwalker/ • Foursquare: https://foursquare.com/ • Laura Chau on LinkedIn: https://www.linkedin.com/in/laura-chau/ • Canaan Partners: https://www.canaan.com/ • Andreessen Horowitz: https://a16z.com/ • Sequoia Capital: https://www.sequoiacap.com/ • Greylock: https://greylock.com/ • The Women Who Venture (WoVen) Podcast: https://www.canaan.com/woven/podcasts • Imposter syndrome: https://www.psychologytoday.com/us/basics/imposter-syndrome • Gary Loveman and Harrah’s Entertainment: https://www.gsb.stanford.edu/faculty-research/case-studies/gary-loveman-harrahs-entertainment • “If you need help, just ask”: Underestimating compliance with direct requests for help: https://www.gsb.stanford.edu/faculty-research/publications/if-you-need-help-just-ask-underestimating-compliance-direct-requests • Life story of Kathleen Frances Fowler: https://www.forevermissed.com/kathleenfowler/lifestory • Jason Calacanis on LinkedIn: https://www.linkedin.com/in/jasoncalacanis/ • Jason Calacanis: A Case Study in Creating Resources: https://www.gsb.stanford.edu/faculty-research/case-studies/jason-calacanis-case-study-creating-resources • You’re Invited: The Art and Science of Connection, Trust, and Belonging: https://www.amazon.com/Youre-Invited-Science-Cultivating-Influence/dp/0063030977 • View from the Top: https://www.gsb.stanford.edu/experience/learning/guest-speakers/view-top • Omid Kordestani on LinkedIn: https://www.linkedin.com/in/omid-kordestani-46515151/ • Netscape: https://en.wikipedia.org/wiki/Netscape •  Esther Wojcicki on LinkedIn:  https://www.linkedin.com/in/estherwojcicki/ • Leanne Williams: https://med.stanford.edu/profiles/leanne-williams • Precision Psychiatry: Using Neuroscience Insights to Inform Personally Tailored, Measurement-Based Care: https://www.amazon.com/Precision-Psychiatry-Neuroscience-Personally-Measurement-Based/dp/1615371583 • Mark Granovetter on LinkedIn: https://www.linkedin.com/in/mark-granovetter-8161704/ • The Strength of Weak Ties: https://snap.stanford.edu/class/cs224w-readings/granovetter73weakties.pdf • Getting a Job: https://www.amazon.com/Getting-Job-Study-Contacts-Careers/dp/0226305813 • Acting with Power: https://www.amazon.com/Acting-Power-More-Powerful-Believe/dp/110190397X • Articles by Herminia Ibarra: https://herminiaibarra.com/articles/ • Kingdom of the Planet of the Ape: https://www.imdb.com/title/tt11389872/ • Jim Collins’s website: https://www.jimcollins.com/ • Dana Carney on LinkedIn: https://www.linkedin.com/in/danarosecarney/ • Baba Shiv: https://www.gsb.stanford.edu/faculty-research/faculty/baba-shiv • Tony Hayward: https://en.wikipedia.org/wiki/Tony_Hayward • Lloyd Blankfein: https://en.wikipedia.org/wiki/Lloyd_Blankfein • Regis McKenna: https://en.wikipedia.org/wiki/Regis_McKenna • Jack Valenti: https://en.wikipedia.org/wiki/Jack_Valenti • Salman Rushdie quote: https://www.pinterest.com/pin/434175220328596286/ • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • Carole Robin’s 15% rule: https://pen-name.notion.site/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb • Karlie Kloss on Instagram: https://www.instagram.com/karliekloss • Lindsey Graham’s website: https://www.lindseygraham.com/ • Was Microsoft’s Empire Built on Stolen Code? We May Never Know: https://www.wired.com/2012/08/ms-dos-examined-for-thef/ • Who’s who of Jeffrey Epstein’s powerful friends, associates and possible co-conspirators: https://www.cnn.com/2019/08/12/us/jeffrey-epstein-associates-possible-accomplices/index.html • Why Did Martha Stewart Go to Prison? A Look Back at Her 2004 Fraud Case: https://people.com/martha-stewart-fraud-case-prison-sentence-look-back-8550277 • Dianne Feinstein: https://www.congress.gov/member/dianne-feinstein/F000062 • Richard Blum: https://en.wikipedia.org/wiki/Richard_C._Blum • Athena Care Network: https://www.athenacarenetwork.org • James G. March: https://en.wikipedia.org/wiki/James_G._March • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Trump Organization fined $1.6 million for tax fraud: https://apnews.com/article/politics-legal-proceedings-new-york-city-donald-trump-manhattan-e2f1d01525dafb64be8738c8b4f32085 • Rudy Giuliani: https://en.wikipedia.org/wiki/Rudy_Giuliani • Harvard president resigns amid claims of plagiarism and antisemitism backlash: https://www.theguardian.com/education/2024/jan/02/harvard-president-claudine-gay-resigns • Stanford president resigns after fallout from falsified data in his research: https://www.npr.org/2023/07/19/1188828810/stanford-university-president-resigns • Rudy Crew: https://en.wikipedia.org/wiki/Rudy_Crew — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Uri Levine is the co-founder of Waze, the world’s largest community-based traffic and navigation app, acquired by Google for over $1 billion. He’s also founded nine other companies, been on the board of 20 companies, and advised more than 50 companies. He’s most recently the author of Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs, hailed by Steve Wozniak as the “Bible for entrepreneurs.” Uri is dedicated to creating impactful startups that solve real-world problems and has seen everything from failure to moderate success to big success. In our conversation, we dig into: • Why falling in love with the problem is key to startup success • The phases of the startup journey and how to navigate them • Why firing is more important than hiring • How Waze iterated to achieve product-market fit • Tactics for telling a compelling story when fundraising • Much more — Brought to you by: • Vanta—Automate compliance. Simplify security • Mercury—The powerful and intuitive way for ambitious companies to bank • LinkedIn Ads—Reach professionals and drive results for your business — Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-uri-levine — Where to find Uri Levine: • X: https://twitter.com/urilevine1 • LinkedIn: https://www.linkedin.com/in/uri-levine • Website: https://urilevine.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Uri’s background (02:50) Falling in love with the problem (09:03) Signs this is a big enough problem (10:54) The importance of passion (12:06) A pivot example (14:01) Where to find startup ideas (21:57) Finding product-market fit at Waze (29:45) The different phases of a startup journey (36:47) What investors don’t want to hear (39:53) Fundraising tips (48:02) How to make your presentations stronger (50:32) A wild fundraising story (53:46) Firing and hiring (59:50) The 30-day test (01:04:12) Understanding users (01:12:10) Talking to the right users (01:15:36) Lightning round — Referenced: • Fall in Love with the Problem, Not the Solution: A Handbook for Entrepreneurs: https://www.amazon.com/Fall-Love-Problem-Solution-Entrepreneurs/dp/1637741987 • Waze: https://www.waze.com/ • Ben Horowitz on LinkedIn: https://www.linkedin.com/in/behorowitz/ • Ben Horowitz quote: https://quotefancy.com/quote/1635284/Ben-Horowitz-As-a-startup-CEO-I-slept-like-a-baby-I-woke-up-every-2-hours-and-cried • Michael Jordan quote: https://www.forbes.com/quotes/11194/#:~:text=I've%20lost%20almost%20300,that%20is%20why%20I%20succeed. • Steph Curry: https://en.wikipedia.org/wiki/Stephen_Curry • How Airbnb Used Word of Mouth to Change the Travel Industry Forever: https://truested.com/story/airbnb • Space Mountain: https://en.wikipedia.org/wiki/Space_Mountain_(Disneyland) • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence • Steve Wozniak on LinkedIn: https://www.linkedin.com/in/wozniaksteve/ • Uri’s post about the conference in Guatemala with Steve Wozniak: https://www.linkedin.com/posts/uri-levine_jewishnewyear-speakers-book-activity-6980089544079486976-0ADa/ • Leonardo da Vinci quote: https://www.goodreads.com/quotes/9010638-simplicity-is-the-ultimate-sophistication-when-once-you-have-tasted • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead • Nana Korobi Ya Oki: https://ikigaitribe.com/vlog/nana-korobi-ya-oki/ • That Will Never Work: The Birth of Netflix and the Amazing Life of an Idea: https://www.amazon.com/That-Will-Never-Work-Netflix/dp/0316530204 • Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones: https://www.amazon.com/Atomic-Habits-Proven-Build-Break/dp/0735211299 • 8 Great Chess Apps for Beginners and Grand Masters: https://www.wired.com/story/best-chess-apps/ • Pontera: https://pontera.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Cameron Adams is the co-founder and chief product officer of Canva. Canva is one of the world’s most valuable private software companies, used by 95% of Fortune 500 companies. Since its launch in 2013, Canva has grown to over 150 million monthly users in more than 190 countries, generating $2.3 billion in annual revenue. Prior to Canva, Cameron ran a design consultancy, worked at Google on Google Wave, and founded the email startup Fluent. He is also an author of five web design books and a regular speaker at global conferences. In our conversation, we discuss: • Why they spent a year building their minimum viable product (MVP) before launch • Why Canva has no managers, and their unique approach to coaching and performance reviews • Why they encourage employees to “give away their Legos” • Insights into Canva’s SEO growth strategy • Their three-pillar framework for integrating AI into their product • Stories from the early days — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Attio—The powerful, flexible CRM for fast-growing startups • Vanta—Automate compliance. Simplify security. — Find the transcript at: https://www.lennysnewsletter.com/p/inside-canva-with-cameron-adams — Where to find Cameron Adams: • X: https://twitter.com/themaninblue • LinkedIn: https://www.linkedin.com/in/themaninblue • Website: https://themaninblue.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Cameron’s background (02:00) Reflecting on the success of Canva (04:50) Reflecting on hard times (10:01) Canva’s product-obsessed culture (12:02) Why they prioritize internal promotions and hires (13:56) What makes Canva unique (16:31) The concept of giving away your Legos (21:44) Why Canva has no managers (24:29) Product management at Canva (27:56) Reflections on working with a married couple (30:37) Why they spent a year building their MVP before launch (33:49) Advice for building an MVP (41:23) Canva’s onboarding transformation (44:25) Canva’s SEO strategy (50:37) The success of Canva’s freemium strategy (54:24) Integrating AI into Canva’s product (01:01:50) Where to find Cameron — Referenced: • Canva: https://www.canva.com/ • Melanie Perkins on LinkedIn: https://www.linkedin.com/in/melanieperkins • Cliff Obrecht on LinkedIn: https://www.linkedin.com/in/cliff-obrecht-79ba9920 • Jennie Rogerson, Head of People, LinkedIn post about “season opener” events: https://www.linkedin.com/posts/jennierogerson_season-opener-is-one-of-my-favourite-events-activity-7006815614556135424-73bD/ • Game of Thrones on HBO: https://www.hbo.com/game-of-thrones • Woodstock: https://en.wikipedia.org/wiki/Woodstock • ‘Give Away Your Legos’ and Other Commandments for Scaling Startups: https://review.firstround.com/give-away-your-legos-and-other-commandments-for-scaling-startups/ • Minimum viable product (MVP): https://www.productboard.com/glossary/minimum-viable-product-mvp • Canva’s SEO Strategy Is Elite: https://thegrowthplaybook.substack.com/p/canvas-seo-strategy-is-elite • The SEO Strategy That Led Canva to a $40 Billion Valuation: https://www.youtube.com/watch?v=INyGKt6LAqM • Andrianes Pinantoan on LinkedIn: https://www.linkedin.com/in/andrianes/ • Canva Create: https://www.canva.com/canva-create/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matt Dixon is one of the world’s foremost experts in sales and the author of The Challenger Sale, which sold over a million copies worldwide and was a #1 Amazon and Wall Street Journal bestseller. His most recent book, The JOLT Effect, focuses on overcoming customer indecision—one of the biggest challenges to closing deals. Outside of writing, Matt co-founded DCM Insights, a boutique consultancy helping organizations understand customer behavior, and is a frequent contributor to the Harvard Business Review, with more than 20 print and online articles to his credit. In our conversation, we discuss: • Why 40% to 60% of qualified sales opportunities are lost due to customer indecision • Why dialing up FOMO doesn’t work, and what to do instead • The “pings and echoes” technique to catch issues early • The JOLT method for overcoming indecision • Key lessons from The Challenger Sale • Practical examples of how to apply these principles to close more deals — Brought to you by: • Enterpret—Transform customer feedback into product growth • Webflow—The web experience platform • Heap—Cross-platform product analytics that converts, engages, and retains customers — Find the transcript at: https://www.lennysnewsletter.com/p/close-more-deals-matt-dixon — Where to find Matt Dixon: • LinkedIn: https://www.linkedin.com/in/matthewxdixon • Website: https://www.jolteffect.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Matt’s background (01:57) The research behind Matt’s books (06:08) Insights from The JOLT Effect (10:15) FOMO vs. FOMU (18:18) An example of selling software (26:04) The JOLT method Step 1: Judge their level of indecision (29:41) The “pings and echoes” technique (34:49) Step 2: Offer a recommendation (38:36) Step 3: Limit the exploration (41:43) Step 4: Take risk off the table (45:58) When to hit the pause button with a customer (47:27) Insights from The Challenger Sale (49:07) An example of a challenger sale (55:23) Where to find Matt — Referenced: • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennysnewsletter.com/p/a-step-by-step-guide-to-crafting • The Challenger Sale: Taking Control of the Customer Conversation: https://www.amazon.com/Challenger-Sale-Control-Customer-Conversation/dp/0670922854 • The JOLT Effect: How High Performers Overcome Customer Indecision: https://www.amazon.com/JOLT-Effect-Performers-Overcome-Indecision/dp/0593538102 • Gartner acquires CEB: https://www.gartner.com/en/about/acquisitions/history/ceb-acquisition • Tiger King on Netflix: https://www.netflix.com/title/81115994 • Why sourdough went viral: https://www.economist.com/1843/2020/08/04/why-sourdough-went-viral • Neil Rackham: https://en.wikipedia.org/wiki/Neil_Rackham • Status quo bias in decision-making: https://en.wikipedia.org/wiki/Status_quo_bias • Omission bias: https://thedecisionlab.com/biases/omission-bias • Gartner Magic Quadrant & Critical Capabilities: https://www.gartner.com/en/research/magic-quadrant • Dunning-Kruger effect: https://en.wikipedia.org/wiki/Dunning%E2%80%93Kruger_effect • Stop Losing Sales to Customer Indecision: https://hbr.org/2022/06/stop-losing-sales-to-customer-indecision • Dentsply Sirona: https://www.dentsplysirona.com/ • “We happy?” Briefcase scene from Tarantino’s Pulp Fiction: https://www.youtube.com/watch?v=FGchDuOpbhE • Nupro Freedom Cordless Prophy System: https://www.dentsplysirona.com/en-us/discover/discover-by-category/preventive/hygiene-handpieces.html — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Bangaly Kaba was an early growth PM at Facebook, head of growth at Instagram, and VP of Product at Instacart and is currently Director of Product at YouTube overseeing a global team working on creator monetization. Bangaly has also been a growth advisor to dozens of companies, including Twitter, on the board of multiple companies, and is an active angel investor. In our conversation, we discuss: • A simple framework for choosing where to work and what to work on • The importance of “understand work” • The “adjacent users” theory and how it can help you drive growth • Advice for coaching product managers • Invaluable lessons from his time at Instagram, Facebook, and YouTube • Much more — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Mercury—The powerful and intuitive way for ambitious companies to bank • Vanta—Automate compliance. Simplify security. — Find the transcript and references at: https://www.lennysnewsletter.com/p/frameworks-for-growing-your-career-bangaly-kaba — Where to find Bangaly Kaba: • X: https://twitter.com/iambangaly • LinkedIn: https://www.linkedin.com/in/iambangaly/ • Instagram: https://www.instagram.com/iambangaly/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Bangaly’s background (06:31) Choosing where to work and what to work on (08:39) The impact factor (10:53) Evaluating the environment (15:53) The manager component (18:27) The skills part of the equation (23:49) Advice on finding a mentor (25:42) The power of “understand work” (31:17) Operationalizing understand work (37:55) Balancing understand work (41:25) Managing complex change (45:26) Effective management of product managers (51:35) The role of product managers as coaches and team leaders (54:52) Driving growth through flywheels and value proposition (01:03:14) Understanding adjacent users (01:08:41) The role of partnerships and SEO in Instagram’s early growth (01:16:08) The secret behind Instagram’s growth (01:25:37) Lessons from Facebook (01:29:15) Failure corner (01:31:58) Lightning round — Referenced: • Impact = Environment x Skills: How to Make Career Decisions: https://www.reforge.com/blog/how-to-make-career-decisions • Thinking beyond frameworks | Casey Winters (Pinterest, Eventbrite, Airbnb, Tinder, Canva, Reddit, Grubhub): https://www.lennysnewsletter.com/p/thinking-beyond-frameworks-casey • Casey Winters’s blog: https://caseyaccidental.com/ • Ben Thompson’s newsletter: https://stratechery.com/about/ • Elena Verna on how B2B growth is changing, product-led growth, product-led sales, why you should go freemium not trial, what features to make free, and much more: https://www.lennysnewsletter.com/p/elena-verna-on-why-every-company • George Lee on LinkedIn: https://www.linkedin.com/in/geolee/ • Bangaly Kaba: The Path to 1 Billion: Lessons Learned from Growing Instagram—CXL LIVE 2018: https://www.youtube.com/watch?v=L9ZHlb6kj_E • What Is ‘Dogfooding’?: https://www.nytimes.com/2022/11/14/business/dogfooding.html • Bloom’s taxonomy: https://en.wikipedia.org/wiki/Bloom%27s_taxonomy • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/ • Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/ • LeBron James: https://en.wikipedia.org/wiki/LeBron_James • Kobe Bryant: https://en.wikipedia.org/wiki/Kobe_Bryant •  Mike Krzyzewski: https://en.wikipedia.org/wiki/Mike_Krzyzewski • John Calipari: https://en.wikipedia.org/wiki/John_Calipari • Stripe: https://stripe.com/ • Chief: https://chief.com/ • Jobs to be done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • The Adjacent User: https://brianbalfour.com/quick-takes/the-adjacent-user • How the biggest consumer apps got their first 1,000 users: https://www.lennysnewsletter.com/p/how-the-biggest-consumer-apps-got • Alex Zhu on LinkedIn: https://www.linkedin.com/in/keepsilence/ • From Brush to Canvas with Alex Zhu of Musical.ly: https://www.youtube.com/watch?v=ey15v81pwII • Selena Gomez on Instagram: https://www.instagram.com/selenagomez/ • Kim Kardashian on Instagram: https://www.instagram.com/kimkardashian/ • Rob Andrews on LinkedIn: https://www.linkedin.com/in/robby-andrews-64669720/ • Instagram’s growth speeds up as it hits 700 million users: https://techcrunch.com/2017/04/26/instagram-700-million-users/ • Range: Why Generalists Triumph in a Specialized World: https://www.amazon.com/Range-Generalists-Triumph-Specialized-World/dp/0735214484 • Deep Work: Rules for Focused Success in a Distracted World: https://www.amazon.com/Deep-Work-Focused-Success-Distracted/dp/1455586692 • Start at the End: How to Build Products That Create Change: https://www.amazon.com/Start-End-Products-Create-Change/dp/0525534423 • Flighty app: https://www.flightyapp.com/ • Adam Grant on Instagram: https://www.instagram.com/adamgrant/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kenneth Berger coaches startup leaders on how to prevent burnout, advocate for their desired lifestyle, and make a meaningful impact on the world. He’s spent more than 20 years in the tech industry, is a former founder backed by top investors, and was the first product manager at Slack. Kenneth’s core mission is to help startup leaders change the world by learning to ask for what they want, living with integrity, and building genuine relationships even with the people they find most challenging. Currently he is writing a book, Ask for What You Want, in which he aims to share his actionable strategies for creating change in the world. In our conversation, we explore: • Why asking for what you want is so impactful • Three steps to effectively ask for what you want • Challenges that arise when people struggle to ask for what they want • Why hearing “no” is a normal part of the process • The “dream behind the complaint” technique for uncovering desires • Kenneth’s experience of being fired three times from Slack • How embracing fear and discomfort is key to getting what you want • Why discipline is overrated — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers • Webflow—The web experience platform • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/ask-for-what-you-want-kenneth-berger — Where to find Kenneth Berger: • X: https://twitter.com/kberger • Threads: https://www.threads.net/@kberger • LinkedIn: https://www.linkedin.com/in/kberger/ • Website: https://kberger.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kenneth’s background (04:31) The importance of asking for what you want (06:36) Challenges that arise when people struggle to ask for what they want (08:09) A personal example of failing to ask for what you want (09:17) Signs this is a skill you need to work on (10:49) How to get better at knowing what you want (15:28) Why hearing “no” is a normal part of the process (17:29) Getting a “yes” vs. a “hell yes” (19:20) Step 1: Articulate what you want (24:07) Doing an integrity check (26:56) Step 2: Ask for what you want intentionally (30:45) Understanding your influence (34:48) Using complaints as inspiration (36:24) Internal family systems (38:00) Giving feedback (41:24) Step 3: Accept the response (45:22) Kenneth’s experience of being fired three times from Slack (57:30) Advice on being the first PM at a company or startup (01:04:58) Contrarian corner: anti-discipline (01:05:52) Lightning round — Referenced: • Joining as the first product manager: https://www.lennysnewsletter.com/p/joining-as-the-first-product-manager • Internal Family Systems: https://ifs-institute.com/ • How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • Leaders in Tech: https://leadersintech.org/ • The Three Realities Framework | The 15% Rule | Feedback Guidelines: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin • T-group weekends at Stanford: https://www.gsb.stanford.edu/experience/learning/leadership/interpersonal-dynamics/facilitation-training-program/intro-tgroup • DBT skill DEAR MAN: https://www.therapistaid.com/therapy-worksheet/dbt-dear-man • Dialectical behavior therapy (DBT): https://my.clevelandclinic.org/health/treatments/22838-dialectical-behavior-therapy-dbt • Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product at Figma): https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor • Stewart Butterfield on LinkedIn: https://www.linkedin.com/in/butterfield/ • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennysnewsletter.com/p/how-to-fire-people-with-grace-work • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • Jonny Miller’s Nervous System Mastery course: https://nsmastery.com/lenny • Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable-ebook/dp/B00R3MHWUE • Break Point on Netflix: https://www.netflix.com/title/81569920 • Living on Netflix: https://www.netflix.com/title/81582076 • Wimbledon tennis: https://www.wimbledon.com • Wenshan Baozhong tea: https://redblossomtea.com/products/wenshan-baozhong?variant=31629962820 • Tea From Taiwan: https://www.teafromtaiwan.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jag Duggal is chief product officer at Nubank, a decacorn neobank founded in Brazil. It’s valued at over $30 billion, is bigger than Coinbase, Robinhood, Affirm, and SoFi combined, has 100 million customers (more than Bank of America!) while only operating in three countries in Latin America, and 80% to 90% of its growth comes through word of mouth. Prior to Nubank, Jag was a director of product management at Facebook, a senior vice president at Quantcast, and a product leader at Google. In our conversation, we discuss: • How Nubank builds a fanatical user base • Tactics for driving word-of-mouth growth • Measuring customer love through the Sean Ellis score • The importance of strategic clarity • The role of category design in creating successful products • Why companies should strive to be “fundamentally different,” not “incrementally better” • Nubank’s vision for an AI-powered banking future — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Mercury—The powerful and intuitive way for ambitious companies to bank • OneSchema—Import CSV data 10x faster — Find the transcript at: https://www.lennysnewsletter.com/p/be-fundamentally-different-jag-duggal — Where to find Jag Duggal: • LinkedIn: https://www.linkedin.com/in/jagduggal/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jag’s background (04:34) Nubank’s remarkable achievements (06:01) Nubank’s product development process (11:23) Nubank’s values (12:16) Building products people love fanatically (15:21) The Sean Ellis score (21:27) An example project using the Sean Ellis score (25:07) Picking up the phone and calling customers (28:20) The importance of starting small and iterating (30:42) Pushing back effectively (34:10) Uncovering pain points through customer research (37:53) An example of setting a clear hypothesis (42:01) Developing a strategy (52:16) “Be fundamentally different, not incrementally better” (53:10) Category design (57:37) Nubank’s founding story and goals for the future (01:00:46) Advice for adding new product lines (01:03:46) The future of fintech and banking (01:09:23) AI corner (01:12:34) Failure corner (01:20:24) Key takeaways (01:22:11) Lightning round — Referenced: • Nubank: https://nubank.com.br/en/ • Coinbase: https://www.coinbase.com/ • Robinhood: https://www.robinhood.com/ • SoFi: https://www.sofi.com/ • Affirm: https://www.affirm.com/ • Lemonade: https://www.lemfi.com/ • Bank of America: https://www.bankofamerica.com/ • Nubank achieves a world record with more than 7 million people participating in NuBolão in one month: https://building.nubank.com.br/nubank-achieves-world-record-with-nubolao • Nu México carries out first financial transaction 20 meters under the depth of the sea: https://www.bnamericas.com/en/news/nu-mexico-carries-out-first-financial-transaction-20-meters-under-the-depth-of-the-sea • David Vélez on LinkedIn: https://www.linkedin.com/in/david-v%C3%A9lez-1004875 • Cristina Junqueira on LinkedIn: https://www.linkedin.com/in/crisjunqueira • Edward Wible on LinkedIn: https://www.linkedin.com/in/adamedwardwible • Sequoia Capital: https://www.sequoiacap.com/ • Churrascaria: https://en.wikipedia.org/wiki/Churrascaria • Nubank’s real foundation: our culture and values: https://building.nubank.com.br/nubank-culture-and-values/ • Working Backwards Press Release Template and Example: https://www.linkedin.com/pulse/working-backwards-press-release-template-example-ian-mcallister/ • Sean Ellis test: https://productcoalition.com/using-sean-ellis-test-for-measuring-your-product-market-fit-c8ac98053c2c • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ • Ultravioleta: Nubank expands its premium card offer and adds new features on the product’s first anniversary: https://international.nubank.com.br/company/ultravioleta-nubank-expands-its-premium-card-offer-and-adds-new-features-on-the-products-first-anniversary/ • Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast #405: https://www.youtube.com/watch?v=DcWqzZ3I2cY • The Innovation Method Behind Swiffer Madness: https://www.fastcompany.com/3006797/innovation-method-behind-swiffer-madness • Kevin Systrom on LinkedIn: https://www.linkedin.com/in/kevinsystrom/ • Good Strategy, Bad Strategy | Richard Rumelt: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard • Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 • The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/ • How to become a category pirate | Christopher Lochhead (author of Play Bigger, Niche Down, Category Pirates, more): https://www.lennysnewsletter.com/p/how-to-become-a-category-pirate-christopher • Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets: https://www.amazon.com/Play-Bigger-Dreamers-Innovators-Dominate/dp/0062407619 • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market • Citi: https://www.citi.com/ • Santander Bank: https://www.santanderbank.com/ • Fidji Sumo on LinkedIn: https://www.linkedin.com/in/fidjisimo/ • Harvard Kennedy School: https://www.hks.harvard.edu/ • Susan Wojcicki on LinkedIn: https://www.linkedin.com/in/susan-wojcicki-b136a99/ • Coldplay—“Lost+” ft. Jay-Z: https://www.youtube.com/watch?v=PkCDRm_YRFg • Google Buys DoubleClick for $3.1 Billion: https://www.nytimes.com/2007/04/14/technology/14DoubleClick.html • Real-time bidding: https://support.google.com/authorizedbuyers/answer/6136272 • From Third World to First: The Singapore Story: 1965-2000: https://www.amazon.com/Third-World-First-Singapore-1965-2000/dp/0060197765/ • The Gilded Age on HBO: https://www.hbo.com/the-gilded-age • Lomi: https://lomi.com/ • Nubank careers: https://international.nubank.com.br/careers/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Vikrama Dhiman heads all things product at Gojek, including product management, design, program management, and research, across Indonesia, Singapore and India. He has over 16 years of experience building internet products, consults with Fortune 500 companies, and is among the most well-known and respected product leaders in all of Asia. In our conversation, we discuss: • The most common traits among successful product managers • The 3 W’s framework for PM career growth • The Four A’s of leveling up in product management • The right way to push back as a PM • Common pitfalls that stall PM careers • Vikrama’s advice for transitioning into product management • Why intent alone is not enough — Brought to you by: • Uizard—AI-powered prototyping for visionary product leaders • Webflow—The web experience platform • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/a-framework-for-pm-skill-development — Where to find Vikrama Dhiman: • X: https://twitter.com/vikramadhiman • LinkedIn: https://www.linkedin.com/in/vikrama/ • Website: https://www.vikramadhiman.