Stay Wealthy Retirement Podcast

Two retirees. Same $1 million portfolio. Same 60/40 allocation. Same 4% withdrawal rate. Same 30-year retirement. The only difference? One retired in 1973. The other retired in 1975.  Fast forward 30 years: one finished with about $280,000 and the other finished with over $3 million. Same plan. Just two years apart. In this episode, I'm breaking down new research that analyzes nearly a century of market history to answer a question most retirement plans don't spend enough time on: "How much does your exact retirement date shape the outcome of your plan?" Here's what you'll learn: → Why retirement timing may matter more than your withdrawal rate or asset allocation  → Why a larger nest egg at retirement has historically led to worse outcomes → A 3-part playbook, in priority order, for protecting your plan when the starting point looks unfavorable Most retirement strategies focus on what happens after you retire. But this research suggests the year you walk away from work may deserve a much bigger seat at the planning table. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Many retirement savers assume the anxiety will lift once they hit a certain number. Maybe it's $1 million. Maybe $2 million. Maybe $5 million or more. And then the account crosses the line, the headlines turn ugly, and the worry is still there. A recent Wall Street Journal headline put it bluntly: "Even Rich Retirees Fear Outliving Their Money." In this episode, I'm sharing new research from Fidelity that helps explain why having "enough" so often still doesn't feel like enough. I'm also sharing the four things I consistently see in retirees who feel genuinely secure.  Here's what you'll learn: → The retirement planning factor that more than doubles confidence → A cognitive concept that explains why retirement anxiety has very little to do with your account balance → The question many well-prepared retirees still can't answer — and why ignoring it can be so costly Not one of the four pillars has anything to do with the size of your portfolio. Which raises the real question: what's actually keeping wealthy retirees up at night? *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

The math behind "wait until 70" for Social Security is real. Hold off claiming from 62 to 70 and your monthly benefit climbs by roughly 77%. So why would anyone walk away from a number that big? The short answer is that the standard break-even analysis only measures one variable.  And for retirees with healthy pre-tax savings, there are other factors at play that can make "waiting" a more expensive decision than it looks. In this episode, I'm turning the mic over to Josh Rendler — a partner at our firm — who walks through a case study of a 62-year-old woman with a $1.5 million IRA and the question most retirees are wrestling with. Here's what you'll learn: → The reframe that makes "wait until 70" fall apart for retirees with healthy pre-tax balances → How Social Security timing and Roth conversions compete for the same bracket space (and why claiming earlier can actually EXPAND your conversion runway) → The planning window that opens at 61, and what gets harder to fix once it closes The biggest claiming-age check isn't always the biggest after-tax outcome. And a well-built plan shouldn't make you choose between doing the math right and actually enjoying the retirement you spent 35 years earning. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Tax season is finally over. The returns are filed, the stress is behind you, and the last thing you probably want to do is think about taxes again. But the weeks right after tax season are one of the most valuable windows you have all year. Every number from last year is fresh, every missed opportunity is still visible, and every mistake you just uncovered is a clue about what to fix going forward. In this episode, I sit down with Josh Rendler, CFP®, a partner at our firm and someone who spends his days deep inside client tax returns. Together, we're answering some of the biggest questions we're hearing from retirees right now. Here's what you'll learn: → The 3 numbers on last year's return that reveal your biggest 2026 planning opportunities → How to know if charitable giving belongs in your plan (plus the QCD detail that keeps it "invisible" to the IRS) → A fresh, counterintuitive take on Social Security timing While last year's return is still on your desk: what's hiding in there that could make 2026 better? 🤔 *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

One of the biggest decisions you'll make in your 70s and 80s has nothing to do with your portfolio. It's not about Social Security timing. And it's not about Roth conversions. It's about where you'll live and, more importantly, how care will be delivered, coordinated, and paid for if your health changes later on. Most people think of this as a lifestyle decision. But in reality, it's a housing-and-care decision, and it's one most retirement plans barely address. In this episode, I'm breaking down the later-life housing choices most retirement savers haven't fully thought through. Here's what you'll learn: → The four main housing options later in life—and how they differ in cost, care, and flexibility → What Continuing Care Retirement Communities (CCRCs) actually are (+ a little-known tax planning tip) → The four types of risk every housing decision really involves → When this decision usually needs to be made, and what can happen if you wait too long Because "we'll just stay in the house" isn't a plan...it's an assumption. And assumptions tend to get tested at the worst possible moment. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

According to the FBI, Americans lost nearly $21 billion to cyber-enabled fraud last year—a 26% increase from the year before. And the single largest category? Investment-related fraud, with more than $8.6 billion in losses. But what's most unsettling isn't the scale... it's how simple some of these scams really are. A retired couple recently lost thousands of dollars from their IRA after a scammer tricked them into sharing a single six-digit verification code over the phone. No hacking. No stolen password. Just one text message and one phone call. In this episode, I'm breaking down how "account takeover" scams work, why they're so effective, and the specific steps you can take to close the security gap. Here's what you'll learn: → The 3-step pattern behind most account takeover scams  → Why your personal information may already be compromised (and what that means for your account security) → What to do—and what not to do—when a financial institution contacts you about suspicious activity → 3 simple upgrades to better protect your accounts that most people overlook In a world where scammers only need a few seconds to strike, your ability to slow down and take back control of the moment may be the most valuable layer of protection you have. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

A viral claim keeps making the rounds: that a 1% advisory fee will drain hundreds of thousands of dollars from your retirement savings. The math looks alarming... and that's exactly the point. But as with most things in finance (and life!), the truth is more nuanced than a headline or social media post makes it seem. In this episode, I break down research from Derek Tharp, Ph.D., CFP®, that puts this widely shared math to the test and reveals where it falls apart.  Here's what you'll learn: → The misleading assumptions behind the popular "1% fee" calculation  → How alternative fee models can be 3x more expensive using the same math → What academic research says about quantifying the value of a good advisor → A smarter way to evaluate whether hiring an advisor makes sense for your specific situation This episode isn't about defending any particular fee model. It's about making sure you have the right information to evaluate the cost, the value, and the role financial advice may play in your retirement planning.  *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Saving for retirement is one challenge. Feeling comfortable (and confident) enough to actually enjoy it is another. Even when the numbers say you're okay, uncertainty about the future can make it hard to use money for the things that matter most. Today, I'm revisiting a conversation with Dr. Daniel Crosby where we talk about money, happiness, and why spending is often harder than saving.  It's especially relevant for me as my family currently navigates some big financial decisions... and a birthday trip for my oldest son that almost didn't happen. 🫣 In this episode, we discuss: → What the research gets wrong about the link between money and happiness → Why certain types of spending leave a bigger impact than others → A simple mindset shift that can make spending feel safer in retirement → What people near the end of life rarely regret—and what they wish they had done more of This conversation is a good reminder that money is a tool, and the goal is to use it to support the life you truly value. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

If you're in or near retirement, one bad investment decision can have lasting consequences. And new research shows just how risky stock picking can be:  Over the last 100 years, nearly 60% of all U.S. stocks underperformed Treasury bills—one of the safest investments you can own. Even more surprising, fewer than 4% of companies created all of the stock market's net wealth. In other words, the odds of consistently picking the right stocks are far lower than most people realize. In this episode, I'm breaking down this eye-opening research and what it means for protecting your portfolio and retirement plan. Here's what you'll learn: → Why owning a handful of well-known, familiar stocks can be far riskier than it feels → What the research reveals about where long-term market returns actually come from → The 3 actions you can take to better position and optimize your portfolio for the years ahead Because in retirement, successful investing isn't about hitting home runs—it's about avoiding unnecessary mistakes and stacking the odds in your favor. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Now that the One Big Beautiful Bill Act has made the 2017 tax rates permanent, more retirees are taking a fresh look at Roth conversions. But there's one rule that even reputable sources struggle to explain clearly—and the confusion can lead to costly mistakes. In this episode, I'm simplifying the Roth conversion 5-year rule and sharing: → Why the rule is so confusing (and what most people get wrong) → The fastest way to determine how the rule applies to your specific situation → 4 real-world scenarios so you can see exactly how it works  If Roth conversions aren't a fit today, I'm also sharing one simple step everyone can take right now to make future conversions much easier. *** 📝 GRAB THE ROTH 5-YEAR FLOWCHART (PDF) Want to apply what you learned in this episode to your unique situation? Subscribe to the Stay Wealthy Retirement Newsletter and I'll send you my freshly updated Roth 5-Year Flowchart (PDF). It's a simple guide to help you navigate this tricky rule step by step. Grab your copy here. *** 📆 BOOK A CALL WITH OUR TEAM: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

📝 Note: The 6.5% withdrawal rate is based on an 80% stock portfolio, a 30-year time horizon, and a 90% "confidence score." Thanks for your patience while we update the episode to include that information. ~Taylor *** Most people spend far less in retirement than they likely could. In fact, one study found married households age 65+ with more than $100k in savings withdrew just 2.1% per year on average. And ironically, the traditional 4% rule may be one reason why. In this episode, I'm breaking down new research on retirement withdrawal strategies—and what it reveals about how retirees may be able to spend more. Here's what you'll learn: → 5 strategies that (safely) support higher retirement income → The overlooked key to sustainable and confident retirement spending → 3 factors that can push starting withdrawal rates to as high as 6.5%  The goal of retirement planning isn't just making your money last…it's making sure you actually use it. Which raises an important question: "Could you afford to spend more in retirement than you think?" *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Health insurance is keeping millions of Americans stuck in jobs they'd otherwise leave. In fact, 1 in 5 workers ages 50–64 say they're staying put because of their employer health coverage. And with recent changes to the ACA, that pressure is only growing.  In this episode, I cover: → Why healthcare before Medicare has become a psychological roadblock to early retirement → Why the real cost of waiting until 65 may not be what you think  → The options many people overlook and the tradeoffs worth understanding Because for most people, the healthcare challenge does have a solution. And the worst thing you can do is never explore your options at all. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

For 30 or 40 years, a paycheck simply showed up. Then one day, it stops. Now you're staring at a portfolio and asking: "How do I turn this into reliable income for the rest of my life…without overpaying the IRS or outliving my money?"  It's no surprise so many retirees gravitate toward dividends. They feel like a replacement paycheck. In fact, the majority of investors say they prefer dividends and interest over capital gains to fund retirement. But retirement income planning isn't just about generating cash flow. It's about creating sustainable income from a finite pool of capital while coordinating taxes and the rest of your retirement plan. In this episode, I break down new research on dividend investing and explain why the most popular income strategy may be far less efficient than it appears. I also share what the evidence suggests about building a portfolio and a plan that actually supports long-term retirement success. Because when it comes to funding your retirement, small structural decisions compound into very large outcomes. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Markets move every day. Headlines change every hour. But the greatest threat to your retirement plan isn't volatility... it's something far less visible. In this episode, I'm breaking down: → The three components of risk most investors focus on (and the one they ignore) → Why rare, extreme events have an outsized impact on long-term wealth → How to build a retirement plan designed to survive (and even benefit from) uncertainty I'm also sharing why many "downside-protection" strategies sound compelling in theory, but are risky and difficult to execute in the real world. *** 📆 BOOK A CALL: Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Your retirement involves complex, interconnected decisions—taxes, income, healthcare, estate planning, investments.  See how they fit together in one coordinated strategy built around your numbers. 👉 Learn More and Book a Call ----- Strong rallies make people uneasy. So does the fear that one bad crash could undo decades of careful saving. Recently, Morningstar published a great article centered around a chart mapping nearly 100 years of U.S. market history. When you zoom out, several widely accepted beliefs about market crashes and bull markets start to look far less certain. In this episode, I break down the three common myths the article explores. I also share what the data actually tells us about bear markets and what's far more likely to derail your retirement than a crash. Not to predict the future or eliminate risk. But to help you think more clearly about the environment we're in and how it fits into a disciplined, long-term retirement plan. ----- EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Annuities are often sold as a simple solution to a complicated retirement problem. Guaranteed income. Protection from market volatility. Peace of mind that your money won't run out. But behind those promises is a much more complex set of trade-offs that many investors don't consider.  Because while annuities can play a role in retirement planning, evaluating them in isolation often leads to unintended consequences (higher fees, reduced flexibility, extra taxes).  So in today's episode, I break down how annuities actually work. We'll walk through the major types of annuities, how "guarantees" are structured, what you're really paying for, and where the risks tend to show up later in retirement. I'll also explain when annuities may make sense, when they don't, and how to evaluate them as part of a coordinated retirement plan so you can make informed decisions with confidence. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

What makes an investment "good?" It seems like a straightforward question, but the answer is more subjective than most people realize.  Recently, my wife asked why I thought real estate was such a BAD investment when others she knows call it the BEST they've ever made.  Hearing it framed that way struck a different chord. And rather than quickly defending my position with data and facts, I found myself reconsidering the question entirely. In today's episode, I share how to evaluate investments in the real world, what separates good investments from bad ones, and why some popular metrics can mislead. If you've ever wondered why an investment looks great paper but doesn't feel right—or why others swear by strategies you'd never touch—this episode will give you a clearer framework for thinking about your own portfolio. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

