Your Money Guide on the Side

Epizodes

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  The Withdrawal Order Nobody Taught You (And How to Save 10% on Taxes Annually in Retirement) 27.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: Caldera+ Lab⁠: → If you've been meaning to take better care of your skin, head to CalderaLab.com/TYLER and use code TYLER for 20% off your first order. This has been a game-changer for me. ⁠⁠⁠⁠Copilot Money: → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months, and learn why this is the only budgeting app that makes it into our group texts. Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order! ⁠⁠LMNT⁠: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. And On to the Show Notes! Most retirement advice gives you a simple withdrawal order: Taxable.Traditional.Roth. Useful? Yes. Always right? Not even close. In Part 2 of the Art of Decumulation series, Tyler digs into what actually determines where your retirement income should come from each year — taxes, healthcare, market conditions, account type, and the life you’re trying to fund. Because retirement withdrawals aren’t a problem you solve once. They’re a decision you revisit every year. In this episode, Tyler covers: Why the “taxable → traditional → Roth” rule is only a starting point How to use low tax brackets strategically instead of simply minimizing withdrawals Why asset location matters just as much as asset allocation How sequence-of-returns risk changes the early years of retirement Monthly vs. annual withdrawals — and why the mathematically “best” answer may not be the best life answer When ACA subsidies and Roth conversions should override the usual withdrawal order Why the Roth is often best preserved for last The core idea: The best withdrawal strategy changes with the year in front of you. Do the math carefully. But remember what the math is for. This is Part 2 of the Art of Decumulation series. Next week: Roth conversions, RMDs, and IRMAA. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The 6 Money Moves to Make Before You Retire 20.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠DeleteMe⁠ → joindeleteme.com/tyler20⁠ Use code Tyler20 for up to 20% off! Caldera+ Lab⁠ → CalderaLab.com/TYLER and use code TYLER for 20% off your first order. ⁠Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! Gelt → ⁠⁠joingelt.com/tyler⁠ because having the right tax strategist changes the game entirely. If you're a business or a high-net worth individual, you might want to check this one out today. And on to the show notes!! Most financial advice is about building wealth. Far less is about what comes next. In this episode, Tyler kicks off a five-part series on the art of decumulation—the transition from saving for retirement to confidently spending what you've spent decades building. Because retirement isn't just a financial shift. It's a life shift. In this episode, Tyler covers: Why the first year of retirement is often the most emotionally challenging How to build a 12–24 month cash buffer before leaving work What to do with your 401(k) when you retire How to think about Social Security and the healthcare gap before Medicare Why every retiree should review beneficiaries and prepare their spouse to manage the finances How to reposition your portfolio before retirement—not after The core idea: A successful retirement starts long before your last day at work. The more decisions you make in advance, the less likely you'll be forced into emotional ones later. This is Part 1 of Tyler's five-part series on retirement spending. Next week, he dives into one of the biggest decisions retirees face: which accounts to withdraw from first—and why the order matters. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The $2 Million Portfolio: Two Funds, Three Funds, or Five? 13.07.2026 36min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Fabric⁠ → ⁠meetfabric.com/tyler⁠ Made for busy parents like you; all online, on your schedule, right from your couch. You could be covered in under 10 minutes, often with no health exam required. LMNT⁠ → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. ⁠⁠⁠Copilot Money → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ ⁠Bilt⁠ → ⁠joinbilt.com/tyler⁠ So you can choose the card that fits your lifestyle without missing out on points and exclusive benefits. And on to the show notes!! Most investors think a better portfolio is a more complicated portfolio. It usually isn't. In this episode, Tyler revisits his retirement portfolio framework and answers one of the most common questions he's received: How many funds do you actually need? From a simple two-fund portfolio to more complex five-fund allocations, Tyler explains where diversification adds real value—and where it simply adds complexity. In this episode, Tyler covers: The differences between two-, three-, and five-fund portfolios Why simplicity often outperforms complexity over the long run The difference between bond funds and money market funds Whether international stocks are actually necessary When adding more funds becomes an active bet, not diversification Why rebalancing once a year is usually enough The behavioral advantage of owning a portfolio you can actually stick with The core idea: The best portfolio isn't the most sophisticated. It's the one you'll hold through the next bear market. Because long-term investing isn't won by finding the perfect allocation. It's won by keeping costs low, staying invested, and resisting the urge to tinker. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  5 Money Milestones and the Lie Each One Tells 06.07.2026 43min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Thrive Market⁠: → ⁠⁠thrivemarket.com/tyler for⁠ $20 off your first three orders plus you’ll get a FREE $60 gift! ⁠Gelt: → ⁠⁠⁠joingelt.com/tyler⁠⁠ because Q3 is where strategic businesses make game-changing tax moves before the yearis over. If you're a business or a high-net worth individual, check out Gelt today. Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough. ⁠Facet⁠⁠: → ⁠⁠⁠facet.com/tyler⁠⁠ for an exclusive $550 kickstart offer! And on to the show notes!! We spend a lot of our lives chasing financial milestones. A six-figure salary. Coast FIRE. Retirement. The next big achievement. But what if those milestones were never meant to make us feel complete? In this episode, Tyler steps away from spreadsheets and investment strategies to explore what literature can teach us about money, ambition, and the illusion that one more milestone will finally make everything click. Drawing on works by C.P. Cavafy, Samuel Johnson, Kazuo Ishiguro, and David Foster Wallace, Tyler reflects on why so many financial goals feel strangely empty once we reach them—and what that means for how we should build our lives. In this episode, Tyler explores: Why a six-figure salary often changes less than we expect What Coast FIRE really gives us—and what it doesn't The hidden myth at the heart of retirement planning Why major achievements rarely deliver lasting fulfillment The importance of always having another "Ithaca" on the horizon The one financial milestone that genuinely does transform people's lives: getting out of high-interest debt The core idea: Financial milestones matter—but not because they complete us. They give us direction. The real value isn't in arriving. It's in the person you become on the way there. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  How to Build an Inflation-Proof Portfolio (And 3 Mistakes to Avoid) 29.06.2026 39min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: LMNT⁠: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! ⁠⁠⁠⁠⁠Copilot Money⁠⁠: → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ ⁠⁠Fabric⁠⁠: → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next step you should take today. And on to the show notes!! Inflation doesn't usually destroy wealth overnight. It does it slowly. A little bit each year. A little less purchasing power. A little more expensive to maintain the same lifestyle. And over a long retirement, those small changes add up. In this episode, Tyler breaks down how investors can build portfolios that are designed to keep pace with inflation, rather than slowly fall behind it. Because protecting your money isn't just about growing it. It's about preserving what it can actually buy. In this episode, Tyler covers: Why inflation is one of the biggest long-term risks retirees face The asset classes that have historically done the best job of outpacing rising prices Why stocks remain the most powerful long-term inflation hedge How TIPS (Treasury Inflation-Protected Securities) work The role of real estate and infrastructure in an inflation-resistant portfolio Why traditional bond-heavy portfolios can struggle when inflation rises The hidden cost of holding too much cash How overreacting to inflation headlines can hurt returns more than inflation itself Tyler also walks through three increasingly sophisticated portfolio approaches, ranging from a simple stock-and-TIPS allocation to a more diversified strategy incorporating real assets. The core idea: Inflation isn't a market event. It's a permanent feature of the system. The goal isn't to predict it. The goal is to build a portfolio that's prepared for it. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  13 Money Moves They're Betting You Won't Make 22.06.2026 38min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: Keeper: → keepersecurity.com/tyler for 60% off personal and family plans for our podcast listeners only! Use this link, so they know we sent you. ⁠⁠Bilt⁠: → ⁠joinbilt.com/tyler⁠ to find the card that fits your lifestyle! ⁠⁠⁠⁠⁠Gelt⁠⁠: → joingelt.com/tyler⁠ because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today. And on to the show notes!! Most people assume the listed price is the real price. It often isn't. In this episode, Tyler shares a collection of practical money-saving strategies he's used himself — from negotiating internet bills to appealing property tax assessments — and explains why so many financial opportunities come down to one simple skill: Asking. Because companies routinely offer discounts, credits, and incentives that never appear on their websites. In this episode, Tyler covers: Why calling the retention department can save hundreds per year How often to shop auto insurance for the best results The medical bill strategy that can dramatically reduce healthcare costs Why HSAs may be the most underrated retirement account available How Roth conversions can create major tax savings in low-income years The surprisingly effective property tax appeal process Hidden consumer tricks involving credit cards, Costco pricing, and price protection policies Why unclaimed property databases are worth checking at least once The common thread through all of these strategies is simple: Most savings opportunities aren't hidden because they're complicated. They're hidden because most people never ask. The companies know it. The people who save money know it. And now you do too. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors 15.06.2026 33min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠⁠⁠⁠Superpower: → superpower.com⁠ Use code Tyler for $20 off your membership! And remember, wealth means nothing without your health. Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! ⁠⁠Copilot Money⁠: → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months.⁠ ⁠Fabric⁠: → ⁠meetfabric.com/tyler⁠ because if someone depends on your income, term life insurance is the next step you should take today. And on to the show notes!! Most investors spend their lives trying to beat the market. The problem? The market is already made up of millions of people trying to do the exact same thing. In this episode, Tyler explores what he calls "the tyranny of the benchmark" — the idea that comparing ourselves to the S&P 500 often creates more anxiety, more mistakes, and worse outcomes than simply owning the market in the first place. Because for most investors, matching the market isn't mediocrity. It's success. In this episode, Tyler covers: How index funds changed investing forever Why the S&P 500 became a benchmark that many investors misunderstand The hidden psychological cost of constantly comparing performance Why beating the market is mathematically harder than most people realize What you're really competing against when you try to outperform The behavioral mistakes that consistently hurt returns Why missing just a handful of the market's best days can dramatically reduce long-term wealth How fees, overconfidence, and market timing quietly work against investors Tyler also explains why the greatest threat to most portfolios isn't Wall Street. It's the person checking the portfolio. The core idea: The goal isn't to outsmart the market. It's to stop getting in your own way. Own it cheaply. Hold it patiently. Let time do the heavy lifting. Because the most remarkable investing outcomes often come from the most unremarkable investing stories. If the show's been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  Why I Will Never Retire. And Why the Premise Itself Might Be Wrong. 08.06.2026 31min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠tyler.gardner.com/book⁠⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠Square⁠⁠⁠: → ⁠⁠⁠⁠⁠⁠square.com/go/tyler⁠ Get up to $200 off Square hardware and run your business smarter today. ⁠Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for up to 35% off your first order!⁠ ⁠Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough. And on to the show notes!! We’ve been sold a very specific version of success: Work for forty years.Retire at sixty-five.Finally enjoy your life. But what if retirement, at least as we think about it, is the wrong goal entirely? In this episode, Tyler makes the case that the wealthiest people don’t retire — they redesign work. Because the real goal isn’t escaping your life. It’s building one you don’t constantly want to escape from. In this episode, Tyler covers: Why retirement is a relatively modern invention — and why the system was built for a different world What people like Warren Buffett, John D. Rockefeller, and Jeff Bezos have in common Why autonomy, purpose, and meaningful work matter more than most financial plans acknowledge The hidden traps of lifestyle inflation and “golden handcuffs” Why so many people stay in jobs they dislike (even when they know it) The difference between trading time for money and building assets that buy time back Why purpose matters just as much as portfolio size Tyler also shares a more personal reflection on leaving a stable career to build something of his own — and why uncertainty, while uncomfortable, can be worth it. The core idea: Real wealth isn’t retiring from your life. It’s building one you don’t need to retire from. Because the goal was never the finish line. It was finding a game worth playing for a very long time. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The 80% Problem: Why Wealthy People Don't Save for a Rainy Day 01.06.2026 30min

  Pre-order Tyler's book, Real Wealth, at ⁠⁠tyler.gardner.com/book⁠⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! LMNT⁠: → drinklmnt.com/tyler Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. ⁠⁠Gelt⁠⁠: → ⁠⁠joingelt.com/tyler⁠ because Q2 is where strategic businesses (like mine!) make game-changing tax moves. If you're a business or a high-net worth individual, I'd encourage you to check this one out today. ⁠ Keeper: → keepersecurity.com/tyler for 60% off personal and family plans for our podcast listeners only! Use this link, so they know we sent you. And now, on to the show notes!! We’ve been taught that saving money is responsible: Save for a rainy day. Delay gratification. Spend less. Save more. But what if the way most people save is actually making them slightly poorer? In this