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Vikrama’s background (03:56) Three common traits among great PMs (07:09) The first W: What you produce (15:40) The second W: What you bring to the table (18:58) The third W: What’s your operating model? (20:36) Three traits that make you a great PM to work with (21:49) How to improve the quality and quantity of your outputs (23:26) The art of the pushback (26:55) Common factors that impede career growth (33:39) Vikrama’s personal reflections (39:33) Choosing which skill(s) to focus on developing (46:28) The ambiguity of the PM role (51:47) The 8 axis for PM growth (56:57) Contrarian corner: Why intent alone is not enough (59:30) Lightning round — Referenced: • Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek): https://www.lennysnewsletter.com/p/taxi-mafias-cash-vaults-and-100-mom • How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu: https://www.lennysnewsletter.com/p/how-to-hire-for-measure-and-unlock • Gojek: https://www.gojek.com/en-id • SQL: https://en.wikipedia.org/wiki/SQL • Oracle: https://www.oracle.com/ • Crystal Widjaja on LinkedIn: https://www.linkedin.com/in/crystalwidjaja • Raditya Wibowo: https://www.linkedin.com/in/raditya-wibowo-a0845436/?originalSubdomain=id • Sidu Ponnappa on LinkedIn: https://www.linkedin.com/in/sidup • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennysnewsletter.com/p/leveraging-mentors-to-uplevel-your • Kevin Aluwi on LinkedIn: https://www.linkedin.com/in/kaluwi/ • Workday: https://www.workday.com/ • Salesforce: https://www.salesforce.com/ • Small Data: The Tiny Clues That Uncover Huge Trends: https://www.amazon.com/Small-Data-Clues-Uncover-Trends/dp/1250080681 • Originals: How Non-Conformists Move the World: https://www.amazon.com/Originals-How-Non-Conformists-Move-World/dp/014312885X • Thinking, Fast and Slow: https://www.amazon.com/Thinking-Fast-Slow-Daniel-Kahneman/dp/0374533555 • Miss Congeniality on Prime Video: https://www.amazon.com/Miss-Congeniality-Sandra-Bullock/dp/B002R5HQDK • Schitt’s Creek on Prime Video: https://www.amazon.com/Schitts-Creek/dp/B083LDRW9F • DramaBox: https://www.dramaboxapp.com/ • Am I Overthinking This?: Over-Answering Life’s Questions in 101 Charts: https://www.amazon.com/Am-Overthinking-This-Over-answering-questions/dp/1452175861/ • Crazy Rich Asians on Prime Video: https://www.amazon.com/Crazy-Rich-Asians-Constance-Wu/dp/B07JGJFXBF • 9 Best Hawker Centers in Singapore—and What to Eat There: https://www.afar.com/magazine/best-hawker-centers-in-singapore-and-what-to-eat-there — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Hamilton Helmer is one of the world’s leading experts on business strategy and the author of the seminal book 7 Powers: The Foundations of Business Strategy, which provides a comprehensive framework for understanding what it really takes to achieve and sustain a competitive advantage. With more than three decades of experience in the strategic consulting industry, Hamilton has advised over 200 companies—from burgeoning startups to Fortune 100 giants—on how to identify, build, and leverage their unique strategic powers. In our conversation, we discuss: • Potential sources of power that startups should develop from an early stage • Common misconceptions among companies about the types of power they possess • How power relates to strategy • The difference between a moat and a power • Practical strategies for non-leaders to leverage insights about power and strategy in their work • AI’s impact on competitive advantages and barriers to entry — Brought to you by: • WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs • Vanta—Automate compliance. Simplify security • Paragon—Ship every SaaS integration your customers want — Find the transcript and references at: https://www.lennysnewsletter.com/p/business-strategy-with-hamilton-helmer — Where to find Hamilton Helmer: • X: https://twitter.com/hamiltonhelmer • LinkedIn: https://www.linkedin.com/in/hamilton-helmer-42983/ • Website: https://7powers.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Hamilton’s background (04:08) When power becomes important (08:24) How strategy relates to power (12:09) How power informs strategy (14:46) The sequence of powers (21:13) Common misconceptions (24:39) Network effects vs. network economies (26:58) Uber’s success (29:16) Moats vs. powers (31:12) Strategies for non-leaders to leverage power and strategy (37:51) Advice on how to become a strategic thinker (39:27) AI’s impact on the seven powers (45:43) Why moving fast is not a power (50:24) Three things that create value in a company (51:16) The debt trajectory of the U.S. (56:35) Optimism for the future (59:25) Lightning round — Referenced: • 7 Powers: The Foundations of Business Strategy: https://www.amazon.com/7-Powers-Foundations-Business-Strategy/dp/0998116319 • John von Neumann: https://en.wikipedia.org/wiki/John_von_Neumann • Pearl Harbor: https://www.history.com/topics/world-war-ii/pearl-harbor • Where the Japanese Went Wrong at Pearl Harbor: https://pearlharbor.org/blog/where-japanese-went-wrong-pearl-harbor/ • The ‘7 Powers’ of business success—from one of Netflix’s early investors: https://www.qualitycompounders.com.au/post/the-7-powers-of-business-success-from-one-of-netflix-s-early-investors • 7 Powers: Foundations of Business Strategy (Key Takeaways): https://www.linkedin.com/pulse/7-powers-foundations-business-strategy-key-takeaways-nikita-maloo/ • Strategy Capital: https://strategycapital.com/ • Warren Buffett: https://www.forbes.com/profile/warren-buffett/ • Charlie Munger: https://www.forbes.com/profile/charles-munger/ • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.stripe.press/poor-charlies-almanack • Bill Gates reveals why Warren Buffett was an invaluable source of support during the stormiest period of his career: https://www.businessinsider.com/bill-gates-interview-warren-buffett-support-microsoft-antitrust-lawsuit-2019-6 •  Billionaire Warren Buffett’s Secret Love Affair With Castles, Revealed: https://www.thestreet.com/opinion/billionaire-warren-buffett-s-secret-love-affair-with-castles-revealed-14290973 • Netflix didn’t kill Blockbuster—how Netflix almost lost the movie rental wars: https://www.cnbc.com/2020/09/22/how-netflix-almost-lost-the-movie-rental-wars-to-blockbuster.html • Michael Porter on LinkedIn: https://www.linkedin.com/in/professorporter/ • What Is Strategy?: https://hbr.org/1996/11/what-is-strategy • TSMC: https://www.tsmc.com/english • Toyota Production System: https://en.wikipedia.org/wiki/Toyota_Production_System • America will be left with ‘severe, irreversible scars’ if national debt goes unchecked. Now, a blockbuster report warns the bill is higher than believed, hitting $141T by 2054: https://fortune.com/2024/04/01/america-social-economic-scars-us-debt-gomes-price/ • Ben S. Bernanke: https://www.federalreservehistory.org/people/ben-s-bernanke • Forty-four of 50 U.S. states worsen inequality with ‘upside-down’ taxes: https://www.theguardian.com/us-news/2024/jan/10/states-wealth-inequality-taxes • Joseph A. Schumpeter: https://en.wikipedia.org/wiki/Joseph_Schumpeter • Theory of Economic Development: https://www.amazon.com/Theory-Economic-Development-Science-Classics/dp/0878556982 • The Road to Reality: A Complete Guide to the Laws of the Universe: https://www.amazon.com/Road-Reality-Complete-Guide-Universe/dp/0679776311 • The Gene: An Intimate History: https://www.amazon.com/Gene-Intimate-History-Siddhartha-Mukherjee/dp/147673352X • American Fiction on Prime Video: https://www.amazon.com/American-Fiction-Jeffrey-Wright/dp/B0CQKR72NX • Farahan Sarouk rugs: https://nazmiyalantiquerugs.com/persian-sarouk-farahan-rugs/ • Rory Sutherland on LinkedIn: https://www.linkedin.com/in/rorysutherland • Ogilvy: https://www.ogilvy.com/ • Clint Eastwood quote: https://www.brainyquote.com/quotes/clint_eastwood_168005 • Winston Churchill: https://en.wikipedia.org/wiki/Winston_Churchill • Michelangelo, God’s Architect: The Story of His Final Years and Greatest Masterpiece: https://www.amazon.com/Michelangelo-Gods-Architect-Greatest-Masterpiece/dp/0691195498 • The Last Judgment: https://en.wikipedia.org/wiki/The_Last_Judgment_(Michelangelo) • Theodore Roosevelt: https://www.whitehouse.gov/about-the-white-house/presidents/theodore-roosevelt/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Annie Duke is a former professional poker player, a decision-making expert, and a special partner at First Round Capital. She is the author of Thinking in Bets (a national bestseller) and Quit: The Power of Knowing When to Walk Away and the co-founder of the Alliance for Decision Education, a nonprofit whose mission is to improve lives by empowering students through decision skills education. In our conversation, we cover: • What Annie learned from the late Daniel Kahneman • The power of pre-mortems and “kill criteria” • The relationship between money and happiness • The power of “mental time travel” • The nominal group technique for better decision quality • How First Round Capital improved their decision-making process • Many tactical decision-making frameworks — Brought to you by: • Vanta—Automate compliance. Simplify security. • UserTesting—Human understanding. Human experiences. • LinkedIn Ads—Reach professionals and drive results for your business — Find the transcript at: https://www.lennysnewsletter.com/p/making-better-decisions-annie-duke — Where to find Annie Duke: • X: https://twitter.com/AnnieDuke • LinkedIn: https://www.linkedin.com/in/annie-duke/ • Website: https://www.annieduke.com/ • Substack: https://www.annieduke.com/substack/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Annie’s background (03:53) Lessons from Daniel Kahneman: humility, curiosity, and open-mindedness (09:15) The importance of unconditional love in parenting (15:15) Mental time travel and “nevertheless” (20:06) The extent of improvement possible in decision-making  (24:54) Independent brainstorming for better decisions (35:36) Making sure people feel heard (42:41) The “3Ds” framework to make better decisions (44:49) Decision quality (55:46) Improving decision-making at First Round Capital (01:05:05) Using pre-mortems and kill criteria (01:10:15) Making explicit what’s implicit (01:10:55) The challenges of quitting and knowing when to walk away (01:19:23) Where to find Annie — Referenced: • Daniel Kahneman, Who Plumbed the Psychology of Economics, Dies at 90: https://www.nytimes.com/2024/03/27/business/daniel-kahneman-dead.html • Adversarial collaboration: https://en.wikipedia.org/wiki/Adversarial_collaboration • Does more money correlate with greater happiness?: https://penntoday.upenn.edu/news/does-more-money-correlate-greater-happiness-Penn-Princeton-research# • Income and emotional well-being: A conflict resolved: https://pubmed.ncbi.nlm.nih.gov/36857342/ • Strategic decisions: When can you trust your gut?: https://www.mckinsey.com/capabilities/strategy-and-corporate-finance/our-insights/strategic-decisions-when-can-you-trust-your-gut • Cass Sunstein on X: https://twitter.com/CassSunstein • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside • A framework for finding product-market fit | Todd Jackson (First Round Capital): https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market • First Round Capital: https://firstround.com/ • Brett Berson on X: https://twitter.com/brettberson • Renegade Partners: https://www.renegadepartners.com/ • Renata Quintini on X: https://twitter.com/rquintini • Roseanne Wincek on X: https://twitter.com/imthemusic • Josh Kopelman on X: https://twitter.com/joshk • Bill Trenchard on X: https://twitter.com/btrenchard • Linnea Gandhi on X: https://twitter.com/linneagandhi • Maurice Schweitzer on X: https://twitter.com/me_schweitzer • Problems with premortems: https://sjdm.org/presentations/2021-Poster-Gandhi-Linnea-debiasing-premortem-selfserving~.pdf • Create a Solid Plan on How to Fail Big This Year: https://www.forbes.com/sites/forbesfinancecouncil/2020/02/07/create-a-solid-plan-on-how-to-fail-big-this-year/ • Quit: The Power of Knowing When to Walk Away: https://www.amazon.com/Quit-Power-Knowing-When-Walk/dp/0593422996/ • Richard Thaler on X: https://twitter.com/R_Thaler • Stewart Butterfield on X: https://twitter.com/stewart • Glitch: https://en.wikipedia.org/wiki/Glitch_(video_game) • How the Founder of Slack & Flickr Turned Colossal Failures into Billion-Dollar Companies: https://medium.com/swlh/how-the-founder-of-slack-flickr-turned-failures-into-million-and-billion-dollar-companies-7bcaf0d35d66 • The Most Fascinating Profile You’ll Ever Read About a Guy and His Boring Startup: https://www.wired.com/2014/08/the-most-fascinating-profile-youll-ever-read-about-a-guy-and-his-boring-startup/ • The Alliance for Decision Education: https://alliancefordecisioneducation.org/ • Make Better Decisions course on Maven: https://maven.com/annie-duke/make-better-decisions — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kayvon Beykpour was the longest-serving head of product at Twitter and was GM of Twitter’s consumer division until the platform was acquired by Elon Musk. He originally joined Twitter in 2015 through the acquisition of his company, Periscope, the largest live video streaming platform at the time. Periscope pioneered technology that inspired Instagram Live, TikTok Live, Facebook Live, and other social networks’ expansion into video streaming. In our conversation, we discuss: • The story of being let go from Twitter after Elon’s acquisition • How he turned Twitter’s stagnant culture around • Kayvon’s thoughts on the limitations of frameworks like Jobs to Be Done • Why Periscope failed • Advice for building consumer products • When to copy, when to innovate — Brought to you by: • Enterpret—Transform customer feedback into product growth • OneSchema—Import CSV data 10x faster • Heap—Cross-platform product analytics that convert, engage, and retain customers — Find the transcript at: https://www.lennysnewsletter.com/p/twitters-former-head-of-product-kayvon-beykpour — Where to find Kayvon Beykpour: • X: https://twitter.com/kayvz • LinkedIn: https://www.linkedin.com/in/kayvz/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kayvon’s background (04:31) Getting Elon up to speed at Twitter (11:34) The story of being let go from Twitter after Elon’s acquisition (21:09) Changing the product culture at Twitter (29:44) Building the “hide replies” feature (32:02) Sacred crows, taking bold bets, and reigniting growth (34:28) Aquihires and their impact (42:40) Tips for successful acquisitions and staffing (47:00) The limitations of frameworks like JTBD (53:20) Signs you’ve gone too far with a framework (57:44) Lessons from building Periscope (01:00:41) Reasons why Periscope failed (01:07:24) The challenges of implementing video at Twitter (01:12:05) Copying ideas in good taste (01:17:58) How to get better at building consumer products (01:19:51) What Kayvon is building (01:20:31) Lightning round — Referenced: • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • What it’s like to sell your startup for ~$120 million before it’s even launched: Meet Twitter’s new prized possession, Periscope: https://www.businessinsider.com/what-is-periscope-and-why-twitter-bought-it-2015-3 • Walter Isaacson on LinkedIn: https://www.linkedin.com/in/walter-isaacson-b8b81520/ • Elon Musk on X: https://twitter.com/elonmusk • Parag Agrawal on LinkedIn: https://www.linkedin.com/in/parag-agrawal-5a14742a/ • Jack Dorsey on LinkedIn: https://www.linkedin.com/in/jack-dorsey-a43b07242/ • Blackboard: https://en.wikipedia.org/wiki/Blackboard_Inc. • Keith Coleman on X: https://twitter.com/kcoleman • Esther Crawford on LinkedIn: https://www.linkedin.com/in/esthercrawford/ • Twitter acquires Chroma Labs: https://tech.hindustantimes.com/tech/news/twitter-acquires-chroma-labs-story-aqvcRPAoYXqXJuAbefA6cN.html • John Barnett on LinkedIn: https://www.linkedin.com/in/johnbarnettt/ • Jobs to Be Done framework: https://jobs-to-be-done.com/jobs-to-be-done-a-framework-for-customer-needs-c883cbf61c90 • Hot takes and techno-optimism from tech’s top power couple: https://www.lennyspodcast.com/hot-takes-and-techno-optimism-from-techs-top-power-couple-sriram-and-aarthi/ • Nike Is Unveiling the Kobe 11 Tomorrow Using Periscope: https://sneakernews.com/2015/12/13/nike-is-unveiling-the-kobe-11-tomorrow-using-periscope/ • Chris Sacca’s website: https://chrissacca.com/ • Facebook Live: https://www.facebook.com/formedia/tools/facebook-live • Kevin Hart on X: https://twitter.com/KevinHart4real • Clubhouse: https://www.clubhouse.com/ • Vine: https://en.wikipedia.org/wiki/Vine_(service) • Paul Davison on LinkedIn: https://www.linkedin.com/in/davison/ • Rohan Seth on LinkedIn: https://www.linkedin.com/in/rohanseth/ • Cryptonomicon: https://www.amazon.com/Cryptonomicon-Neal-Stephenson/dp/0380788624 • Reamde: https://www.amazon.com/Reamde-Novel-Neal-Stephenson-ebook/dp/B004XVN0WW • The Name of the Wind: https://www.amazon.com/Name-Wind-Kingkiller-Chronicle-Book-ebook/dp/B0010SKUYM • Star Trek official site: https://www.startrek.com/ • Dune: part 2: https://www.dunemovie.com/ • Oppenheimer on Peacock: https://www.peacocktv.com/stream-movies/oppenheimer • Tokyo Vice on Max: https://www.max.com/shows/tokyo-vice/e7d93204-7f98-4e62-ab52-6c1da053f942 • Devs on Hulu: https://www.fxnetworks.com/shows/devs • Nick Offerman on X: https://twitter.com/nick_offerman • 3 Body Problem on Netflix: https://www.netflix.com/title/81024821 • Perplexity AI: https://www.perplexity.ai/ • Particle: https://www.particle.news/ • Crokinole board game: https://boardgamegeek.com/boardgame/521/crokinole — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Carole Robin spent over 20 years teaching the Stanford Graduate School of Business course Interpersonal Dynamics, affectionately known as “Touchy Feely.” After leaving Stanford, she founded a nonprofit called Leaders in Tech, which applies the Touchy Feely principles to help Silicon Valley executives build their leadership and interpersonal skills. Carole co-authored the popular book Connect: Building Exceptional Relationships with Family, Friends, and Colleagues, which shares key insights from her decades of teaching these courses. In our conversation, we discuss: • The benefits of building robust relationships, in life and work • The 15% rule, and how it will help you build better relationships • The power of vulnerability • Examples of how to practice vulnerability • Why mental models you build early in life hold you back later • The “three realities” and “the net” • The art of inquiry • Practical tips for avoiding defensiveness when getting feedback • The impact of long Covid on Carole’s life — Brought to you by: • Eppo—Run reliable, impactful experiments • CommandBar—AI-powered user assistance for modern products and impatient users • The a16z Podcast—Featuring conversations with the founders and technologists shaping our future — Find the transcript at: https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin — Where to find Carole Robin: • LinkedIn: https://www.linkedin.com/in/carole-robin/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Carole’s background (05:17) The importance of building robust relationships (10:20) The “Touchy Feely” course at Stanford (13:29) An example of the in-class experience (17:19) Leaders in Tech: developing interpersonal competence (21:36) Progressive disclosure and the 15% rule (24:28) Appropriate disclosure (26:52) The power of vulnerability (34:57) Admitting mistakes and sharing feelings (37:08) Understanding mental models (42:57) The “three realities” framework (53:52) The power of feedback and personal change (58:47) The art of inquiry (01:03:27) How to get better at giving feedback (01:07:47) Exercises and continued learning (01:10:49) “Advice hinders relationships” (01:16:49) Failure corner: AFOG (01:20:30) Takeaways (01:21:51) Lessons from long Covid — Referenced: • How to Build Better Relationships: https://www.gsb.stanford.edu/insights/how-build-better-relationships • Connect: Building Exceptional Relationships with Family, Friends, and Colleagues: https://www.amazon.com/Connect-Building-Exceptional-Relationships-Colleagues-ebook/dp/B0894279WZ • Leaders in Tech: https://leadersintech.org/ • Leaders in Tech Fellows: https://leadersintech.org/learnaboutfellows • Steve Jobs: https://www.forbes.com/profile/steve-jobs/ • Sheryl Sandberg on X: https://twitter.com/sherylsandberg • Ursula Burns: https://www.forbes.com/profile/ursula-burns/ • Application for Leaders in Tech: https://leadersintech.org/programs-and-applications • Vygotsky’s Zone of Proximal Development and Scaffolding Theory: https://www.simplypsychology.org/zone-of-proximal-development.html • The Best Leaders Aren’t Afraid to Be Vulnerable: https://hbr.org/2022/07/the-best-leaders-arent-afraid-of-being-vulnerable • The Surprising Benefits of Admitting Mistakes: 5 Ways to Build Intellectual Humility: https://www.forbes.com/sites/tracybrower/2021/12/29/the-surprising-benefits-of-admitting-mistakes-5-ways-to-build-intellectual-humility/ • How to Build Conflict Skills—The Pinch/Crunch Model: https://www.forbes.com/sites/hannahart/2023/12/15/how-to-build-conflict-skills-the-pinchcrunch-model/ • Slides mentioned (The Three Realities Framework | The 15% Rule | Feedback Guidelines): https://www.notion.so/pen-name/Carole-Robin-on-Lenny-s-Podcast-dc7159208e4242428f4b11ebc92285eb • Mindset: The New Psychology of Success: https://www.amazon.com/Mindset-Psychology-Carol-S-Dweck/dp/0345472322 • Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey • Long COVID: major findings, mechanisms and recommendations: https://www.nature.com/articles/s41579-022-00846-2 • Leadership, acceptance, and self-management: my journey with long COVID: https://www.linkedin.com/pulse/leadership-acceptance-self-management-my-journey-long-carole-robin/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Mihika Kapoor is a design-engineer-PM hybrid at Figma, where she was an early PM on FigJam and is now spearheading development on a new product at the company that’s coming out this June. She’s known as the go-to person at Figma for leading new 0-to-1 products, and, as you’ll hear in our conversation, beloved by everyone she works with. Her background includes founding Design Nation, a national nonprofit focused on democratizing design education for undergraduates; spearheading product launches at Meta; and community building within the NYC AI startup scene. In our conversation, we discuss: • How to effectively take ideas from 0 to 1 at larger companies • How to craft a compelling vision • The importance of vulnerability and feedback • The role of intuition and product sense in making decisions • How to practically communicate your vision • How to balance collaboration and strong opinions • Advice for building a strong team culture • Pivoting with grace and enthusiasm • The current AI revolution and its impact on PM — Brought to you by: • Paragon—Ship every SaaS integration your customers want • Lenny’s Talent Team—Hire the best product people. Find the best product gigs • Vanta—Automate compliance. Simplify security — Find the transcript at: https://www.lennysnewsletter.com/p/vision-conviction-hype-mihika-kapoor — Where to find Mihika Kapoor: • X: https://twitter.com/mihikapoor • LinkedIn: https://www.linkedin.com/in/mihikakapoor/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Mihika’s background (04:29) Core attributes of great product managers (07:34) Crafting a compelling vision (12:12) The vision behind FigJam  (18:25) Delivering a vision without design or engineering skills (21:52) Creating momentum (26:36) The importance of strong conviction (27:45) Direct communication (32:48) Building hype (42:20) Immersing yourself in user insights (47:16) Operationalizing user insights   (50:33) Caring deeply about what you build (54:01) Finding passion in your work (57:00) Building a strong culture (01:07:07) Pivoting with grace and enthusiasm (01:11:48) Design Nation (01:13:15) Mihika’s weaknesses (01:16:07) Building new products at larger companies (01:20:50) Coming up with a great idea (01:22:49) The key to going from 0 to 1 (01:26:47) Spreading the idea across the company (01:29:15) Closing thoughts (01:32:11) Lightning round — Referenced: • Figma: https://www.figma.com/ • Sho Kuwamoto on LinkedIn: https://www.linkedin.com/in/shokuwamoto/ • The Medici Effect: What Elephants and Epidemics Can Teach Us About Innovation: https://www.amazon.com/Medici-Effect-Preface-Discussion-Guide/dp/1633692949 • FigJam: https://www.figma.com/figjam/ • Cognition: https://www.cognition-labs.com/ • Devin: https://www.cognition-labs.com/introducing-devin • David Hoang on LinkedIn: https://www.linkedin.com/in/dhoang2/ • Replit: https://replit.com/ • The Making of Maker Week at Figma: https://www.figma.com/blog/the-making-of-maker-week/ • Yuhki Yamashita on LinkedIn: https://www.linkedin.com/in/yuhki/ • Jeff Bezos’ Simple Decision-Making Framework Will Give You Clarity, Conviction, and Courage: https://medium.com/illumination/jeff-bezos-simple-decision-making-framework-will-give-you-clarity-conviction-and-courage-adf8d0183625 • Alice Ching on LinkedIn: https://www.linkedin.com/in/aliceching/ • Karl Jiang on LinkedIn: https://www.linkedin.com/in/karl-jiang-4a07424/ • Kris Rasmussen on LinkedIn: https://www.linkedin.com/in/kristopherrasmussen/ • Config: https://config.figma.com/ • Dev Mode: https://www.figma.com/dev-mode/ • Asana: https://asana.com/ • Julie Zhuo on LinkedIn: https://www.linkedin.com/in/julie-zhuo/ • StrengthsFinder test: https://www.gyfted.me/personality-quiz/strengthsfinder-test-free • Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/ • Vishal Shah on LinkedIn: https://www.linkedin.com/in/vishalnshah/ • Design Disruptors: https://www.invisionapp.com/films/design-disruptors • Daniel Burka on LinkedIn: https://www.linkedin.com/in/dburka/ • Jamie Myrold on LinkedIn: https://www.linkedin.com/in/jamiemyrold/ • Design Nation: https://dn.businesstoday.org/ • Stuart Weitzman on X: https://twitter.com/StuartWeitzman • Joe Gebbia on LinkedIn: https://www.linkedin.com/in/jgebbia/ • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/ • Jambot: https://www.figma.com/community/widget/1274481464484630971/jambot • Hestia: https://en.wikipedia.org/wiki/Hestia • Harry Potter series: https://www.amazon.com/Harry-Potter-Paperback-Box-Books/dp/0545162076 • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927/ • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Expanded-Overcoming-Inspiration/dp/0593594649 • The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X • Severance on AppleTV+: https://tv.apple.com/us/show/severance/umc.cmc.1srk2goyh2q2zdxcx605w8vtx • Dune on Max: https://www.max.com/movies/dune/e7dc7b3a-a494-4ef1-8107-f4308aa6bbf7 • Dune: Part 2: https://www.dunemovie.com/ • Arc browser: https://arc.net/ • Pika: https://pika.art/home • The power of recognition: Why you should celebrate your employees | Josh Miller: https://www.lennyspodcast.com/videos/the-power-of-recognition-why-you-should-celebrate-your-employees-josh-miller/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dalton Caldwell is Managing Director and Group Partner at Y Combinator. Prior to YC, he was the co-founder and CEO of imeem (acquired by MySpace in 2009) and the co-founder and CEO of App.net. During his time at YC, he’s advised more than 35 YC unicorns, including DoorDash, Amplitude, Webflow, and Retool, and has worked across 21 different YC batches. He’s also racked up more than 6,500 office hours with founders. In our conversation, we discuss: • Why founders need to adopt the mindset “Just don’t die” • The most common reason startups fail • When to pivot, and characteristics of a good pivot • The concept of “tar pit ideas” and examples of bad startup ideas • Why investors say no to startups • The importance of market size in investment decisions • The pitfalls of founders over-delegating • Effective ways to talk to customers • 20 ideas Dalton is looking to fund — Brought to you by: • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security • Coda—The all-in-one collaborative workspace — Find the transcript at: https://www.lennysnewsletter.com/p/lessons-from-1000-yc-startups — Where to find Dalton Caldwell: • X: https://twitter.com/daltonc • LinkedIn: https://www.linkedin.com/in/daltoncaldwell/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Dalton’s background (04:41) The value of simple advice (07:04) Dalton’s advice: “Just don’t die” (08:39) Knowing when to stop (11:45) Deciding to pivot (14:26) Characteristics of a good pivot (17:53) Knowing when to pivot (19:03) Zip’s journey and finding a market (21:22) Why Dalton says to “Move towards the mountains and the desert” (23:45) Tar pit ideas (26:49) Understanding why investors say no (29:14) The importance of market size (32:16) Avoiding over-delegation and hiring senior people too early (36:43) Why startups fail (40:30) Effectively talking to customers (45:17) Examples of startups hustling to talk to customers (48:01) Patterns of successful startups (52:05) YC’s Request for Startups (55:37) Early days of Silicon Valley (01:05:33) Contrarian corner: growth hacking for early startups (01:09:28) Failure corner (01:11:15) Closing thoughts (01:12:22) Lightning round — Referenced: • Y Combinator: https://www.ycombinator.com/ • Tiger Woods’s website: https://tigerwoods.com/ • Co-Founder Mistakes That Kill Companies & How to Avoid Them: https://www.youtube.com/watch?v=dlfjs_eEEzs • Daniel Alberson’s LinkedIn post about Y Combinator: https://www.linkedin.com/posts/alberson_i-left-my-dream-job-as-a-product-manager-activity-7089677882431533056-jJ9H • Companies in Y Combinator W17 Batch: https://www.ycdb.co/batch/w17 • Brex: https://www.brex.com/ • Retool: https://retool.com/ • Segment: https://segment.com/ • Mixpanel: https://mixpanel.com/ • Whatnot: https://www.whatnot.com/ • Andreessen Horowitz: https://a16z.com/ • Airbnb’s CEO says a $40 cereal box changed the course of the multibillion-dollar company: https://fortune.com/2023/04/19/airbnb-ceo-cereal-box-investors-changed-everything-billion-dollar-company/ • Rujul Zaparde on LinkedIn: https://www.linkedin.com/in/rujulz/ • Zip: https://ziphq.com/ • Lu Cheng on LinkedIn: https://www.linkedin.com/in/lu-cheng-973b7830/ • Avoid these tempting startup tar pit ideas: https://www.ycombinator.com/library/Ij-avoid-these-tempting-startup-tarpit-ideas • Airbnb acquires Localmind to create crowdsourced advice about neighborhoods: https://skift.com/2012/12/13/airbnb-acquires-localmind-to-create-crowdsourced-advice-about-neighborhoods/ • Foursquare: https://foursquare.com/ • Razorpay: https://razorpay.com/ • Total Addressable Market: https://www.productplan.com/glossary/total-addressable-market/ • Lenny Bogdonoff on LinkedIn: https://www.linkedin.com/in/rememberlenny/ • Milk Video: https://milkvideo.com/ • Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb): https://www.lennyspodcast.com/lessons-from-working-with-600-yc-startups-gustaf-alstromer-y-combinator-airbnb/ • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups • Collison installation: https://news.ycombinator.com/item?id=18400504 • Stripe: https://stripe.com/ • Patrick Collison on LinkedIn: https://www.linkedin.com/in/patrickcollison/ • John Collison on LinkedIn: https://www.linkedin.com/in/johnbcollison/ • Tony Xu on LinkedIn: https://www.linkedin.com/in/xutony/ • Grant LaFontaine on LinkedIn: https://www.linkedin.com/in/grantlafontaine/ • Ryan Petersen on LinkedIn: https://www.linkedin.com/in/rpetersen/ • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • YC’s latest Request for Startups: https://www.ycombinator.com/blog/ycs-latest-request-for-startups • ERPs: https://www.ycombinator.com/rfs#new-enterprise-resource-planning-software • Commercial open source companies: https://www.ycombinator.com/rfs#commercial-open-source-companies • New space companies: https://www.ycombinator.com/rfs#new-space-companies • A way to end cancer: https://www.ycombinator.com/rfs#a-way-to-end-cancer • Spatial computing: https://www.ycombinator.com/rfs#spatial-computing • New defense technology: https://www.ycombinator.com/rfs#new-defense-technology • Bringing manufacturing back to America: https://www.ycombinator.com/rfs#bring-manufacturing-back-to-america • Better enterprise glue: https://www.ycombinator.com/rfs#better-enterprise-glue • Small fine-tuned models, as an alternative to giant generic ones: https://www.ycombinator.com/rfs#small-finetuned-models-as-an-alternative-to-giant-generic-ones • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ • Sam Altman on X: https://twitter.com/sama • Sean Parker on LinkedIn: https://www.linkedin.com/in/parkersean/ • Owen Van Natta on LinkedIn: https://www.linkedin.com/in/owen-van-natta-444a7/ • Marc Andreessen on X: https://twitter.com/pmarca • Picplz 1, Instagram 0 as VC firm Andreessen Horowitz chooses photo app rival: https://www.reuters.com/article/idUS2587232395/ • Gustaf Alstromer—How to Get Users and Grow: https://www.youtube.com/watch?v=T9ikpoF2GH0 • Getting to Yes: Negotiating Agreement Without Giving In: https://www.amazon.com/Getting-Yes-Negotiating-Agreement-Without/dp/0143118757 • Founding Sales: The Early Stage Go-to-Market Handbook: https://www.amazon.com/Founding-Sales-Go-Market-Handbook-ebook/dp/B08PMK17Z1 • Founder-led sales | Pete Kazanjy (Founding Sales, Atrium): https://www.lennyspodcast.com/founder-led-sales-pete-kazanjy-founding-sales-atrium/ • The Sopranos on HBO: https://www.hbo.com/the-sopranos • The Wire on HBO: https://www.hbo.com/the-wire • Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA • Oura ring: https://ouraring.com/ • Apple watch: https://www.apple.com/watch/ • SiPhox: https://siphoxhealth.com/ • Dalton & Michael on YouTube: https://www.youtube.com/playlist?list=PLQ-uHSnFig5Nd98Sc9I-kkc0ZWe8peRMC • How Future Billionaires Get Sh*t Done: https://www.youtube.com/watch?v=ephzgxgOjR0 • The Student’s Guide to Becoming a Successful Startup Founder: https://www.youtube.com/watch?v=O5KCB2p6SB8 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

David DeSanto is the chief product officer of GitLab, which is the largest remote-only company in the world. They share many of their team meetings on YouTube, and they’ve grown from being an open-source code management product competing with GitHub to a multi-product platform that covers security, compliance, continuous integration, project management, and deployment tools, many of which are infused with AI magic. In our conversation, we discuss: • How GitLab operationalizes transparency • The philosophy behind recording and sharing team meetings on YouTube • Their extensive public employee handbook • GitLab’s core value of having “short toes” • Challenges and advice for doing remote work well • Strategies for ensuring effective communication in a remote work environment • GitLab’s breadth-over-depth strategy • The company’s unique approach to AI • The value of using humor in high-stakes conversations — Brought to you by: • Orb—The flexible billing engine for modern pricing • Eppo—Run reliable, impactful experiments • Paragon—Ship every SaaS integration your customers want — Find the transcript at: https://www.lennysnewsletter.com/p/the-gitlab-way — Where to find David DeSanto: • X: https://twitter.com/david_desanto • LinkedIn: https://www.linkedin.com/in/ddesanto/ • Threads: https://www.threads.net/@david.the.beard — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) David’s background (04:20) Maintaining an epic beard (05:29) Why GitLab publicly shares team meetings (09:49) The GitLab Handbook (11:30) GitLab’s issue tracker (14:29) How to successfully build a culture of transparency (18:11) Benefits of operating with transparency (19:55) The value of building in public (21:53) How GitLab implements their core value of kindness (25:16) What it means to have “short toes” (27:41) Other core values (32:16) Common reasons for not fitting in at GitLab (34:42) Advice for remote teams (42:04) Advice for getting into product (43:52) Advice for PMs who are struggling in a remote world (48:25) Specific tools that help with remote work (53:13) Time zones and remote work (57:18) Breadth-over-depth strategy (01:04:14) AI at GitLab (01:13:11) GitLab’s products and solutions (01:14:54) Lightning round — Referenced: • GitLab: https://about.gitlab.com/ • UX Showcase—David DeSanto introduction to UX team and AMA: https://www.youtube.com/watch?v=fEdsmnVKNj4 • The GitLab Handbook: https://handbook.gitlab.com/ • Sid Sijbrandij on LinkedIn: https://www.linkedin.com/in/sijbrandij/ • Y Combinator: https://www.ycombinator.com/ • GitLab issues: https://docs.gitlab.com/ee/user/project/issues/ • Salesforce: https://www.salesforce.com/ • GitLab values: https://handbook.gitlab.com/handbook/values • GitLab organizational structure: https://handbook.gitlab.com/handbook/company/structure • GitLab direction: https://about.gitlab.com/direction/ • Dogfooding: A simple practice to help you build better products: https://medium.com/agileinsider/dogfooding-a-simple-practice-to-help-you-build-better-products-b5954af4d5f7 • The ultimate guide to adding a PLG motion | Hila Qu (Reforge, GitLab): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-adding-a-plg • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • HubSpot: https://www.hubspot.com/ • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: https://www.lennyspodcast.com/geoffrey-moore-on-finding-your-beachhead-crossing-the-chasm-and-dominating-a-market/ • Open-core model: https://en.wikipedia.org/wiki/Open-core_model • GitLab Duo: https://about.gitlab.com/gitlab-duo/ • GitLab Docs: https://docs.gitlab.com/ • Anthropic: https://www.anthropic.com/ • GitLab Acquires UnReview to Expand Its DevOps Platform with Machine Learning Capabilities: https://about.gitlab.com/press/releases/2021-06-02-gitlab-acquires-unreview-machine-learning-capabilities/ • Essentialism: The Disciplined Pursuit of Less: https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382 • The Mission Critical Core/Context Model for Product Managers: https://secretpmhandbook.com/the-mission-critical-corecontext-model-for-product-managers/ • The Devil’s Hour on AppleTV+: https://tv.apple.com/us/show/the-devils-hour/umc.cmc.3zw4tyzd4lvor5mwhujms63x3 • Glass Onion: A Knives Out Mystery on Netflix: https://www.netflix.com/title/81458416 • Taylor Swift’s The Eras Tour on Prime Video: https://www.amazon.com/TAYLOR-SWIFT-ERAS-EXTENDED-VERSION/dp/B0CP99SN2B • The STAR method: https://capd.mit.edu/resources/the-star-method-for-behavioral-interviews/ • Artifact News: https://artifact.news/ • Superhuman: https://superhuman.com/ • Arc browser: https://arc.net/ • An inside look at how The Browser Company builds product: https://www.lennysnewsletter.com/p/competing-with-giants-an-inside-look — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Todd Jackson is a Partner at First Round Capital. Before moving into venture capital, he played a crucial role as VP of Product and Design at Dropbox, guiding the company until its IPO in 2018. Prior to Dropbox, Todd led product management for Twitter’s Content and Discovery teams after selling his startup, Cover, to Twitter in 2014. Before Cover, Todd oversaw product development for Facebook’s Newsfeed, Photos, and Groups. He kickstarted his career at Google as an associate product manager and eventually led product for Gmail, witnessing its growth from beta to 200 million users. In our conversation, we discuss: • Why product-market fit (PMF) matters • First Round Capital’s four-part PMF framework • Level one: Nascent product-market fit • Level two: Developing product-market fit • Level three: Strong product-market fit • Level four: Extreme product-market fit • Examples of companies at each level • How to know if you’re stuck at a level, and how to get unstuck • What to change if you’re stuck: persona, problem, promise, and product • The goals and challenges at each stage — Brought to you by: • WorkOS—The modern API for auth and user identity • Eppo—Run reliable, impactful experiments • CommandBar—AI-powered user assistance for modern products and impatient users — Find the full transcript at: https://www.lennysnewsletter.com/p/a-framework-for-finding-product-market — Where to find Todd Jackson: • X: https://twitter.com/tjack • LinkedIn: https://www.linkedin.com/in/toddj0/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Todd’s background (06:07) First Round Capital’s PMF framework (09:07) Why product-market fit is so important (11:02) Who can benefit from this framework (12:55) The product-market fit method (16:54) Broad overview of the framework (21:35) Level one: nascent product-market fit (33:16) The four P’s (39:13) Level two: developing product-market fit (49:13) Signs you’re stuck at level two, and what to do (55:12) Level three: strong product-market fit (01:00:17) Signs you’re stuck at level three, and what to do (01:02:22) Level four: extreme product-market fit (01:06:55) Rough timelines for each level (01:11:18) A quick recap of the framework (01:12:15) Diving deeper on the four P’s: what to do if you’re stuck (01:13:56) Dollar-driven discovery (01:25:11) Apply for the product-market-fit method program — Referenced: • First Round: https://firstround.com/ • Twitter Acquires Cover: https://www.vox.com/2014/4/7/11625332/twitter-acquires-cover-an-android-mobile-startup • Dropbox: https://www.dropbox.com/ • Rahul Vohra on LinkedIn: https://www.linkedin.com/in/rahulvohra/ • How Superhuman Built an Engine to Find Product Market Fit: https://review.firstround.com/how-superhuman-built-an-engine-to-find-product-market-fit/ • How to validate your startup idea: https://www.lennysnewsletter.com/p/validating-your-startup-idea • How the most successful B2B startups came up with their original idea: https://www.lennysnewsletter.com/p/how-the-most-successful-b2b-startups • How to know if you’ve got product-market fit: https://www.lennysnewsletter.com/p/how-to-know-if-youve-got-productmarket • A guide for finding product-market fit in B2B: https://www.lennysnewsletter.com/p/finding-product-market-fit • Product-market fit method: http://pmf.firstround.com/ • Stripe: https://stripe.com/ • Plaid: https://plaid.com/ • Paths to PMF: https://review.firstround.com/series/product-market-fit/ • WeWork: https://www.wework.com/ • Casper: https://casper.com/ • Vanta: https://www.vanta.com/ • Christina Cacioppo on LinkedIn: https://www.linkedin.com/in/ccacioppo/ • Ramp: https://ramp.com/ • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/ • Jack Altman on LinkedIn: https://www.linkedin.com/in/jackealtman/ • Lattice: https://lattice.com/ • Zachary Perret on LinkedIn: https://www.linkedin.com/in/zperret/ • Positioning: https://www.lennysnewsletter.com/p/positioning • Retool: https://retool.com/ • David Hsu on LinkedIn: https://www.linkedin.com/in/dvdhsu/ • Persona: https://withpersona.com/ • Rick Song on LinkedIn: https://www.linkedin.com/in/rick-song-25198b24/ • Lloyd Tabb on LinkedIn: https://www.linkedin.com/in/lloydtabb/ • Looker: https://en.wikipedia.org/wiki/Looker_(company) • Jason Boehmig on LinkedIn: https://www.linkedin.com/in/jboehmig/ • Ironclad: https://ironcladapp.com/ • Lessons in leadership | Scaling an org and tactical management advice | Jack Altman (Lattice): https://www.youtube.com/watch?v=cZzXqf61mrQ • Filip Kaliszan on LinkedIn: https://www.linkedin.com/in/kaliszan/ • Verkada: https://www.verkada.com/ • Ali Ghodsi on LinkedIn: https://www.linkedin.com/in/alighodsi/ • Databricks: https://www.databricks.com/ • Stripe Radar: https://stripe.com/radar • Stripe Atlas: https://stripe.com/atlas • Square Stand: https://squareup.com/shop/hardware/us/en/products/ipad-pos-stand-integrated-card-reader • Cash App: https://cash.app/ • Square Checking: https://squareup.com/us/en/campaign/banking/checking • Square Loan: https://squareup.com/help/us/en/article/5654-get-started-with-square-capital • Casey Winters on LinkedIn: https://www.linkedin.com/in/caseywinters/ • How to sell your ideas and rise within your company | Casey Winters, Eventbrite: https://www.lennyspodcast.com/how-to-sell-your-ideas-and-rise-within-your-company-casey-winters-eventbrite/ • Josh Kopelman on LinkedIn: https://www.linkedin.com/in/jkopelman/ • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennyspodcast.com/videos/the-art-and-science-of-pricing-madhavan-ramanujam-monetizing-innovation-simon-kucher/ • Simon Kucher: https://www.simon-kucher.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Claire Vo is the chief product officer at LaunchDarkly and the founder of ChatPRD, likely the most popular PM-specific AI product out there. Before LaunchDarkly, she was a longtime chief product officer at Color and Optimizely. Claire has founded and managed two other companies, Pretty HQ and Experiment Engine, the latter of which Optimizely acquired in 2017. In our conversation, we discuss: • Knowing what you want in your career and being clear about it • Finding your zone of genius and how to operate within it • How to maintain a fast pace in larger companies • How to make it easy for your boss to help you achieve your goals • Advice for navigating the tech industry as a woman • The role of a CPTO and the benefits it brings to organizations • Why she built ChatPRD • Tips for building your own AI tools • The impact of AI on product management and what skills will continue to be important — Brought to you by: • Orb—The flexible billing engine for modern pricing • Dovetail—Bring your customer into every decision • Vanta—Automate compliance. Simplify security — Find the full transcript at: https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor — Where to find Claire Vo: • X: https://twitter.com/clairevo • LinkedIn: https://www.linkedin.com/in/clairevo/ • TikTok: https://www.tiktok.com/@chiefproductofficer — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Claire’s background (04:50) How to achieve career progression (10:11) Avoiding promotion obsession (13:50) How Claire stepped into leadership roles (17:24) Operating in your zone of genius (23:03) How to maintain a fast pace (27:46) Setting a high bar for quality and talent (29:54) Normalizing feedback (33:09) Being a woman in tech (47:09) The role of a CPTO (54:19) Building ChatPRD (59:39) Tips for building a GPT (01:02:27) The impact of AI on product management (01:08:08) How AI is changing the product management role (01:14:36) Efficiency gains with ChatPRD (01:16:39) Contrarian corner: sales-led product organizations (01:20:11) Lightning round — Referenced: • LaunchDarkly: https://launchdarkly.com/ • Define your zone of genius: Laura Garnett at TEDxMillRiver: https://www.youtube.com/watch?v=gQ7_r2oWlrw • Energy Audit: https://beta.mocharymethod.com/blog-post/energy-audit • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary: https://www.lennyspodcast.com/videos/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary/ • Radical Candor: From theory to practice with author Kim Scott: https://www.lennyspodcast.com/radical-candor-from-theory-to-practice-with-author-kim-scott/ • Optimizely: https://www.optimizely.com/ • GitLab: https://about.gitlab.com/ • ChatPRD: https://www.chatprd.ai/ • You should be playing with GPTs at work: https://www.lennysnewsletter.com/p/you-should-be-playing-with-gpts-at • SpaceX’s Starship: https://www.spacex.com/vehicles/starship/ • GitHub Copilot: https://github.com/features/copilot • Product management theater | Marty Cagan (Silicon Valley Product Group): https://www.lennyspodcast.com/product-management-theater-marty-cagan-silicon-valley-product-group/ • High Growth Handbook: Scaling Startups from 10 to 10,000 People: https://www.amazon.com/High-Growth-Handbook-Elad-Gil/dp/1732265100 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Stripe Press: https://press.stripe.com/ • Circe: https://www.amazon.com/Circe-Madeline-Miller/dp/0316556327 • Poor Things: https://www.imdb.com/title/tt14230458/ • Mythic Quest on AppleTV+: https://tv.apple.com/us/show/mythic-quest/umc.cmc.1nfdfd5zlk05fo1bwwetzldy3 • Silicon Valley on HBO: https://www.hbo.com/silicon-valley • Chrysler Pacifica: https://www.chrysler.com/pacifica.html • Waymo: https://waymo.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Dharmesh Shah is the co-founder and CTO of HubSpot (currently valued at $30 billion) and one of the most fascinating founders I’ve ever met. Dharmesh is the keeper of HubSpot’s Culture Code, built ChatSpot (an AI chatbot built on top of HubSpot CRM) and a game called WordPlay (which grew to 16 million users), and also founded and writes for OnStartups, a top-ranking startup blog and community with more than 1M members. He’s also invested in 100+ startups including OpenAI, AngelList, Coinbase, and Dropbox. In our conversation, we discuss: • The biggest lessons he has learned from building HubSpot • The importance of leaning into your strengths • Dharmesh’s data-oriented approach to public speaking • How he developed HubSpot’s culture code • The decision-making process at HubSpot • His contrarian approach to building products • Why founders and product teams are all fighting the second law of thermodynamics • How “flash tags” can save your teams time • How to decide what ideas are worth investing in — Brought to you by: • Explo—Embed customer-facing analytics in your product • Vanta—Automate compliance. Simplify security • LinkedIn Ads—Reach professionals and drive results for your business — Find the full transcript at: https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building — Where to find Dharmesh Shah: • X: https://twitter.com/dharmesh • LinkedIn: https://www.linkedin.com/in/dharmesh/ • Website: https://dharmesh.