After decades of filing taxes together, most couples assume their retirement plan will continue largely unchanged if one spouse passes away. But for many surviving spouses, the first surprise is a higher tax bill, even when income hasn't changed much. In this episode, I explain how a feature of the tax code can increase taxes after the loss of a spouse. Using a real-world example, I show why tax brackets shrink, why retirement income often doesn't, and how that mismatch can quietly drive taxes higher over time. More importantly, I share a planning framework couples can use while both spouses are still alive. We'll cover common mistakes, why the "married window" matters, and how small, intentional decisions made years in advance can meaningfully protect the surviving spouse. This isn't about fear or worst-case scenarios—it's about avoiding unnecessary surprises and making thoughtful, proactive decisions that support confidence throughout retirement. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Every year, Wall Street rolls out its market predictions. Targets get published, expectations get set, and the headlines make it sound like the future is just a spreadsheet away. But markets have a long history of humbling even the most confident forecasts, and that creates a real problem for retirement savers. Because, while short-term forecasts are usually noise, ignoring market expectations altogether isn't the answer either.  So in today's episode, I break down how to think about market outlooks the right way. We'll cover why forecasts so often miss the mark, when long-term assumptions actually matter, and how market research can be used as a planning tool (not a prediction engine). I also share key themes from Vanguard's Economic and Market Outlook for 2026, focusing on growth, inflation, and expected returns—and why all of that matters for your portfolio and retirement plan. *** 📆 BOOK A CALL: For two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Every January, we go through the same routine. Limits adjust, brackets shift, and most years it's just a quick refresh. But 2026 is different. Sweeping tax legislation passed last summer is introducing some of the biggest changes we've seen in a while. And buried inside those updates are two new rules that have already caused widespread confusion (even among experts). In this bonus episode, I walk through the most important tax updates for 2026 and explain why they matter for your retirement plan. I also also break down those two unique rules, sharing how they work, who they apply to, and why they matter. So even if you feel up to speed on the 2026 changes, I'm confident you'll walk away with at least one new and useful insight. *** 📆 BOOK A CALL: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click to Learn More and Schedule *** EPISODE RESOURCES: →  Download the 2026 Tax Cheat Sheet →  Grab the Episode Show Notes →  Learn About the Total Retirement System™

After decades of saving and doing the right things, most people expect retirement to feel clear.  But for many, it doesn't. Not necessarily because they didn't save enough, but because key financial decisions were made in isolation. In this episode, I walk through the seven questions every retirement saver should be able to answer. I also share the exact planning framework my team and I use to make sure those questions are addressed in a thoughtful, coordinated way. By the end of today's episode, you'll have a clearer framework for evaluating your retirement decisions. And more importantly, you'll understand what it actually takes to feel confident about the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Learn More *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

It's that time of year again—time to step back from the complex tax strategies, Roth conversion debates, and retirement planning deep dives… and have a little fun. 😊 In this annual "surprising stats" episode, I'm sharing 7 counterintuitive facts about the markets and investing. Some are counterintuitive. A few might make you question things you've believed for years. And at least one involves math that should make anyone considering complex insurance products hit the pause button. By the end of today's episode, you'll walk away feeling more confident in the proven (sometimes boring!) academic approach to investing that we talk about so often here on the show. And if nothing else, you'll have a few holiday-dinner stats to drop between bites of pie. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Learn More *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™ →  Download the 2026 Tax Cheat Sheet

💥 Download the freshly updated 2026 Tax Planning Cheat Sheet (PDF): www.youstaywealthy.com/cheatsheet *** Most year-end tax advice is generic... max out your 401(k), bunch your deductions, donate to charity. But for diligent retirement savers with healthy nest eggs, the real opportunities are more nuanced.  In this episode, I break down three tax strategies that can help you avoid overpaying the IRS and reduce your lifetime tax bill. You'll learn how to evaluate whether each move makes sense for your situation, so you're making informed decisions rather than chasing aimless deductions.  If you're nearing retirement or already there, this episode will help you close out the year with a clearer tax picture and a smarter plan for the years ahead. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule a Call *** EPISODE RESOURCES: →  Download the 2026 Tax Cheat Sheet →  Grab the Episode Show Notes →  Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™ →  Careers at Define Financial

The Oracle of Omaha is officially "going quiet."  In a rare and deeply personal announcement, Warren Buffett published what appears to be his final press release to shareholders. This episode isn't about taxes, investing, or the latest market headlines. It's about how one of the most successful investors of all time is thinking about money, family, aging, and what actually matters when the scoreboard stops moving. In this Thanksgiving special, I break down: ▶ Why he chose to say this now (at age 95!) ▶ What retirement savers and investors can learn from his message ▶ How his parting wisdom can change the way you use your time and wealth If you've ever wondered what your future self might wish you'd paid more attention to today, this conversation is for you. Tune in for the deeper meaning behind Buffett's Thanksgiving sign-off ("yes, even the jerks") and what it reveals about redefining success in the second half of life. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, we've have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

"Just buy the index." It's the simple advice that built your wealth and got you to the finish line. But here's what often gets overlooked: The strategy that got you to retirement won't necessarily keep you there. When you switch from saving to spending, the math changes. Suddenly, relying on a "simple" S&P 500 strategy exposes you to risks that didn't matter when you had a paycheck. In this episode, we cover: ▶ The Simplicity Trap: Why "decision fatigue" lures smart retirees into risky, overly concentrated portfolios. ▶ S&P 500 Reality Check: Why the "safe" default option is actually dangerous for your retirement income.  ▶ The "Flatline" Defense: How to build a retirement portfolio that protects your purchasing power during downturns.  ▶ Beyond Investing: How to align your investments, taxes, and legacy for true peace of mind. If you are approaching retirement and wondering if your "set it and forget it" strategy is enough to last a lifetime this episode is for you. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Everyone fears running out of money in retirement—even millionaires.  What most people don't realize is that research shows most retirees rarely spend down their savings. In fact, many actually see their wealth grow throughout retirement, even during some of the toughest markets in history. In this episode, we unpack: ▶ Why that happens ▶ What the data really says about retirement spending ▶ How to find the right balance between confidence and caution By the end, you'll see why most retirees worry far more than they need to, and how to feel confident spending your own money. *** 📆 SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: For nearly two decades, my team and I have helped hundreds of families across the U.S. plan smarter retirements—from tax strategies and investments to income and legacy planning. The result? Less stress. Lower taxes. More confidence about the future. If you're looking for clarity and a proven, personalized process, we'd be honored to have a conversation. 👉 Click Here to Schedule Your FREE Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Sales of "traditional" long-term care insurance have fallen 92% since 2002. Meanwhile, hybrid policies have surged to over 500,000 sales a year.  But which option actually makes sense for your situation?  In this episode, I break down everything you need to know before buying long-term care insurance, including: ▶ The optimal age to purchase ▶ Traditional vs. hybrid policies (the real pros and cons beyond the sales pitch) ▶ The actual costs of proper coverage I'm also sharing three critical implementation details that can make or break your coverage when you need it most. If you're approaching retirement and wondering how to protect yourself from potentially catastrophic long-term care costs, this episode will give you the clarity you need to make an informed decision. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule Your FREE Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

You've heard it before—70% of Americans over 65 will need long-term care. While that number is technically true, it's also misleading. Because here's what many people don't realize: the vast majority of retirees will never face a catastrophic, six-figure care event. In fact, nearly two-thirds will spend ZERO out of pocket during their lifetime! 🤯 So how do you prepare responsibly without overpaying for protection you may never use?  In this episode, I walk you through a simple 5-step process to decide if you can safely "self-fund" your long-term care needs, while still protecting your retirement plan and peace of mind. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Americans lost a record $16 billion to scams in 2024—nearly 40% from investment fraud alone. The trend is moving in the wrong direction.  In this episode, I share the story of a small-town financial advisor who built trust over decades, until that trust unraveled into one of the most devastating scams they'd ever seen. More importantly, I break down 8 red flags that experts say could indicate you're being conned. Because here's the truth: falling for a scam doesn't mean you're careless or foolish—it means you're human. And understanding the psychology behind deception is the best way to protect yourself. If you think you're immune, that confidence might be exactly what scammers are counting on. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Most experts say the smartest Social Security move is to wait until age 70 to claim. On paper, the logic seems simple—delay claiming, and you'll lock in a larger monthly check for life. But here's what's interesting: only about 10% of Americans actually wait that long. 🤯 Nearly one-third claim Social Security at 62, and the majority file before full retirement age.  So are millions of retirees making a huge mistake… or is the conventional wisdom missing something? In today's episode, I'm sharing findings from a new research paper showing why delaying until 70 isn't always the clear-cut, no-brainer strategy it's made out to be. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

We've been told our whole lives that retirement happens at 65—maybe 62 if you're lucky. But in my experience, that traditional timeline isn't always the reality. In fact, for many people, retirement may be much closer than they realize. After nearly 20 years of building retirement plans, I've noticed a recurring theme: Most people overestimate how much they think they need and underestimate how ready they already are. That's why in this episode, I'm breaking down 7 signs that could mean you're closer to early retirement than you realize. These aren't about chasing some arbitrary savings target—they're practical, real-world markers that can help you rethink your timeline and gain confidence in your next chapter. If even a few of these resonate with you, it may change the way you think about retirement and the life you've worked so hard to create. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Even if you're not on Medicare right now, chances are someone you love is—and sooner or later, you'll face those decisions yourself. That's why it's worth paying attention to an important letter that arrives every September: the Annual Notice of Change. Most people glance at it, toss it aside, and never think twice. But with big shifts coming in 2026, ignoring it could be a costly mistake. And that letter is just the beginning. There are three other Medicare traps that cost people thousands each year and, in some cases, wreck entire retirement plans. In this episode, I'll walk you through the 2026 changes you (and your loved ones!) need to prepare for, plus the three mistakes to avoid no matter what year it is. By the end, you'll know exactly what to watch for and how to feel confident about Medicare—whether you're enrolled now, preparing for it soon, or helping someone you care about. *** SCHEDULE A (FREE) RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Learn About the Total Retirement System™

Despite making insurance decisions almost daily, many retirement savers don't truly understand what they're buying or why they need it. In today's episode, I'm breaking down life insurance into simple, actionable terms. Specifically, I'm sharing: ‣ The 3 essential steps to managing insurable risks ‣ The key differences between term and permanent life insurance ‣ The exact questions to ask yourself before buying (or hanging onto) any policy  I'm also sharing a few little-known facts and tips to help you properly evaluate options you may be considering. Even if you think you know everything about life insurance as it relates to your retirement plan, today's episode will provide valuable and important reminders as you continue managing your ongoing insurance needs. *** SCHEDULE A RETIREMENT STRATEGY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Strategy Session *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Schedule Your Free Retirement Strategy Session  

Retirement is about so much more than money—it's a complete life transition. In this episode, I'm sharing my recent conversation with Adam Cmejla, where we explore the often-overlooked aspects of retirement planning. We discuss: ‣ Why retirement can feel like a grieving process—and how to navigate it ‣ The surprising role responsibility and community play in long-term happiness ‣ Smarter ways to approach Monte Carlo simulations, taxes, and cash management We also share our favorite retirement and investing charts that reinforce the principles essential to keeping financial plans grounded. Whether you're 10 years out from retirement or already there, this conversation challenges common assumptions and offers a helpful perspective on this stage of life. *** SCHEDULE YOUR FREE DISCOVERY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Discovery Meeting *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Get Your FREE Retirement & Tax Analysis!

Required Minimum Distributions (RMDs) could force you to withdraw as much as 15% of your retirement account balance in a single year. But do RMDs really put you at risk of outliving your money? Why does the IRS expect you to live so much longer than the Social Security Administration does? And what proactive steps can you take before age 73 to avoid giving the IRS more than its fair share? In this episode, I'm unpacking: ‣ How RMDs are actually calculated ‣ Why the IRS tables are more conservative than most people realize ‣  The pros and cons of using RMDs to build a dynamic withdrawal strategy I'm also sharing tax planning tips and strategies for navigating your RMDs.  If you're concerned about how RMDs might impact your retirement plan—or you're looking to optimize your tax situation before they kick in—this episode is for you. *** SCHEDULE YOUR FREE DISCOVERY MEETING: My team and I have guided hundreds of families across the U.S. through retirement's biggest challenges over the last two decades. The result? Smarter tax strategies, better investment decisions, and a more confident retirement. If you're seeking clarity and a proven retirement planning process, we'd be honored to help. 👉 Schedule a Complimentary Discovery Meeting *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Get Your FREE Retirement & Tax Analysis!

Is retiring in your 50s actually realistic for everyday Americans? According to a recent NerdWallet survey, the average target retirement age for households earning $100,000+ isn't 65—it's 58. And these aren't tech moguls or lottery winners. They're teachers, small business owners, and dual-income couples who've steadily built their nest eggs and now want to enjoy their healthy, active years while they can. But retiring in your 50s requires a very different kind of plan. One that accounts for early withdrawal penalties, health insurance gaps, and delayed Social Security. These obstacles are the "triple threats" of early retirement. In today's episode, I'll share how to combat them and provide a simple 5-step process for turning your retirement vision into a reality.  *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Schedule a Complimentary Discovery Meeting to Learn More. *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Get Your FREE Retirement & Tax Analysis!