episode, Tyler challenges one of personal finance’s most sacred ideas: that keeping large amounts of money sitting in savings is the safest thing you can do. Because safety and stagnation are not the same thing. In this episode, Tyler covers: Why inflation quietly destroys the value of traditional savings The hidden cost of opportunity cost — and what cash could have become if invested Why banks profit from your savings more than you do The problem with oversized emergency funds sitting idle Why fear — not math — drives many financial decisions Smarter alternatives for liquidity, from Treasury bills to Roth IRAs Why retirees often die with most of their wealth untouched The difference between saving as a tool vs. saving as an identity Tyler also makes a more personal argument: That many of us inherit financial beliefs built around scarcity, caution, and delayed gratification — even when we no longer need them. The core idea: Money is meant to support your life, not become the thing preventing you from living it. Invest broadly. Keep reasonable liquidity. Spend intentionally on the things that actually matter. And maybe, every once in a while… Eat the shrimp instead of the mashed potatoes. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course) 25.05.2026 39min

  Pre-order Tyler's book, Real Wealth, at ⁠tyler.gardner.com/book⁠ and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠⁠Wispr Flow: → wisprflow.ai/tyler for one free month of Wispr Flow Pro free! (And to make your life immensely more efficient.) ⁠⁠Copilot Money⁠: → ⁠www.copilot.money/tyler⁠ — use code TYLER2 for two free months and find out why my entire finance-friend group chat uses Copilot Money daily. ⁠Bilt⁠: → joinbilt.com/tyler to see which credit card is right for you and to start getting rewarded for your biggest annual expense: your rent or mortgage!⁠ ⁠Fabric⁠: → ⁠meetfabric.com/tyler⁠ because if ANYONE depends on your income, getting term life needs to be moved to the top of your priority list today. And on to the show notes! The average American spends roughly $12,000 per year on their car. For many people, that’s more than they invest. In this episode, Tyler breaks down the real cost of car ownership — not just the sticker price, but the hidden financial drag of depreciation, financing, insurance, fuel, and maintenance. Because most people buy cars emotionally… and only look at the math afterward. In this episode, Tyler covers: Why the monthly payment is the least important number in a car purchase The true long-term cost of luxury cars, trucks, and financed EVs Why used Toyotas and Hondas dominate on total cost of ownership The financial trap of buying older German luxury cars out of warranty Why a financed Tesla can be far more expensive than people realize The surprising math behind the Toyota Prius and Corolla Why “boring” cars quietly create wealth over time The difference between a vehicle as a tool vs. a lifestyle purchase Tyler also explains why he believes people should stop optimizing every dollar purely for efficiency. Because personal finance isn’t about removing joy from your life. It’s about being intentional enough to know which things are genuinely worth spending on — and cutting ruthlessly everywhere else. The episode ends with Tyler revealing the one category where he knowingly ignores his own financial advice: A brand-new GMC Sierra Denali. Not because it’s the best financial decision. Because it’s the thing he genuinely loves. The core idea: Don’t spend blindly. But don’t optimize the humanity out of your life either. Know your “no’s.” Then spend unapologetically on your “yes.” If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between) 18.05.2026 42min

  Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book and be eligible for all monthly incentives between now and December 1st! And as always, a MASSIVE thank you to this week's sponsors: ⁠Gelt⁠: → ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, you might want to check this one out today. Momentous⁠: → ⁠⁠livemomentous.com⁠ Use code Tyler for 35% for up to 35% off your first order! Facet⁠: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! LMNT⁠: → drinklmnt.com/tyler⁠ Become an INSIDER by ordering the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors like my new favorite, lemonade iced tea! And now, on to the show notes! Most people who get financially devastated by divorce didn’t lose because they were reckless. They lost because they weren’t prepared to operate independently when life changed unexpectedly. In this episode, Tyler breaks down the financial side of divorce — not just for people currently going through one, but for anyone building a life with another person. Because financial awareness inside a marriage is not distrust. It’s maturity. In this episode, Tyler covers: Why both partners should fully understand the household finances The importance of shared access to accounts, passwords, and financial documents Why every adult should have their own individual emergency account The financial reality of “winning” the house in a divorce What a QDRO is — and why misunderstanding it can cost tens of thousands Why beneficiary designations matter more than most wills How to build independent credit before you need it Why recently divorced people are especially vulnerable to bad financial advice The importance of a 6–12 month financial freeze before making major decisions Tyler also explains how some advisors specifically target recently divorced people — and how to tell the difference between real guidance and someone capitalizing on vulnerability. The core idea: Financial independence inside a relationship is not a backup plan. It’s part of being an adult. Because whether a marriage lasts five years or fifty, every person deserves the ability to confidently understand and manage their own financial life. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  What I'd Do If $1,000,000 Landed in My Account Tomorrow: 3 Moves, 3 Mistakes, 3 Red Flags 11.05.2026 45min