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Dharmesh’s background (04:20) Fun facts about Dharmesh (06:31) His data-oriented approach to public speaking (11:45) Advice for adding humor to your presentations (15:28) Why he has no direct reports (18:46) You can shape the universe to your liking (20:02) Lessons from building HubSpot (23:43) Contrarian ways of running a company (37:26) Fighting the second law of thermodynamics (40:29) The importance of simplicity in running a business (45:22) Succeeding in the SMB market (50:29) Zigging when others are zagging (54:17) When it makes sense to go “wide and deep” (57:33) Using flashtags to communicate opinions (01:02:44) HubSpot’s decision-making process (01:09:41) Deciding what ideas to invest in (01:15:26) Defining and maintaining company culture (01:30:46) The potential of AI (01:37:03) Practical advice for learning AI (01:40:07) Where to find Dharmesh — Referenced: • WordPlay: https://wordplay.com/article/unlimited • ChatSpot: https://chatspot.ai/ • Indian-origin entrepreneur buys ‘chat.com’ for over $10 million, then sells, donates $250,000 to Khan Academy: https://www.businesstoday.in/technology/news/story/indian-origin-entrepreneur-buys-chatcom-for-over-10-million-then-sells-donates-250000-to-khan-academy-382907-2023-05-26 • Kipp Bodnar on LinkedIn: https://www.linkedin.com/in/kippbodnar/ • The surprising metric presenters should analyze: https://lars-sudmann.com/the-surprising-metric-presenters-should-analyze/ • SoloWare: https://www.linkedin.com/posts/dharmesh_for-3-decades-now-in-addition-to-my-day-activity-7166500611247583232-kZgb/ • Brian Halligan on LinkedIn: https://www.linkedin.com/in/brianhalligan/ • First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles • Peter Thiel on LinkedIn: https://www.linkedin.com/in/peterthiel/ • The second law of thermodynamics: https://en.wikipedia.org/wiki/Second_law_of_thermodynamics • What is an SMB?: https://www.techtarget.com/whatis/definition/SMB-small-and-medium-sized-business-or-small-and-midsized-business • Shopify: https://www.shopify.com/ • Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Christopher Miller (VP of Product, Growth and AI): https://www.lennyspodcast.com/relentless-curiosity-radical-accountability-and-hubspots-winning-growth-formula-christopher-mil/ • FlashTags: A Simple Hack for Conveying Context Without Confusion: https://www.onstartups.com/flashtags-a-simple-hack-for-conveying-context-without-confusion • What it means to “disagree and commit”: https://news.ycombinator.com/item?id=16949021 • A Simple Decision Framework: Debate, Decide and Unite: https://connectingdots.com/p/debate-decide-unite • Dharmesh Shah’s Frameworks for Creating a $1 Billion Net Worth: https://hakune.co/dharmesh-shah-networth/ • Zip: https://ziphq.com/ • The HubSpot Culture Code: Creating a Company We Love: https://blog.hubspot.com/blog/tabid/6307/bid/34234/the-hubspot-culture-code-creating-a-company-we-love.aspx • How defining values and culture helped Airbnb achieve worldwide success: https://lattice.com/library/how-defining-values-and-culture-helped-airbnb-achie • What is SQL?: https://aws.amazon.com/what-is/sql/ • GrowthBot: https://community.hubspot.com/t5/Releases-and-Updates/Meet-GrowthBot-from-HubSpot-Labs/ba-p/417985 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matt Abrahams is a renowned communication expert, with decades of teaching, coaching, and consulting experience. At Stanford University, he teaches a business school class on strategic communication. Beyond academia, he’s a sought-after keynote speaker and consultant, guiding presenters from IPO road shows to prestigious platforms like TED, the World Economic Forum, and the United Nations. His acclaimed podcast, Think Fast, Talk Smart, garners millions of listeners, and his book, Think Faster, Talk Smarter, equips speakers with practical skills for impromptu success. With a previous bestseller, Speaking Up Without Freaking Out, Matt has empowered countless individuals to speak confidently and authentically. In our conversation, we discuss: • The concept of “daring to be dull” • The power of visualization to desensitize oneself to speaking situations • Managing negative self-talk • The WHAT structure for delivering toasts (why we are here, how you are connected, anecdote, thanks) • The ADD structure for Q&As (answer, detailed example, describe relevance) • Breathing techniques to reduce anxiety, such as the double exhale • Concrete speaking structures like What? So What? Now What? and the Four I’s (information, impact, invitation, implications) • Much more — Brought to you by: • Sprig—Build a product people love • Dovetail—Bring your customer into every decision • Coda—Meet the evolution of docs — Find the transcript and references at: https://www.lennysnewsletter.com/p/how-to-speak-more-confidently-and — Where to find Matt Abrahams: • X: https://twitter.com/tftsthepod • LinkedIn: https://www.linkedin.com/in/maabrahams/ • Website: https://mattabrahams.com/ • Podcast: https://open.spotify.com/show/6ll0MwobDt1JW9gYaOONEo — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Matt’s background (04:50) Techniques for managing anxiety in public speaking (10:57) Dare to be dull (13:40) Reframing anxiety as excitement (16:08) Using mantras to boost confidence (18:45) Managing negative self-talk (20:03) Normalizing speaking anxiety (23:12) Using conversation as a communication technique (24:52) Using the double-exhale breathing technique (28:29) Getting present-oriented (29:46) Using tongue twisters (33:34) Broad advice for speaking on the spot (38:35) The PREP structure (38:59) The What? So What? Now What? structure (42:10) Toastmasters and improv (45:31) Getting better at small talk (51:05) The importance of sharing back (52:33) Giving feedback (56:31) Improving toasts and tributes (01:02:57) Mastering Q&A sessions (01:07:25) Apologizing effectively (01:09:29) Closing thoughts — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kunal Shah is one of the most well-known and admired product leaders in India. He is the CEO and founder of CRED, an Indian-based fintech startup valued at over $6 billion. Prior to CRED, he founded three other startups, including Freecharge, which he sold for over $400 million to Snapdeal. He has also been an advisor to India’s most influential organizations. In our conversation, we discuss: • The prevalence of successful Indian immigrants in top CEO roles across the tech industry • Why companies in India can grow DAUs but not ARPU—and what that means for building products for India • What most sets India’s market apart • Challenges and opportunities in the Indian market • The Delta 4 framework for building new products • Lessons from building CRED so far • The power of curiosity and second-order thinking • Lessons from failure — Brought to you by: • WorkOS—The modern API for auth and user identity • Orb—The flexible billing engine for modern pricing • Dovetail—Bring your customer into every decision — Find the transcript and references at: https://www.lennysnewsletter.com/p/kunal-shah-on-winning-in-india-second — Where to find Kunal Shah: • X: https://twitter.com/kunalb11 • LinkedIn: https://www.linkedin.com/in/kunalshah1/ • Podcast: https://www.youtube.com/@CRED_club — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kunal’s background (04:22) The Delta 4 framework (11:00) The success of Indian CEOs in the U.S. (19:55) Challenges and opportunities in India (23:04) DAUs vs. ARPU in Indian markets (25:50) The perception of time in India (27:55) The curse of focus in Asian markets (30:33) Challenges and opportunities in India (continued) (33:23) Lessons learned from building CRED (36:40) Profit pools can provide valuable insights into the values of a country (37:55) Founders’ role in company growth (39:55) Profitability and Indian business culture (43:24) Advice for staying positive amid criticism (44:41) The promising market in India (47:35) The power of curiosity (52:59) Who Kunal looks up to (55:31) Kunal’s favorite sources of content (58:42) Asking great questions (01:02:54) Contrarian corner: Wealth is nothing but storage of energy (01:05:26) Failure corner (01:08:57) Closing thoughts: Share your learnings (01:09:38) Lightning round — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Emilie Gerber is the founder and CEO of Six Eastern, a top PR agency that’s worked with over 100 tech companies, from stealth startups to publicly traded companies. Before starting her own firm, she worked at Uber, where she led PR for the business development team and B2B programs. Prior to that, she worked at Box on product communications, with a focus on product launches and partnership announcements. In our conversation, we discuss: • Why, and when, getting press is worth your time • Common misconceptions about the impact press can have • The second-order effects of press • Which areas each publication (TechCrunch, Axios, The Verge, etc.) cares most about • How to craft your pitch • How to find and reach reporters • How pitching press is different from pitching customers • The effectiveness of direct communication through social media versus traditional press — Brought to you by: • Sprig—Build a product people love • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security. — Find the full transcript at: https://www.lennysnewsletter.com/p/the-ultimate-guide-to-pr-emilie-gerber — Where to find Emilie Gerber: • Substack: http://onbackgroundintel.substack.com • LinkedIn: https://www.linkedin.com/in/emilie-gerber-59612230/ • Website: https://sixeastern.com/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Emilie’s background (04:56) The value of press and second-order effects (13:00) When press is not worth your time (17:01) Different publications and their suitability (25:36) Avoiding negative stories (27:23) Finding aligned podcasts and awards (31:12) Advice for reaching out to reporters (37:23) Controversial pitches (41:16) Avoiding category creation (43:26) Examples of pitches that have worked well (53:32) Pitching to Lenny (55:46) Effective pitching strategies (57:45) Improving pitch announcements (01:03:01) Press releases (01:07:06) Crafting a compelling story (01:09:43) Traditional press vs. newsletters, podcasts, and social media (01:15:50) Building a social media presence (01:17:51) How to get a Morning Brew feature (01:19:32) Advice on choosing a PR agency (01:22:25) Timing and budget for PR (01:25:39) Lightning round — Referenced: • Perplexity: https://www.perplexity.ai/ • Who is Lenny Rachitsky? And what does he know that you don’t about making millions writing online?: https://www.fastcompany.com/90940453/lenny-rachitsky-newsletter-podcast-job-board-substack • 42-year-old brings in an average of $41,000 a month from his podcast and works on it just 5 hours a week: https://www.cnbc.com/2024/01/11/lenny-rachitsky-podcast-brings-in-more-than-500k-a-year-heres-how.html • How This Newsletter Writer Got More Than 300,000 Subscribers, and Now Makes “Significantly More” Than He Did at His Day Job: https://www.entrepreneur.com/starting-a-business/how-this-newsletter-writer-got-more-than-300000/447172 • Business Insider: https://www.businessinsider.com/ • Contraline: https://www.contraline.com/ • Forbes: https://www.forbes.com/ • TechCrunch: https://techcrunch.com/ • Axios: https://www.axios.com/ • Fortune: https://fortune.com/ • Term Sheet: https://fortune.com/tag/term-sheet/ • The Verge: https://www.theverge.com/ • Wall Street Journal: https://www.wsj.com/ • New York Times: https://www.nytimes.com/ • Found podcast: https://techcrunch.com/tag/found/ • Equity podcast: https://techcrunch.com/tag/equity-podcast/ • VentureBeat: https://venturebeat.com/ • Fast Company: https://www.fastcompany.com/ • Clockwise: https://www.getclockwise.com • Shopify deleted 322,000 hours of meetings. Should the rest of us be jealous?: https://www.npr.org/2023/02/15/1156804295/shopify-delete-meetings-zoom-virtual-productivity • Shopify canceled all recurring meetings. Should you too?: https://www.getclockwise.com/blog/shopify-cancels-meetings • Shopify’s new meeting cost calculator is well intentioned—but it’s not addressing the issue: https://www.fastcompany.com/90930137/shopifys-new-meeting-cost-calculator-is-well-intentioned-but-its-not-addressing-the-issue • Matt Martin on LinkedIn: https://www.linkedin.com/in/voxmatt/ • Ramp: https://ramp.com/welcome • Corporate card start-up Ramp targets Bill.com with free payments software: https://www.cnbc.com/2021/10/26/corporate-cards-ramp-targets-billcom-with-free-payments-software.html • Bill: https://www.bill.com/ • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennyspodcast.com/velocity-over-everything-how-ramp-became-the-fastest-growing-saas-startup-of-all-time-geoff-charl/ • Column Tax: https://www.columntax.com/ • Propel: https://www.joinpropel.com/ • Gamma: https://gamma.app/ • Gamma brings in $7M to bring the slide deck into the 21st century: https://techcrunch.com/2021/10/28/gamma-brings-in-7m-to-bring-the-slide-deck-into-the-21st-century/ • NewBank: https://www.newbankusa.com/ • Backed by a16z, Relay races to market with Zapier in its crosshairs: https://techcrunch.com/2023/10/11/relay-a16z-zapier-google/ • Zapier: https://zapier.com/ • Rajiv Ayyangar’s thread on X about tag lines: https://twitter.com/rajivayyangar/status/1758179077629100482 • Entropy: https://entropytechnologydesign.com/ • Money 20/20: https://www.money2020.com/ • Jim Bankoff on LinkedIn: https://www.linkedin.com/in/jimbankoff/ • Ramping Up: https://www.notboring.co/p/ramping-up • Aaron Levie on LinkedIn: https://www.linkedin.com/in/boxaaron/ • Aaron Levie on X: https://twitter.com/levie • Duolingo on TikTok: https://www.tiktok.com/@duolingo • Morning Brew: https://www.morningbrew.com/ • Tech Brew: https://www.emergingtechbrew.com/ • HR Brew: https://www.hr-brew.com/ • Mark Zuckerberg on Morning Brew Daily: https://www.youtube.com/watch?v=xQqsvRHjas4&t=1309s • How to Change Your Mind: What the New Science of Psychedelics Teaches Us About Consciousness, Dying, Addiction, Depression, and Transcendence: https://www.amazon.com/Change-Your-Mind-Consciousness-Transcendence/dp/1594204225 • The Walking Dead on Netflix: https://www.netflix.com/title/70177057 • Yellowjackets on Paramount+: https://www.paramountplus.com/shows/yellowjackets/ • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • Apple Vision Pro: https://www.apple.com/apple-vision-pro • TNB Tech Minute: Startup Perplexity Challenges Google With AI Search: https://www.wsj.com/podcasts/tech-news-briefing/tnb-tech-minute-startup-perplexity-challenges-google-with-ai-search/984362d5-a8f0-48b4-8b55-ad7e570a74d2 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Noam Lovinsky has had a distinguished career in product, leaving an indelible mark at Facebook, YouTube, Thumbtack, and currently as the chief product officer at Grammarly. At Facebook, Noam helped establish the New Product Experimentation team; at Thumbtack, he was chief product officer; and at YouTube, he was one of the early product leaders overseeing the consumer experience. In our conversation, we discuss: • Challenges and lessons from reviving growth at YouTube and Thumbtack • Lessons from building Facebook’s New Product Experimentation team • Insights into Grammarly’s success • Knowing when it’s time to kill your project • Why diversifying your growth channels is critical • The power of visioning and storytelling in shaping product strategy • How to create space for innovation at large companies • The resilience and motivation of Grammarly’s team in Ukraine — Brought to you by: • Whimsical—The iterative product workspace • Vanta—Automate compliance. Simplify security. • LinkedIn Ads—Reach professionals and drive results for your business — Where to find Noam Lovinsky: • X: https://twitter.com/noaml • LinkedIn: https://www.linkedin.com/in/noaml/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Noam’s background (04:18) Noam’s lack of online presence (08:06) Lessons from YouTube: advocating for what’s best for yourself and the team (14:31) Prioritizing what’s best for the business (19:37) Knowing when it’s time to kill a project (21:47) Lessons from Thumbtack: diversifying growth channels and overcoming challenges (26:24) How Thumbtack turned growth around (31:44) Building Airbnb’s instant booking feature (35:28) Lessons from Thumbtack: team collaboration and product strategy (38:38) Lessons from Facebook: building the New Product Experimentation team (40:43) The importance of starting small and building community density (46:07) Advice for building a startup within a startup (48:52) Having an incentive system (49:34) Lessons from Grammarly: adapting to changing user needs and building for the masses (54:20) The scrappiness and profitability of Grammarly (56:56) The resilience and motivation of the Grammarly team in Ukraine (59:08) General career advice (01:01:02) When to pull back (01:02:58) Closing thoughts (01:03:56) Lightning round — Referenced: • Substack: https://substack.com/ • Hunter Walk on LinkedIn: https://www.linkedin.com/in/hunterwalk/ • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/ • Salar Kamangar on LinkedIn: https://www.linkedin.com/in/salar-kamangar-5a059712/ • Grammarly: https://www.grammarly.com/ • Thumbtack: https://www.thumbtack.com/ • FRED on YouTube: https://www.youtube.com/FRED • How Airbnb Proved That Storytelling Is the Most Important Skill in Design: https://www.inc.com/yazin-akkawi/the-surprising-technique-airbnb-uses-to-better-sell-an-experience.html • Google+: https://en.wikipedia.org/wiki/Google%2B • Marco Zappacosta on LinkedIn: https://www.linkedin.com/in/marcozappacosta/ • Bryan Schreier on LinkedIn: https://www.linkedin.com/in/bryanschreier/ • Whitney Steele on LinkedIn: https://www.linkedin.com/in/whitneydsteele/ • David Shein on LinkedIn: https://www.linkedin.com/in/davidshein/ • The magic of thinking big, by Lenny Rachitsky: https://www.mindtheproduct.com/the-magic-of-thinking-big-by-lenny-rachitsky/ • What Seven Years at Airbnb Taught Me About Building a Business: https://www.lennysnewsletter.com/p/what-seven-years-at-airbnb-taught • New apps, new experiences: NPE Team, from Facebook: https://tech.facebook.com/engineering/2019/7/npe-team-from-facebook/ • The Origin Story of the BRC Trash Fence: https://journal.burningman.org/2016/05/black-rock-city/leaving-no-trace/the-origin-story-of-the-brc-trash-fence/ • Nike opens high-tech research and innovation lab: https://www.just-style.com/news/nike-opens-high-tech-research-and-innovation-lab/ • ChatGPT: https://chat.openai.com/ • Microsoft Copilot: https://copilot.microsoft.com/ • How to grow a subscription business | Yuriy Timen (Grammarly, Canva, Airtable): https://www.lennyspodcast.com/how-to-grow-a-subscription-business-yuriy-timen-grammarly-canva-airtable/ • “The cave you fear to enter holds the treasure you seek”: https://gointothestory.blcklst.com/the-cave-you-fear-to-enter-holds-the-treasure-you-seek-d624e28c3848 • Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Fargo TV series on Hulu: https://www.fxnetworks.com/shows/fargo • Arc browser: https://arc.net/ • Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO): https://www.lennyspodcast.com/competing-with-giants-an-inside-look-at-how-the-browser-company-builds-product-josh-miller-ceo/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Marty Cagan is a luminary in the world of product. He’s the author of two of the most foundational books for product teams and product leaders (Inspired and Empowered), he’s the founder of Silicon Valley Product Group (one of the longest-running product advisory groups), and he’s almost certainly worked with more product leaders and teams than any human alive. Now he’s releasing his newest book, Transformed, which is sure to become a staple of tech-powered companies worldwide. Marty’s previous appearance on our show remains one of the most popular episodes to date. In this conversation, we discuss: • The rise of “product management theater” • Changes in the PM role post-ZIRP and the shift from growth to build functions • The disconnect between good product companies and online product advice • How over-hiring has created challenges in the product industry • The most important skills for PMs to build • How to know if you’re on a “feature team” • The potential disruption of product management by AI • Marty’s new book, Transformed: Moving to the Product Operating Model • Four new competencies required for successful product organizations — Brought to you by: • Sprig—Build a product people love • Eppo—Run reliable, impactful experiments • Vanta—Automate compliance. Simplify security. — Find the full transcript at: https://www.lennysnewsletter.com/p/product-management-theater-marty — Where to find Marty Cagan: • X: https://twitter.com/cagan • LinkedIn: https://www.linkedin.com/in/cagan/ • Silicon Valley Product Group: https://www.svpg.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Marty’s background (04:46) His take on the state of product management (12:08) Product management theater (18:33) Feature teams vs. empowered product teams (24:48) Skills of a real product manager (29:27) The product management reckoning is here (32:05) Taking control of your product management career (34:59) The challenge of finding reliable product management advice (40:18) The disconnect between good product companies and the product management community (44:23) Top-down vs. bottom-up cultures (47:06) The shift in product management post-ZIRP era (49:44) The changing landscape of product management (52:05) The disruption of PM skills by AI (55:56) The purpose and content of Marty’s new book, Transformed (01:02:05) The product operating model (01:08:27) New competencies required for successful product teams (01:11:25) Marty’s thoughts on product ops (01:15:13) Advice for founders who don’t want product managers (01:18:06) Lightning round — Referenced: • Transformed: Moving to the Product Operating Model: https://www.amazon.com/Transformed-Becoming-Product-Driven-Company-Silicon/dp/1119697336 • Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507 • Empowered: Ordinary People, Extraordinary Products: https://www.amazon.com/EMPOWERED-Ordinary-Extraordinary-Products-Silicon/dp/111969129X • The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/ • Product Leadership Theater: https://www.svpg.com/product-leadership-theater/ • Product Management Theater: https://www.svpg.com/product-management-theater/ • Linear: https://linear.app/ • How Linear builds product: https://www.lennysnewsletter.com/p/how-linear-builds-product • Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/ • Mamas, don’t let your babies grow up to be coders, Jensen Huang warns: https://www.theregister.com/2024/02/27/jensen_huang_coders/ • Epic Waste: https://www.svpg.com/epic-waste/ • What is scrum and how to get started: https://www.atlassian.com/agile/scrum • CSPO: https://www.scrumalliance.org/get-certified/product-owner-track/certified-scrum-product-owner • PSPO: https://www.scrum.org/courses/professional-scrum-product-owner-training • Jira: https://www.atlassian.com/software/jira • Continuous Discovery Habits: Discover Products That Create Customer Value and Business Value: https://www.amazon.com/Continuous-Discovery-Habits-Discover-Products/dp/1736633309 • Shreyas Doshi on LinkedIn: https://www.linkedin.com/in/shreyasdoshi/ • Ben Erez’s LinkedIn post: https://www.linkedin.com/feed/update/urn:li:activity:7168978777966891008/ • Oracle: https://www.oracle.com/ • The essence of product management | Christian Idiodi (SVPG): https://www.lennyspodcast.com/the-essence-of-product-management-christian-idiodi-svpg/ • Making Meta | Andrew ‘Boz’ Bosworth (CTO): https://www.lennyspodcast.com/making-meta-andrew-boz-bosworth-cto/ • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennyspodcast.com/building-a-long-and-meaningful-career-nikhyl-singhal-meta-google/ • Partners at SVPG: https://www.svpg.com/team/ • Trainline: https://www.thetrainline.com/ • Almosafer: https://global.almosafer.com/ • Expedia: https://www.expedia.com/ • Shopify: https://www.shopify.com/ • Salesforce: https://www.salesforce.com/ • The ultimate guide to product operations | Melissa Perri and Denise Tilles: https://www.lennyspodcast.com/the-ultimate-guide-to-product-operations-melissa-perri-and-denise-tilles/ • Understanding the role of product ops | Christine Itwaru (Pendo): https://www.lennyspodcast.com/understanding-the-role-of-product-ops-christine-itwaru-pendo/ • Build: An Unorthodox Guide to Making Things Worth Making: https://www.amazon.com/Build-Unorthodox-Guide-Making-Things/dp/0063046067 • What’s Our Problem?: A Self-Help Book for Societies: https://www.amazon.com/Whats-Our-Problem-Self-Help-Societies/dp/B0BVGH6T1Q • Rivian: https://rivian.com/ • AI-1 airbag vest: https://www.klim.com/Ai-1-Airbag-Vest-3046-000 • Leslie Lamport’s quote: https://quotefancy.com/quote/3702194/Leslie-Lamport-If-you-re-thinking-without-writing-you-only-think-you-re-thinking • Joan Didion’s quote: https://www.goodreads.com/quotes/264509-i-don-t-know-what-i-think-until-i-write-it — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ray (Jiayi) Cao is the global head of product strategy and operations for monetization product at TikTok. Prior to TikTok, Ray spent six years at Google helping scale Google Shopping globally. In our conversation, we discuss: • TikTok’s internal culture and core values • How TikTok’s product team operates • How working at TikTok is different from working at Google • How TikTok rolls out to new markets • TikTok’s core principle of “context, not control” • How their sales and product teams work together • Lessons (and mistakes) from building TikTok’s early go-to-market team • The importance of hiring for quality rather than quantity • Insights on being successful on TikTok as a creator, a business, and an advertiser — Brought to you by: • WorkOS—The modern API for auth & user identity • Eppo—Run reliable, impactful experiments • OneSchema—Import CSV data 10x faster — Find the full transcript at: https://www.lennysnewsletter.com/p/inside-tiktok-culture-strategy-monetization — Where to find Ray Cao: • LinkedIn: https://www.linkedin.com/in/jiayiraycao/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Ray’s background (04:55) Cultural differences between Google and TikTok (08:24) Fine-tuning the algorithm for different markets (12:15) Examples of fine-tuning the algorithm (15:11) Core principles and values of TikTok (19:34) Hiring at TikTok (21:38) Embracing the “always day one” mentality (25:09) Collaboration between teams (28:38) Amazon’s cultural influence (31:14) Setting up the product organization for speed and innovation (35:38) Building the go-to-market team (40:18) What makes people successful at TikTok (43:02) Thoughts on putting in long hours (44:40) OKRs and planning at TikTok (49:12) Tips for how to be successful on TikTok (53:49) Tips for advertising on TikTok (01:04:03) Getting started with TikTok Ads (01:08:42) Common mistakes to avoid with TikTok advertising (01:09:44) Ray’s favorite TikTok account (01:10:54) Where to find Ray — Referenced: • TikTok: https://tiktok.com/ • Google Shopping: https://shopping.google.com/ • Eugene Wei’s blog: https://www.eugenewei.com/ • TikTok and the Sorting Hat: https://www.eugenewei.com/blog/2020/8/3/tiktok-and-the-sorting-hat • How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennyspodcast.com/how-netflix-builds-a-culture-of-excellence-elizabeth-stone-cto/ • Inside OpenAI | Logan Kilpatrick (head of developer relations): https://www.lennyspodcast.com/inside-openai-logan-kilpatrick-head-of-developer-relations/ • Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/ • Lead with Context not Control: https://www.svpg.com/lead-with-context-not-control/ • Shuba on TikTok: https://www.tiktok.com/@tiktokbrownchick • Duolingo on TikTok: https://www.tiktok.com/@duolingo • Duolingo leagues: https://duolingo.fandom.com/wiki/League • CapCut: https://www.capcut.com/ • Amanda Talijan (silent baby item reviews) on TikTok: https://www.tiktok.com/@amanda_talijan/video/7321700482018233642 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Andrew Bosworth—or Boz, as most people know him—is the chief technology officer at Meta and head of Reality Labs, the company’s augmented reality/virtual reality (AR/VR) organization, which he created in 2017. Boz joined Facebook in 2006 as their approximately 10th engineer, and in his 18-year tenure he built the original News Feed, Messenger, and Groups, as well as many early anti-abuse and infrastructure systems. At various times he has been the engineering director overseeing Events, Places, Photos, Videos, Timeline, Privacy, and more. Before Reality Labs, he ran the Ads and Business Platform product group, where he led engineering, product, research, analytics, and design, taking annual revenue from $4 billion to $40 billion in five years. Andrew currently leads Meta’s efforts in AR, VR, AI, and consumer hardware across Quest, Ray-Ban Meta glasses, and more. In our conversation, we discuss: • Stories from the early days of Facebook • Lessons from Meta’s downturn and recent turnaround • Meta’s culture of transparency • Boz’s thoughts on the Apple Vision Pro • Why communication is the job • Why you should regularly seek help from your manager • Lessons in setting incentives and avoiding their misuse • Why you should optimize for a variety in experience in your career • The importance of trusting your own expertise and not being swayed by external opinions • Stories of failures and personal growth — Brought to you by: • Vanta—Automate compliance. Simplify security. • Eppo—Run reliable, impactful experiments • Explo—Embed customer-facing analytics in your product — Find the full transcript at: https://www.lennysnewsletter.com/p/making-meta-andrew-boz-bosworth-cto — Where to find Andrew Bosworth: • Facebook: https://www.facebook.com/boz/ • Instagram: https://www.instagram.com/boztank/ • X: https://twitter.com/boztank • LinkedIn: https://www.linkedin.com/in/andrew-bosworth-8247a01/ • Website: https://boz.com/ • Photography website: https://wardenshortbow.