What if everything you've learned about money completely changes once you cross the $1 million mark? Many people think a healthy 7-figure nest egg means the hardest part is done, but ironically, that's when the biggest financial challenges start. Today, Nick Maggiulli returns to share his latest retirement research, which inspired his new book, "The Wealth Ladder." In this conversation, we explore: ▸ Why retirement savers with $1-10 million often feel "stuck" ▸ The surprising reason wealthy retirees are more likely to LOSE wealth than those with less money ▸ Why your investment portfolio becomes more important than your income at this stage ▸ The academic research showing good health is worth $400,000 per year If you're nearing retirement (or already there), you'll learn why crossing the million-dollar mark isn't the finish line—it's when the game changes entirely. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Schedule a Complimentary Discovery Meeting to Learn More. *** EPISODE RESOURCES: →  Grab the Episode Show Notes → Join the Stay Wealthy Retirement Newsletter →  Get Your FREE Retirement & Tax Analysis!

A recent study reported that 76% of retirees regret not saving more money. But after working with hundreds of successful retirees and analyzing thousands of survey responses, I've discovered something interesting:  Their deepest regrets actually have little to do with financial shortfalls. Instead, they revolve around critical aspects of financial planning that significantly impact purpose, independence, and fulfillment in your golden years. In this episode, I'm revealing three (3) retirement regrets that many people don't consider until it's too late. I'm also sharing how to avoid the same mistakes so YOUR retirement is fulfilling instead of filled with regret. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter 📊  Get Your FREE Retirement & Tax Analysis!

Wondering how the new 'One Big Beautiful Bill Act' affects you and your retirement plan? Don't want to read 870 pages of Congressional jargon? I've got you covered! In this episode, I'm breaking it all down and sharing the 5 biggest things retirement savers need to know. I'm also addressing several broader provisions in the bill and clarifying some common misconceptions. This giant (and confusing!) economic package touches nearly every aspect of your financial life. So, pour yourself some coffee—or something stronger if you need it—and hit play. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Looking to hire a retirement and tax planning expert? We help 100+ families in 40 states across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter 📊  Get Your FREE Retirement & Tax Analysis!

Think you need millions of dollars to retire comfortably? Think again. Most people believe they're "behind" on retirement savings because they're measuring against arbitrary benchmarks that don't reflect their unique situation. But what if retiring at 62 is actually more achievable than you've been led to believe? In this episode, I'm sharing: ► Why you should ignore popular savings benchmarks ► Why delaying Social Security isn't always the right move (and how taking it early might preserve MORE wealth) ► A simple 4-step process to build your personalized early retirement plan If you're tired of feeling behind and want to discover how early retirement might be within reach right now, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need retirement & tax planning guidance?  We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter

"I planned for 30 years of expenses—but zero years of purpose." This was a recent client's confession, and she's not alone. In fact, nearly 40% of retirees say they wish they had waited longer to retire (and it's not about money).  In this episode, I'm revealing why even the most financially prepared retirees fall into identity crises and regret. I'm also sharing my 5-step "Bridge Strategy" to help you retire with clarity and purpose, not just a seven-figure portfolio.  If you're planning FOR retirement but haven't considered what you're retiring TO, this episode is for you. *** SCHEDULE A COMPLIMENTARY DISCOVERY CALL: Need professional retirement & tax planning help?  We help 100+ families across the country navigate retirement, optimize investments, and reduce taxes. 🗓️ Learn more and schedule a Discovery Meeting with us. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📫 Join the Stay Wealthy Retirement Newsletter

"Cash is king" has guided investors since the 1987 market crash. But what if this so-called "king" is actually putting your retirement plan at risk? Millions of retirees are lured by today's enticing cash yields, confusing safety nets for sound investment strategies. In this episode, I'm revealing why cash (even at 4-5%) is a deceptive long-term investment. I'm also sharing details about a critical investment performance metric to help you make more informed portfolio decisions. If you're wondering how to balance safety and growth in today's uncertain market, this episode is for you.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes

You've finally made it to retirement! But what if some of the choices you're making right now are quietly pulling you back to work? Every year, countless retirees are forced back into the workplace. Not because they were reckless, but because they followed advice that sounded smart and safe. In this episode, I'm sharing 7 of the most common retirement pitfalls that can derail even the best-laid plans. I'm also sharing our Total Retirement System™—a comprehensive framework to ensure you retire once and never look back.  If you're approaching retirement (or already there) and want to avoid mistakes that force people back to work, this episode is for you. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes

"I'll just work a few more years." It's the retirement safety net millions of Americans often count on. In large part because the financial industry has convinced everyone that retiring later is the most sensible backup plan if your savings fall short. But what if this common advice is actually setting you up for one of the most costly mistakes of your life? In this episode, I'm sharing why the real danger may not be running out of money in retirement, but rather working too long. I'm also sharing why choosing the right withdrawal strategy may help you retire sooner AND give you more confidence to spend in retirement.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes

Today I'm diving into the tariff-induced market mania that has been dominating every news headline. Specifically, I'm joined by Cullen Roche, monetary economics expert and founder of Discipline Funds, to discuss three important things: ► How tariffs actually work and why economists across the political spectrum overwhelmingly agree they are bad ► What the recent tariff proposal means for the economy (and American consumers) ► What yesterday's "90-day pause" means for the markets going forward We also discuss how retirement investors should approach their portfolios during this period of economic uncertainty + what changes are prudent to make. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes

ESG investing is exploding in popularity—but it's also a giant, confusing mess. Over $35 trillion in global assets now follow ESG guidelines. 🤯 But despite the rapid growth, most retirement investors still don't fully understand ESG investing... ...or how to spot legitimate ESG strategies from clever marketing hype. To help break through the confusion, Liz Simmie joins me to discuss: ➤ What ESG investing is and how it differs from Socially Responsible Investing (SRI) ➤ How retirement savers should evaluate ESG funds, particularly in terms of cost and performance ➤ The #1 data point Liz screens for when evaluating an ESG investment We also explore how investors can cut through ESG marketing hype to find genuinely responsible investment solutions. *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  View the Episode Show Notes

Morningstar recently published its annual "State of Retirement Income" research report. This year's report finds the highest 30-year safe withdrawal rate for retirees is... 3.7% 🤯 In this episode, you'll learn: ► How researchers arrive at different recommended withdrawal rates ► Why popular withdrawal strategies are (likely) too conservative ► 3 proven strategies for boosting retirement income And since there is no one-size-fits-all, you'll also learn the pros and cons of each retirement income strategy discussed! *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Subscribe to "The Go-Go" Retirement Newsletter

Today I'm discussing the biggest retirement investment risk. As Morgan Housel put it, "It's the hardest risk for people to understand...  ...and it's the only one that really matters." In this episode, you'll learn: ► What the three sides of risk are ► Why tail risk is all that matters ► How to mitigate this risk in your retirement plan You'll also learn why most investors should (probably) stay away from investment products promising you lots of upside with limited downside.  *** 2025 TAX CHEATSHEET Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you,  you'll receive my recently updated 2025 Tax Cheatsheet (PDF).  You'll also receive weekly retirement and investing tips from yours truly. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Worried about Medicare IRMAA eating into your retirement savings?  Whether you're 10+ years away from Medicare or already enrolled, this episode will help you navigate this pesky surcharge and protect your retirement savings. Key topics covered: ► Updated 2025 IRMAA brackets  ► Answers to common planning questions  ► 3 strategies to minimize (or avoid) IRMAA You'll also learn how to project future IRMAA brackets for better planning. If you want a clear roadmap for making informed decisions about your future healthcare costs, you'll enjoy today's episode. *** RETIREMENT & TAX PLANNING: Looking to hire a financial planner with retirement & tax planning expertise? My team and I only have a few more openings for Discovery Meetings with new clients.  If you're seeking professional help, we would love to have a conversation! 👉 Learn more about our process and grab one of the remaining slots. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Markets tend to operate in cycles—yesterday's winners often become tomorrow's losers (and vice versa).  The most unloved asset classes can quietly become the best performers, while the most popular ones frequently disappoint. Yet, many investors fall into the trap of assuming recent trends will continue indefinitely. But markets don't work that way. No asset class outperforms or underperforms forever. To help you avoid falling into this trap (and make more informed portfolio decisions), I'm sharing key takeaways from Vanguard's 2025 Market & Economic Report in this episode.  I'm also sharing 5 actions retirement savers can take right now to prepare for success over the next decade and beyond. *** Looking to hire a financial planner with retirement & tax planning expertise? My team and I only have a few more openings for Discovery Meetings with new clients.  If you're seeking professional help, we would love to have a conversation! 👉 Learn more about our process and grab one of the remaining slots. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network  

Looking to hire a financial planner with retirement & tax planning expertise? My team and I have availability for 25 Discovery Meetings over the next 8 weeks. If you're seeking professional retirement planning help, we would love to have a conversation! 👉 Learn more about our process and grab one of the 25 meeting slots. We intentionally limit the number of new clients we take on each year. This ensures we can provide each family with highly customized investment, retirement, and tax planning services. Once these 25 meetings are scheduled, we will not have availability to meet with new clients until later this year. Schedule your Discovery Meeting. *** Today I'm sharing the essential steps for evaluating and selecting the right financial advisor for your unique situation.  Specifically, I cover 5 important things: ► How to identify and document your financial challenges, needs, and goals before starting your search ► Critical questions to ask yourself about the type of professional you want ► Guidance for conducting background checks ► Non-obvious questions to ask potential advisors ► The importance of a well-defined evaluation process (and why you shouldn't rush your decision) You'll learn how to navigate through the sea of 300,000+ financial advisors to find the right one for you. Whether you want a short-term or long-term engagement, this episode provides actionable steps to help you make the right choice. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Grab your Tax Planning Cheatsheet (updated for 2025!) by clicking here. The 2-page PDF guide includes every important number you'll need for your retirement & tax planning next year. Updated federal income tax brackets, AMT annual limits, standard deductions, Social Security taxation summary, estate and gift tax annual limits…and more. 👉 Download it now.  *** In our final episode of the year, I'm taking a break from the usual nerdy retirement planning talk to share twelve (12) insightful, fun, and humourous investing statistics.  These stats cover topics such as: ➤ The McRib Effect: Can a fast-food favorite influence markets? ➤ Shiller P/E Ratio History: What does this popular valuation signal suggest for the market's future? ➤ Netflix Drawdowns: A stock's wild history of recovery. ➤ Berkshire Hathaway: A long-term (unbelievable) investment story unfolds. ➤ Pet Spending: A surprising shift in American priorities. Whether you're a market enthusiast or just here for the entertaining stories, you'll love this lighthearted yet insightful end-of-year episode. Thank YOU for making this year so special by tuning in and engaging with the show. Enjoy the holidays, reflect on the year behind us, and prepare to dive into 2025 with fresh market insights and retirement planning strategies.  Here's to "staying wealthy" next year and beyond! 🎉 *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