  Pre-order Tyler's book, Real Wealth, at ⁠tyler.gardner.com/book⁠ and receive two chapters that didn't make the final cut in digital form in early June. And as always, a MASSIVE thank you to this week's sponsors: Keeper: → keepersecurity.com/tyler for 60% off personal and family plans for our podcast listeners only! Use this link, so they know we sent you. Anthropic⁠: → ⁠⁠claude.ai/tyler ⁠to find out why they continue to be my number one strategic thought partner. Thrive Market⁠: → ⁠⁠thrivemarket.com/tyler for⁠ $20 off your first three orders plus you’ll get a FREE $60 gift! Copilot Money⁠: → ⁠www.copilot.money/tyler — use code TYLER2 for two free months. And now on with the show notes! You wake up tomorrow morning and there’s $1 million sitting in your account. What’s the first thing you do? Most people think they know the answer. In reality, most people panic, freeze, or make expensive decisions out of emotion. In this episode, Tyler walks through exactly what he would do with a sudden lump sum of money — practically, immediately, and without turning it into a fantasy exercise. Because having money doesn’t automatically make people better with money. It just makes mistakes more expensive. In this episode, Tyler covers: Why the first move is protecting the cash, not investing it immediately The difference between parking money in a checking account vs. a money market fund Why paying off high-interest debt is often the best guaranteed return available The “bucket framework” for investing based on when you need the money, not your age Why low-cost index funds still beat most “sophisticated” strategies How investing in your primary residence can improve both lifestyle and tax efficiency Why most people confuse complexity with competence in investing The psychological traps that show up once you have money Tyler also explains why he wouldn’t immediately buy expensive depreciating assets — and why the goal is to get the principal working hard enough that the returns eventually pay for the lifestyle instead. The core idea: A million dollars isn’t the destination. It’s the infrastructure. The real question isn’t what you buy. It’s what kind of life the money gives you the freedom to build. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  My Interview with Burton Malkiel (That You Will Never Hear) 04.05.2026 42min

  Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book And as always, a MASSIVE thank you to this week's sponsors: Fabric: → ⁠meetfabric.com/tyler⁠ because if you have dependents, and you don't have term life, getting term life insurance is the financial step you need to take right now. Gelt: ⁠→ ⁠joingelt.com/tyler because Q2 is where strategic businesses make game-changing tax moves LMNT: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. Facet: → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And see for yourself why I've partnered with Facet for almost TWO YEARS! And now on with the show notes! What if the most important investing conversation you’ve ever had… never got recorded? That’s what happened here. In this episode, Tyler reconstructs a lost interview with Burton Malkiel, author of A Random Walk Down Wall Street, and uses it to tell a bigger story — one about index investing, behavior, and why the simplest strategy is still the hardest to follow. Because this isn’t just about theory. It’s about what actually works in real life — and why people still struggle to stick with it. In this episode, Tyler walks through: The origin of index investing — and why Wall Street fought it for decades Why most active managers fail to beat the market after fees The role of academics like Markowitz, Fama, and Samuelson in shaping modern investing How fear and behavior — not knowledge — derail most investors Why trying to time the market (even when you’re right) can still cost you returns The risk of concentration in modern index funds — and why it’s not a new problem Malkiel’s core principle: you will never consistently outguess the market Tyler also shares one of the most important takeaways from the conversation: Even Burton Malkiel feels fear. He just doesn’t act on it. And that’s the difference. The core idea: Investing isn’t about being right. It’s about staying consistent when it’s hardest to do so. The episode closes with a broader reflection on retirement — not just how to invest, but how to live. Because according to Malkiel, the goal isn’t to stop working. It’s to stay engaged — with ideas, with learning, and with life itself. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The 0% Tax Bracket Most Retirees Walk Right Past 27.04.2026 41min

