Year One

When Papermark founder Marc Seitz accused insurance startup Corgi of copying his open-source dataroom software word for word, the stakes escalated fast: Corgi's own CEO admitted their AI 'vibe-coding' had produced near-identical pages, then responded with cease-and-desist letters, including one over an unrelated joke tweet. On this episode of Year One, Miles and Grant break down what actually happened, why identical wording (not identical code) is the real legal vulnerability, and how this compares to the 2024 PearAI cloning scandal. They dig into Corgi's rapid climb to a $2.6 billion valuation, the seven-day-workweek culture stories swirling around it, and whether repeat litigation spooks enterprise buyers doing due diligence. With Papermark still holding off on a lawsuit, the hosts pose an open question for the AI-native era: does aggressive legal posturing protect founders, or does it eventually cost them. Essential listening for YC founders navigating fast growth, AI tooling, and the fine line between speed and recklessness.

A YC-backed insurtech called Corgi shipped its Dataroom product on June 24th and was facing a public plagiarism accusation within twenty-four hours. The stakes were immediate: an AGPL-licensed open-source competitor posted side-by-side screenshots, Corgi blamed vibe coding, then sent cease-and-desist letters to the accuser and a founder who tweeted a joke about it. In this episode of Year One, Miles and Grant talk to an S26 founder who admits they can only explain sixty to seventy percent of their AI-generated codebase and never ran a license audit before shipping — which turns out to be Corgi's exact problem at a smaller scale. They break down the four-layer IP exposure every vibe-coded startup carries: AGPL strict liability, the Copyright Office's January 2025 ruling on AI-generated output, and the invention assignment gap that quietly kills YC Series A deals before founders know what hit them. If you're shipping with AI-assisted tools and haven't thought seriously about license scanning or invention assignment agreements, this one is required listening.

A founder inside YC's Summer 2026 batch describes day one of S26 — not the pitch, not the Demo Day narrative, the unedited version. The room was quieter than expected, and before office hours existed, real decisions were already being made: who to trust, which signals to act on, and whether to build the chip or the scheduler. In this episode of Year One, Miles and Grant pull apart the first uninvited choices S26 founders made, break down the structural information asymmetry between founders and YC partners in week one, and analyze the Summer 2026 Request for Startups as a conviction map — not a checklist. Eight of fifteen RFS categories require hardware or capital, and one partner's name appears on three of them. That's not an accident. Grant frames what partners are actually tracking earliest, Miles connects a live Inference Chips founder decision to the utilization gap hiding in the RFS, and neither of them knows how it ends — because the batch just started. If you're a founder inside YC right now, or trying to read where it's placing its bets, this one is built for you.

Jorge B. Macías had to figure out how to sell an AI product to medical offices from Puerto Rico, scale it to millions in ARR, and do it as the first founder from the island to take a company through YC—without a traditional sales background. The stakes were high: represent a whole ecosystem on the YC stage while carrying the pressure of proving a repeatable way to win B2B deals far from Silicon Valley. You have to hear this one because Jorge breaks down how he turned industrial engineering tools into a “GTM engineering” system that took BrainHi from messy first calls to a structured sales engine. He talks about growing up trying to escape his family’s sales legacy, then realizing that process thinking—not charisma—is what closes and scales deals. Along the way, he unpacks the emotional hit of constant rejection, the mindset shift from fighting gatekeepers to winning them over, and the hidden differences between B2B and consumer selling that trip most founders up. This Year One episode also touches on YC expectations, Demo Day hindsight, and why his real career turned out to be building systems, not carrying a quota. Published June 11, 2026, it is especially relevant for early-stage B2B founders who know they need sales but do not yet have a sales engine.

Sam Altman walked into a YC event and offered every startup in the current batch $2 million in API tokens for an uncapped equity stake — and founders had to decide on the spot whether that was a gift or a trap. In this Year One episode, we get inside the deal mechanics behind OpenAI's tokenmaxxing offer: what an uncapped SAFE actually does to your cap table, and why the real cost stays invisible until you're in the Series A room. Two founders from the same YC batch made opposite calls — one signed for the signal value, one walked over vendor lock-in — and their reasoning cuts straight to the fault lines of the deal. A YC partner then runs the numbers on stacked unconverted SAFEs, which can consume 35 to 45 percent of a cap table before a Series A dollar comes in, and flags why most founders won't feel the consequences for years. This one is essential listening for any early-stage founder weighing infrastructure partnerships that also hand your investor a permanent seat at the table. If you know a Year One founder with a story worth telling, reach out at [email protected].

Two founders applied to YC S26. One got in. One didn't. In this episode of Year One, Miles and Grant sit with both of them inside the moment the decision email arrived — and what happened next reveals more about each founder than the application itself did. The accepted founder had reverse-engineered proof-of-velocity signals specifically for YC's evaluation criteria. The rejected founder had spent her final six weeks rewriting her bio. A YC partner breaks down the two signals that move an application from interesting to interview — traction curve shape and founder-problem fit — and both founders' stories map almost exactly onto what the partner describes. Grant pushes hard on the rejected founder's traction number, pointing out she had evidence she simply didn't lean into. With Demo Day on September 10th, one founder has $500k and 14 weeks; the other has roughly 90 days before the next deadline and, when the hosts last spoke to her, still no plan. If you're preparing a YC application or trying to understand why a strong company didn't get in, this one is worth your full attention.