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Boz’s background (04:48) Fun facts about him (07:20) Early days at Facebook (11:11) Advice for founders (13:22) Leveraging leaders (19:27) Tips for communicating with managers (22:10) Transparency at Meta (27:01) The importance of clear guidelines (29:11) Involvement in the details (33:15) Building the News Feed (37:28) Passion and career growth (40:25) Exploring new opportunities (42:02) The value of variety in experience (45:01) Giving and receiving feedback (47:38) Boz’s tattoos (51:30) Communication is the job (01:00:47) Comparing VR headsets: Meta Quest 3 and Apple Vision Pro (01:10:41) Meta’s downturn and turnaround (01:16:10) Navigating org changes (01:20:43) Lessons from failure (01:26:33) Closing thoughts (01:29:57) Lightning round — Referenced: • Reality Labs: https://about.meta.com/realitylabs/ • Quest: https://www.meta.com/quest/ • Ray-Ban Meta smart glasses: https://www.ray-ban.com/usa/ray-ban-meta-smart-glasses • Taekwondo: https://en.wikipedia.org/wiki/Taekwondo • 4-H: https://4-h.org/ • David Copperfield’s website: https://www.davidcopperfield.com/html/ • MC Hammer on Instagram: https://www.instagram.com/mchammer/ • George W. Bush: https://www.whitehouse.gov/about-the-white-house/presidents/george-w-bush/ • Fry’s Electronics: https://en.wikipedia.org/wiki/Fry%27s_Electronics • Association for Computing Machinery: https://www.acm.org • Get It Done: https://boz.com/articles/get-it-done • Patrick Stewart on X: https://twitter.com/sirpatstew • The FB Exec Practice That Changed the Way I Lead (about HPMs): https://livingos.substack.com/p/fb-exec-hpm • Mark Zuckerberg on Facebook: https://www.facebook.com/zuck • Chris Cox on LinkedIn: https://www.linkedin.com/in/chris-cox-2896b841/ • Javier Olivan on LinkedIn: https://www.linkedin.com/in/javierolivan/ • Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/ • Eye of Sauron: https://lotr.fandom.com/wiki/Eye_of_Sauron • Ruchi Sanghvi on LinkedIn: https://www.linkedin.com/in/rsanghvi/ • Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-e-schmidt/ • Sheryl Sandberg on LinkedIn: https://www.linkedin.com/in/sheryl-sandberg-5126652/ • Best Advice Sheryl Sandberg Received: If Offered a Seat on Rocket Ship, Get On: https://news.yahoo.com/blogs/newsmakers/best-advice-sheryl-sandberg-received-don-t-idiot-161459450.html • Veritas: https://en.wikipedia.org/wiki/Veritas • Communication is The Job: https://boz.com/articles/communication-is-the-job • Repetition does not spoil the prayer: https://www.linkedin.com/pulse/repetition-does-spoil-prayer-constantine-constantinides-m-d-ph-d--1f/ • Janet Lansbury’s website: https://www.janetlansbury.com/ • Dr. Becky on Instagram: https://www.instagram.com/drbeckyatgoodinside • Boz to the Future Episode 18: The Future According to Matthew Ball: https://www.meta.com/blog/quest/boz-to-the-future-episode-18-matthew-ball-metaverse-epyllion/ • Apple Vision Pro: https://www.apple.com/apple-vision-pro • Quest 3 headset: https://www.meta.com/quest/quest-3/ • Virtual desktop: https://www.meta.com/experiences/2017050365004772/ • Meta Horizon Workrooms: https://www.meta.com/experiences/2514011888645651/  • After trying the Vision Pro, Mark Zuckerberg says Quest 3 ‘is the better product, period’: https://www.theverge.com/2024/2/13/24072413/mark-zuckerberg-apple-vision-pro-review-quest-3 • Lou Holtz on X: https://twitter.com/CoachLouHoltz88 • Gell-Mann amnesia effect: https://en.wiktionary.org/wiki/Gell-Mann_Amnesia_effect • “Wet streets cause rain”: https://news.ycombinator.com/item?id=19026568 • Michael Crichton on X: https://twitter.com/CrichtonBooks • AI research at Meta: https://ai.meta.com/research/ • Llama 2: https://llama.meta.com/ • Warren Buffett quote: https://www.brainyquote.com/quotes/warren_buffett_383933 • Mark Slee on LinkedIn: https://www.linkedin.com/in/mcslee/ • Dave Fetterman on LinkedIn: https://www.linkedin.com/in/davefetterman/ • Emacs and Vim: https://dev.to/george_udonte/emacs-and-vim-an-overview-for-beginners-2e65 • Ami Vora on LinkedIn: https://www.linkedin.com/in/amvora/ • The Dream Machine: https://www.amazon.com/Dream-Machine-M-Mitchell-Waldrop/dp/1732265119 • Alan Turing: https://en.wikipedia.org/wiki/Alan_Turing • Good Inside: A Guide to Becoming the Parent You Want to Be: https://www.amazon.com/Good-Inside-Guide-Becoming-Parent/dp/B09Y4WG7RJ • Dr. Becky’s website: https://www.goodinside.com/ • The Mandalorian on Disney+: https://www.disneyplus.com/series/the-mandalorian/3jLIGMDYINqD • Scott Trowbridge on LinkedIn: https://www.linkedin.com/in/scott-trowbridge-b70866/ • Dave Filoni on X:  https://twitter.com/dave_filoni • Jon Favreau on X: https://twitter.com/jon_favreau • Mercedes-Benz AMG EQS Sedan: https://www.mbusa.com/en/vehicles/model/eqs/sedan/amgeqsv4 • Tracey Emin “Trust Yourself”: https://www.artsy.net/artwork/tracey-emin-trust-yourself • Tracey Emin on Instagram: https://www.instagram.com/traceyeminstudio • Rick Rubin: Protocols to Access Creative Energy and Process | Huberman Lab Podcast: https://www.youtube.com/watch?v=GpgqXCkRO-w • Ansel Adams: https://en.wikipedia.org/wiki/Ansel_Adams — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Donna Lichaw is an internationally sought-after executive coach, keynote speaker, and best-selling author. She helps visionary founders, CEOs, and executive teams level up their leadership and scale their impact while staying true to their mission, purpose, and themselves. Donna works with leaders at companies like Google, Disney, Twitter, Microsoft, Mailchimp, and Adobe, as well as a plethora of mission-driven startups and nonprofits. In our conversation, we discuss: • How our personal narratives influence our success and failure • Why identifying your superpowers (and kryptonite) is so important, and how to do it • The value of doubling down on your strengths rather than trying to fix weaknesses • How to acknowledge and reframe feelings of impostor syndrome • The Double Diamond framework for personal growth and goal-setting • The power of visualization and how it can fuel motivation and creativity — Brought to you by: • OneSchema—Import CSV data 10x faster • Sendbird—The (all-in-one) communications API platform for mobile apps • Sprig—Build a product people love — Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-discover-your-superpowers — Where to find Donna Lichaw: • LinkedIn: https://www.linkedin.com/in/dlichaw/ • Website: https://www.donnalichaw.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Donna’s background (04:25) Donna’s origin story and transition to coaching (08:38) The power of storytelling in leadership (11:36) Becoming the hero of your own story (14:49) Changing your story (21:19) Understanding and shifting others’ stories (25:41) Imposter syndrome (31:28) Exploring different types of kryptonite (36:41) Identifying and leveraging strengths (43:53) Identifying superpowers (56:39) Running experiments (01:01:52) Using product frameworks for personal growth (01:12:41) Identifying subconscious goals (01:15:27) Envisioning impact (01:16:44) Lightning round — Referenced: • The Leader’s Journey: Transforming Your Leadership to Achieve the Extraordinary: https://www.amazon.com/Leaders-Journey-Transforming-Leadership-Extraordinary/dp/1959029134 • Effective Leadership Is Transformational, by Ken Blanchard: https://www.chieflearningofficer.com/2019/06/13/effective-leadership-is-transformational/ • Ken Blanchard’s website: https://www.blanchard.com/ • How to write a kickass README: https://dev.to/scottydocs/how-to-write-a-kickass-readme-5af9 • This Week #5: Overcoming impostor syndrome, introducing growth to an org, and how to partner with your Data Scientist: https://www.lennysnewsletter.com/p/this-week-overcoming-impostor-syndrome • Community Wisdom: Dealing with impostor syndrome as a PM: https://www.lennysnewsletter.com/p/community-wisdom-dealing-with-impostor • Stuart Smalley: https://en.wikipedia.org/wiki/Stuart_Smalley • Kryptonite: https://en.wikipedia.org/wiki/Kryptonite • How Dyslexic Thinking Gives Entrepreneurs a Competitive Edge: https://www.forbes.com/sites/alisoncoleman/2023/05/16/how-dyslexic-thinking-gives-entrepreneurs-a-competitive-edge/ • Characterizing Creative Thinking and Creative Achievements in Relation to Symptoms of Attention-Deficit/Hyperactivity Disorder and Autism Spectrum Disorder: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9283685/ • Robert Iger: https://thewaltdisneycompany.com/leaders/robert-a-iger/ • CliftonStrengths test: https://www.gallup.com/cliftonstrengths/en/252137/home.aspx • VIA Character Strengths: https://www.viacharacter.org/ • How to fire people with grace, work through fear, and nurture innovation | Matt Mochary (CEO coach): https://www.lennyspodcast.com/how-to-fire-people-with-grace-work-through-fear-and-nurture-innovation-matt-mochary-ceo-coach/ •10 Steve Jobs Quotes That’ll Stick With You Long After You Read Them: https://www.themuse.com/advice/10-steve-jobs-quotes-thatll-stick-with-you-long-after-you-read-them • Gestalt coaching: https://gestaltcenterforcoaching.com/ • Gestalt therapy: https://www.psychologytoday.com/us/therapy-types/gestalt-therapy • Head, Heart and Hands: http://creatingminds.org/tools/head_heart_hands.htm • Managing nerves, anxiety, and burnout | Jonny Miller (Nervous System Mastery): https://www.lennyspodcast.com/managing-nerves-anxiety-and-burnout-jonny-miller-nervous-system-mastery/ • The User’s Journey: Storymapping Products That People Love: https://www.amazon.com/Users-Journey-Storymapping-Products-People/dp/1933820314 • For All Mankind on AppleTV+: https://tv.apple.com/us/show/for-all-mankind/umc.cmc.6wsi780sz5tdbqcf11k76mkp7 • Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/umc.cmc.vtoh0mn0xn7t3c643xqonfzy • The Art of Possibility: Transforming Professional and Personal Life: https://www.amazon.com/Art-Possibility-Transforming-Professional-Personal/dp/0142001104 • IMPRESA Monkey Noodle Stretchy String Fidget/Sensory Toys: https://www.amazon.com/IMPRESA-Glitter-Stretchy-Phthalate-Latex-Free/dp/B0868X6NRQ • Dolly Parton quote: https://www.goodreads.com/quotes/21268-find-out-who-you-are-and-do-it-on-purpose • Donna’s favorite fidgets: https://pen-name.notion.site/Donna-Lichaw-s-Favorite-Fidgets-f84f241d31704a498d71d3502af1821b?pvs=4 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Elizabeth Stone is the chief technology officer of Netflix. She previously served as vice president of product data science and engineering, and as vice president of data and insights, at Netflix. Before Netflix, Elizabeth was vice president of science at Lyft, chief operating officer at Nuna, a trader at Merrill Lynch, and an economist at Analysis Group. In our conversation, we discuss: • Elizabeth’s advice for career advancement • Netflix’s unique high-performance culture • How, and why, Netflix maintains a high bar for excellence • Intentional leadership practices • How to foster an “open door” culture within your team • The Keeper Test and how it contributes to maintaining a high bar for excellence • The power of transparent communication • Much more — Brought to you by: • Vanta—Automate compliance. Simplify security. • Sendbird—The (all-in-one) communications API platform for mobile apps • Explo—Embed customer-facing analytics in your product — Find the full transcript at: https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence — Where to find Elizabeth Stone: • LinkedIn: https://www.linkedin.com/in/elizabeth-stone-608a754/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Elizabeth’s background (04:36) Life as CTO vs. VP of Data (05:57) The role of economists in tech companies (08:32) Using economics to understand incentives (10:07) Success and career growth (20:15) Setting expectations (25:02) Advice for how to avoid burnout (27:44) Netflix culture: high talent density (30:31) Netflix culture: candor and directness (31:45) The Keeper Test (39:01) Maintaining a high bar for excellence (43:54) Netflix culture: freedom and responsibility (46:18) Unconventional processes at Netflix (47:55) Examples of candor (51:44) Data and insights team structure (01:00:12) Staying close to teams (01:02:31) Advice on being present (01:07:40) Lightning round — Referenced: • What to Know About the Netflix Cup, Today’s First-Ever Live Sports Event: https://www.netflix.com/tudum/articles/netflix-cup-live-event-date-news • Ann Miura Ko interview | The Tim Ferriss Show (Podcast): https://www.youtube.com/watch?v=h2GO0Ks_VGg • Netflix culture: https://jobs.netflix.com/culture • No Rules Rules: Netflix and the Culture of Reinvention: https://www.amazon.com/No-Rules-Netflix-Culture-Reinvention/dp/1984877860 • Reed Hastings on LinkedIn: https://www.linkedin.com/in/reedhastings/ • Netflix’s “Keeper Test” and Why You Need It | Lorne Rubis: https://www.highlights.lornerubis.com/2015/08/the-netflix-keeper-test-and-the-courage-to-take-it/ • The Hunger Games: https://en.wikipedia.org/wiki/The_Hunger_Games • Nan Yu on LinkedIn: https://www.linkedin.com/in/thenanyu/ • Work Life Philosophy: https://jobs.netflix.com/work-life-philosophy • The Scoop: Netflix’s historic introduction of levels for software engineers: https://blog.pragmaticengineer.com/netflix-levels/ • Chaos Monkey: https://www.techtarget.com/whatis/definition/Chaos-Monkey • Ali Rauh on LinkedIn: https://www.linkedin.com/in/ali-rauh/ • Keith Henwood on LinkedIn: https://www.linkedin.com/in/keith-henwood/ • Jeff Bezos’ Morning Routine of Puttering Around—How It Works: https://medium.com/illumination/jeff-bezos-morning-routine-of-puttering-around-how-it-works-9d73f359ac8d • What I Talk About When I Talk About Running: A Memoir: https://www.amazon.com/What-Talk-About-When-Running/dp/0307389839 • A Fine Balance: https://www.amazon.com/Fine-Balance-Rohinton-Mistry/dp/140003065X • Triangle of Sadness on Hulu: https://www.hulu.com/movie/triangle-of-sadness-f60937bd-45f4-469a-938f-db95026953a1 • Beef on Netflix: https://www.netflix.com/title/81447461 • Fellow pour-over coffee set: https://fellowproducts.com/products/stagg-xf-pour-over-set • Peloton bikes: https://www.onepeloton.com/shop/bike — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jason Lemkin created and runs SaaStr, the world’s largest community for B2B/SaaS founders, and is the managing director of SaaStr Fund, a $90 million venture capital firm specializing in early-stage enterprise investments. He is also the mastermind behind two major tech conferences each year—one in the Bay Area, drawing in over 15,000 people, and another in Europe, with a crowd of more than 3,000 SaaS executives, founders, and entrepreneurs. Before SaaStr, Jason wore many hats: CEO and co-founder of EchoSign (later bought by Adobe), vice president at Adobe Systems, co-founder and president of NanoGram Devices Corp., vice president of NeoPhotonics, and a senior director at BabyCenter. In our conversation, we discuss: • How far you should go without a salesperson • Signs it’s time to hire salespeople • Why you need to hire two salespeople • How to compensate your salespeople • How to interview salespeople • When to hire a VP of Sales • How to prevent their flaming out • How to scale your sales org • How to improve the relationship between your sales and product teams • Much more — Brought to you by: • CommandBar—AI-powered user assistance for modern products and impatient users • Vanta—Automate compliance. Simplify security. • LinkedIn Ads—Reach professionals and drive results for your business — Find the full transcript at: https://www.lennysnewsletter.com/p/building-a-world-class-sales-org — Where to find Jason Lemkin: • X: https://twitter.com/jasonlk • LinkedIn: https://www.linkedin.com/in/jasonmlemkin/ • Website: https://www.saastr.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jason’s background (06:18) The importance of sales in B2B businesses (11:23) Signs that you should start hiring salespeople (14:19) Attributes to look for in early sales reps (19:08) Hiring a VP of Sales (26:43) The role of a VP of Sales (30:06) Interviewing salespeople (45:16) Determining sales compensation and quota (53:34) Transitioning from 100% commission to a smaller percentage (56:58) Indicators of a hard-to-sell product (59:39) Scaling the sales organization (01:05:26) Understanding sales roles and titles (01:10:02) Product involvement in sales, and vice versa (01:20:32) Thoughts on product teams taking on P&L responsibilities (01:27:23) One thing founders can do to become better at sales (01:31:02) The ideal trial length for a free trial sales team (01:39:50) Closing thoughts (01:41:43) Lightning round — Referenced: • Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/ • Snowflake: https://www.snowflake.com/en/ • Yamini Rangan on LinkedIn: https://www.linkedin.com/in/yaminirangan/ • Salesforce: https://www.salesforce.com/ • HubSpot: https://www.hubspot.com/ • Twilio: https://www.twilio.com/ • Cloudflare: https://www.cloudflare.com/ • GitHub: https://github.com/ • Columbo: https://www.imdb.com/title/tt1466074/ • What is Davos and why is it important? Your guide to the World Economic Forum’s annual meeting: https://www.euronews.com/next/2024/01/15/what-is-davos-and-why-is-it-important-your-guide-to-the-world-economic-forums-annual-meeti • Adobe: https://www.adobe.com/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Glengarry Glen Ross on Prime Video: https://www.amazon.com/Glengarry-Glen-Ross-James-Foley/dp/B002NN5F7A • The Wolf of Wall Street on Prime Video: https://www.amazon.com/Wolf-Wall-Street-Leonardo-DiCaprio/dp/B00IIU9FQY • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/ • Pipedrive: https://www.pipedrive.com/ • Sam Blond on LinkedIn: https://www.linkedin.com/in/sam-blond-791026b/ • Gong: https://www.gong.io/ • Zendesk: https://www.zendesk.com/ • ZoomInfo: https://www.zoominfo.com/ • Apollo: https://www.apollo.io/ • Daniel Chait on LinkedIn: https://www.linkedin.com/in/dhchait/ • SAP: https://www.sap.com/ • Lessons on building product sense, navigating AI, optimizing the first mile, and making it through the messy middle | Scott Belsky (Adobe, Behance): https://www.lennyspodcast.com/lessons-on-building-product-sense-navigating-ai-optimizing-the-first-mile-and-making-it-through-t/ • VistaPrint: https://www.vistaprint.com/ • Procore: https://www.procore.com/ • Matt Mullenweg on LinkedIn: https://www.linkedin.com/in/mattm/ • Wordpress: https://wordpress.com/ • SaaStr University: https://app.saastruniversity.com/collections/20252 • From Impossible to Inevitable: How SaaS and Other Hyper-Growth Companies Create Predictable Revenue: https://www.amazon.com/Impossible-Inevitable-Hyper-Growth-Companies-Predictable/dp/1119531691 • Pavilion: https://www.joinpavilion.com/ • Top 10 Learnings about Free Trials with Tomasz Tunguz: https://www.youtube.com/watch?v=tfQNJpnxmMw • The Terminal List on Prime Video: https://www.amazon.com/The-Terminal-List-Season-1/dp/B09HYNH8TK • Top Gun: Maverick on Paramount: https://www.paramountmovies.com/movies/top-gun-maverick • OpusClip app: https://www.opus.pro/ • OnePlus Open smartphone: https://www.amazon.com/OnePlus-Dual-SIM-Unlocked-Smartphone-Hasselblad/dp/B0CHN7M531/ • SaaStr conferences: https://www.saastr.com/events/ • Marketo: https://go.marketo.com/about-marketo-landingpage-emea.html • Zoomtopia: https://zoomtopia.com/ • Money20/20: https://us.money2020.com/ • Shoptalk: https://shoptalk.com/ • Jeff Lawson on LinkedIn: https://www.linkedin.com/in/jeffiel/ • Eric Kwan on LinkedIn: https://www.linkedin.com/in/erickwan/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jake Knapp and John Zeratsky are the authors of best-selling books Sprint and Make Time. They have helped more than 300 teams design new products and bring them to market, including those at YouTube, Gusto, One Medical Group, and Slack. Jake and John are co-founders of the venture capital firm Character, where they support startups with capital and sprints. Previously, they were operating partners at Google Ventures and, before that, design leaders at Google, where John worked on Google Ads and YouTube and Jake helped build Gmail and co-founded Google Meet. In our conversation, we discuss: • “Busy bandwagon” and “infinity pools” • Creating one “highlight” each day • Their four-part framework for productivity • How to use the calendar to design your day • How creating friction can help you avoid distractions • Tips on creating a distraction-free phone • Strategies for managing email and distractions • The importance of reflecting on the day and making time for meaningful work • Design sprints — Brought to you by: • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers • Whimsical—The iterative product workspace • WorkOS—The modern API for auth and user identity — Find the full transcript at: https://www.lennysnewsletter.com/p/making-time-for-what-matters-jake — Where to find Jake Knapp: • X: https://twitter.com/jakek • LinkedIn: https://www.linkedin.com/in/jake-knapp/ • Website: https://jakeknapp.com/ — Where to find John Zeratsky: • X: https://twitter.com/jazer • LinkedIn: https://www.linkedin.com/in/johnzeratsky/ • Website: https://johnzeratsky.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) About Jake and John (04:10) Recording the audiobook for Make Time (06:06) What people often get wrong when trying to become more productive (11:24) The busy bandwagon and infinity pools (15:22) Real talk: Jake and John’s productivity levels (20:10) The four-part framework for getting more done: Highlight, Laser, Energize, Reflect (25:15) Step 1: Highlight (28:08) Designing your day with a calendar (30:52) The Groundhog Day mentality (35:10) Tactical advice for implementing the highlight method (39:30) An example of a failed highlight (48:08) Step 2: Laser (51:12) Creating intentional friction to avoid distractions (57:28) Curating a distraction-free phone (01:07:58) Resetting expectations and slowing your inbox (01:14:51) Systems over willpower (01:18:14) Managing email distractions (01:18:49) Step 3: Energize (01:22:05) Step 4: Reflect (01:26:30) Introduction to Sprint — Referenced: • Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422 • Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days: https://www.amazon.com/Sprint-audiobook/dp/B019R2DQIY • Make Time blog: https://maketime.blog/ • Make Time blog on X: https://twitter.com/maketimeblog • Character: https://www.character.vc/ • Google Ventures: https://www.gv.com/ • Character Labs: https://www.character.vc/labs • Strategies for becoming less distracted and improving focus | Nir Eyal (author of Indistractable and Hooked): https://www.lennyspodcast.com/strategies-for-becoming-less-distracted-and-improving-focus-nir-eyal-author-of-indistractable-and/ • Groundhog Day on Prime Video: https://www.amazon.com/Groundhog-Day-Bill-Murray/dp/B000SP1SH6 • Reclaim.ai: https://reclaim.ai/ • Feed Blocker for LinkedIn: https://chromewebstore.google.com/detail/feed-blocker-for-linkedin/eikaafmldiioljlilngpogcepiedpenf • The Lord of the Rings: https://www.amazon.com/Lord-Rings-J-R-R-Tolkien/dp/0544003411 • MagSafe charger: https://www.amazon.com/Apple-MHXH3AM-A-MagSafe-Charger/dp/B08L5NP6NG/ • Nanit app: https://www.nanit.com/pages/nanit-app • Arianna Huffington’s Phone Bed Charging Station: https://www.amazon.com/Arianna-Huffingtons-Charging-Station-Walnut/dp/B0799ZG1LY • Cell Phone Lock Box with Timer: https://www.amazon.com/Portable-Android-Self-Discipline-Achieve-Addiction/dp/B0CG8V4YG3?th=1 • The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich: https://www.amazon.com/4-Hour-Workweek-Escape-Live-Anywhere/dp/0307465357 • The Economist: https://www.economist.com/ • Odysseus: https://www.britannica.com/topic/Odysseus • Mailman: https://www.mailmanhq.com/ • Future: https://www.future.co/ • Notion: https://www.notion.so/ • Miro: https://miro.