  As always, a MASSIVE thank you to this week's sponsors! LMNT⁠: → ⁠drinklmnt.com/tyler⁠ Become an INSIDER, just order the INSIDER Bundle–four boxes for the price of three, best value they offer–and get early access to limited time flavors and cool surprise gifts along the way. ⁠Bilt⁠: → ⁠joinbilt.com/tyler⁠ to get rewarded for your biggest annual expense! ⁠Copilot Money⁠: → ⁠try.copilot.money/tyler⁠ and use code TYLER2 for two free months. ⁠Gelt⁠: → ⁠joingelt.com/tyler and see if you can get your business tax planning to the next level in 2026 and beyond! And now, on with the show notes! Most retirement withdrawal conversations focus on one number: 4%? 5%? 6%? But that misses a much bigger variable: Taxes. In this episode, Tyler revisits his $2 million retirement portfolio framework and explains why the real issue isn’t just how much you withdraw — it’s how much you keep after taxes. Because two retirees can withdraw the exact same amount and end up with very different lifestyles depending on how their accounts are structured. In this episode, Tyler covers: Why after-tax returns matter more than headline portfolio returns The hidden cost of relying too heavily on traditional IRAs and 401(k)s How Roth conversions can reduce future tax pain Why taxable brokerage accounts are one of the most underrated retirement tools How the 0% capital gains bracket can legally lower taxes in retirement Why withdrawal order matters: taxable, pre-tax, and Roth accounts each play different roles How poor tax planning can quietly reduce spending power for decades Tyler also explains why the classic withdrawal-rate debate often misses the point entirely. A 6% withdrawal with poor tax planning may feel like 4.75%. A well-structured 6% withdrawal may feel like…6%. The core idea: The goal was never to withdraw less. The goal was always to keep more. This episode isn’t about tax gimmicks or loopholes. It’s about understanding the rules well enough to make smarter decisions with the money you’ve already built. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About Snowbirding 20.04.2026 40min

  As always, a MASSIVE thank you to this week's sponsors! Momentous: → ⁠livemomentous.com Use code Tyler for 35% off your first order! Thrive Market: → ⁠thrivemarket.com/tyler $20 off your first three orders plus you’ll get a FREE $60 gift! Facet: → ⁠facet.com/tyler for an exclusive $550 kickstart offer! Anthropic: → ⁠claude.ai/tyler if you're looking for the best business and thought partner I have EVER had. And on to the show notes! Most financial advice focuses on optimization. This episode is about something else entirely: alignment. In this more personal episode, Tyler shares five lessons from spending two months “snowbirding” in Sedona — and what the experience revealed about money, time, and the life we think we want. Because sometimes the biggest financial insights don’t come from spreadsheets. They come from living differently long enough to notice what actually matters. In this episode, Tyler reflects on: Why buying back time only works if you know what to do with it The idea of a “path dividend” — testing lifestyles before committing to them How lifestyle upgrades quickly become your new normal (and lose their impact) Why major life changes require understanding what you’re leaving, not just gaining The illusion that a new place will create a new version of you Along the way, Tyler connects everyday moments — cooking dinner, staying in Airbnbs, almost buying a house — to deeper financial decisions around spending, relocation, and retirement. The core idea: Wherever you go, there you are. Money can change your environment. It doesn’t automatically change you. This episode isn’t about maximizing efficiency. It’s about building a life that actually fits — before you build the plan to fund it. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  5 Hard Truths About Investing From 26 Years at Motley Fool | Chris Hill 13.04.2026 37min

  Pre-Order Tyler's First Book, Real Wealth, ⁠⁠here⁠⁠ & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EDT, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: LMNT just dropped a limited-time Pink Lemonade flavor — exclusively for LMNT INSIDERs, which means you need to order the INSIDER Bundle (four boxes for the price of three) to get it. If you like your electrolytes without the sugar and your hydration without the regret, this one's for you: → drinklmnt.com/tyler Fabric: ten minutes online, no health exam, no phone calls, a million dollars in coverage for less than a dollar a day — and if you're young and healthy, there's no better window to lock this in than right now. → meetfabric.com/tyler Copilot Money tracks your spending, net worth, investments, subscriptions, and savings goals in one place — and it's the only personal finance app to win an Apple Editor's Choice Award, with a 4.8-star rating from over 25,000 reviews. → try.copilot.money/tyler — use code TYLER2 for two free months. And on to the show notes! Most people think investing is about finding the next big thing. The reality is much less exciting — and far more effective. In this episode, Tyler sits down with Chris Hill, longtime host of Motley Fool Money, to talk about what actually drives long-term success in