How do we fix the housing affordability problem in the U.S.? Will lower interest rates really improve the real estate market? How have Zillow and Airbnb contributed to the current housing challenges?   What are tariffs (+ benefits and drawbacks)? What's next for the U.S. economy?  These are just a few of the questions I'm exploring in this episode with author and economic expert, Kyla Scanlon.  *** BOOK GIVEAWAY I'm giving away 10 copies of Kyla's beautifully written and designed book, "In This Economy? How Money & Markets Actually Work." To put your name in the hat and receive a free copy, be sure you're subscribed to the Stay Wealthy Retirement Newsletter by visiting https://www.youstaywealthy.com/email. Next week, my team will randomly select 10 lucky readers to give our copies away to.  👉 Join the newsletter! *** FREE RETIREMENT PLANNING RESOURCES: As a bonus for subscribing to the Stay Wealthy Retirement Newsletter, you'll also receive three (3) of my MOST popular retirement & tax cheatsheets.  *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm discussing the challenges of spending money in retirement.  To help, Brian Portnoy, one of the world's leading experts on the psychology of money, joins us to discuss three big things: ➤ Why it's so difficult for retirement savers to transition from saving to spending ➤ What you can do to prepare for the (well-documented!) challenges of retirement spending  ➤ How to use Brian's "Four C's" to achieve true wealth in retirement We also delve into the meaning behind Brian's famous quote, "Diversification always means having to say your sorry," and how it can help you make better investing decisions. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Emerging Markets are the world's primary drivers of global growth (and wealth accumulation). Just over 50% of the world's economic output comes from these countries. 🤯 They play a crucial role in shaping global economic trends... ...but most retirement investors don't fully understand this asset class. To help break it down for us, Emerging Markets expert and founder of Life + Liberty Indexes, Perth Tolle, stops by to discuss:  ➤ What Emerging Markets are and why retirement savers should consider investing in this asset class ➤ Why traditional, low-cost Emerging Market funds may produce lower returns ➤ The pros/cons of excluding countries like China and Russia from an Emerging Markets fund  We also discuss why "freedom" plays an important role in this asset class and how investors can (potentially) use freedom metrics to capture higher returns.  *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Why are most people planning for the wrong things in retirement? What should they be planning for that they're not? To help answer these important questions, Psychologist & Behavioral Finance Expert Dr. Daniel Crosby stops by to discuss: ➤ What our happiness is determined by ➤ Why (contrary to popular research) more money can ACTUALLY make us happier ➤ What is the "PERMA model" and how can we use it to improve retirement success We also discuss why retirees are more depressed than everyone else and what they can do to mitigate this risk. *** THE SOUL OF WEALTH:  Grab a copy of Daniel's new book, The Soul of Wealth.  The book explores what wealth really is and provides practical suggestions for how to change your thinking and your actions in small, powerful ways, for a wealthier life. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm talking about navigating the risks of concentrated investments. Specifically, Peter Lazaroff, CIO of Plancorp, joins me to answer three BIG questions: ➤ How do you know if you have a "concentrated investment?" ➤ What are some little-known risks investors aren't considering? ➤How do you (tax-efficiently) diversify concentrated investments? I also share a specific exercise investors can follow to decide if they should sell some or all of their concentrated holding(s). *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm sharing how retirement investors can take action in this final episode of our Small Cap Value series.  Specifically, I'm discussing three things:  ➤ Why paying MORE for an investment can pay off ➤ How to easily and properly evaluate different funds  ➤ What small-cap value funds to consider  I'm also sharing two important reminders before taking action and investing in this popular asset class. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm diving into part two of our Small Cap Value investing series. Specifically, I'm addressing three big questions: ➤ How do small-cap value stocks reduce risk + improve returns  ➤ What criteria does an investment need to meet to be included in a portfolio ➤ Why value investing is still alive and well While there is no shortage of research in favor of this dominant asset class... ...I'm also sharing why investors don't necessarily need small-cap value stocks to reach their retirement goals. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm kicking off a two-part series on Small Cap Value investing. Specifically, I'm addressing three big questions: ➤ What exactly are small-cap value stocks? ➤ Why have small-cap value stocks, historically, outperformed most major asset classes? ➤ Does the recent 20-year underperformance suggest that the strategy is dead and won't work in the future?  I'm also sharing critical differences between small-cap value funds + how to take action if you want to include this asset class in your portfolio. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm sharing key takeaways from three of the BEST retirement articles I read this month. 1️⃣ The first article is about the future of taxes in this country and specifically makes a strong case for why they will be higher. 2️⃣ The second reveals why investors missed out on 15% of investment returns over the last decade. 😳 3️⃣ Lastly, the third article is a real-life account of what it actually feels like to transition from the working world into retirement. Didn't get a chance to read everything that was published last month? Don't worry—I've got you covered! *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter! 👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today, I'm sharing FIVE surprising statistics about the economy, markets, and retirement. For example, one stat highlights a "stock market indicator" that has a 100% success rate 😳  Another emphasizes a growing insurance risk that everyone needs to protect against. Along with being entertaining, these stats bring important investing and planning topics to the surface.  They also serve as important reminders. If you're ready to have some fun learning about the history of the markets and little-known investing facts, this episode is for you. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Are you ready to get answers to some BIG retirement questions? Questions such as: ➤ What role does the equity in my home play in my retirement plan? ➤ Why should I do Roth conversions to help mitigate taxes on my kids' inheritance? ➤ Are closed-end funds a good investment? ➤ How do I properly evaluate pension vs. lump-sum decisions? Today on the show, I'm answering these questions (and more!) with my good friend, Roger Whitney. I'm also providing an update on the Retirement Podcast Network after taking a hint from 1,000+ retirement savers.   *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Required Minimum Distributions (RMDs) begin at age 73 for most retirement savers. These forced withdrawals can be a burden for those who don't need (or want) the taxable income. Since they are "required," many assume that they don't have any control over their RMDs. But that's not necessarily the case. In fact, one of the 5 strategies I'm sharing with you today allows you to delay unwanted (mandatory) distributions well past age 73 😳 Applying these strategies and gaining control of your RMDs can potentially help you: ➤ Lower lifetime taxes ➤ Reduce catastrophic risks  ➤ Improve risk-adjusted investment returns It doesn't matter if you're still working or already taking RMDs—if you want to optimize your long-term plan, you'll enjoy today's episode. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

In the final episode of this series, I'm answering the BEST listener questions I've received about dividend investing. Questions such as: ➤ If dividend investing is NOT a great way to create retirement income, what is?  ➤ What dividend-focused funds should investors consider if they insist on investing for yield?  ➤ What is the counterargument for stock buybacks? Why are some people against them? Tune in to hear my answers to these great questions! FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter.  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

In today's episode, I'm sharing everything you need to know about stock buybacks. Specifically, I'm sharing: ➤ Why stock buybacks are referred to as a "flexible" dividend ➤ What a stock buyback is (and how it works) ➤ How stock buybacks are more tax-friendly than traditional dividends If you want to learn more about this increasingly popular "flexible dividend" strategy, you'll enjoy this episode. FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter.  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm continuing our multi-part series on Dividend Investing. Specifically, in part two, I'm sharing: ➤ What the long-term performance has been for dividend-focused funds ➤ Why popular dividend investing charts can be incomplete (or misleading) ➤ The 3 primary reasons dividend strategies typically underperform If you want to learn more about dividend investing and why it may not be the magical solution it's often marketed as, you'll enjoy this episode.  *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter.  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm kicking off a multi-part series on Dividend Investing. While dividends are a normal occurrence in the global markets, their role in a retirement portfolio is often misunderstood. ➤ What is a dividend, and why do some companies pay them?  ➤ How do they affect an investor's return? ➤ Where do dividends fit in the portfolio construction process?  ➤ What are the little-known problems with this investment strategy? ➤ And what does my upcoming birthday have to do with dividends? 🥳 I'm covering all of these questions (and more!) in this investing series.  *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm sharing a story about a couple who lost $2 million to an investment scam. I'm also sharing (new!) resources to help protect your personal data in 2024. Financial scams are getting more sophisticated and losses are skyrocketing. In fact, last year, Americans lost $10 billion to financial scams. That's $1 billion more than 2022, and is the highest-ever reported annual loss in FTC history. Everyone is at risk. And everyone needs to regularly take proactive steps to stay safe. Tune in to learn more. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

There is no shortage of questions when it comes to navigating and planning for retirement. ➤ How much do I need to save?  ➤ How do I optimize my tax bill and avoid overpaying the IRS?  ➤ When do I take Social Security?  ➤ What should I invest in? (And what should I avoid?!) The list goes on. And while you've likely read (or heard) helpful answers to most of the big questions, it never hurts to revisit them or get a different perspective. In fact, some studies suggest that it can take hearing something 7 times before you retain it 🤯 Today on the show, I'm answering listener questions with the Retirement Answer Man himself, Roger Whitney. Questions like, "What account type is the best retirement account type to fund after you've reached your savings goals?"  And, "What's the best process for making important changes to your investments after learning you aren't invested properly?"  If you want to hear our answers to these great questions (and more!), you'll enjoy this episode. *** FREE RETIREMENT PLANNING RESOURCES: Subscribe to the Stay Wealthy Retirement Newsletter! As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Inflation hit a 40-year high of 9.1% in June 2022. Today, inflation is hovering around 3%. If inflation is back in line with long-term historical averages, why does everything still feel so expensive? When voters were asked what they would most like to see improved in our economy... ...why did 64% of them say "lower prices?"  In this episode, I'm digging into the current state of inflation, why prices still feel high, and where inflation might be headed. I'm also sharing tactics for how to successfully navigate challenging time periods. If, like most retirement savers, things still feel outrageously expensive to you, you're going to enjoy this episode.  *** RETIREMENT & TAX PLANNING TOOLS: Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive three (3) of my MOST popular retirement & tax cheatsheets.  You'll also receive my weekly retirement newsletter :)  👉 Click here to subscribe and grab your cheatsheets. *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network  

Want an easy way to learn how the "Roth 5-Year Rule" affects your unique situation?  Subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive my one-page flowchart (PDF) for navigating this confusing rule. 👉 Click here to join the newsletter! *** TODAY'S EPISODE: The "Trump-era tax cuts" are set to expire in 2026. In other words, retirement savers only have two more years to take advantage of today's lower tax rates. One of the popular strategies to do this is through (aggressive) Roth conversions. As a result, I've had more questions than ever about the wildly confusing "Roth IRA 5-year rule"... ...specifically as it relates to Roth conversions. To help simplify this rule, I'm sharing TWO simple questions you can answer to understand how the rule works. I'm also sharing several real-life examples + my thoughts on what an election year might mean for the Tax Cuts and Jobs Act (TCJA). *** EPISODE RESOURCES: 📊  Get Your FREE Retirement & Tax Analysis! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network    

Today I'm talking through four (rarely-discussed) retirement planning misconceptions. In fact, some of these misconceptions might not be misconceptions at all... ...they might be concepts that you've never even considered! For example, is retirement planning a complex problem OR a complicated problem? (And why does it matter?)  And, should you develop a retirement plan from the outside in OR the inside out? To help answer these important questions, I'm joined by Roger Whitney, host of the Retirement Answer Man podcast.  Along with being a great person and expert retirement planner, Roger is also a deep, critical thinker who will definitely get your wheels turning in this episode. WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2024 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. ----- EPISODE RESOURCES: 📊  Get Your Free Retirement Assessment! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

It's an election year. As a result, many retirement investors believe that the market MUST be in for a wild ride. But is that true?  Over the last 100 years, how have markets behaved during election years? What have been the best and worst returns?  How has the market performed during every 4-year presidential term since 1929? And is it "different this time?"  To help retirement savers invest wisely during this period of heightened uncertainty, I'm answering these questions (and more). --- WANT THE CHARTS & DATA REFERENCED IN TODAY'S EPISODE? Join the Stay Wealthy Newsletter by clicking here. I'll be sending the 12-page PDF to all newsletter readers this week and next 😊 Click here to subscribe. --- EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement Assessment! 📘  Check Out the Retirement Podcast Network

The U.S. national debt recently crossed $34 trillion. Without causing some serious pain, paying off this debt is nearly impossible to do. We would have to dramatically cut spending in some VERY important areas, increase taxes, or both. This debacle has led many to label this situation as catastrophic... ...as a "building that we're stuck in that will need to collapse on us before we can leave." But is it really as bad as some make it out to be? Is $34 trillion of debt truly an issue?  Should we really be focused on paying down (or paying off) this debt?  To help answer these questions and shed light on this complex topic, I'm joined today by Cullen Roche, monetary economic expert and CIO of Discipline Funds. ----- WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2024 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. ----- EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement Assessment! 📘  Check Out the Retirement Podcast Network

With over 300,000 in the U.S., finding a financial advisor is easy. On the other hand, properly evaluating an advisor AND choosing the right expert to help with your unique needs is a challenging task. To help, I'm providing an actionable framework for evaluating financial advisors in this episode. I'm also sharing 3 critical things everyone should consider before entering into a new advisory relationship. It doesn't matter if you are looking for short-term help or a long-term relationship...if you're considering a financial advisor this year, you'll enjoy this episode. WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2024 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. ----- EPISODE RESOURCES: 📊  Get Your Free Retirement Assessment! ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm talking about stock market predictions. Specifically, I'm sharing: ‣ What happened in the markets in 2023 ‣ What may lie ahead for us in 2024 ‣ Why we should prepare for the biggest crash of our lifetime I'm also sharing an exciting announcement that will directly benefit you! 😊 WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2024 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. ----- EPISODE RESOURCES: 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Check Out the Retirement Podcast Network

Today I'm sharing 4 (important!) retirement and tax planning updates for 2024. I'm also sharing my freshly updated two-page tax cheatsheet 😊 One listener recently said: "This is the best two-page cheat sheet that I've seen! I do a lot of planning around taxes, IRMAA's, etc., and it is very helpful."  If you're wrapping up your year-end planning + starting to think about 2024 and beyond, you'll enjoy today's episode. RETIREMENT & TAX PLANNING RESOURCES: ‣ Grab Your 2024 Tax Cheatsheet ‣ Join the Stay Wealthy Newsletter (My Top 5 Year-End Checklists Going to Subscribers ONLY Next Week!) EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your FREE Retirement & Tax Analysis

Year-end is a popular time for tax planning strategies. Roth conversions. Charitable gifts. Squeezing in those final tax-deductible contributions. And, of course, the crowd favorite...good ol' tax-loss harvesting! ‣ Who should consider tax-loss harvesting (and who should stay away from it)? ‣ How can you increase the benefit of tax-loss harvesting? ‣ When can harvesting losses backfire? If you're a retirement saver wanting to learn more about this popular tax strategy, you'll love today's episode.  *** ✏️  Grab the Episode Show Notes 📬  Subscribe to the Stay Wealthy Newsletter! 📊  Get Your FREE Retirement & Tax Analysis

Navigating the Medicare world is confusing and challenging.  As a result, many retirees make Medicare decisions without clearly understanding the long-term implications. Long-term implications that, in worst-case scenarios, can put a retirement plan in jeopardy. To help you avoid making costly Medicare mistakes, I'm sharing three (3) big pitfalls to avoid in this episode. If you want to brush up on your Medicare knowledge before turning 65—or you're looking to change your current Medicare plan—you'll love today's episode. *** NAVIGATING IRMAA (2024 UPDATED) Click here to view the 2024 IRMAA brackets and learn how to avoid this surcharge.  *** WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Read My New Book: More Than Money