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Logan Kilpatrick leads developer relations at OpenAI, supporting developers building with the OpenAI API and ChatGPT. He is also on the board of directors at NumFOCUS, the nonprofit organization that supports open source projects like Jupyter, Pandas, NumPy, and more. Before OpenAI, Logan was a machine-learning engineer at Apple and advised NASA on open source policy. In our conversation, we discuss: • OpenAI’s fast-paced and innovative work environment • The value of high agency and high urgency in your employees • Tips for writing better ChatGPT prompts • How the GPT Store is doing • OpenAI’s planning process and decision-making criteria • Where OpenAI is heading in the next few years • Insight into OpenAI’s B2B offerings • Why Logan “measures in hundreds” — Brought to you by: • Hex—Helping teams ask and answer data questions by working together • Whimsical—The iterative product workspace • Arcade Software—Create effortlessly beautiful demos in minutes — Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/inside-openai-logan-kilpatrick-head Today’s transcript will be live by 8 a.m. PT. — Where to find Logan Kilpatrick: • X: https://twitter.com/OfficialLoganK • LinkedIn: https://www.linkedin.com/in/logankilpatrick/ • Website: https://logank.ai/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Logan’s background (03:49) The impact of recent events on OpenAI’s team and culture (08:20) Exciting developments in AI interfaces (09:52) Using OpenAI tools to make companies more efficient (13:04) Examples of using AI effectively (18:35) Prompt engineering (22:12) How to write better prompts (26:05) The launch of GPTs and the OpenAI Store (32:10) The importance of high agency and urgency (34:35) OpenAI’s ability to move fast and ship high-quality products (35:56) OpenAI’s planning process and decision-making criteria (40:22) The importance of real-time communication (42:33) OpenAI’s team and growth (44:47) Future developments at OpenAI (47:42) GPT-5 and building toward the future (50:38) OpenAI’s enterprise offering and the value of sharing custom applications (52:30) New updates and features from OpenAI (55:09) How to leverage OpenAI’s technology in products (58:26) Encouragement for building with AI (59:30) Lightning round — Referenced: • OpenAI: https://openai.com/ • Sam Altman on X: https://twitter.com/sama • Greg Brockman on X: https://twitter.com/gdb • tldraw: https://www.tldraw.com/ • Harvey: https://www.harvey.ai/ • Boost Your Productivity with Generative AI: https://hbr.org/2023/06/boost-your-productivity-with-generative-ai • Research: quantifying GitHub Copilot’s impact on developer productivity and happiness: https://github.blog/2022-09-07-research-quantifying-github-copilots-impact-on-developer-productivity-and-happiness/ • Lesson learnt from the DPD AI Chatbot swearing blunder: https://www.linkedin.com/pulse/lesson-learnt-from-dpd-ai-chatbot-swearing-blunder-kitty-sz57e/ • Dennis Yang on LinkedIn: https://www.linkedin.com/in/dennisyang/ • Tim Ferriss’s blog: https://tim.blog/ • Tyler Cowen on X: https://twitter.com/tylercowen • Tom Cruise on X: https://twitter.com/TomCruise • Canva: https://www.canva.com/ • Zapier: https://zapier.com/ • Siqi Chen on X: https://twitter.com/blader • Runway: https://runway.com/ • Universal Primer: https://chat.openai.com/g/g-GbLbctpPz-universal-primer • “I didn’t expect ChatGPT to get so good” | Unconfuse Me with Bill Gates: https://www.youtube.com/watch?v=8-Ymdc6EdKw • Microsoft Azure: https://azure.microsoft.com/ • Lennybot: https://www.lennybot.com/ • Visual Electric: https://visualelectric.com/ • DALL-E: https://openai.com/research/dall-e • The One World Schoolhouse: https://www.amazon.com/One-World-Schoolhouse-Education-Reimagined/dp/1455508373/ref=sr_1_1 • Why We Sleep: Unlocking the Power of Sleep and Dreams: https://www.amazon.com/Why-We-Sleep-Unlocking-Dreams/dp/1501144324 • Gran Turismo: https://www.netflix.com/title/81672085 • Gran Turismo video game: https://www.playstation.com/en-us/gran-turismo/ • Manta sleep mask: https://mantasleep.com/products/manta-sleep-mask • WAOAW sleep mask: https://www.amazon.com/WAOAW-Sleep-Sleeping-Blocking-Blindfold/dp/B09712FSLY — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Megan Cook is the head of product for Atlassian’s Jira software, which is used by 75% of Fortune 500 companies, has over 125,000 customers globally, over 15 different products, and is by far the most popular project management tool in the world. Megan has been at Atlassian for just under 11 years, and before this role, she was an analyst, a developer, and an Agile coach. In our conversation, we discuss: • How to get buy-in for your ideas • The value of starting small • How, and why, creating space for play is so essential • How Jira stays ahead of endless competition • Atlassian’s approach to launching new product lines • Tactical tips for making remote work, work • A personal failure and the lessons learned from it — Brought to you by: • Teal—Your personal career growth platform • Sprig—Build a product people love • Vanta—Automate compliance. Simplify security. — Find the transcript for this episode and all past episodes at: https://www.lennysnewsletter.com/p/lessons-from-atlassian-launching Today’s transcript will be live by 8 a.m. PT. — Where to find Megan Cook: • X: https://twitter.com/meganwcook • LinkedIn: https://www.linkedin.com/in/cookmegan — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Megan’s background (03:50) Creating space for play and psychological safety on teams (07:36) Peer feedback groups (10:30) Sharing stories of failure (13:33) The “10 dollar” game for priorities (15:24) Advice on making remote work, work (24:16) Getting buy-in for your ideas (28:33) The importance of staying open-minded (34:05) A quick summary of how to get buy-in (36:45) Fighting the good fight (38:15) Identifying customer pain points (43:04) Starting small and showing success (46:08) Launching new product lines (53:35) Atlassian’s gated process for new product ideas (58:00) How Jira stays ahead of competitors (01:04:28) Learning from failure (01:08:30) Fight club (01:10:08) Lightning round — Referenced: • Jira: https://www.atlassian.com/software/jira • Atlassian: https://www.atlassian.com/ • Bitbucket: https://bitbucket.org/product • Ben Crowe on LinkedIn: https://www.linkedin.com/in/ben-crowe-67299714/ • Ash Barty on X: https://twitter.com/ashbarty • Atlassian’s blog, Work Life: https://www.atlassian.com/blog • Lessons learned: 1,000 days of distributed at Atlassian: https://www.atlassian.com/blog/distributed-work/distributed-work-report • New research: How to make time for the work that matters: https://www.atlassian.com/blog/distributed-work/calendar-redesign-experiment • Atlas: https://www.atlassian.com/software/atlas • Confluence: https://www.atlassian.com/software/confluence • Lenny’s swag store: https://lennyswag.com/ • What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat • The UX research reckoning is here | Judd Antin (Airbnb, Meta): https://www.lennyspodcast.com/the-ux-research-reckoning-is-here-judd-antin-airbnb-meta/ • Charlie Sutton on LinkedIn: https://www.linkedin.com/in/charliesutton/ • Nokia 6100: https://en.wikipedia.org/wiki/Nokia_6100 • Compass: https://www.atlassian.com/software/compass • Jira Product Discovery: https://www.atlassian.com/software/jira/product-discovery • Canva: https://www.canva.com/ • Inspired: How to Create Tech Products Customers Love: https://www.amazon.com/INSPIRED-Create-Tech-Products-Customers/dp/1119387507 • Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212 • Foundation on AppleTV+: https://tv.apple.com/us/show/foundation/umc.cmc.5983fipzqbicvrve6jdfep4x3 • Foundation book series: https://www.amazon.com/Foundation-3-Book-Boxed-Set-Empire/dp/0593499573 • Traeger smoker: https://www.traeger.com/shop/wood-pellet-grills — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jonny Miller is the founder of Nervous System Mastery, a course that has helped hundreds of founders and tech leaders cultivate calm, reduce nervousness, enhance resilience, and elevate their sense of aliveness. Having personally benefited from Jonny’s teachings, I’m especially excited to have him on the show. In this episode, we discuss: • How shifting your focus from the mind to the body can help ease nervousness • The power of breath in changing states • The importance of “interoception” • Specific breathing exercises to both calm and excite your nervous system • The A.P.E. (awareness, posture, and emotion) framework for recognizing body signals • The “feather, brick, dump truck” phenomenon • The concept of emotional debt and how to release it • The competitive advantage of feeling emotions — Jonny’s five-week boot camp, Nervous System Mastery, will equip you with evidence-backed protocols to cultivate greater calm and agency over your internal state. Learn to rewire maladaptive stress responses and improve your sleep (use code LENNY for $250 discount). Apply here. — Brought to you by: • Teal—Your personal career growth platform • Vanta—Automate compliance. Simplify security. • Miro—A collaborative visual platform where your best work comes to life — Find the full transcript at: https://www.lennysnewsletter.com/p/managing-nerves-anxiety-and-burnout — Where to find Jonny Miller: • X: https://twitter.com/jonnym1ller • LinkedIn: https://www.linkedin.com/in/jonnym1ller/ • Website: https://www.jonnymiller.co/ • Podcast: podcast.curioushumans.com  • Email: [email protected] • Course: https://nsmastery.com/lenny — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jonny’s background (07:19) The bottom-up approach to nervousness and anxiety (09:42) The power of breath in changing states (11:47) The concept of state over story (13:56) Personal experiences with nervousness (15:01) Breathing exercises to calm you down (20:40) The “espresso” breath exercise to give you energy (25:44) Interoception and the A.P.E. framework (34:47) The “feather, brick, dump truck” phenomenon (37:40) Recognizing emotional debt and avoiding burnout (40:47) Using somatic-oriented therapy for healing (45:26) Telltale signs of emotional debt (48:13) The competitive advantage of “feeling the feels” (50:20) Advice for people overwhelmed by stimuli (52:36) The NSDR (non-sleep deep rest) practice for emotional release (55:38) Daily practices for emotional well-being (58:23) Thoughts on meditation (01:01:26) The Body Keeps the Score (01:01:58) Contrarian corner (01:04:43) Lightning round — Jonny’s If [This] Then [Breathe] Recipes: • If [overwhelmed], then [hum] • If [anxious], then [breath of calm] • If [lethargic], then [espresso breath] — Referenced: • The Operating Manual for Your Nervous System: https://every.to/p/the-operating-manual-for-your-nervous-system • Afferent vs. Efferent Neurons: https://www.osmosis.org/answers/afferent-vs-efferent-neurons • Insular cortex: https://en.wikipedia.org/wiki/Insular_cortex • Jonny’s TED Talk, “The gifts of grief”: https://www.ted.com/talks/jonny_miller_the_gifts_of_grief/details • Humming (Simple Bhramari Pranayama) as a Stress Buster: A Holter-Based Study to Analyze Heart Rate Variability (HRV) Parameters During Bhramari, Physical Activity, Emotional Stress, and Sleep: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10182780/ • 14-Minute Guided NSDR (non-sleep deep rest) practice: https://www.youtube.com/watch?v=vjXX2c72fYY • Breathing Techniques to Reduce Stress and Anxiety | Dr. Andrew Huberman on the Physiological Sigh: https://www.youtube.com/watch?v=kSZKIupBUuc • Interoception: the hidden sense that shapes well-being: https://www.theguardian.com/science/2021/aug/15/the-hidden-sense-shaping-your-wellbeing-interoception • Exteroception: https://dictionary.apa.org/exteroception • Interoceptive Awareness and ADHD: https://chadd.org/adhd-news/adhd-news-adults/interoceptive-awareness-and-adhd/ • Childhood Trauma Affects Stress-Related Interoceptive Accuracy: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6813623/ • The Hour Between Dog and Wolf: How Risk Taking Transforms Us, Body and Mind: https://www.amazon.com/Hour-Between-Dog-Wolf-Transforms/dp/0143123408 • Somatic Experiencing: https://www.somaticexperiencing.com/ • Hakomi Institute: https://hakomiinstitute.com/ • Decisions and Desire (about Antonio Damasio’s work): https://hbr.org/2006/01/decisions-and-desire • When enough is enough | Andy Johns (ex-FB, Twitter, Quora): https://www.lennyspodcast.com/when-enough-is-enough-andy-johns-ex-fb-twitter-quora/ • What Is Yoga Nidra?: https://health.clevelandclinic.org/what-is-yoga-nidra • Becoming Fully Yourself, What AI Wants, Family Rituals & Rites of Passage, with Kevin Kelly: https://podcast.curioushumans.com/episodes/becoming-fully-yourself-what-ai-wants-rites-of-passage-with-kevin-kelly • Tim Ferriss: https://tim.blog/ • The Power of Sensations: Intermediate’s Vipassana Body Scan: https://insighttimer.com/carola.ananda/guided-meditations/the-power-of-sensations-intermediates-vipassana-body-scan-meditation • Vipassana Meditation: https://www.dhamma.org/en/index • The Body Keeps the Score: Brain, Mind, and Body in the Healing of Trauma: https://www.amazon.com/Body-Keeps-Score-Healing-Trauma/dp/0670785938 • Waking the Tiger: Healing Trauma: https://www.amazon.com/Waking-Tiger-Healing-Peter-Levine/dp/155643233X • Consolations: The Solace, Nourishment and Underlying Meaning of Everyday Words: https://www.themarginalian.org/2015/04/29/david-whyte-consolations-words/ • The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904/ • The Conscious Leadership Group: https://conscious.is/ • Recapture the Rapture: Rethinking God, Sex, and Death in a World That’s Lost Its Mind: https://www.amazon.com/Recapture-Rapture-Rethinking-Death-World/dp/0062905465 • Kubo and the Two Strings on Prime Video: https://www.amazon.com/Kubo-Two-Strings-Charlize-Theron/dp/B01K5BSWX0 • Wolfwalkers on AppleTV+: https://tv.apple.com/us/movie/wolfwalkers/umc.cmc.amuoq00hqelfi98j0gvg641x • Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4 • Jerry Colonna on LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/ • Ra Optics “Sunset” blue-light blockers: https://raoptics.com/collections/night-lenses • Nurosym vagal stimulation device: https://my.nurosym.com/vns1564/ • Pulsetto vagal stimulation device: https://pulsetto.tech/new-year/?gc_id=20124962116&h_ad_id=686249897188&gad_source=1 • Apollo vagus nerve stimulator: https://apolloneuro.com/products/apollo-wearable — Additional research: • Cellular allostatic load is linked to increased energy expenditure and accelerated biological aging: https://www.sciencedirect.com/science/article/pii/S0306453023003001 • Somatic experiencing: using interoception and proprioception as core elements of trauma therapy: https://www.frontiersin.org/articles/10.3389/fpsyg.2015.00093/full • Relationship between interoception and emotion regulation: New evidence from mixed methods: https://www.sciencedirect.com/science/article/abs/pii/S0165032718323723 • Out-of-the-blue panic attacks aren’t without warning: body sends signals for hour before: https://pubmed.ncbi.nlm.nih.gov/21783179/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Geoffrey Moore is an author, speaker, and advisor, widely known for his seminal book Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers, which many consider the most important book ever written on go-to-market strategy. Moore’s work is focused on the market dynamics surrounding disruptive innovations, and how one overcomes the challenge of transitioning from serving early adopters to the mainstream. In this episode, we discuss: • What “crossing the chasm” means • What steps to take before you try crossing the chasm • The importance of winning a marquee customer • The role of executive sponsors in the sales process • The differences between visionaries and pragmatists, and how to build for each • Geoffrey’s four go-to-market playbooks based on stage: Early Market, Bowling Alley, Tornado, and Main Street • The problem with discounting before crossing the chasm • “Deadly sins” to avoid when crossing the chasm — Brought to you by: • CommandBar—AI-powered user assistance for modern products and impatient users • WorkOS—An API platform for quickly adding enterprise features • Arcade Software—Create effortlessly beautiful demos in minutes — Find the full transcript at: https://www.lennysnewsletter.com/p/geoffrey-moore-on-finding-your-beachhead — Where to find Geoffrey Moore: • X: https://twitter.com/geoffreyamoore • LinkedIn: https://www.linkedin.com/in/geoffreyamoore/ • LinkedIn posts: https://www.linkedin.com/in/geoffreyamoore/recent-activity/articles/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Geoffrey’s background (04:03) What people often get wrong about Crossing the Chasm (05:58) Finding your beachhead segment (09:29) The four inflection points of the technology adoption lifestyle (15:45) Geoffrey’s bonfire and bowling alley analogies (18:36) Steps to take before trying to cross the chasm (22:19) Signs you’re ready to cross the chasm (25:19) Advice for startups on where to start (27:31) Thoughts on venture capital (27:53) A general timeline for crossing the chasm (30:52) What exactly is the “chasm”? (32:35) The difference between visionaries and pragmatists (36:05) Finding the compelling reason to buy (43:45) The Early Market playbook (45:46) The Bowling Alley playbook (48:39) Different sales approaches for early market and bowling alley (51:26) Changing the value state of the company (53:28) The Tornado playbook (57:35) Why combining playbooks doesn’t work (59:10) Using generative AI in different market phases (01:03:02) The risks of discounting (01:04:21) Other “deadly sins” of crossing the chasm (01:09:09) Positioning in crossing the chasm (01:10:36) Product-led growth and crossing the chasm (01:13:54) The challenges of software and entrepreneurship (01:16:35) How Geoffrey’s thinking has evolved (01:19:30) The importance of entrepreneurship and impact (01:20:42) His book The Infinite Staircase (01:23:58) Connect with Geoffrey Moore — Referenced: • Crossing the Chasm: Marketing and Selling Disruptive Products to Mainstream Customers: https://www.amazon.com/Crossing-Chasm-3rd-Disruptive-Mainstream/dp/0062292986 • Oracle: https://www.oracle.com/ • Documentum: https://www.opentext.com/products/documentum • Figma: https://www.figma.com/ • Notion: https://www.notion.so/ • Salesforce: https://www.salesforce.com/ • Intel: https://www.intel.com/ • Jason Fried challenges your thinking on fundraising, goals, growth, and more: https://www.lennyspodcast.com/jason-fried-challenges-your-thinking-on-fundraising-goals-growth-and-more/ • The Mayo Clinic: https://www.mayoclinic.org/ • Coda: https://coda.io/ • An inside look at how Figma ships product: https://coda.io/@yuhki/figma-product-roadmap • Dylan Field on LinkedIn: https://www.linkedin.com/in/dylanfield/ • Regis McKenna on Crunchbase: https://www.crunchbase.com/organization/regis-mckenna-inc • Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove • A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome and Sales Pitch): https://www.lennyspodcast.com/a-step-by-step-guide-to-crafting-a-sales-pitch-that-wins-april-dunford-author-of-obviously-awesom/ • Sales Pitch: How to Craft a Story to Stand Out and Win: https://www.amazon.com/Sales-Pitch-Craft-Story-Stand/dp/1999023021 • B2B Go-to-Market Playbooks and the Technology Adoption Life Cycle: https://www.linkedin.com/pulse/b2b-go-to-market-playbooks-technology-adoption-life-cycle-moore/ • Juniper: https://www.juniper.net/us/en.html • Sal Khan on LinkedIn: https://www.linkedin.com/in/khanacademy/ • Khan Academy: https://www.khanacademy.org/ • How the Star Wars Kessel Run Turns Han Solo Into a Time-Traveler: https://www.wired.com/2013/02/kessel-run-12-parsecs/ • Atlassian: https://www.atlassian.com/ • Martin Casado on LinkedIn: https://www.linkedin.com/in/martincasado/ • The Infinite Staircase: What the Universe Tells Us About Life, Ethics, and Mortality: https://www.amazon.com/Infinite-Staircase-Universe-Ethics-Mortality/dp/1950665984 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Richard Rumelt is a legend in the world of strategy. He’s the author of Good Strategy/Bad Strategy and The Crux: How Leaders Become Strategists, both of which are often recommended by guests on this podcast. From his early days teaching in Iran at a Harvard-sponsored business school to teaching at Harvard Business School itself to over four decades teaching at UCLA’s Anderson School of Management, Richard’s impact resonates globally. His strategic insights are sought after by major corporations including Microsoft, Shell, Apple, AT&T, Intel, and Commonwealth Bank and by governmental organizations such as the U.S. Army Special Operations Command. In this episode, we discuss: • The essential components of a good strategy • The importance of coherence in strategy • Common pitfalls that create a bad strategy • How “power” plays into strategy, and common sources of power • The value of knowing history when developing effective strategies • Why a strategy should simply be called an “action agenda” • The need for one decider in an organization — Brought to you by: • CommandBar—AI-powered user assistance for modern products and impatient users • Miro—A collaborative visual platform where your best work comes to life • Vanta—Automate compliance. Simplify security. — Find the full transcript at: https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard — Where to find Richard Rumelt: • Email: [email protected] • LinkedIn: https://www.linkedin.com/in/richard-rumelt-18520828/ • Website: https://thecruxbook.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Richard’s background (04:29) What is a strategy? (06:23) The essential components of a good strategy (the “kernel”) (15:04) An example of good strategy (16:55) Bad strategy (25:17) The importance of focus and power (28:19) Identifying and utilizing power (34:38) Types of power (41:13) Implementing power (48:15) The importance of historical knowledge (55:23) How to write an action agenda (01:02:47) The crux (01:10:40) Challenges to executing a strategy (01:15:44) The need for a decider (01:20:39) Strategy for startups (01:26:04) Richard’s “value denials” exercise (01:31:01) Closing thoughts (01:33:57) Lightning round — Referenced: • China’s Xi says ‘reunification’ with Taiwan is inevitable: https://www.cnbc.com/2023/12/31/chinas-xi-says-reunification-with-taiwan-is-inevitable.html • The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240 • Good Strategy/Bad Strategy: The Difference and Why It Matters: https://www.amazon.com/Good-Strategy-Bad-Difference-Matters/dp/0307886239 • Fundamental Issues in Strategy: A Research Agenda: https://www.amazon.com/Fundamental-Issues-Strategy-Research-Agenda/dp/0875843433/ • Strategy, Structure, and Economic Performance: https://www.amazon.com/Strategy-Structure-Economic-Performance-Richard/dp/0875841090 • There’s more than the CIA and FBI: The 17 agencies that make up the U.S. intelligence community: https://www.latimes.com/nation/la-na-17-intelligence-agencies-20170112-story.html • Programme for International Student Assessment: https://www.oecd.org/pisa/ • Gerstner: Changing Culture at IBM—Lou Gerstner Discusses Changing the Culture at IBM: https://hbswk.hbs.edu/archive/gerstner-changing-culture-at-ibm-lou-gerstner-discusses-changing-the-culture-at-ibm • Marvin Lieberman on LinkedIn: https://www.linkedin.com/in/marvin-lieberman-2a6b72/ • S&P 500: https://www.spglobal.com/spdji/en/indices/equity/sp-500/#overview • Battle of Tora Bora: https://en.wikipedia.org/wiki/Battle_of_Tora_Bora • Milton Friedman: https://en.wikipedia.org/wiki/Milton_Friedman • The Louvre: https://www.louvre.fr/en • How does SpaceX build its Falcon 9 reusable rocket?: https://www.sciencefocus.com/space/how-does-spacex-build-its-falcon-9-reusable-rocket • Charles Darwin: History’s most famous biologist: https://www.nhm.ac.uk/discover/charles-darwin-most-famous-biologist.html • Donald Rumsfeld: https://www.defense.gov/About/Biographies/Biography/Article/602800/ • Bush: The Decider-in-Chief: https://www.cbsnews.com/news/bush-the-decider-in-chief/ • Woodrow Wilson: https://www.whitehouse.gov/about-the-white-house/presidents/woodrow-wilson/ • How the Sinking of Lusitania Changed World War I: https://www.history.com/news/how-the-sinking-of-lusitania-changed-wwi • Nokia: https://www.nokia.com/ • The Rise and Fall of Nokia: https://www.hbs.edu/faculty/Pages/item.aspx?num=46041 • Salesforce: https://www.salesforce.com/ • These New Windows Let the Summer Breeze In, But Block the Street Noise: https://www.smithsonianmag.com/smart-news/these-new-windows-let-the-summer-breeze-in-but-block-the-street-noise-7906121/ • Stop it! (Bob Newhart): https://www.youtube.com/watch?v=jvujypVVBAY • The Innovator’s Dilemma: The Revolutionary Book That Will Change the Way You Do Business: https://www.amazon.com/Innovators-Dilemma-Revolutionary-Change-Business/dp/0062060244 • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • Steve Jobs: https://www.amazon.com/Steve-Jobs-Walter-Isaacson/dp/1982176865 • Only the Paranoid Survive: How to Exploit the Crisis Points That Challenge Every Company: https://www.amazon.com/Only-Paranoid-Survive-Exploit-Challenge/dp/0385483821 • Titan: The Life of John D. Rockefeller, Sr.: https://www.amazon.com/Titan-Life-John-Rockefeller-Sr/dp/1400077303/ • Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone • Smart telescopes: https://milehighastro.com/collections/smart-telescopes • Cassandra Clare: https://cassandraclare.com/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Heidi Helfand is the author of Dynamic Reteaming, which outlines practical strategies for orchestrating successful team and company org changes. Her work is informed by more than 20 years in the tech industry at notable companies like AppFolio, Procore, and Expertcity/GoToMeeting. Today, she dedicates her efforts to sharing her knowledge through workshops, comprehensive courses, and consultative services, helping organizations navigate and optimize their team structures. In this episode, we discuss: • The importance of reteaming and reorging • The benefits of embracing reteaming • The five patterns of reteaming: one by one, grow and split, merging, isolation, and switching • Examples of successful reteaming • Why stable teams are not always ideal • How change can lead to great career opportunities • The RIDE framework for decision-making • Advice on how to set up isolated teams for success • The anti-patterns of reteaming and the challenges that can arise • Tactical tips for becoming a better listener — Brought to you by: • Productroadmap.ai—AI to connect your roadmaps to revenue • Hex—Helping teams ask and answer data questions by working together • Ahrefs—Improve your website’s SEO for free — Find the full transcript at: https://www.lennysnewsletter.com/p/the-art-and-wisdom-of-changing-teams — Where to find Heidi Helfand: • X: https://twitter.com/heidihelfand • LinkedIn: https://www.linkedin.com/in/heidihelfand/ • Website: https://www.heidihelfand.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Heidi’s background (03:40) How Heidi got involved with reteaming and reorgs (07:37) Advice for people dealing with reorgs (11:56) The benefits of change and the RIDE framework (17:11) The five patterns of reteaming (20:00) The power of isolation (27:38) Advice on how to be successful by isolating small teams (33:27) Supporting and protecting internal startups (34:33) The one-by-one pattern (36:44) The grow and split pattern (39:20) The merging pattern (42:14) The switching pattern (50:18) Anti-patterns of reteaming (52:49) Embracing change and growth (58:48) How to become a better listener (01:01:28) Lightning round — Referenced: • Dynamic Reteaming: The Art and Wisdom of Changing Teams: https://www.amazon.com/Dynamic-Reteaming-Wisdom-Changing-Teams/dp/1492061298 • O’Reilly: https://www.oreilly.com/ • Procore Technologies: https://www.procore.com/ • Kristian Lindwall on LinkedIn: https://www.linkedin.com/in/kristianlindwall/ • Chris Smith on LinkedIn: https://www.linkedin.com/in/chrissmithagile • Transitions: Making Sense of Life’s Changes: https://www.amazon.com/Transitions-Making-Changes-Revised-Anniversary/dp/073820904X • Pat Wadors on LinkedIn: https://www.linkedin.com/in/patwadors/ • The Four Steps to the Epiphany: Successful Strategies for Products That Win: https://www.amazon.com/Four-Steps-Epiphany-Successful-Strategies/dp/1119690358 • GoToMyPC: https://get.gotomypc.com/ • Teamwork: https://www.amazon.com/Teamwork-Right-Wrong-Interpersonal-Communication/dp/0803932901 • AppFolio: https://www.appfolio.com/ • SecureDocs: https://www.securedocs.com/ • Citrix: https://www.citrix.com/ • The Culture Code: The Secrets of Highly Successful Groups: https://www.amazon.com/Culture-Code-Secrets-Highly-Successful/dp/0804176981 • Tuckman’s stages of group development: https://en.wikipedia.org/wiki/Tuckman%27s_stages_of_group_development • Rich Sheridan on LinkedIn: https://www.linkedin.com/in/menloprez/  • Menlo Innovations: https://menloinnovations.com/ • Drive: The Surprising Truth About What Motivates Us: https://www.amazon.com/Drive-Surprising-Truth-About-Motivates/dp/1594484805 • Toyota Kata: Managing People for Improvement, Adaptiveness and Superior Results: https://www.amazon.com/Toyota-Kata-Managing-Improvement-Adaptiveness/dp/0071635238 • Paulo Freire: https://en.wikipedia.org/wiki/Paulo_Freire • Jon Walker on LinkedIn: https://www.linkedin.com/in/jwalker/ • Managing Corporate Lifecycles: https://www.amazon.com/Managing-Corporate-Lifecycles-Ichak-Adizes/dp/9381860548 • The Adizes Institute: https://www.adizes.com/ • John Cutler on Lenny’s Podcast: https://www.lennyspodcast.com/what-differentiates-the-highest-performing-product-teams-john-cutler-amplitude-the-beautiful-mes/ • Co-Active Training Institute: https://coactive.com/ • Co-Active Coaching: The proven framework for transformative conversations at work and in life: https://www.amazon.com/Co-Active-Coaching-Fourth-transformative-conversations/dp/1473674980 • Creating Intelligent Teams: https://www.amazon.com/Creating-Intelligent-teams-Anne-R%C3%B8d/dp/186922583X • The Surprising Power of Liberating Structures: Simple Rules to Unleash a Culture of Innovation: https://www.amazon.com/Surprising-Power-Liberating-Structures-Innovation/dp/0615975305 • Facilitator’s Guide to Participatory Decision-Making: https://www.amazon.com/Facilitators-Participatory-Decision-Making-Jossey-bass-Management/dp/1118404955 • The Bear on Hulu: https://www.hulu.com/series/the-bear-05eb6a8e-90ed-4947-8c0b-e6536cbddd5f — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Ethan Evans is a writer, career coach, course instructor, and retired VP at Amazon. During his 15 years at Amazon, he helped invent Prime Video, Amazon Video, the Amazon Appstore, Prime Gaming (formerly Twitch Prime), and Twitch Commerce. Prior to Amazon, Ethan spent 12 years in technical leadership roles at several East Coast startups. He writes a newsletter, Level Up, which publishes candid career advice and has a growing community of ambitious professionals to connect with. Ethan also offers a range of Leadership Development Courses via live online classes and on-demand courses. In this episode, we discuss: • The Magic Loop framework: a five-step process to grow your career • A handful of reasons why people get stuck in their career growth • Advice on how to break out of a career plateau • How to cultivate inventiveness in your work • How to stand out in interviews • A personal story of failing Jeff Bezos and lessons learned • Contrarian opinions on the return-to-office movement and doing business on a handshake — Brought to you by Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Sprig—Build a product people love | Arcade Software—Create effortlessly beautiful demos in minutes — Find the full transcript at: https://www.lennysnewsletter.com/p/taking-control-of-your-career-ethan — Where to find Ethan Evans: • LinkedIn: https://www.linkedin.com/in/ethanevansvp/ • Substack: https://levelupwithethanevans.