investing — and why so many people get distracted along the way. From launching a podcast during the 2008 financial crisis to interviewing some of the biggest names in business and finance, Chris shares lessons from decades inside one of the most influential investing platforms. In this conversation, Tyler and Chris discuss: How Motley Fool Money started during a crisis — and why simplicity won Why investors obsess over “hot stocks” and excitement (and why that hurts returns) The importance of time in the market — and not interrupting compounding Why the best companies are often the ones everyone already knows The balance between simple index investing vs. active stock picking Chris also reflects on what makes a great investor over time — and it’s not intelligence or access. It’s patience. Discipline. And the ability to ignore noise when it matters most. The core idea: Investing isn’t about being clever. It’s about staying consistent long enough for compounding to do its job. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  The $172,000 Retirement Surprise (And Exactly How to Avoid It) 06.04.2026 46min

  Pre-Order Tyler's First Book, Real Wealth, ⁠here⁠ & be immediately eligible for exclusive bonuses between now and December 1st! April Bonus: Free two-hour digital live event on Wednesday, May 6th from 7-9pm EST, where Tyler will answer the most commonly asked questions and walk through what you can expect from the book! And as always, a MASSIVE thank you to this week's sponsors: Thrive Market: Get $20 off your first three orders plus a FREE $60 gift if you order at thrivemarket.com/tyler today. Facet: find out why I have been endorsing Facet for over 18 months now by checking out ⁠facet.com/tyler⁠. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. And on to the show notes! No one wants to think about long-term care. Which is exactly why most people don’t plan for it. In this episode, Tyler tackles one of the most uncomfortable — and most overlooked — parts of financial planning: what happens if you live long enough to need care. Because longevity is a gift. And financially, it’s also a risk. In this episode, Tyler covers: The reality that ~70% of people over 65 will need some form of long-term care What long-term care actually means (it’s not just nursing homes) The real costs — from home care to assisted living to memory care Why long-term care is separate from normal retirement planning The four ways to pay for it: self-insuring, Medicaid, traditional insurance, and hybrid policies Why Medicare doesn’t cover what most people think it does How to estimate your true long-term care exposure (and why it can reach seven figures) The biggest mistakes people make — including relying on kids or “figuring it out later” Tyler also lays out a clear, practical framework: Understand your numbers. Decide who pays. And make the decision before you need it. The core idea: A retirement plan isn’t complete until it answers one question — what happens if care is required? Because this isn’t just a financial decision. It’s a decision that affects your spouse, your kids, and how the last chapter of your life actually plays out. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  Why I'm Taking Social Security at 62 (And Why the "Wait Until 70 Crowd" Might Want to Pay Attention) 30.03.2026 39min

  Pre-Order Tyler's First Book, Real Wealth, here & be immediately eligible for exclusive bonuses between now and December 1st! As always, a MASSIVE thank you to this week's sponsors: LMNT⁠: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink ⁠LMNT⁠ daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try ⁠drinklmnt.com/tyler⁠ today and let me know what your favorite flavor is! Copilot Money⁠: if you are looking for one of the most well-designed money apps out there, check out ⁠Copilot Money⁠ today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out ⁠try.copilot.money/tyler ⁠today and use code TYLER2 for two free months, so you can see if it works for you! Anthropic⁠: I use Claude AI every single day as a thought partner and business strategist. To become more efficient and solve problems more quickly and effectively, check out ⁠claude.ai/tyler⁠ today. There is no single business move I have made in the past year that has been more worthwhile and productive. And on to the show notes! When should you take Social Security? It’s one of the most debated — and most personal — financial decisions you’ll ever make. In this episode, Tyler makes a serious, data-backed case for taking benefits at 62 — not as a blanket recommendation, but as a counterpoint to the conventional advice to always wait. Because this decision isn’t just math. It’s math layered on top of real life. In this episode, Tyler covers: The break-even math between taking benefits at 62, 67, and 70 Why waiting only “wins” if you live past your late 70s or early 80s The idea that a dollar at 62 isn’t equal to a dollar at 82 How the “go-go, slow-go, no-go” phases of retirement change how money is experienced The often-overlooked healthcare gap between 62 and 65 — and what it can cost How the earnings test reduces (but doesn’t eliminate) benefits if you keep working Why Social Security decisions should factor in your spouse’s survivor benefit Tyler also introduces a practical framework — six key questions — to help you make the decision based on your own life, not a generic rule: Health. Healthcare. Work status. Income needs. Spousal impact. And how you actually want to spend your time. The core idea: This isn’t about maximizing dollars. It’s about maximizing life. For some people, waiting is the right call. For others, taking it early — and using that money when it matters most — may be the better decision. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  5 AI Prompts That Will Change How You Manage Money (And 3 Things It Still Gets Dead Wrong) 23.03.2026 37min