In part two of my series on bonds, I'm tackling three BIG questions: 1.) With cash yielding 5%, does it make sense to use money market funds (or t-bill) as a bond alternative? 2.) What should investors do if they own the wrong bonds and need to make changes? 3.) Does the current landscape shift how retirement investors should approach bonds going forward? If you're ready to dive deep into the research to understand this asset class better, you'll love this episode. ----- WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. ----- EPISODE RESOURCES: 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Read My New Book: More Than Money

Bonds are down 20%+ over the past three years.  Meanwhile, riskier asset classes (like U.S. stocks) are UP ~30% during the same period. ‣ What the %@#! is happening to bonds right now? ‣ Why are safe asset classes down double digits while risky asset classes scream upward? ‣ Should retirement investors consider changes? ‣ Are money market funds and CDs a better solution than bond funds?  ‣ And what might all of this mean for the future of bond investing? I'm answering these questions (and more!) in this 2-part series on bonds. --- WANT MORE RETIREMENT PLANNING TIPS? Join 5,000+ listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Read My New Book: More Than Money

Today I'm sharing nine fun facts about the economy, markets, and retirement.  Along with being entertaining, these facts bring important planning topics to the surface. They also help to address and answer common questions. For example: ‣ How correlated is the economy to the stock market? ‣ What are the actual odds of a catastrophic long-term care event? ‣ Should average life expectancy assumptions be used in retirement projections? If you're ready to have some fun learning about the history of the markets and little-known facts about investing, this episode is for you. --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Read My New Book: More Than Money

Everyone should freeze their credit. But most retirement savers I talk to have not tackled this simple (and free!) task. After commenting briefly about credit freezes in an episode last month, I've received dozens of GREAT questions from listeners. Questions like... ‣ Should minor children freeze their credit even if they don't have a credit score? ‣ After freezing with the "big three" (Equifax, Transunion, Experian), what other agencies should I freeze my credit with? ‣ How will freezing my credit affect my credit score? ...and more! Tune in to get answers to these questions and learn more about this critical financial planning task that continues to be overlooked. --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📖  How to Freeze Your Credit (Step-by-Step) 📊  Get Your Free Retirement + Tax Analysis ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money

Last June, inflation hit a 40-year high of 9.1%. Since then, it's been falling month over month, hitting 3.2% in July of this year. The Fed's aggressive rate hikes seemed to be doing their job, and their 2% inflation target appeared to be in sight. But then, the August CPI report came out a few weeks ago... ...and we saw inflation spike, jumping up to 3.7%. What happened? Where does inflation go from here? And should we be worried about this recent uptick? --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📊  Get Your Free Retirement and Tax Analysis ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money

Year after year, investors underperform the funds they invest in by almost 2%. 🤯 Not because of fees or taxes...but because of poorly-timed investing decisions. In today's episode, I'm sharing the results of this year's "Mind the Gap" study from Morningstar.  I'm also sharing: ‣ The asset classes with the highest and lowest behavior gap over the last 10 years ‣ The relationship between volatility and investing returns ‣ Three things retirement investors can do to earn more of the returns generated by their investments --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📊  Get Your Free Retirement and Tax Analysis ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money

Consumers reported losing nearly $9 billion to fraud in 2022 — a 30% increase from the year prior. And those are just the incidents that are reported. In fact, some reports suggest that the ACTUAL amount is closer to $40 billion! One thing every report seems to agree on is that scams are becoming more prevalent and more sophisticated. So to help protect retirement investors from becoming victims, today I'm sharing the three financial scams to watch out for. I'm also sharing how you can protect yourself (and your loved ones) from each scam. --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 📊  Get Your Free Retirement and Tax Analysis ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money  

In this episode, we're answering listener questions! Specifically, guest host Jeremy Schneider is answering questions like: What are the best index funds to invest in How do you access retirement money early What are the little-known pitfalls of early retirement Jeremy also shares important tips on transferring money from old investment accounts.  If you want to get answers to these great questions (and hear from a surprise guest who snuck their way in!), this episode is for you.  --- WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. --- EPISODE RESOURCES: 👉  Follow Jeremy Schneider on Instagram ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money 📊  Get Your Free Retirement and Tax Analysis

Almost every day, I (guest host Jeremy Schneider) hear someone mention their credit score. After being in school our entire young lives, we must all crave for someone to give us another grade. And when the ol' FICO corporation is slapping a big number on all of us... ...we excitedly spend every waking moment trying to improve (or maintain) it. But here's the problem: Focusing on your credit score is a TERRIBLE way to win with money. You're putting your energy towards precisely the wrong thing. In today's episode, I'm sharing why you shouldn't care about your credit score + what you should be focusing on instead! WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners around the country and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 👉  Follow Jeremy Schneider on Instagram ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money 📊  Get Your Free Retirement and Tax Analysis

Today we're talking about the Backdoor Roth IRA. Specifically, guest host Jeremy Schneider is sharing: What the Backdoor Roth IRA strategy is Why you should (or shouldn't) pursue it How to execute it the right way If you're interested in learning more about this unique strategy for getting more money into a Roth IRA, this episode is for you. *** WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 👉  Follow Jeremy Schneider on Instagram ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money 📊  Get Your Free Retirement and Tax Analysis

If YOU were to unexpectedly die tomorrow, would your loved ones know how to access your information?  Your bank accounts? Insurance policies? Debts? Access to your home and car? Your devices? Approximately 2/3 of Americans don't have any estate planning documents! To help you avoid leaving a financial mess behind, guest host Jeremy Schneider is sharing how he's PERSONALLY prepared his family for an untimely death. Specifically, he's sharing: ➡ What information and documents he has gathered  ➡ Where and how he (securely) stores it ➡ His process for keeping everything updated If you need actionable ideas (and motivation!) to tackle this critical planning task, today's episode is for you. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 👉  Follow Jeremy Schneider on Instagram ✏️  Grab the Episode Show Notes 📘  Check Out My New Book: More Than Money 📊  Get Your Free Retirement and Tax Analysis

Today I'm discussing a new retirement withdrawal strategy.  The strategy is simple + allows retirees to (safely) spend more money than the 4% rule. It also protects against one of the biggest threats to retirement—Sequence Risk! If you want to avoid leaving behind a mattress full of money and learn about a simpler approach to boosting retirement income, you'll enjoy today's episode. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

What separates a good investment from a bad one? How do you evaluate different investment options? Why are some very well-known metrics flawed and problematic? I'm answering these questions + sharing a personal story that caused me to change my approach when giving opinions about different asset classes.  WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Last year, I published an episode titled, 5 Reasons Not to Do a Roth Conversion.  The 5 reasons shared were: 1️⃣ - Shadow taxes  2️⃣ - No undo button  3️⃣ - Lack of cash flow to pay the tax bill  4️⃣ - You just don't want to :)  5️⃣ - Future charitable giving goals Today I'm sharing three (more) reasons not to convert + why it might be ok to leave money in your pre-tax IRA. Roth conversions can be a wildly beneficial tax planning move for the right person... ...but they aren't a "no-brainer" for everyone.  If you want to learn more about situations when converting money to a Roth IRA does NOT make sense, today's episode is for you.  WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

"Cash is king." But is it a great investment?  Historically, investors have built up dry powder to fund emergencies or survive market downturns. But with cash now yielding close to 5%... ...many investors are viewing cash as a way to make money. Today I'm sharing why cash — even at today's rates — is a bad investment. I'm also sharing how much cash a retirement investor should consider holding. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

For the last 53 years, U.S. stocks have significantly outperformed international stocks. (It's not even close.) As a result, many retirement investors are left wondering if they should own this asset class. Today I'm sharing why owning international stocks over the last 5 decades -- despite the disappointing track record -- was actually a smart decision. I'm also sharing why owning international stocks for the next 50 years and beyond is likely a wise decision, too.  WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Today I'm joined by Phil Huber, Chief Investment Officer at Savant Wealth Management. Phil joins me to take the other side of the alternative investment debate and shares three big insights: 1.) What exactly defines an "alternative investment" 2.) Why traditional stock/bond portfolios will be challenged in the years ahead 3.) How alternatives can help to reduce risk and improve investment returns He also addresses common misconceptions about this complex asset class.   If you're looking to expand your investment knowledge and learn how alternatives might enhance your retirement portfolio, this episode is for you. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out My New Book: More Than Money ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Today I'm talking about the bond market. Specifically, what it's currently telling us about where the economy might be headed. In fact, we've never seen bond yields sound the recession alarm this loudly. 🚨 But, how reliable is the bond market? What does this "recession warning" mean for retirement savers? And how might the current environment impact investment decisions? I'm answering these questions (and more) in this episode! WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Check Out the More Than Money Book ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Today we're talking about expectations vs reality. To help, I'm joined by Rubin Miller, founder and CIO of Peltoma Capital. Rubin and I talk about three BIG things:  Why chess players don't make great investors How retirement savers should think about their current and future investment returns What investment assumptions should be used when running retirement planning projections We also talk about "risk-free" investments, the hidden dangers of an investor's time horizon, and growth vs value stocks. If you want to learn how to be a successful investor + how we can use evidence to make informed retirement planning decisions, today's episode is for you. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Grab Your Copy of the More Than Money Book ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Today I'm talking about the current banking crisis. Why? Silicon Valley Bank and Signature Bank were the 2nd and 3rd largest bank failures in history. In addition to explaining how we got here + why these banks collapsed... ...I'm answering three (3) important questions that retirement investors are asking. If you're ready to understand what this banking debacle means and what to do in response, today's episode is for you! WANT MORE RETIREMENT PLANNING TIPS? Join 2,000+ retirement savers and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis 📘  More Than Money is Available Everywhere!

*** More Than Money is officially out! Click here to grab your copy now. *** (All net proceeds being donated to non-profit organizations dedicated to improving financial literacy and diversity in the profession.)  --- Today I'm sharing my recent conversation with Joe Saul-Sehy from Stacking Benjamins.  Together, Joe and I break down two real-life case studies from my (just released!) book, More Than Money. We cover: Why the "making work optional" exercise is so empowering  How to have constructive money conversations How a widow overcame the newfound challenge of managing the finances We also talk about retirement planning misconceptions, how my wife and I track our expenses (😲), and more! WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: 📘  Grab Your Copy of the More Than Money Book ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis

Today I'm discussing risk. Specifically, a type of risk known as "tail risk." As Morgan Housel puts it, it's the hardest for people to understand... ...and it's the only one that really matters.  If you want to learn what tail risk is, why it's important, and how to mitigate it, today's episode is for you. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis 📘  Pre-Order the More Than Money Book

Today I'm talking about alternative investments. An "alternative" is an asset that doesn't fall into one of the three traditional investment categories (stocks, bonds, and cash). For example, private equity, venture capital, and managed futures. These complex strategies often claim to reduce risk + deliver "uncorrelated" returns.  But do they live up to the hype? Do they provide compelling risk-adjusted returns?  Should retirement savers include alternative investments in their portfolio?  I'm answering those questions (and more) in this episode. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis 📘  Pre-Order the More Than Money Book

Today I'm addressing the January inflation report. In fact, contrary to expectations, inflation increased last month. Specifically, the Consumer Price Index (CPI) jumped 0.5% after increasing by only 0.1% in December.  Why are prices increasing again? Was the report positive or negative? What does this mean for the long-term inflation trend?  I'm answering these questions + we have a special guest that drops by to share his thoughts. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis 📘  Pre-Order the More Than Money Book

Today I'm talking about investing and planning for retirement during uncertain times. In fact, I was recently invited to discuss this topic with Caleb Silver, Editor-in-Chief at Investopedia. Caleb hosts the Investopedia Express Podcast and has had conversations with everyone from Ray Dalio & Liz-Ann Sonders to Eli Manning & David Rubenstein. Needless to say, it was an honor to be on his show and share: How to build a plan for your cash and why it's so important What mistakes investors should watch out for in today's choppy markets How to create a tax-efficient withdrawal strategy in retirement  I also shared my "hottest" 2023 investing take, my favorite financial term, and what the future of financial planning looks like. WANT MORE RETIREMENT PLANNING TIPS? Join thousands of listeners and subscribe to the Stay Wealthy Retirement Newsletter. As a thank you, you'll receive a copy of my 2023 Tax Planning Cheatsheet. 👉 Click here to subscribe and grab your cheatsheet. *** EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📊  Get Your Free Retirement and Tax Analysis 📘  Pre-Order the More Than Money Book

Today I'm wrapping up our series on Financial Advisors by answering five common questions. Questions such as: How important are professional designations like CFP or CFA? What is the process for firing a financial advisor? Will I incur fees and taxes when transferring investment accounts to another financial institution?  I'm also sharing more about financial coaches + what to do if you are a victim of bad financial advice. NEED TAX & RETIREMENT PLANNING HELP? Click to Learn more about our FREE Retirement & Tax Analysis. We help people aged 50+ lower taxes, invest smarter, and (safely) create a retirement paycheck. Our Free Retirement Assessment™ will answer your BIG questions and help you properly evaluate our firm. 👉 Learn more here! *** Episode Resources: 📬  Join the Stay Wealthy E-Newsletter ✏️  Grab the Episode Show Notes 📘  Pre-Order the More Than Money Book