Alex Benz is applying to YC Summer 2026 while already sitting on $10k MRR, four enterprise customers, and a live AI podcast platform that actually works in production—and he has to decide whether to double down now or wait for more signal. The stakes are real: timing this YC application could determine whether Mato becomes infrastructure for big podcast networks or stalls as a niche tool. You have to hear this one because Alex breaks down how Mato’s AI hosts run live interviews with real humans, auto-generate full episodes from RSS feeds and custom topics, and ship edited audio, transcripts, show notes, cover art, and ads with almost no human lift. He walks through landing early deals with networks like iHeart and Blaze, the scrappy channel partner who unlocked his first customers, and how his 14 years in UX shaped a product non-technical producers actually adopt. A YC partner weighs in on what “enough traction” means at $10k MRR two months in and how YC thinks about AI infrastructure versus point solutions. Published May 6, 2026, this Year One episode is especially relevant if you’re on the fence about YC timing or building anything in the podcast or media automation space.

Fourteen companies in the YC W26 batch hit a million in ARR before Demo Day ended — three times more than the previous winter batch and the highest count in YC history. The question Miles and Grant press on in this episode of Year One isn't whether that number is impressive; it's what it actually costs to get there in ninety days, and whether the valuation it commands is earned or a cap table trap. They pull apart Hex Security, which reached $1M ARR in eight weeks by deploying AI agents for continuous penetration testing, and examine why their batch-as-first-customer strategy worked — and where it gets harder. They also surface a counter-intuitive finding across the full W26 batch: the fastest-growing companies didn't pivot, they held course. With the default round now sitting at $4M on a $40M post-money — double what W23 commanded — the Series A math deserves a hard look. This episode is especially relevant for early-stage founders deciding when to price their first round. Know a YC founder in their first year who'd tell their story? Reach out at [email protected].

Two founders applied to YC S26 in the same window. One got the interview invite. One hit June 2 in silence. This Year One episode follows both through the moment the decision became real — and what each story reveals about how YC partners actually filter thousands of applications down to a batch. The accepted founder walks through the traction question that nearly ended her interview, the four seconds of silence that felt terminal, and the evening phone call that changed everything. The rejected founder already had a rehearsed answer about what went wrong — twelve users, no paid revenue — and Miles and Grant examine whether that diagnosis is honest or just the version that's easier to say out loud. Grant breaks down why the written application is the real filter, not the interview, and what separates founders who can defend a number under pressure from those who can't. If you're rebuilding for W27 or trying to understand what YC partners are actually watching, this one is worth your full attention.

A founder walks into an all-hands meeting running the best quarter of her company's life, and realizes mid-sentence she has nothing left. Not tired. Empty. In this episode of Year One, Miles and Grant trace her burnout from month four to month nine, anchored in CEREVITY's shadow burnout research showing 73% of founders experience persistent exhaustion while still hitting their targets, and Sifted's 2025 survey finding only 6% of founders reported zero mental health issues. A therapist who works exclusively with founders breaks down the three clinical markers that separate burnout from high-functioning stress, including the identity fusion trap that makes asking for help feel like admitting the company itself is failing. The episode also examines what YC partners actually observe when a founder starts deteriorating, and whether investors are structurally positioned to intervene, with early efforts like Felicis Ventures' 1% Founder Development Pledge and the foundermental.health clinical survey offering a partial answer. There is no clean resolution here. If you are a first-year founder who has been performing fine while feeling nothing, this one is for you.

Jon Yoo closed a seed round for Suger, his YC Winter 2023 marketplace startup, and then his co-founder walked out. What followed was five weeks with zero customers, a solo rebuild, and a run from $500K to $2M ARR in six months with a team of five. In this episode of Year One, Miles and Grant go deep on the moment Jon knew the split was coming and why neither side said it out loud sooner, the deliberate customer-sequencing strategy he used to climb from early logos like Fivetran toward Snowflake, and what YC partner data actually says about co-founder breakups as a leading killer of otherwise fundable startups. They also surface a complicating detail: Suger's Series A press materials still list two co-founders, leaving the solo-founder narrative murkier than the headline suggests. The episode closes on the structural question that outlasts the people drama: can a company scale past Series A when one person is still the single point of failure? Essential listening for any founder navigating a co-founder split or building toward their first institutional round.

A W26 founder walks into an investor meeting and one question about OpenAI exposure dismantles the entire pitch in real time. The stakes are immediate: was this a company or a feature with better branding? In this episode of Year One, the founder recounts the moment they froze, and what it forced them to admit about what they had actually built. Miles and Grant dig into the W26 Demo Day batch data, where 60% of companies are AI-powered and narrative alone no longer works as cover. A YC partner names the one-sentence tell that separates a real structural moat from a well-packaged story: what would the customer have to rebuild if they left? Eight months out, the founder faces a fundraise in three months that will reveal whether the pivot produced something genuinely defensible or just a cleaner deck. With Gartner projecting enterprise AI agent adoption jumping from under 5% to 40% by end of 2026, good timing can mask weak positioning, but only for so long. This episode is essential listening for any early-stage AI founder approaching their first institutional raise.

A W26 founder signed a $40M post-money SAFE at 2am in a parking lot and thought she had made it. Six months later, three stacked SAFEs had quietly committed 30% of her company before a Series A conversation even started. In this episode of Year One, Miles and Grant walk through the exact dilution math with the founder herself, uncovering how a single cap concession to close one reluctant investor triggered an MFN cascade she never modeled and never saw coming. She admits she did not know what Most Favored Nation meant when she signed YC's standard docs. A YC partner then breaks down the two fear-based SAFE cap mistakes they see again and again post-Demo Day, and why founders who treat the cap as a confidence signal end up with a Series A math problem they cannot solve. No clean resolution here — her cap table is still on the table. This episode is essential listening for any first-time founder heading into Demo Day or sitting with an unsigned term sheet right now.