  As always, a MASSIVE thank you to this week's sponsors: Gelt: I will forever regret not prioritizing a tax strategist early in my solopreneur journey. Don't make the same mistake I did and leave money on the table. If you are a business owner or a high net worth individual, check out Gelt today at joingelt.com/tyler. Fabric: there is a reason that term life insurance is number 4 in my financial order of operations, before an Emergency Fund, and before funding the Roth IRA. If anyone else depends on your income, cross this off your list today in ten minutes at meetfabric.com/tyler. And on to the show notes! AI isn’t replacing financial advisors. But it is getting surprisingly good at doing one of the most valuable parts of the job: stopping you from making bad decisions. In this episode, Tyler breaks down how to actually use AI as a financial tool — not for stock picks or shortcuts, but for clarity, structure, and behavioral coaching. Because the biggest gap in investing isn’t information. It’s execution. In this episode, Tyler covers: Why most investors underperform the market — and how behavior drives that gap How to build a complete financial snapshot for better decision-making How to use AI to uncover your real risk tolerance (not the one you think you have) How to create a simple, diversified investment strategy using structured prompts Why asset location (where you hold investments) matters more than most people realize How to stress test your plan using worst-case scenarios and Monte Carlo thinking How to use AI as a behavioral guardrail during market volatility The real risks: privacy concerns, bad prompts, and AI hallucinations The core idea: AI is a tool, not a replacement for judgment. Used well, it can help you think more clearly, avoid emotional decisions, and build a plan you actually understand. Used poorly, it can give you confident-sounding answers to the wrong questions. If you take one thing from this episode, it’s this: Better inputs lead to better decisions. And if AI helps you slow down, ask better questions, and avoid one major mistake, it’s already paid for itself. If the show’s been helpful, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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  How to Make Your Child Absurdly Wealthy for Absurdly Little 16.03.2026 47min

  As always, a MASSIVE thank you to this week's sponsors: LMNT: regardless of who much money you have, if you're not feeling your best physically and mentally, it means very little. That's why I drink LMNT daily (well, multiple times a day) to continue to be as productive as I can be after my workouts. Try drinklmnt.com/tyler today and let me know what your favorite flavor is! Copilot Money: if you are looking for one of the most well-designed money apps out there, check out Copilot Money today. My friends and family continue to rave about it, and they now have all of their money needs in one place. Check out try.copilot.money/tyler today and use code TYLER2 for two free months, so you can see if it works for you! Facet: find out why I have been endorsing Facet for over 18 months now by checking out facet.com/tyler. They are a one-stop shop for financial planning, investment management, tax strategy, and retirement planning. And best part: it's all for one flat annual membership fee. Check out facet.com/tyler and see if they're the right fit for you! And on to the show notes! Many parents want to help their kids financially — but often focus on the wrong things. Saving for a wedding, helping with a down payment, or paying for grad school can help in the moment. But the biggest advantage you can give a child financially is time. In this episode, Tyler breaks down how investing small amounts early in a child’s life can turn into millions thanks to compound growth — and walks through the most practical ways parents can do it. In this episode, Tyler covers: How investing $3,000 per year for a decade could grow into millions over a lifetime The power of giving a child 20–30 extra years of compounding How UGMA/UTMA accounts work and their tax implications Why a custodial Roth IRA can create completely tax-free retirement wealth A lesser-known strategy: investing in your own brokerage account and passing assets down with a step-up in basis Why 529 plans are useful — but often overhyped and less flexible The key takeaway: when it comes to investing for your kids, starting early matters far more than the amount you invest. Even small, consistent contributions can grow into life-changing sums over decades. If this episode helped clarify your approach to investing for your family, consider leaving a quick review on Apple Podcasts or Spotify — it helps others find the show.