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Ethan’s background (04:25) The Magic Loop (08:31) The goal of the Magic Loop (10:59) Clarifications on the framework (12:46) Success stories (17:22) The importance and effectiveness of the Magic Loop (19:01) A quick summary of the steps in the Magic Loop (21:46) What if you’re not pursuing a promotion? (23:09) How to break out of a career plateau (28:52) How to become systematically inventive (36:04) Interview advice and how to stand out (40:43) A story of failing Jeff Bezos (50:31) Lessons learned from that failure (57:30) What Ethan would have done differently (01:00:35) Amazon’s leadership principles (01:08:52) Contrarian corner: Returning to the office vs. staying remote (01:10:39) Contrarian corner: Doing business on a handshake (01:11:52) Lightning round — Referenced: • The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop • SDE levels: https://www.masaischool.com/blog/understanding-sde-levels-sde-1-vs-sde-2-vs-sde-3-differences/ • What Got You Here Won’t Get You There: How Successful People Become Even More Successful: https://www.amazon.com/What-Got-Here-Wont-There/dp/1401301304 • Thomas Edison’s quote: https://www.brainyquote.com/quotes/thomas_a_edison_109928 • Jeff Bezos: Amazon and Blue Origin | Lex Fridman Podcast: https://www.youtube.com/watch?v=DcWqzZ3I2cY • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennyspodcast.com/unpacking-amazons-unique-ways-of-working-bill-carr-author-of-working-backwards/ • Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595 • Jeff Wilke on X: https://twitter.com/jeffawilke • Andy Jassy on LinkedIn: https://www.linkedin.com/in/andy-jassy-8b1615/ • Werner Vogels on LinkedIn: https://www.linkedin.com/in/wernervogels/ • Amazon’s Silk browser explained: https://www.androidpolice.com/amazon-silk-browser-explainer/ • Chickens and pigs: https://www.scrum.org/resources/chickens-and-pigs • 58% of tech employees experience imposter syndrome. Here’s how to overcome it: https://medium.com/wearefutureworks/58-of-tech-employees-experience-imposter-syndrome-heres-how-to-overcome-it-78172d8a2258 • Jeff Bezos to exec after product totally flopped: ‘You can’t, for one minute, feel bad’: https://www.cnbc.com/2020/05/22/jeff-bezos-why-you-cant-feel-bad-about-failure.html • Amazon’s leadership principles: https://www.amazon.jobs/content/en/our-workplace/leadership-principles • Sam Altman on X: https://twitter.com/sama • Decisive: How to Make Better Choices in Life and Work: https://www.amazon.com/Decisive-Make-Better-Choices-Life/dp/0307956393 • Leadership and Self-Deception: Getting Out of the Box: https://www.amazon.com/Leadership-Self-Deception-Getting-Out-Box/dp/1523097809 • The Almanack of Naval Ravikant: A Guide to Wealth and Happiness: https://www.amazon.com/Almanack-Naval-Ravikant-Wealth-Happiness/dp/1544514212/ • Angel list: https://venture.angellist.com/naval/syndicate • Naval Ravikant on X: https://twitter.com/naval • 1923 on Paramount+: https://www.paramountplus.com/shows/1923/ • Yellowstone on Paramount+: https://www.paramountnetwork.com/shows/yellowstone • Chuckit! dog toys: https://www.chuckit-toys.co.uk/ • Luke 12:48: https://law.utk.edu/2016/05/10/to-whom-much-is-given-much-will-be-required • The Challenger space shuttle disaster: https://en.wikipedia.org/wiki/Space_Shuttle_Challenger_disaster • Ethan’s popular course on Maven: https://maven.com/ethan-evans/break-through-to-executive — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sam Schillace is deputy CTO and corporate vice president at Microsoft. Prior to working at Microsoft, Sam started a company called Writely, which was acquired by Google and became the foundation of what today is Google Docs. While at Google, Sam helped lead many of Google’s consumer products, including Gmail, Blogger, PageCreator, Picasa, Reader, Groups, and more recently Maps and Google Automotive Services. Sam was also a principal investor at Google Ventures, has founded six startups, and was the SVP of engineering at Box through their IPO. In this episode, we discuss: • The journey of building Google Docs • The importance of taking risks, embracing failure, and finding joy in your work • The importance of asking “what if” questions vs. “why not” • Why convenience always wins • How, and why, Sam stays optimistic • Inside Microsoft’s culture • Why you should solve problems without asking for permission • Early-career advice • Why “pixels are free” and “bots are docs” — Brought to you by Teal—Your personal career growth platform | Vanta—Automate compliance. Simplify security | Ahrefs—Improve your website’s SEO for free — Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-be-more-innovative-sam-schillace — Where to find Sam Schillace: • LinkedIn: https://www.linkedin.com/in/schillace/ • Newsletter: https://sundaylettersfromsam.substack.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sam’s background (03:45) The first Google Docs file (06:45) Disruptive innovation (10:11) First-principles thinking (11:00) Recognizing disruptive ideas (13:17) Examples of first-principles thinking (15:46) The power of optimism (19:47) Sam’s motto: Get to the edge of something and f**k around (21:53) User value and laziness (24:31) People are lazy (and what to do about it) (28:36) Building Google Docs (31:06) The evolution of Google Docs (37:15) Finding product-market fit (39:52) The future of documents (44:57) The value of playing with technology (47:58) Taking risks and embracing failure (49:21) Thinking in the future (53:48) Finding joy in your work (01:01:20) Just do the best you can (01:02:34) The transformational power of AI (01:09:27) Advice for approaching AI (01:13:07) The culture at Microsoft (01:16:51) Closing thoughts (01:17:32) Lightning round — Referenced: • Google Docs began as a hacked-together experiment, says creator: https://www.theverge.com/2013/7/3/4484000/sam-schillace-interview-google-docs-creator-box • Edna Mode: https://disney.fandom.com/wiki/Edna_Mode • Sergey Brin’s profile on Forbes: https://www.forbes.com/profile/sergey-brin/ • People Who Were No Smarter Than You: https://medium.com/thrive-global/people-who-were-no-smarter-than-you-4e1c88c3fee6 • Nat Torkington (O’Reilly Media): https://www.oreilly.com/people/nathan-torkington/ • How Tesla Has Shaken (Not Stirred) Established Carmakers—and Why It Really Matters: https://www.forbes.com/sites/jenniferdungs/2021/04/23/how-tesla-has-shaken-not-stirred-established-carmakersand-why-it-really-matters/ • First Principles: Elon Musk on the Power of Thinking for Yourself: https://jamesclear.com/first-principles • Ashton Tate: https://en.wikipedia.org/wiki/Ashton-Tate • Learning by Doing: https://www.linkedin.com/pulse/learning-doing-sam-schillace • Kevin Scott on LinkedIn: https://www.linkedin.com/in/jkevinscott/ • How do we make sense of all of this?: https://sundaylettersfromsam.substack.com/p/how-do-we-make-sense-of-all-of-this • Steve Newman on LinkedIn: https://www.linkedin.com/in/stevescalyr/ • Eric Schmidt on LinkedIn: https://www.linkedin.com/in/eric-schmidt-02158951/ • Michael Arrington on X: https://twitter.com/arrington • TechCrunch: https://techcrunch.com/ • “Hello, Computer” scene from Star Trek: https://www.youtube.com/watch?v=hShY6xZWVGE • Writely—Process Words with your Browser: https://techcrunch.com/2005/08/31/writely-process-words-with-your-browser/ • Satya Nadella on LinkedIn: https://www.linkedin.com/in/satyanadella/ • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack • Calvinism: https://en.wikipedia.org/wiki/Calvinism • This Quote from Seth Godin Could Change How You Think About Pursuing Your Passion: https://friedchickenandsushi.com/blog/2021/7/5/this-quote-from-seth-godin-could-change-how-you-think-about-pursuing-your-passion • AI isn’t a feature of your product: https://sundaylettersfromsam.substack.com/p/ai-isnt-a-feature-of-your-product • Introducing Gemini: our largest and most capable AI model: https://blog.google/technology/ai/google-gemini-ai/ • Invisible Cities: https://www.amazon.com/Invisible-Cities-Italo-Calvino/dp/0156453800 • The Wasp Factory: https://www.amazon.com/WASP-FACTORY-NOVEL-Iain-Banks/dp/0684853159 • Where Good Ideas Come From: The Natural History of Innovation: https://www.amazon.com/Where-Good-Ideas-Come-Innovation/dp/1594485380/ • Slow Horses on Apple TV+: https://tv.apple.com/us/show/slow-horses/umc.cmc.2szz3fdt71tl1ulnbp8utgq5o • Monarch: Legacy of Monsters on Apple TV+: https://tv.apple.com/us/show/monarch-legacy-of-monsters/umc.cmc.62l8x0ixrhyq3yaqa5y8yo7ew?mttn3pid • Scavengers Reign on Max: https://www.max.com/shows/scavengers-reign/50c8ce6d-088c-42d9-9147-d1b19b1289d4 • 2023 Mustang Mach-E: https://www.ford.com/suvs/mach-e/ • Boccalone Salumeria (now closed) on X: https://twitter.com/boccalone — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Will Larson is Chief Technology Officer at Carta. Prior to joining Carta, he was the CTO at Calm and held engineering leadership roles at Stripe, Uber, and Digg. He is the author of two foundational engineering career books, An Elegant Puzzle and Staff Engineer, and The Engineering Executive’s Primer, which will be released in February. In our conversation, we discuss: • Systems thinking: what it is and how to apply it • Advice for product managers on fostering productive relationships with engineering managers • Why companies should treat engineers like adults • How to best measure developer productivity • Writing and its impact on his career • How to balance writing with a demanding job • How to develop your company values — Brought to you by DX—A platform for measuring and improving developer productivity | OneSchema—Import CSV data 10x faster | Vanta—Automate compliance. Simplify security. — Find the full transcript at: https://www.lennysnewsletter.com/p/the-engineering-mindset-will-larson — Where to find Will Larson: • X: https://twitter.com/Lethain • LinkedIn: https://www.linkedin.com/in/will-larson-a44b543/ • Website: https://lethain.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Will’s background (04:12) Changes in the field of engineering (06:27) We need to stop treating engineers like children (08:32) Systems thinking (13:23) Implementing systems thinking in hiring (16:32) Engineering strategy (20:21) Examples of engineering strategies (25:08) How to get good at strategy (26:48) The importance of writing about things that excite you (32:40) The biggest risk to content creation is quitting too soon (35:24) How to make time for writing (37:41) Tips for aspiring writers (41:18) Building productive relationships between product managers and engineers (43:45) Giving the same performance rating to EMs and PMs (48:24) Measuring engineering productivity (55:53) Defining company values (01:02:10) Failure corner: the Digg rewrite (01:11:05) Will’s upcoming book, The Engineering Executive’s Primer (01:12:04) Lightning round — Referenced: • The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom • Work on what matters: https://lethain.com/work-on-what-matters/ • Sheryl Sandberg to Harvard Biz Grads: “Find a Rocket Ship”: https://www.forbes.com/sites/kashmirhill/2012/05/24/sheryl-sandberg-to-harvard-biz-grads-find-a-rocket-ship/?sh=708c9a93b37a • What Is Systems Thinking?: https://www.snhu.edu/about-us/newsroom/business/what-is-systems-thinking • Introduction to systems thinking: https://lethain.com/systems-thinking/ • Thinking in Systems: https://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/1603580557 • Silent Spring: https://www.amazon.com/Silent-Spring-Rachel-Carson/dp/0618249060 • Writing an engineering strategy: https://lethain.com/eng-strategies/ • Carta: https://carta.com/ • Eric Vogl on LinkedIn: https://www.linkedin.com/in/ericvogl/ • Good Strategy/Bad Strategy: The difference and why it matters: https://www.amazon.com/Good-Strategy-Bad-difference-matters/dp/1781256179 • The Crux: How Leaders Become Strategists: https://www.amazon.com/Crux-How-Leaders-Become-Strategists/dp/1541701240/ • How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything in Between: https://www.amazon.com/How-Big-Things-Get-Done/dp/0593239512/ • Technology Strategy Patterns: Architecture as Strategy: https://www.amazon.com/Technology-Strategy-Patterns-Architecture/dp/1492040878/ • The Value Flywheel Effect: Power the Future and Accelerate Your Organization to the Modern Cloud: https://www.amazon.com/Value-Flywheel-Effect-Accelerate-Organization/dp/1950508579 • The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win: https://www.amazon.com/Phoenix-Project-DevOps-Helping-Business/dp/1942788290 • The Engineering Executive’s Primer: Impactful Technical Leadership: https://www.amazon.com/Engineering-Executives-Primer-Impactful-Leadership/dp/1098149483 • An Elegant Puzzle: Systems of Engineering Management: https://press.stripe.com/an-elegant-puzzle • Staff Engineer: Leadership beyond the management track: https://www.amazon.com/Staff-Engineer-Leadership-beyond-management-ebook/dp/B08RMSHYGG • Gergely Orosz’s newsletter: https://blog.pragmaticengineer.com/author/gergely/ • Leaving big tech to build the #1 technology newsletter | Gergely Orosz (The Pragmatic Engineer): https://www.lennyspodcast.com/videos/leaving-big-tech-to-build-the-1-technology-newsletter-gergely-orosz-the-pragmatic-engineer/ • The art of product management | Shreyas Doshi (Stripe, Twitter, Google, Yahoo): https://www.lennyspodcast.com/videos/the-art-of-product-management-shreyas-doshi-stripe-twitter-google-yahoo/ • Henry Ward on LinkedIn: https://www.linkedin.com/in/heward/ • Vrushali Paunikar on LinkedIn: https://www.linkedin.com/in/vrushali-paunikar/ • Accelerate: The Science of Lean Software and DevOps: Building and Scaling High Performing Technology Organizations: https://www.amazon.com/Accelerate-Software-Performing-Technology-Organizations/dp/1942788339 • How to measure and improve developer productivity | Nicole Forsgren (Microsoft Research, GitHub, Google): https://www.lennyspodcast.com/how-to-measure-and-improve-developer-productivity-nicole-forsgren-microsoft-research-github-goo/ • DORA: https://dora.dev/ • Setting engineering org values: https://lethain.com/setting-engineering-org-values/ • Digg: https://digg.com/ • Kevin Rose on LinkedIn: https://www.linkedin.com/in/kevinrose/ • Digg’s v4 launch: an optimism born of necessity: https://lethain.com/digg-v4/ • Dash Gopinath on LinkedIn: https://www.linkedin.com/in/dashgopinath/ • Rich Schumacher on LinkedIn: https://www.linkedin.com/in/richschumacher/ • The ALL NEW Don’t Think of an Elephant!: Know Your Values and Frame the Debate: https://www.amazon.com/ALL-NEW-Dont-Think-Elephant-ebook/dp/B00NP9LHFA • Top Chef on Peacock: https://www.peacocktv.com/watch-online/tv/top-chef/5172289448907967112 • Hard to work with: https://lethain.com/hard-to-work-with/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Judd Antin has spent 15 years leading research and design teams at companies like Yahoo, Meta, and Airbnb. His direct reports have gone on to lead user research at Figma, Notion, Slack, Robinhood, Duolingo, AllTrails, and more. In our conversation, we unpack the transformation that the user-research field is experiencing. Specifically: • Where user research went wrong over the past decade • The three types of research—macro, middle-range, and micro—and the purpose of each • How to effectively integrate researchers into the product development process • The “user-centered performance” phenomenon and why it’s a waste of time • Common tropes about PMs, from researchers • The ideal ratio of researchers in a company • Why Judd says NPS is useless, and what to use instead — Brought to you by Teal—Your personal career growth platform | Vanta—Automate compliance. Simplify security | Ahrefs—Improve your website’s SEO for free — Find the full transcript at: https://www.lennysnewsletter.com/p/the-ux-research-reckoning-is-here — Where to find Judd Antin: • LinkedIn: https://www.linkedin.com/in/juddantin/ • Website: https://juddantin.com/ • Blog: https://medium.com/onebigthought — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Judd’s background (04:16) Critiques and responses to Judd’s post “The UX Research Reckoning Is Here” (07:33) The state of user research (08:53) Macro, middle-range, and micro research (14:05) What teams get wrong when it comes to research (15:46) The importance of integrating research from the beginning (17:30) Traits of great researchers (19:53) Advice for evaluating user researchers (21:10) Balancing business and product focus (23:55) User-centered performance (26:42) The role of intuition in product development (30:15) Checking your gut instincts (32:54) Common tropes about PMs, from researchers (41:02) A/B testing vs. user research (43:15) Hindsight bias and narrative fallacy (44:55) Making recommendations based on research (47:26) Advice for teams on how to leverage researchers (51:18) How product managers can be better partners to user researchers (56:53) The ideal ratio of researchers in a company (59:43) Empowering user researchers to drive impact (01:03:39) The limitations of NPS as a metric (01:06:48) The risks of dogfooding (01:08:51) Lightning round — Referenced: • Matt Gallivan on LinkedIn: https://www.linkedin.com/in/mattgallivan/ • Janna Bray on LinkedIn: https://www.linkedin.com/in/janna-bray-a4046a25/ • Celeste Ridlen on LinkedIn: https://www.linkedin.com/in/celesteridlen/ • Rebecca Gray on LinkedIn: https://www.linkedin.com/in/rebeccagray2/ • Hannah Pileggi on LinkedIn: https://www.linkedin.com/in/hannah-pileggi-43169314/ • Louise Beryl on LinkedIn: https://www.linkedin.com/in/louise-beryl-13225833/ • The UX Research Reckoning Is Here: https://medium.com/onebigthought/the-ux-research-reckoning-is-here-c63710ea4084 • The end of the “free money” era: https://www.theguardian.com/technology/2023/apr/11/techscape-zirp-tech-boom • Cognitive biases: https://en.wikipedia.org/wiki/List_of_cognitive_biases • IDEO design thinking: https://designthinking.ideo.com/ • Everything Is Obvious: How Common Sense Fails Us: https://www.amazon.com/Everything-Obvious-Common-Sense-Fails/dp/0307951790 • Patrick Collison’s tweet: https://twitter.com/patrickc/status/1443215022029619200?lang=en • Brian Chesky on LinkedIn: https://www.linkedin.com/in/brianchesky/ • Brian Chesky on Lenny’s Podcast: https://www.lennyspodcast.com/brian-cheskys-new-playbook/ • NPS: https://en.wikipedia.org/wiki/Net_promoter_score • What is CSAT and how do you measure it?: https://www.qualtrics.com/experience-management/customer/what-is-csat/ • Michael Murakami on LinkedIn: https://www.linkedin.com/in/michaelhmurakami/ • Bad Leadership: What It Is, How It Happens, Why It Matters: https://www.amazon.com/Bad-Leadership-Happens-Matters-Common/dp/1591391660 • Demon Copperhead: https://www.amazon.com/Demon-Copperhead-Novel-Barbara-Kingsolver/dp/0063251922 • All Systems Red: The Murderbot Diaries: https://www.amazon.com/All-Systems-Red-Murderbot-Diaries/dp/0765397536 • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • Belay glasses: https://www.amazon.com/Belay-Glasses-Climbing-Comfortable-Sturdy/dp/B08GSBYDKQ/ • Epictetus: Control What You Can—Especially Yourself: https://www.shortform.com/blog/epictetus-control/ • The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Nir Eyal is the author of two best-selling books, Hooked: How to Build Habit-Forming Products and Indistractable: How to Control Your Attention and Choose Your Life. He writes, consults, and teaches at the intersection of psychology, technology, and business. His books have sold over 1 million copies in more than 30 languages; he has taught at Stanford’s Graduate School of Business and its Design School; and he has started and sold two startups since 2003. In our conversation, we discuss: • Strategies for becoming less distractible and improving focus • The difference between distraction and “traction” • Reactive work vs. reflexive work and why you should book time in your calendar • The 10-minute rule to overcome internal triggers and stay focused • The problem with to-do lists, and what to do instead • The value of creating a timebox schedule that aligns with personal values and priorities • The use of pacts as a last line of defense against distraction • How to develop a high-agency mindset • Advice for leaders on helping employees improve focus in the workplace — Brought to you by Vanta—Automate compliance. Simplify security | Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Teal—Your personal career growth platform — Find the full transcript at: https://www.lennysnewsletter.com/p/strategies-for-becoming-less-distractible — Where to find Nir Eyal: • X: https://twitter.com/nireyal • LinkedIn: https://www.linkedin.com/in/nireyal/ • Website: https://www.nirandfar.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Nir’s background (04:20) How to become less distractible (07:43) Understanding distraction and traction (12:52) The four steps to becoming indistractable (13:53) Mastering internal triggers (18:49) Surfing the urge with a 10-minute timer (23:20) Making time for traction with a timebox schedule (25:02) How to turn your values into time (28:36) Booking deep work time (29:22) Making pacts to prevent distraction (31:00) The problem with to-do lists (34:31) The drawback of deadlines (36:08) Distraction is an emotion regulation problem (39:54) Hacking back external triggers (45:03) Preventing distraction with pacts (48:18) Specific tools to hold you accountable (53:42) Managing emotions and discomfort (56:37) Taking responsibility and being high-agency (01:00:09) Becoming indistractable at work (01:05:04) Schedule syncing to align with managers (01:09:36) We are not as hooked on technology as people think (01:16:00) Life purpose and personal responsibility (01:17:38) Lightning round — Referenced: • Indistractable: How to Control Your Attention and Choose Your Life: https://www.amazon.com/Indistractable-Control-Your-Attention-Choose/dp/194883653X • Hooked: How to Build Habit-Forming Products: https://www.amazon.com/Hooked-How-Build-Habit-Forming-Products/dp/1591847788 • Dorothy Parker’s quote: https://twitter.com/nireyal/status/1472280598723108866 • “Writing is bleeding” quote: https://www.hemingwaysociety.org/quotation-controversy-writing-and-bleeding • The Pomodoro Technique Explained: https://www.forbes.com/sites/bryancollinseurope/2020/03/03/the-pomodoro-technique/ • Timeboxing: Why It Works and How to Get Started in 2024: https://www.nirandfar.com/timeboxing/ • Using your working time well - Issue 22: https://www.lennysnewsletter.com/p/time-management-issue-22 • All-In podcast: https://www.allinpodcast.co/ • Nir’s post about “the planning fallacy”: https://www.linkedin.com/posts/nireyal_why-do-tasks-always-seem-to-take-longer-than-activity-7137440438939959297-XIUB/ • How the Ancient Greeks Beat Distraction: https://www.nirandfar.com/tantalizing-distractions/ • Jeremy Bentham: https://iep.utm.edu/jeremy-bentham • An overview of Sigmund Freud’s pleasure principle: https://www.sciencedirect.com/topics/nursing-and-health-professions/pleasure-principle • The Matrix “There is no spoon” scene: https://www.youtube.com/watch?v=uAXtO5dMqEI • Outlet timer: https://www.amazon.com/Century-Indoor-24-Hour-Mechanical-Outlet/dp/B01LPSGBZS • Forest app: https://www.forestapp.cc/ • Focusmate: https://www.focusmate.com/ • Have We Been Thinking About Willpower the Wrong Way for 30 Years?: https://hbr.org/2016/11/have-we-been-thinking-about-willpower-the-wrong-way-for-30-years • We Need Social Antibodies to Fight the Disease of Distraction: https://nireyal.medium.com/we-need-social-antibodies-to-fight-the-disease-of-distraction-51f9187be016 • The Mere Presence of Your Smartphone Reduces Brain Power, Study Shows: https://news.utexas.edu/2017/06/26/the-mere-presence-of-your-smartphone-reduces-brain-power • Leading in Tough Times: HBS Faculty Member Amy C. Edmondson on Psychological Safety: https://www.hbs.edu/recruiting/insights-and-advice/blog/post/leading-in-tough-times • If Tech Is So Distracting, How Do Slack Employees Stay So Focused?: https://www.nirandfar.com/slack-use/ • Managing up: https://www.lennysnewsletter.com/p/managing-up • Duolingo: https://www.duolingo.com/ • FitBot: https://www.fitbotapp.com/ • Paulo Coelho’s quote: https://twitter.com/paulocoelho/status/416264984188825600 • Alchemy: The Dark Art and Curious Science of Creating Magic in Brands, Business, and Life: https://www.amazon.com/Alchemy-Curious-Science-Creating-Business/dp/006238841X • The Experience Machine: How Our Minds Predict and Shape Reality: https://www.amazon.com/Experience-Machine-Minds-Predict-Reality/dp/1524748455 • Empire of the Sun on Prime Video: https://www.amazon.com/Empire-Sun-Christian-Bale/dp/B001N3JY82 • Sesame grinder: https://www.miyacompany.com/450-014-450-014 • Muji pens: https://www.muji.us/collections/pen-pencils — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Sarah Tavel is a General Partner at Benchmark and sits on the boards of Chainalysis, Hipcamp, Rekki, Cambly, and Medely. She is a founding member of All Raise, the nonprofit organization working to accelerate the success of women in the venture-capital and VC-backed startup ecosystem. Before Benchmark, Sarah was a partner at Greylock Partners. She joined Pinterest in 2012 as their first PM and launched their first search and recommendations features. She also led three acquisitions as she helped the company scale through a period of hypergrowth. In this episode, we discuss: Sarah’s Hierarchy of Engagement framework for growing a consumer startup • The three levels of the Hierarchy of Engagement: core action, retention, and self-perpetuation • The importance of measuring cohorts and maintaining focus on the core action • Examples of core user actions from Pinterest and YouTube Sarah’s Hierarchy of Marketplaces framework for building a marketplace startup • The three vectors of growth for dominating a marketplace • Advice on “tipping the marketplace” and ultimately dominating the market • The value of focusing on a constrained market • How to avoid disruption — This entire episode is brought to you by Gelt—Redefine your approach to taxes. — Find the full transcript at: https://www.lennysnewsletter.com/p/the-hierarchy-of-engagement-sarah — Where to find Sarah Tavel: • X: https://twitter.com/sarahtavel • LinkedIn: https://www.linkedin.com/in/sarahtavel/ • Substack: https://www.sarahtavel.