Today I'm tackling part four of our series on financial advisors. Specifically, I'm covering three BIG things: What is a fiduciary financial advisor (and should investors work with one) How are 'fee-only' advisors different from 'fee-based' Where can retirement savers search for a financial advisor based on their needs If you want to understand some of the most misunderstood financial terms + learn how to find a qualified advisor, today's episode is for you. NEED TAX + RETIREMENT PLANNING HELP? Click to Learn more about our FREE Retirement & Tax Analysis We specialize in helping people aged 50+ lower taxes, invest smarter, and (safely) create a retirement paycheck. Our Free Retirement Assessment™ will help you evaluate our firm and others you might be considering. 👉 Learn more here! *** Episode Resources: 📬  Join the Stay Wealthy E-Newsletter ✏️  Grab the Episode Show Notes 📘  Pre-Order the More Than Money Book

Today I'm sharing the different ways financial advisors charge for their services. In fact, there are FOUR main fee structures you might come across when interviewing advisors... ...and each one can be a disservice to someone. In this episode, I'm covering three important things: What are the four fee structures and their pros & cons Who is (and isn't) a good fit for each service model How much do financial advisors typically charge for their services I'm also sharing how retirement savers might think about measuring the value of financial advice. If you're ready for a deep dive into financial advisor fees, you're going to enjoy today's episode.  *** WANT MORE RETIREMENT & TAX PLANNING CONTENT? Join thousands of other listeners and subscribe to the Stay Wealthy e-newsletter! EPISODE RESOURCES: ✏️  Grab the Episode Show Notes 📘  Pre-Order the More Than Money Book 📊  Get Your FREE Retirement & Tax Analysis

Want to support my upcoming book and help improve financial literacy? To encourage your support, I'm running a "buy one, give one" campaign.  Here's how it works: Pre-order a copy of More Than Money (Kindle or physical copy) before Dec 31. Email a screenshot of your order to [email protected]. I will personally match your order and send you a second copy to gift to someone in your life. All net proceeds from the book are being donated to non-profit organizations dedicated to improving financial literacy and access to advice.  Pre-order your copy of More Than Money! *** Today I'm tackling part two of our series on Financial Advisors. Specifically, I'm breaking down the 5 different types of advisors (and who might be a good fit for each type). I'm also sharing some thoughts on paying for financial advice and measuring the value you receive. If you're ready to continue learning about the world of financial advisors + how to make sense of the different types you can work with, today's episode is for you. Want more retirement content? Join thousands of other listeners and subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📘  Pre-Order the More Than Money Book 📊  Get Your FREE Retirement & Tax Analysis

Today I'm kicking off a multi-part series on Financial Advisors. (I'm also sharing a BIG announcement with everyone! 🥳)  Here in Part 1, I'm covering three things: What is a financial advisor Why the job title is meaningless What financial advisors do (and don't do) It doesn't matter if you manage your own finances, happily work with a financial advisor, or work with 15 advisors... ..if you want to gain a better understanding of this important (yet confusing!) profession, this series is for you. Want more retirement content? Join thousands of other listeners and subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📘  Pre-Order the More Than Money Book 📊  Get Your FREE Retirement & Tax Analysis

Bonds are on track for their worst year in history. In response, retirement investors are concerned (rightfully so) and questioning their bond allocation. To help address those concerns, I'm covering three things today: Why bond yields are NOT moving in lockstep with interest rates set by the Fed How long it takes for bond losses to recover Why retirement savers should maintain exposure to bonds for the long run I'm also sharing the pros & cons of laddering bank CDs as a bond fund alternative. Want more retirement content? Join thousands of other listeners and subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📊  Get Your FREE Retirement & Tax Analysis

Today I'm talking about state taxes (in retirement!). Specifically, I'm sharing three important facts that often fly under the radar. I'm also clearing up common misconceptions and sharing real-life examples.  If you're ready to learn how state income taxes will impact your bottom line in retirement, this episode is for you. Want more retirement content? Subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📊  Get Your FREE Retirement & Tax Analysis

Today I'm sharing three retirement and tax planning updates for 2023. Specifically, I'm sharing a summary of important changes to: Social Security payments Social Security taxation Medicare Part B premiums  I'm also sharing key highlights from the highly anticipated Secure Act 2.0 bill + when we might expect it to (finally) pass. If you're wrapping up your year-end planning and starting to think about 2023 and beyond, this episode is for you. Want more retirement content? Subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📊  Get Your FREE Retirement & Tax Analysis

Recent headlines suggest stocks could be flat (or negative!) for the next 10 years.  The technical for this is "lost decade." And these headlines have created more concern for investors who are already on edge. So, what exactly does a lost decade mean for retirement savers? How likely is it that we are going to experience one? If we do, how should investors approach their asset allocation? Those are the questions I'm answering in today's episode!  Want more retirement content? Subscribe to the Stay Wealthy e-newsletter! *** ✏️  Grab the Episode Show Notes 📊  Get Your FREE Retirement & Tax Analysis

Today I'm breaking down the current state of the markets and economy. Specifically, I'm sharing: Why markets are falling (and how we got here) How things could get worse before they get better Four (4) reasons for investors to be optimistic right now If you're feeling worried or concerned and want to learn more about the current downturn, this episode is for you. *** ✏️  Grab the Episode Show Notes 📬  Subscribe to the Stay Wealthy Newsletter! 📊  Get Your FREE Retirement & Tax Analysis

The current yield on a one-year U.S.Treasury bond is 4%. But the yield on a ten-year Treasury bond is only…3.5%.  Why is this? What does it mean for retirement savers? And how should investors respond? That's what I'm tackling today on the show! *** ✏️  Grab the Episode Show Notes 📬  Subscribe to the Stay Wealthy Newsletter! 📊  Get Your FREE Retirement & Tax Analysis

Have you joined the Stay Wealthy newsletter? No spam. No fluff. Just one retirement/tax planning article each week...written by yours truly. 😊 Sign up for free here.  *** In today's episode, I'm wrapping up our tax-loss harvesting series. Specifically, I'm answering three BIG questions: What if I don't have any capital gains to offset? How to maximize the benefits of tax loss harvesting? How do I navigate multiple tax lots properly + avoid making a costly mistake? What is direct indexing and why is tax-loss harvesting always advertised as a benefit? If you're a new listener, hit the pause button on today's episode and go listen to part 1 of this series first.  *** ✏️  Grab the Episode Show Notes 📬  Subscribe to the Stay Wealthy Newsletter! 📊  Get Your FREE Retirement & Tax Analysis

Today I'm continuing with our series on tax-loss harvesting. Here in part 2, I'm sharing: Who should consider tax-loss harvesting Who should stay away from it The (top) 3 things that can boost your tax savings I'm also presenting situations where tax loss harvesting can backfire, and do more harm than good. 😬 If you're a retirement saver ready to learn how this tax strategy can be maximized, you're going to love today's episode.  *** ✏️  Grab the Episode Show Notes 📬  Subscribe to the Stay Wealthy Newsletter! 📊  Get Your FREE Retirement & Tax Analysis

Today I'm kicking off a multi-part series on tax-loss harvesting.  In part one, I'm breaking down: What tax-loss harvesting is (and how it works) Why it has become a popular tax strategy 5 little-known things about the wash sale rule If you're a retirement saver ready to learn all about tax-loss harvesting, you're going to love this episode...and this series. *** 📬 Subscribe to the Newsletter 📊 Get Your FREE Retirement & Tax Analysis ✏️ Grab the episode show notes

Today I'm tackling a few retirement and investing questions from our listeners. Specifically, I'm answering the following: How do you make sense of the two conflicting July inflation reports (0% inflation vs 8.5%)?  What are Buffer ETFs and are they a good investment for retirement accounts? What will the 2023 Social Security COLA be and why are news outlets quoting different numbers? If you're ready to get answers to some of the top retirement questions I've received lately, this episode is for you. *** 📊 Get Your FREE Retirement & Tax Analysis ✏️ Grab the episode show notes 📬 Subscribe to the Newsletter

Today I'm talking about the case for (and risk of!) deflation. Specifically, I'm covering: What deflation is How deflation impacts our economy Why it's a risk we should be considering  If you're ready to learn about the often-overlooked risk of deflation, you're going to enjoy this episode. *** 📊 Get Your FREE Retirement & Tax Analysis ✏️ Grab the episode show notes 📬 Subscribe to the Newsletter

Today, Jeremy Schneider unveils his Ultimate Investing Checklist. In fact, you can use this 7-step checklist to measure your current investing strategy. You can also use it to: Optimize your tax bill Maximize your risk-adjusted returns Eliminate costly mistakes If you want to learn how to cut through the nonsense + optimize your investment portfolio, this episode is for you. ----- Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Today we're talking about the best way to invest for kids + grandkids.  In fact, guest host Jeremy Schneider says this is one of the most frequent topics he gets asked about! So, to help our listeners, he explores three BIG things: How to decide if you should invest for your kids...at all The top four (4) investing strategies to use How to optimize for taxes and growth If you have kids (or grandkids!) and want to know the best ways to invest for their future, this episode is for you. ----- Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Today we're talking about I Bonds! Specifically, guest host Jeremy Schneider is discussing: What exactly I Bonds are How I Bonds work Where they belong in a retirement savers portfolio If you want to learn about this unique + (virtually) risk-free investment that's paying 9%+, you're going to love this episode. ----- Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Today Jeremy Schneider dives into Vanguard Target Retirement funds (and the tax problems they're causing).   Specifically, he's sharing: What happened at Vanguard to trigger this giant tax issue Why this occurred in the first place What to do when it happens again   He's also answering two (2) BIG questions from listeners! If you're ready to learn how to avoid future mutual fund tax surprises so you don't overpay the IRS, today's episode is for you. Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Indexed Universal Life Insurance (IUL) is all the rage right now. "10%+ growth potential. Guaranteed security against market risk. Tax-free retirement income." These policies are confusing. And they sound WAY too good to be true. So to get to the bottom of it ... I bought one! I read the fine print. Did the math. And uncovered the ugly truth.  In this episode, I'm sharing the 10 lies told during the IUL sales pitch + the actual financial outcome of buying one. I'm also answering two questions from listeners, including one about using a 3-fund portfolio for retirement investing.  Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Today I'm sharing a fun announcement with everyone. I'm also providing retirement savers with important information on the 2022 Medicare IRMAA brackets. This includes covering three things: What IRMAA is How IRMAA is calculated The 10 best ways to avoid IRMAA If you want to better understand how you can navigate Medicare IRMAA this year (and beyond!), you'll enjoy this episode. *** 📖 Read more about the 2022 Medicare IRMAA brackets 📬 Subscribe to the Newsletter 📊 Get Your FREE Retirement & Tax Analysis ✏️ Grab the episode show notes

Today I'm talking about Grandparent 529 Plans. In fact, a BIG change was recently that seemed to fly under the radar. In addition to discussing this change, Robert Farrington joins me to discuss three (3) important things: How to maximize the tax benefits of a 529 Why 529 plans are great estate planning tools How to invest your money inside a 529 We also talk about alternatives to 529 plans that retirement savers might consider. If you want to learn about the new 529 rules + how to maximize the tax/estate planning benefits of these accounts, you're going to love this episode. Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Today I'm sharing key takeaways from the May inflation (CPI) report. I'm also sharing: What "shadow inflation" is (and why you should ignore it) Why inflation is high What retirement investors can do in response Over age 50? Need retirement + tax planning help?  👉 Get Started With a Free Retirement Assessment  To grab the links mentioned in today's episode, visit the show notes page.

Inflation has skyrocketed this year. In fact, inflation jumped to a 40-year high of 8.5% in March 2022. So why are Treasury Inflation-Protected Securities (TIPS) losing money? What are TIPS exactly? And do they belong in a retirement portfolio? If you want answers to these questions, you're going to love today's episode. On the hunt for a retirement + tax planning expert? 👉 Learn more about getting a Free Retirement Assessment™.  To grab the links mentioned in today's episode, head over to the show notes page here.

Today I'm sharing three (3) big retirement planning mistakes and how to avoid them. Actually, that's not true... I was inspired to add a fourth retirement mistake at the last minute after a recent client meeting. So be sure to stick around to the very end. ;) On the hunt for a retirement + tax planning expert? Learn more about getting a Free Retirement Assessment™.  To grab the links mentioned in today's episode, head over to the show notes page here.

The markets are off to the worst start since 1939! Given that, I'm answering three (3) BIG questions from listeners today: Why are stocks AND bonds down at the same time + what should investors be doing right now to protect their portfolio? How can we improve our mindset and gain optimism in the face of negative economic outlooks? What is the correct order of operations when withdrawing money in retirement? If you're asking similar questions and concerned about the current state of the markets, you're going to love this episode.  Want to Lower Your Tax Bill + Improve Retirement Success? 👉 Click Here to Get Your FREE Retirement & Tax Analysis To grab the links and resources for today's episode, click here.

Today I'm sharing details about a (new) popular financial scam. To help you stay safe, I'm also sharing 3 ways to stay safe and protect yourself in retirement. (Hint: your "complex" password may not be as secure as you think. 😲) If you want to learn about this sophisticated financial scam + tips for protecting your family, this episode is for you. Need Retirement & Tax Planning help?  Click here to learn more about our Free Retirement Assessment™. For the episode show notes and links, click here.

Today I'm talking about investing. Specifically, I'm joined by data scientist and author, Nick Maggiulli, and we're talking about: How to invest in high inflationary environments Why you shouldn't "buy the dip" A unique formula for investing during market drawdowns If you're ready to dive into data and get answers to some of the biggest investing questions, this episode is for you. 👉 Click here to learn more about our Free Retirement Assessment For the episode show notes and links, click here.

Inflation jumped 8.5% through March.  This is the highest reported level since 1981. 😬 It was also the biggest monthly jump in prices since 2005. However...there are some tentative signs that inflation may be slowing. I share more in this episode + provide thoughts on how retirement savers might respond.  👉  Learn more about our Free Retirement Assessment For the episode show notes and links, click here.

Today I'm tackling part two of our series on Roth conversions. Specifically, I'm sharing: How to determine if a Roth conversion makes sense A Roth conversion case study Common mistakes + pitfalls to avoid If you're ready to master Roth conversions and take control of your tax bill, you're going to love today's episode. Need retirement + tax planning help? 👉 Learn more about our Free Retirement Assessment For the episode show notes and links, click here.

Today I'm kicking off a 2-part series on Roth conversions. Specifically, here in part one, I'm breaking down: What a Roth conversion is How a Roth conversion works Why Roth conversions are so popular If you're ready to master the basics of Roth conversions, today's episode is for you. Need tax and retirement planning help? 👉  Learn more about our Free Retirement Assessment For the episode show notes and links, click here.

Today I'm addressing inflation (again), war, and the risk of a recession. Specifically, I'm sharing: An update on the recent inflation report Why my previous inflation comments were wrong The probability of a recession + what retirement savers should be doing If like most investors, you're nervous about the current environment and looking for guidance, today's episode is for you. Need tax and retirement planning help? 👉  Learn more about our Free Retirement Assessment For the episode show notes and links, click here.

Today I'm talking about Roth conversions. But instead of talking about why they're so great... ...I'm sharing 5 reasons why you might NOT do them. To help, Steven Jarvis, CPA, joins me. Together, we share a handful of often-overlooked reasons that might make you pause. If you're ready to learn why you might pass on Roth conversions (today or in the future!), today's episode is for you. 👉  Click Here to Access Show Notes and Links for This Episode

Today I'm sharing what the recent spike in inflation will do to your tax bill.  Why? Because the higher inflation is, the more uneven its impact is on taxes owed by retirement savers. And nobody likes it when Uncle Sam catches them off guard! If you want to know the 6 ways inflation might impact your taxes this year, you're going to love this episode. 👉 Click Here to Access Show Notes and Links for This Episode

Today I'm talking about inflation. In 2021, consumer prices rose 7%...the largest increase in 39 years. Is this good news or bad news? What does this mean for retirement investors? How should our investment strategy change in response? I'm answering these questions and more! If you're ready to address common inflation myths + learn how to take action, today's episode is for you. 👉 Access the Show Notes for This Episode

Today I'm discussing the current stock market volatility. As of a couple days ago, U.S. stocks were off to their worst start since 2016. Bonds are also in negative territory. And inflation is at its highest level in 39 years. Many retirement investors are [understandably] worried about the current state of the financial markets. If you want to learn why + how to respond as a smart investor, you'll love today's episode. 👉 Click Here to Access Show Notes for This Episode

Today I'm tackling part 2 of our life insurance in retirement series. To help, friend and fellow financial planner, Stephanie McCullough stops by. Together, we cover three main things: An academic use case for permanent life insurance to create retirement income A step-by-step process for evaluating an existing policy Tips and resources for getting conflict-free help We also break down 1035 exchanges + how you can help family members with old insurance policies. If you're ready to get into the technical weeds today and tie a bow on permanent insurance in retirement, this episode is for you! 👉  Click Here to Access Show Notes and Links for This Episode

Today I'm kicking off our two-part series on life insurance. Specifically, I'll be tailoring these episodes to those who are in retirement or close to it.  Here are a handful of the things I'll be covering: What are the different types of life insurance (+ pros and cons) How to determine the need for life insurance What are the costs and tax considerations How to analyze an old insurance policy Where to buy life insurance without getting ripped off If you're FINALLY ready to understand life insurance in retirement (in plain English!), you're going to love this series. 👉  Click Here to Access Show Notes and Links for This Episode

A near-record number of tech stocks have fallen by 50% or more from their one-year highs.  Is this the beginning of tech bubble 2.0?  If so, how will other asset classes behave?  How should retirement savers prepare? One of our listeners, John H., recently reached out with these (great) questions. If, like John, some of the recent headlines around tech & growth stocks have you concerned, you'll enjoy this listener mailbag episode.

Today I'm talking about market forecasts and predictions. Why? Unlike the core principles that create a successful investment outcome, the financial + economic environment is always changing. And the current environment drives a lot of our assumptions and decisions about the future. While I think investors should ignore most pundits, I do believe thoughtful forecasts are valuable. If you want to learn more about how to approach stock market forecasts (which there is no shortage of right now!), this episode is for you. 👉 Click Here to Access Show Notes and Links for This Episode

Two weeks ago, my wife and I came home to a major water leak. We've been bouncing around between Airbnb's with three kids and a dog since then. Fortunately, the $50,0000 (and counting!) in damages are being covered by insurance. But I learned that's not always the case. I learned that some VERY large insurance companies have recently stopped covering this type of loss. If you want to learn more about my current situation + how you can ensure your home is properly protected, this episode is for you. And if you want to throw your name in the hat for a custom, high-quality Stay Wealthy hoodie, click here. (I'll be drawing names on January 3rd and shipping them off!) 👉  Click Here to Access Show Notes and Links for This Episode

The Social Security program currently pays more in benefits than it collects in revenue. If no changes are made, Social Security will become insolvent by the year 2034... ...and all beneficiaries (regardless of age or income) will face a sudden 22% benefit cut. Even more, some proposals to fix Social Security include stripping 100% of benefits from high-income retirees. This has led a lot of retirement savers to ask: "Should I include Social Security in my retirement planning projections?" If you have the same question, you're going to love today's episode. 👉  Click Here to Access Show Notes and Links for This Episode

Today I'm sharing key findings from a 22-year study on investing in real estate. In general, there are three primary ways you can invest in real estate: Direct ownership Listed real estate Unlisted real estate  Most investors agree that allocating to real estate is prudent. But they don't always agree on the best investment vehicle to use. If you continue to wrestle with how to invest in real estate, you'll enjoy the recent results I'm sharing from a 22-year study on this popular asset class. 👉  Click Here to Access Show Notes and Links for This Episode *** NOTE: The show notes page I reference in the audio of this episode is incorrect. The correct episode number is 135 and the show notes can be found by going to www.youstaywealthy.com/135 ***

Today I'm sharing 11 surprising facts about tax planning, investing, and retirement. For example, if you: Retired in the year 2000 with $1 million, invested all of it in the U.S. stock market, and withdrew $50,000 (adjusted for inflation) per year...  ...you would have been out of money by 2018! If you want to learn how that could be + have some educational fun with retirement/investing statistics, today's episode is for you. 👉  Click Here to Access Show Notes and Links for This Episode

Today I'm clearing up some confusion from a prior episode. I'm also tackling part 2 of our equity compensation series.  Specifically, I'm sharing: How ESPP Lookback Periods Work Qualifying vs Disqualifying Dispositions Tips for Offsetting an RSU Tax Bill If you want to better understand the tax implications of equity compensation, you're going to love today's episode.  👉  Click Here to Access Show Notes and Links for This Episode

In 2018, GE stock traded at $7/share—an 85% drop from its all-time high.  Who was hit the hardest?  Company retirees...including former factory workers who used equity compensation packages to save for retirement. In part one of our equity comp series, I'm breaking down: What it is Why it exists How to manage the risks Friend and fellow planner, Odaro Aisueni, also drops by to share his wisdom and expertise. If you want to better understand equity compensation + learn about the overlooked risks of company stock, you're going to love today's episode. 👉 Click Here to Access Show Notes and Links for This Episode

Today I'm talking about inflation. While inflation has historically averaged ~3%, the most recent CPI report showed an annual rate of 5.4%. 😲 But I'm going to share why that number doesn't tell the whole story. I'm also sharing how some people are using the recent CPI report to try and scare you before Halloween even starts. Finally, I'll be providing tips for how retirement investors can improve their portfolios if moderately high inflation persists. If you want to know what the current inflation numbers mean for your retirement + how to combat this BIG SCARY threat, today's episode is for you. 👉 Click Here to Access Show Notes and Links for This Episode

Today I'm talking about preferred stocks. Why? One of our listeners, Gene, was recently concerned about the low yields he was getting on bonds & cash. And he was wondering if preferred stocks would be an appropriate alternative. In addition to answering Gene's great question, I'm also breaking down:  What preferred stocks are Why you might invest in them How to spot little-known risks If you're ready to learn all about preferred stocks (in plain English!), today's episode is for you. 👉  Click Here to Access Show Notes and Links for This Episode

Today I'm talking about the U.S. National Debt which currently sits at ~$28 trillion. While that is a GIANT number, I'm sharing why current debt levels are not as big of a problem as most think. If you want to learn why (in plain English!), you're going to love today's episode.  👉  Click here to access show notes for this episode

Today I'm talking about the benefits of Market-Cap-Weighted index funds (e.g., Vanguard Total Stock Market). Why? Last week, I made a brief comment that there were some benefits to owning them...and a number of you reached out asking what those were. If, like these other listeners, you're also curious about the benefits of market-cap-weighted funds, you're going to love today's episode! 👉  Click here to access show notes for this episode

The average interest rate for savings accounts is 0.06%. National home prices just reported their highest one-year gain in history. The U.S. stock market is up ~700% since March 2009. When everything seems risky and overbought, what do retirement savers do? How do you earn a healthy 7-8% return over the next 10-20 years? I break it all down in this week's episode. 👉  Click here to access show notes for this episode

Today I'm sharing the hot off the press results of the annual "Mind the Gap" study. Once again, over the last 10 years, investors earned ~2% per year less than the funds they invested in. (Hint: It's not because of fees or taxes.) If you want to learn... Why this return gap exists What asset classes are most at risk And how you can improve your returns ...you'll love this episode. 👉  Click here to access show notes for this episode

Today I'm talking about Required Minimum Distributions (RMDs). Specifically, I'm sharing: How RMD withdrawal rates can creep up to 12% Why they can cause you to overpay the IRS How to use an RMD-based approach to create retirement income When RMDs can put you at risk of over withdrawing What you can do to reduce your RMD tax bill If you want to get a quick Masterclass on Required Minimum Distributions (RMDs) and take control of your tax bill, this episode is for you! 👉  Click here to access show notes for this episode

Today I'm wrapping up our retirement income series by talking about Dynamic Withdrawal Strategies. Dynamic strategies are designed to: Maximize retirement income Greatly lower the chance of running out of money Combat inflation and maintain purchasing power If you want to learn about dynamic withdrawal strategies, their pros & cons, and how to implement them, today's episode is for you.  👉 Click here to learn more about our Free Retirement Assessment To access the show notes for today's episode, click here.

Today I'm talking about immediate annuities and dividend stocks as potential retirement income solutions. Specifically, I'm sharing the what, why, and how behind each strategy. I'm also sharing their pros + cons. If you want to find out if annuities and dividends will solve your retirement paycheck puzzle, you're going to enjoy this episode! 👉  Click here to access show notes for this episode

Today I'm breaking down the 4% rule. Specifically, I'm sharing: A brief history of the rule Why the creator doesn't follow it The pros and cons I'm also sharing how you might take the current environment into consideration when using the 4% rule.  If you want to understand the most popular retirement income strategy once and for all, this episode is for you.  👉  Click here to access show notes for this episode

Today I'm kicking off a multi-part series on creating a reliable income stream in retirement. To help set the stage for this series, Michael Kitces drops in to share why most retirees will NEVER draw down their portfolio. In fact, he shares how the 4% rule is more likely to quintuple wealth than deplete it over 30-years. If you're ready to learn everything you need to know about creating a retirement paycheck, this series is for you.  👉 Click here to access show notes for this episode

Today I'm talking about car ownership.  Specifically, I'm sharing: The Total Lifetime Cost of Owning a Car How Buying New Can Cost the Same as Buying Used Why Leasing a Car Isn't Always the Wrong Decision I also let you in on a little secret about my personal approach to car ownership. 😲 If you want to better understand the true cost of owning a car (and hear my public confession!), today's episode is for you. 👉 Click here to access show notes for this episode

Today I'm talking about I-Bonds, a type of savings bond that some call "the best kept secret in America."   Specifically, I'm sharing: What they are Why successful retirement savers might NOT be racing out to buy them Who they might be a good fit for  If you're interested in learning about a safe investment designed to combat inflation, today's episode is for you.

Today I'm responding to some constructive criticism I received from a listener. I'm also sharing my conversation with Steve Chen, host of The NewRetirement Podcast. Along with sharing a personal update on having three kids under age 5, we dig into: Tax planning opportunities + misconceptions What to do when you've saved more for retirement than you can spend Why people put off estate planning and how to take action Be sure to stick around to the end where we answer a few listener questions and chat about the current state of the markets. 👉 Click here to access show notes for this episode

Want to learn how to lower your tax bill + improve retirement success? Click Here to Get Your FREE Retirement & Tax Assessment --------------------------------------------- Today I'm tackling part two of our series on Long Term Care (LTC). Specifically, I'm breaking down three big things: The types of LTC insurance available (and the pros and cons of each!) Major pitfalls to avoid Vetted resources to help you take action If you want to understand how to maximize your dollars (and coverage!) when buying long-term care insurance, today's episode is for you. 👉 Click here to access show notes for this episode

Today I'm kicking off a two-part series on Long Term Care (LTC). In part one, I'm sharing: LTC statistics that don't often make headlines Why everyone (yes everyone!) needs a plan for LTC My 5-step process for determining if you can self-fund If Long Term Care is one of those financial planning items you STILL haven't tackled yet, this series is for you! 👉  Click here to access show notes for this episode

Today, guest host Jeremy Schneider talks about retirement accounts. Specifically, he shares why having all of your money locked up in them is a problem + how to access your funds early. He also answers a listener question about where to prioritize investing in a 403(b). If you invest in any type of retirement account (e.g., IRA, 401k, etc.), you don't want to miss his VERY last episode. 👉  Click here to access show notes for this episode (Including a unique Stay Wealthy discount code for Jeremy's  investing course!)

Today, guest host Jeremy Schneider explains why he removed oil and gold from his portfolio. In fact, he broke one of his cardinal rules of investing to do it! He also answers a listener's question about investing money that's being saved for a home down payment. If you're a retirement investor who is curious if gold or oil (a.k.a. commodities) belong in your portfolio, you're going to love this episode! 👉  Click here to access show notes for this episode

Today, guest host Jeremy Schneider breaks down the 5 most common arguments AGAINST index funds. Specifically, he shares how individual investors are impacted + his response as an index fund advocate. He also answers a listener question about paying off debt vs. investing. If you're a retirement saver who loves low-cost index funds as much as we do, today's episode is for you! 👉  Click here to access show notes for this episode

Today, guest host Jeremy Schneider takes a deep dive into the COVID-19 stock market crash of 2020. Specifically, he's talking about: What the trading circuit breaker is and why it exists How the length and severity of the COVID crash stacks up to other historical catastrophic events What retirement investors should consider going forward when reviewing their investments  Jeremy also answers a listener's question about rent vs buy given sky-high real estate prices. If you're a retirement investor interested in using history to make more informed decisions about the future, you're going to love this episode. 👉  Click here to access show notes for this episode

Today, guest host Jeremy Schneider covers three BIG topics: When market timing works How to invest a windfall of money What to do if you're afraid to invest in the stock market If you're a nervous retirement investor concerned about investing at market highs, this episode is for you!  👉  Click here to access show notes for this episode

Learn how to: Lower your tax bill Optimize investments Improve retirement success Click Here to Get Your FREE Retirement Assessment --------------------------------------------- Today I'm sharing two simple tax planning tips. These tips will help you catch common errors we're finding on 2020 tax returns. I'm also sharing some fun (personal) news with our listeners! 😲 If you've filed your 2020 tax return and want to avoid any big surprises this year, today's episode is for you.

Today we're diving into ESG investing.   ESG stands for Environmental, Social, and Corporate Governance.   And because the world of ESG is messy and complicated, I asked Liz Simmie, co-founder of Honeytree Investment Management, to help us break it down.   Liz is wildly knowledgeable about purpose driven investing and addresses three big questions in this episode:   What is ESG investing (in plain English!) How retirement savers should approach fees when investing in ESG funds What is the most important data point to screen for when choosing an ESG strategy   If you want to learn the right way to approach ESG investing and how to integrate it into your retirement portfolio, you're going to love this episode.   👉 Click here to access show notes for this episode

Want to learn how to lower your tax bill, optimize investments, and improve retirement success? Click to get your FREE Retirement Assessment ================================= Today I'm sharing my current thoughts on bitcoin. A special guest also drops by to share his point of view, including why bitcoin should NOT be used as a store of value. If you enjoyed last week's interview and you're craving to hear a different perspective, today's episode is for you. 👉  Click here to access show notes for this episode

Today I'm joined by Isaiah Douglass, MBA, CFP®. Isaiah is wildly knowledgeable (and passionate!) about Bitcoin. He's also very optimistic about its future. I have more questions than answers, so I brought him on the show to share his perspective + challenge my thinking. I asked him questions such as: Why should we trust that 10-years of Bitcoin data is sufficient? Is Bitcoin a speculative investment? What are the best-case and worst-case scenarios for Bitcoin? ...and more!  If you're wondering if Bitcoin will "pop" like the dot-com bubble or if it belongs in your investment portfolio, this episode is for you. 👉  Click here to access show notes for this episode

Today I'm joined by special guest, Lazetta Braxton, MBA, CFP®.  It's almost impossible to miss Lazetta these days!  She's been seen on NBC Nightly News, CNBC's Closing Bell, and she's a regular contributor to the Wall Street Journal Financial Experts blog. Lazetta also co-wrote a new book titled "How I Invest My Money" which was illustrated by friend of the show, Carl Richards. In this conversation, we talk about: How I Invest My Money + Investing in Human Capital Lazetta's "Go to Hell" fund What she's doing to provide broader access to financial advice If you want to learn how investing in human capital can be part of your retirement plan, you're going to love this episode. 👉  Click to access the links and resources for this episode

A quick reminder that we're currently offering a FREE retirement & tax return analysis. Learn how to lower your tax bill, optimize investments, and improve retirement success. Click to learn more. ============================== Today I have a special episode for you. I'm sharing a sneak peek into an incredible new project launched by Tyrone Ross. (You don't want to miss this.) I'm also joined by Caleb Silver, Editor in Chief for Investopedia.com. We talk about three big things: How he thinks about the media's role in financial content and education The biggest investing mistakes readers made in the last 12 months What you need to know about fractional shares, limit orders, and SPACs (in plain English!)  If you want to learn how to be a better investor from the person leading the charge at one of the largest financial information websites, you'll love this episode.

Today I'm wrapping up our two-part series on robo-advisors. Specifically, I'm sharing THREE things: The pros and cons of using a robo-advisor Major pitfalls to watch out for How to choose the right one If you currently use a robo-advisor – or you're considering one in the near future – this episode will help you better understand if it's a good fit + how to avoid costly mistakes.

The stock market has been screaming upwards for over 10 years. In fact, the S&P 500 just crossed 4,000! Many retirement savers are starting to get worried, thinking we must be due for a crash. Is it dangerous to invest at market highs? Should you wait for a correction before investing more money in stocks? What if you're retired? Should you be investing in stocks at all? If you've been asking yourself these same questions lately and feeling a bit nervous about the stock market, today's episode is for you.

Today I'm kicking off a two-part series on robo-advisors by sharing: What a robo-advisor is (in plain English!) Why I argue they've been around since the 1920's Who they are and aren't a good fit for If you're a retirement saver who wants to learn more about these low-cost investing solutions + if they live up to the hype, this episode is for you.

Today I'm talking about Non-Fungible Tokens (NFTs).  Specifically, I'm sharing: What an NFT is (in plain English!) Why they are so valuable If this is an asset class retirement savers should take seriously If you want to know why pixelated drawings and 3-second video clips are trading hands for millions of dollars + what to make of this investing craze, today's episode is for you.

Today I'm sharing 3 of my favorite portfolio analytics tools for retirement investors. I'm also using these tools to provide an update on some of the crazy things happening in the stock market right now. So if you're ready to learn how you can use tech to better understand what you're investing in, today's episode is for you. To learn more about our FREE retirement & tax return analysis, visit www.freeretirementassessment.com. 

Today I'm tackling three listener questions with my good friend, Roger Whitney: Why you don't have to invest in ESG stocks to make an impact How to replenish your emergency fund (+ how much cash is too much)?  How to process retirement account withdrawals if you're trying to stay in the 12% tax bracket If you want to hear our answers to these great (and common!) retirement + investing questions, this episode is for you.

Today I'm sharing my 3 favorite tech tools for retirement savers...that have nothing to do with money! Why? Because if technology can improve your life, save time, and help you become more efficient, you'll have more time to spend on improving your financial plan :)  Be sure to stay until the end because I'm sharing a few bonus tech tools as well! Even if you don't consider yourself tech-savvy, I promise you'll learn something new and easy to adopt that will make your life better...or at least more fun.

Today I'm answering a great question from one of our listeners: "Are we in a stock market bubble?" ~Nancy K., Minnesota In this episode, I share: What a bubble is How to measure stock market valuations My answer to answer to Nancy's question! So if you're a retirement investor concerned about current stock market levels, you're going to love today's episode.

Today I'm wrapping up our mini-series on Portfolio Rebalancing. Specifically, I'm sharing the 5 biggest pitfalls to watch out for. Why? Because making just one of these mistakes could wipe away the benefits of rebalancing entirely. So before you process your next rebalance (or let a computer handle it!), tune in to learn what they are and how to avoid them. 

Today I'm kicking off a 2-part series on Portfolio Rebalancing. In part one, I'm sharing: What portfolio rebalancing is How and where it fits into your retirement plan The top 4 benefits of a systematic rebalancing process If you want to learn how a simple rebalancing plan can boost long-term investment returns, you're going to love this episode.

Today I'm sharing two thoughts on Gamestop and Reddit. Specifically, I'm sharing why individual investors aren't winning this battle + who benefits the most from trading platforms like Robinhood (hint: not its users).   So if you want to learn why Gamestop stock traders were not the biggest beneficiary of last week's events, today's episode is for you. 

Today we're talking about cash!   I'm joined by Gary Zimmerman, founder of MaxMyInterest (MAX), an online platform that helps you earn a higher return on your cash savings.    The best part about MAX?   You can keep your existing banking relationship!   So if you want to learn more about MAX and how to boost the yield on your cash, you're going to love this episode.

Today - with help from Morgan Housel - I'm highlighting two economic stories that are flying under the radar. The first story is that Americans might be in the best financial shape they've ever been in. And the second is that a large percentage of Americans don't agree with the first story. Why? Because they're in the worst financial shape they've ever been in. Tune in to learn more. 

Happy New Year! To kick off 2021, I'm digging into the three BIG topics I know are on every investor's mind right now: Small Cap Value Stocks Bitcoin The Dow Jones Crossing 30,000 I'm sharing updates on each + what they mean for your retirement planning and investment portfolio in 2021 and beyond.

Today I'm sharing 3 simple tax planning strategies to consider before year-end. We have two weeks left in 2020 and my goal is to help you take action before it's too late. So if you want to lower your tax bill today and reduce your future taxes in retirement, today's episode is for you.  

Today I'm talking about tax gain harvesting. While tax-loss harvesting typically gets all the attention, realizing gains and deliberately paying taxes now can oftentimes be more valuable. And once again, this strategy is not just for the ultra-wealthy... In fact, those in the highest tax brackets probably shouldn't pursue this tax planning opportunity. So if you want to learn how to harvest gains and reduce your future tax bill in retirement, today's episode is for you.

Today I'm talking about how to combine roth conversions with charitable giving. In fact, this strategy can help wipe out this year's tax bill, reduce future tax bills, and also support some good causes along the way. The best part? There's no minimum amount of net worth required to take action. So if you want to make a smart tax move while also supporting a good cause, today's episode is for you.

Today I'm wrapping up our four-part series on investing in bonds by talking about...implementation! My goal today is to help you take action. To take what you've learned these last four weeks and make some meaningful improvements to your retirement portfolio. So if you're finally able to wrap your head around the basics of bond investing and ready to take action, today's episode is for you.

Today I'm tackling part 3 of our four-part series on investing in bonds. Specifically, I'm sharing why buying bonds and holding them to maturity might not be the best strategy.  In fact, if interest rates go up and we maintain a normal yield environment, it's possible that holding bonds to maturity will result in inferior returns.  So if you want to continue learning how bond returns are generated and where there might be opportunities in this asset class, today's episode is for you.  

Today I'm sharing part 2 of our four-part series on investing in bonds.  Specifically, I'm going to dive into the two ways you can generate higher expected returns in the bond market.  I'm also going to share how one of the most popular bond index funds in the world is taking more risk than most people know.  As always, the information I'm sharing is based on decades of academic research...not a crystal ball :)  So if you've been blindly buying bonds and you're still not sure exactly what you own or why, today's episode is for you.

Today I'm kicking off our 4-part series on investing in bonds. Contrary to what most people think, the bond market is actually more complex than the stock market. But, don't worry, I'm here to translate everything into plain English. In today's episode, you'll learn three big things about bonds: A short history lesson on savings bonds A breakdown of individual bonds vs bond funds How I think most people should invest in this asset class If you're a retirement saver who wants to better understand the world of bonds and how they work, you're going to love today's episode and this 4-part series.