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Sarah’s background (03:33) Framework 1: The Hierarchy of Engagement (06:03) Level 1: Core action (10:33) Level 2: Retention (14:00) Level 3: Self-perpetuation (19:32) The importance of focus (23:54) The challenge of anonymity (26:04) Advice for founders who want to increase retention (29:34) What founders often get wrong (31:43) Examples of core actions (37:37) Finding your North Star Metric (38:12) Who should use the Hierarchy of Engagement framework (38:54) The Hierarchy of Marketplaces framework (46:09) Level 1: Focus on a constrained opportunity (50:19) Sarah’s “happy GMV” and “minimum viable happiness” concepts (54:47) Thumbtack: a counterexample to this approach (56:36) Signs you’re ready to move to level 2 (58:06) Level 2: Tipping the marketplace (01:04:15) Tipping loops (01:10:53) Not all markets are susceptible to tipping (01:15:55) The challenge of homogeneity in B2B marketplaces (01:20:29) Signs you’re tipping successfully (01:21:43) Level 3: Dominating the market (01:28:29) The opportunity in underestimated markets (01:30:11) The challenges of chasing GMV and losing focus (01:36:36) Recognizing currents and momentum in the market (01:39:20) You can never rest on your laurels (01:41:03) How to apply these frameworks outside of marketplaces (01:42:57) Three ways to find marketplace opportunity (01:45:10 ) Lightning round — Referenced: • Hierarchy of Engagement, Expanded: https://sarahtavel.medium.com/the-hierarchy-of-engagement-expanded-648329d60804 • Pinterest: https://www.pinterest.com/ • Evernote: https://evernote.com/ • Notion: https://www.notion.so/ • Houseparty app: https://en.wikipedia.org/wiki/Houseparty_(app) • Clubhouse: https://www.clubhouse.com/ • How to price your product | Naomi Ionita (Menlo Ventures): https://www.lennyspodcast.com/how-to-price-your-product-naomi-ionita-menlo-ventures/ • TikTok: https://www.tiktok.com/ • Lessons on building a viral consumer app: The story of Saturn: https://www.lennysnewsletter.com/p/lessons-on-building-a-viral-consumer • Saturn: https://www.joinsaturn.com/ • What happened to Secret?: https://www.failory.com/cemetery/secret • How to determine your activation metric: https://www.lennysnewsletter.com/p/how-to-determine-your-activation • Shishir Mehrotra on LinkedIn: https://www.linkedin.com/in/shishirmehrotra/ • The rituals of great teams | Shishir Mehrotra of Coda, YouTube, Microsoft: https://www.lennyspodcast.com/the-rituals-of-great-teams-shishir-mehrotra-coda-youtube-microsoft/ • Engagement Hierarchy: Core Actions: https://sarahtavel.medium.com/engagement-hierarchy-core-actions-dd4f72042100 • Choosing Your North Star Metric: https://www.lennysnewsletter.com/p/choosing-your-north-star-metric • Hierarchy of Marketplaces: https://sarahtavel.medium.com/the-hierarchy-of-marketplaces-introduction-and-level-1-983995aa218e • Mike Williams on LinkedIn: https://www.linkedin.com/in/yoroomie/ • Everything Marketplaces: https://www.everythingmarketplaces.com/ • Fabrice Grinda on LinkedIn: https://www.linkedin.com/in/fabricegrinda/ • OLX: https://www.olx.com/ • DoorDash Loves the ’Burbs as Much as You Do: https://www.wsj.com/articles/doordash-loves-the-burbs-as-much-as-you-do-11605618001 • Thumbtack: https://www.thumbtack.com/ • NPS: https://en.wikipedia.org/wiki/Net_promoter_score • Sean Ellis on LinkedIn: https://www.linkedin.com/in/seanellis/ • Rekki: https://rekki.com/ • Ronen Givon on LinkedIn: https://www.linkedin.com/in/ronen-givon-535b2514 • Hipcamp: https://www.hipcamp.com/ • Demand driving supply: The little-understood growth loop behind a surprising number of iconic billion-dollar companies: https://www.lennysnewsletter.com/p/demand-driving-supply-marketplaces • Inside the Revolution at Etsy: https://www.nytimes.com/2017/11/25/business/etsy-josh-silverman.html • Faire: https://www.faire.com/ • Bill Gurley on LinkedIn: https://www.linkedin.com/in/billgurley/ • Mechanical Turk: https://www.mturk.com/ • Parker Conrad on LinkedIn: https://www.linkedin.com/in/parkerconrad/ • Rippling: https://www.rippling.com/ • “White Space” for Building a Marketplace: How to Find Your Competition’s Vulnerabilities—and Capitalize: https://sarahtavel.medium.com/white-space-for-building-a-marketplace-how-to-find-your-competitions-vulnerabilities-and-79674aa4d399 • Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563935 • The Five Temptations of a CEO: https://www.amazon.com/Five-Temptations-CEO-Anniversary-Leadership/dp/0470267585 • The Five Dysfunctions of a Team: A Leadership Fable: https://www.amazon.com/Five-Dysfunctions-Team-Leadership-Fable/dp/0787960756 • Tesla: https://www.tesla.com/ • Reid Hoffman on LinkedIn: https://www.linkedin.com/in/reidhoffman/ • What Is A Good Activation Rate: https://www.lennysnewsletter.com/p/what-is-a-good-activation-rate — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Christian Idiodi is a partner at Silicon Valley Product Group. After a long product career and founding multiple companies, Christian now spends his time working closely with product leaders at companies big and small to implement and improve their discipline of product management. In today’s episode, we discuss: • Why there’s often a negative perception of product managers, and how we can fix this • The four attributes of a product manager’s job: value, usability, viability, and feasibility • The power of finding reference customers • How Christian developed a process for high-volume hiring to help companies like McDonald’s and Starbucks • Tactical tips for coaching, building relationships, and building trust as a leader — Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams | Vanta—Automate compliance. Simplify security | Teal—Your personal career growth platform — Find the full transcript at: https://www.lennysnewsletter.com/p/the-essence-of-product-management — Where to find Christian Idiodi: • X: https://twitter.com/CIdiodi • LinkedIn: https://www.linkedin.com/in/cidiodi/ • Website: https://www.svpg.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Christian’s background (03:56) The negative perception of product managers (07:58) How to become a PM people want to work with (11:30) The definition of a product manager (14:46) Where new PMs fail (16:59) Reference customers: what they are and why they are so important (24:05) A quick summary of how to build a product that people want and love (26:44) How to determine product-market fit (29:54) The benefits of this approach (34:11) Real examples of using reference customers (40:06) Doing things that don’t scale (48:40) How to get better at coaching and build trust with leaders (55:53) The fastest way to build trust (01:00:01) What to do in the absence of good coaching (01:02:51) How to get into product management (01:04:16) The pitfalls of early promotions (01:11:11) How to train someone for a promotion before giving the promotion (01:13:30) How to find a good coach (01:14:40) Christian’s product work in Africa (01:21:22) The importance of passion and empathy in product work (01:22:54) Lightning round — Referenced: • Marty Cagan on LinkedIn: https://www.linkedin.com/in/cagan/ • The nature of product | Marty Cagan, Silicon Valley Product Group: https://www.lennyspodcast.com/the-nature-of-product-marty-cagan-silicon-valley-product-group/ • Silicon Valley Product Group: https://www.svpg.com/ • Enhanced Product Discovery by SVPG Partner Christian Idiodi at Lean Product Meetup: https://www.youtube.com/watch?v=eQKaFEqhiqc • Geoffrey Moore’s technology adoption curve: https://fourweekmba.com/technology-adoption-curve/ • Stripe: https://stripe.com/ • Building a culture of excellence | David Singleton (CTO of Stripe): https://www.lennyspodcast.com/building-a-culture-of-excellence-david-singleton-cto-of-stripe/ • Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft): https://www.lennyspodcast.com/building-beautiful-products-with-stripes-head-of-design-katie-dill-stripe-airbnb-lyft/ • Rippling: https://www.rippling.com/ • Snagajob: https://www.snagajob.com/ • Howard Schultz on LinkedIn: https://www.linkedin.com/in/howardschultz/ • Tesla portable charger: https://shop.tesla.com/product/mobile-connector • Innovate Africa Foundation: https://www.innovateafrica.io/about/ • Inspire Africa Conference: https://www.inspireafricaconference.com/ • Inspired: How to Create Tech Products Customers Love: https://www.svpg.com/books/inspired-how-to-create-tech-products-customers-love-2nd-edition/ • Empowered: Ordinary People, Extraordinary Products: https://www.svpg.com/books/empowered-ordinary-people-extraordinary-products/ • Transformed: Moving to the Product Operating Model: https://www.svpg.com/books/transformed-moving-to-the-product-operating-model/ • Succession on HBO: https://www.hbo.com/succession • Billions on Showtime: https://www.sho.com/billions • Real sports app: https://www.realapp.link/ — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Jason Fried is the co-founder and CEO of 37signals, the maker of Basecamp and HEY. 37signals is a very different kind of company. With fewer than 80 employees, they have over 100,000 customers, generate tens of millions of dollars in profit each year, and have no investors, board, or any plans to ever raise money or sell the company. In our conversation, we explore a path many tech founders never consider—bootstrapping. We discuss: • Why he and his team prioritize profit above all else • The unexpected challenges with raising venture capital • The “Shape Up” framework for building products • Why, and how, to foster a gut-driven culture • Jason’s thoughts on why work should not feel like war • Advice for starting a bootstrapped business • The philosophy behind Once, 37signals’s new line of software products — Brought to you by Coda—Meet the evolution of docs | Sidebar—Accelerate your career by surrounding yourself with extraordinary peers | Wix Studio—The web creation platform built for agencies — Find the full transcript at: https://www.lennysnewsletter.com/p/jason-fried-challenges-your-thinking — Where to find Jason Fried: • X: https://twitter.com/jasonfried • LinkedIn: https://www.linkedin.com/in/jason-fried/ • Email: [email protected] — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Jason’s background (03:49) The success of 37signals (06:46) When raising money makes sense (09:58) The power of small teams (13:55) Defining success and goals (17:08) Playing “infinite games” in life (20:11) Starting a business vs. staying in business (22:13) Lessons from 25 years in business (27:28) Venture scale vs. bootstrapping (30:30) Choosing the right path for your business (33:19) The “Shape Up” framework (37:59) The drawback of promises (39:56) Adopting a new way of working (41:36) The two-week cooldown (43:53) Trusting intuition and gut (46:41) Creating a gut-driven culture (49:44) What Jason looks for in new hires (56:19) Advice on making changes and adapting (01:00:06) What Jason has changed his mind about (01:02:33) Planning in 6-week stretches and figuring it out as you go (01:06:43) Being proud of the work you do (01:09:05) Jason’s thoughts on why work should not feel like war (01:11:31) Advice for starting a bootstrapped business (01:14:33) You must be at peace with the worst that can happen (01:15:42) The benefits of bootstrapping (01:19:11) The value of constraints in business (01:22:00) Jason’s philosophy: “Just keep making great s**t” (01:23:19) Once, 37signals’s new line of software products (01:26:33) The philosophy behind Once (01:35:47) Closing thoughts (01:37:23) Lightning round — Referenced: • 37 Signals: https://www.smartsheet.com/ • Basecamp: https://basecamp.com/ • Finite and Infinite Games: https://www.amazon.com/Finite-Infinite-Games-James-Carse/dp/1476731713/ • Ingram Micro: https://www.ingrammicro.com/ • Once: https://once.com/ • Basecamp’s Shape Up framework: https://basecamp.com/shapeup • Hill charts: https://basecamp.com/features/hill-charts • Jason Fried’s quote about long-term business planning: https://medium.com/@farkhan569/unless-you-are-a-fortune-teller-long-term-business-planning-is-a-fantasy-jason-fried-quote-a69e8778e9c4 • Brian Chesky’s new playbook: https://www.lennyspodcast.com/brian-cheskys-new-playbook/ • Matt Mullenweg on X: https://twitter.com/photomatt • Leo Polovets on X: https://twitter.com/lpolovets • HEY: https://www.hey.com/ • Redefining success, money, and belonging | Paul Millerd (The Pathless Path): https://www.lennyspodcast.com/redefining-success-money-and-belonging-paul-millerd-the-pathless-path/ • It Doesn’t Have to Be Crazy at Work: https://www.amazon.com/Doesnt-Have-Be-Crazy-Work/dp/0062874780 • Squarespace: https://www.squarespace.com/ • Stoic negative visualization: https://dailystoic.com/premortem/ • Linear: https://linear.app/ • Peter Rahal on LinkedIn: https://www.linkedin.com/in/peter-rahal-037bba43/ • RXBAR: https://www.rxbar.com/en_US/home.html • Jason’s LinkedIn post: https://www.linkedin.com/posts/jason-fried_just-keep-making-great-s**t-keep-your-costs-activity-7130978623523614720-VBGX/?trk=public_profile • Several Short Sentences About Writing: https://www.amazon.com/Several-Short-Sentences-About-Writing/dp/0307279413 • Hell Yeah or No: What’s Worth Doing: https://www.amazon.com/Hell-Yeah-No-whats-worth/dp/1988575117/ • Home-Made: Contemporary Russian Folk Artifacts: https://www.amazon.com/Home-Made-Contemporary-Russian-Folk-Artifacts/dp/0955006139 • Oppenheimer: https://www.oppenheimermovie.com/ • Tom Petty’s “Crawling Back to You” on Spotify: https://open.spotify.com/track/1JenqZNMU6unIwVWmoP3J0 • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://press.stripe.com/poor-charlies-almanack — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Matthew Dicks is a best-selling author, columnist, blogger, podcaster, playwright, and teacher. He wrote my all-time favorite book on storytelling, Storyworthy. He is an elementary school teacher by day and by night teaches storytelling and public speaking to individuals, corporations, universities, religious institutions, and school districts around the world. He’s taught storytelling at Yale, MIT, Harvard, and Purdue, along with Amazon, Salesforce, Slack, Lego, and others. In this conversation, Matthew shares insights and techniques for effective storytelling, including: • The benefits of good storytelling in business • The five-second moment and why it’s so important • Why you should start every story at the end • How to build a vault of stories that can be deployed in business situations • Tips on how to be funnier • His life-changing “Homework for Life” practice • Advice for dealing with nervousness in public speaking • The power of saying yes — Brought to you by OneSchema—Import CSV data 10x faster | Maui Nui Venison—The healthiest red meat on the planet delivered directly to your door | Vanta—Automate compliance. Simplify security. — Find the full transcript at: https://www.lennysnewsletter.com/p/how-to-tell-better-stories-matthew — Where to find Matthew Dicks: • Website: https://matthewdicks.com/ • X: https://twitter.com/MatthewDicks • LinkedIn: https://www.linkedin.com/in/matthew-dicks-84a95711/ • YouTube: https://www.youtube.com/channel/UC4K0fcEJkzJLso5h6CN00LQ • Storyworthy: https://www.storyworthymd.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Matthew’s background (04:27) The five-second moment (10:29) Knowing the ending (14:28) The importance of including a transformation (15:59) The dinner test (18:19) You can’t tell someone else’s story (20:24) Vacation stories (23:14) Adding stakes to the story (25:12) The power of surprise (29:20) The benefits of storytelling in business (32:20) An example of adding stakes (34:02) Storytelling in the workplace (44:29) Using personal inventory to make stories relatable (48:46) Four ways to keep people listening (50:52) Using humor in business storytelling (53:09) Advice for adding humor (58:43) An example of how storytelling helped a biotech company sell product (1:02:06) Advice for people who don’t want to become storytellers (1:06:35) The power of “Homework for Life” (01:15:26) Practical tips for starting Homework for Life (01:19:28) Dealing with nervousness in public speaking (01:24:42) Preparing for a talk or presentation (01:25:24) The power of saying yes (01:30:55) Lightning round — Referenced: • How ‘Star Wars’ answers our biggest religious questions: https://www.washingtonpost.com/posteverything/wp/2015/04/21/how-star-wars-answers-our-biggest-religious-questions/ • When Harry Met Sally on Prime Video: https://www.amazon.com/When-Harry-Sally-Billy-Crystal/dp/B001Q556QG • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): https://www.lennyspodcast.com/persuasive-communication-and-managing-up-wes-kao-maven-seth-godin-section4/ • Kurt Vonnegut’s 8 Tenets of Storytelling: https://www.themarginalian.org/2012/04/03/kurt-vonnegut-on-writing-stories/ • Vertigo on Prime Video: https://www.amazon.com/Vertigo-James-Stewart/dp/B000I9YLXU • Ocean’s Eleven on Prime Video: https://www.amazon.com/Oceans-Eleven-George-Clooney/dp/B001EBV0JE • David Mamet | JCCSF: https://www.youtube.com/watch?v=aZOT1jCHfhI • Pulp Fiction on Prime Video: https://www.amazon.com/Pulp-Fiction-John-Travolta/dp/B005T3AX6E • Charity Thief: Boston Moth StorySLAM: https://www.youtube.com/watch?v=YjrlGhAB4a4 • Boris Levin on LinkedIn: https://www.linkedin.com/in/boris-levin-ab95404/ • Masha Reutovski on LinkedIn: https://www.linkedin.com/in/masha-reutovski/ • Top Three Steve Jobs Speeches: https://www.pcworld.com/article/482269/top_three_steve_jobs_speeches.html • The Javits Center: https://www.javitscenter.com/ • Stranger Things on Netflix: https://www.netflix.com/title/80057281 • 1989 (Taylor’s Version) on Spotify: https://open.spotify.com/album/64LU4c1nfjz1t4VnGhagcg • Classic Sesame Street—one of these things is not like the other: https://www.youtube.com/watch?v=gCxrkl2igGY • Homework for Life: https://matthewdicks.com/homework-for-life/ • Homework for Life | Matthew Dicks | TEDxBerkshires: https://www.youtube.com/watch?v=x7p329Z8MD0 • Seth Meyers: https://en.wikipedia.org/wiki/Seth_Meyers • David Sedaris on MasterClass: https://www.masterclass.com/classes/david-sedaris-teaches-storytelling-and-humor • Happy-Go-Lucky: https://www.amazon.com/Happy-Go-Lucky-David-Sedaris/dp/0316392456 • A life of yes: Matthew Dicks at TEDxSomerville: https://www.youtube.com/watch?v=F3TaQFcaMk4 • New York Comedy Festival: https://nycomedyfestival.com/ • In the Heart of the Sea: The Tragedy of the Whaleship Essex: https://www.amazon.com/Heart-Sea-Tragedy-Whaleship-Essex/dp/0141001828 • The Tale of Despereaux: https://www.amazon.com/Tale-Despereaux-Being-Princess-Thread/dp/0763680893 • I’ll Show Myself Out: Essays on Midlife and Motherhood: https://www.amazon.com/Ill-Show-Myself-Out-Motherhood/dp/0062981595 • You’ll Grow Out of It: https://www.amazon.com/Youll-Grow-Out-Jessi-Klein/dp/1455531200 • David Sedaris books: https://www.amazon.com/stores/David-Sedaris/author/B000AQ3YUW • Sure, I’ll Join Your Cult: A Memoir of Mental Illness and the Quest to Belong Anywhere: https://www.amazon.com/Sure-Ill-Join-Your-Cult/dp/1982168560 • The Last of Us on HBO: https://www.hbo.com/the-last-of-us • Barbie: https://www.barbie-themovie.com/ • Krinner tree genie on Amazon: https://www.amazon.com/Krinner-Genie-Christmas-Stand-Small-Green/dp/B081D78FTP • Power Pod: https://powerpodshop.com/ • Nostalgia hotdog toaster: https://www.amazon.com/Nostalgia-HDT600RETRORED-Pop-Up-Toaster-Retro/dp/B005Q8X6IO — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

In this special compilation episode, we delve into failure—an overlooked source of wisdom. From freezing onstage in front of thousands of people, to coworkers staging an intervention, to huge product investments that went to zero, we’ve pulled our favorite stories of failure from 100+ podcast episodes. I hope these stories serve as a gentle nudge to view failure not as a setback but as a crucial detour toward growth. — Brought to you by Sendbird—The (all-in-one) communications API platform for mobile apps | Eppo—Run reliable, impactful experiments — Find the full transcript at: https://www.lennysnewsletter.com/p/failure — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, you’ll hear from: (00:00) Lenny: Why I’m focusing on failure (03:25) Katie Dill: The single meeting that changed how Katie leads forever (08:03) Paul Adams: Freezing onstage in front of thousands of people (18:38) Tom Conrad: Lessons from Pets.com and Quibi—two of the most famous product disasters of all time (33:19) Sri Batchu: When you fail, make sure you fail conclusively (39:00) Jiaona Zhang (JZ): One of the biggest product misses at Airbnb (44:32) Gina Gotthilf: Everyone has an “A side” and a “B side,” and we should all share our B sides more (57:57) Maggie Crowley: Her favorite interview question about failure, and lessons from a personal failure (1:00:33) Thanks for listening — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

Kim Scott is the author of Radical Candor, currently the #1 most recommended book on this podcast. The book has sold over 1 million copies and has been translated into 23 languages. Before writing, Kim was a CEO coach at Dropbox, Qualtrics, Twitter, and other tech companies. She was also a member of the faculty at Apple University and before that led AdSense, YouTube, and DoubleClick teams at Google. This spring she’ll be launching Radical Respect, which she considers to be a prequel to Radical Candor. In today’s conversation, we go deep on Kim’s popular framework, including: • What separates radical candor and obnoxious aggression • Tactical advice on delivering constructive feedback • How well-meaning empathy can become ruinous • Strategies for effectively soliciting and responding to feedback • The importance of having regular career conversations • The false dichotomy of a good leader versus a kind person • A sneak peek into Radical Respect — Brought to you by Jira Product Discovery—Atlassian’s new prioritization and roadmapping tool built for product teams — Find the full transcript at: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice — Where to find Kim Scott: • X: https://twitter.com/kimballscott • LinkedIn: https://www.linkedin.com/in/kimm4/ • Website: https://www.radicalcandor.com/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Kim’s background (03:13) A brief overview of Radical Candor (06:46) How people fail with ruinous empathy, manipulative insincerity, and obnoxious aggression (08:37) The impact of radical candor on Kim’s life (14:16) How to communicate feedback effectively (20:34) A story illustrating the problem with ruinous empathy and manipulative insincerity (27:50) How to get over the need to be liked (31:31) How to have career conversations with your direct reports (29:40) Reflections on how Kim handled an underperforming employee (33:31) Best practices for soliciting feedback as a leader (35:53) How to respond to feedback (39:22) How often to ask for feedback (41:48) Whether or not to accept “no feedback” as an answer (50:48) Investing time in feedback (54:04) How to ask for feedback as an employee (57:42) Why obnoxious aggression is not the best way to deliver feedback (1:01:23) A notable example of problematic management  (1:03:43) Why context matters when diagnosing obnoxious aggression  (1:07:39) Empathy is a good thing, but empathy can paralyze (1:10:47) Reflections on the limitations of radical candor in a society riddled with biases  (1:14:41) Kim’s new book, Radical Respect (1:15:51) Tactical advice to get better at radical candor (1:16:46) Lightning round — Referenced: • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • Radical Respect: How to Work Together Better: https://www.amazon.com/Radical-Respect-Work-Together-Better/dp/1250623766/ • The Office (American version) on Peacock: https://www.peacocktv.com/stream-tv/the-office • Radical Candor diagram: https://www.radicalcandor.com/our-approach/ • Career conversation templates: https://review.firstround.com/the-power-of-performance-reviews-use-this-system-to-become-a-better-manager/ • A behavioral scientist explains why we should reacquaint ourselves with the telephone: https://news.uchicago.edu/story/nicholas-epley-explains-why-phone-calls-can-connect-us-better-zoom • How to get promoted: https://www.lennysnewsletter.com/p/how-to-get-promoted • When They Win, You Win: Being a Great Manager Is Simpler Than You Think: https://www.amazon.com/When-They-Win-You-Manager/dp/1250279666 • Peter Kazanjy on X: https://twitter.com/Kazanjy • Christa Quarles on LinkedIn: https://www.linkedin.com/in/christaquarles/ • Jason Rosoff on LinkedIn: https://www.linkedin.com/in/jason-r-rosoff/ • Andrew Grove: https://en.wikipedia.org/wiki/Andrew_Grove • Columbo on Prime Video: https://www.amazon.com/Columbo-Season-1/dp/B008SA89HA • Squid Game on Netflix: https://www.netflix.com/title/81040344 • Leveraging mentors to uplevel your career | Jules Walter (YouTube, Slack): https://www.lennyspodcast.com/leveraging-mentors-to-uplevel-your-career-jules-walter-youtube-slack/ • Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger: https://www.amazon.com/Poor-Charlies-Almanack-Essential-Charles/dp/1953953239 • Bridgewater: https://www.bridgewater.com/ • The Fund: Ray Dalio, Bridgewater Associates, and the Unraveling of a Wall Street Legend: https://www.amazon.com/Fund-Bridgewater-Associates-Unraveling-Street/dp/1250276934/ • Tim Cook on X: https://twitter.com/tim_cook • Elon Musk: https://www.amazon.com/Elon-Musk-Walter-Isaacson/dp/1982181281 • Building high-performing teams | Melissa Tan (Webflow, Dropbox, Canva): https://www.lennyspodcast.com/building-high-performing-teams-melissa-tan-webflow-dropbox-canva/ • Middlemarch: https://www.amazon.com/Middlemarch-Penguin-Classics-George-Eliot/dp/0141439548 • The Bluest Eye: https://www.amazon.com/Bluest-Eye-Vintage-International/dp/0307278441 • Song of Solomon: https://www.amazon.com/Song-Solomon-Toni-Morrison/dp/140003342X • Orlando: https://www.amazon.com/Orlando-Biography-Virginia-Woolf/dp/015670160X • The Color Purple: https://www.amazon.com/Color-Purple-Novel-Alice-Walker/dp/0143135694 • The Deptford Trilogy: Fifth Business; The Manticore; World of Wonders: https://www.amazon.com/Deptford-Trilogy-Business-Manticore-Wonders/dp/0140147551 • Grey’s Anatomy on Netflix: https://www.netflix.com/title/70140391 • My year of saying yes to everything: https://www.ted.com/talks/shonda_rhimes_my_year_of_saying_yes_to_everything • Attitude: https://attitudeliving.com/collections/adult-hair-care • Dostoevsky books: https://www.amazon.com/Fyodor-Dostoevsky-Books/s?k=Fyodor+Dostoevsky — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected]. — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe