Your Money Guide on the Side

Tyler Gardner
  • 4.9 (2.6K)
  • Investing
  • Updated Weekly

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 4M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be. 

  1. 11h ago

    The $4.2 Million Man Who Couldn't Spend His Own Money

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠⁠tylergardner.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! Gelt → ⁠⁠joingelt.com/tyler⁠ because Q3 is where strategic businesses make game-changing tax moves. If you're a business or a high-net worth individual, time to make moves. 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. Facet⁠ → ⁠⁠facet.com/tyler⁠ for an exclusive $550 kickstart offer! And on to the show notes!! You can have enough money and still be afraid to spend it. That’s the final problem. In Part 5 of the Art of Decumulation series, Tyler moves beyond withdrawal rates, tax brackets, and portfolio mechanics to the harder question: How do you actually become a spender after spending forty years becoming a saver? Because the transition isn’t really financial. It’s an identity shift. In this episode, Tyler covers: Why saving becomes part of your identity—not just a behavior The real cost of oversaving in retirement Why permission to spend has to come from you How to front-load experiences whose value declines with age Why retirees should explicitly define what the money is for The case for giving money away while you’re still alive to see what it changes Why real wealth is ultimately about control over your time The core idea: The portfolio exists to fund the life. The life does not exist to preserve the portfolio. Spend on the experiences that won’t wait. Give while you can witness the impact. And use the money to buy back the hours you actually care about. This is Part 5 and the final episode of the Art of Decumulation series. 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.

  2. Aug 10

    The Subtle Art of Doing Nothing (And Making More Money While Doing It)

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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. Copilot Money → ⁠⁠www.copilot.money/tyler⁠⁠ — use code TYLER2 for two free months.⁠ Anthropic⁠ → ⁠⁠claude.ai/tyler ⁠to experience AI for minds that don't stop at good enough.⁠ 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!! A market crash doesn’t usually destroy a retirement. Panic does. In Part 4 of the Art of Decumulation series, Tyler explores how retirees can survive market downturns without turning temporary losses into permanent ones. Because the financial news reports the weather. Your retirement plan needs to be built for the climate. In this episode, Tyler covers: Why the first five years of retirement carry the greatest sequence-of-returns risk How a larger cash buffer can prevent forced selling during downturns Why a rising equity glide path may make more sense than becoming increasingly conservative with age How the Guyton-Klinger guardrails adjust spending in good and bad markets Why modest spending cuts can support a higher sustainable withdrawal rate The behavioral cost of panic selling—and why knowledge alone rarely prevents it How writing a decision plan in advance can protect you when markets turn Why almost every apparent catastrophe eventually proves to be ordinary market weather The core idea: The most valuable skill in retirement investing is often the ability to do nothing. Use the cash buffer.Adjust spending when the guardrails require it.Trust the plan you made while thinking clearly. Then let the storm pass. This is Part 4 of the Art of Decumulation series. Next week, the final episode: how to move from saver to spender and give yourself permission to enjoy what you 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.

  3. Aug 3

    The $250,000 Mistake Most Retirees Never Know They Made

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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 Q3 is where strategic businesses make game-changing tax moves. If you're a business owner or a high-net worth individual, time to make moves! Facet → ⁠⁠⁠facet.com/tyler⁠⁠ for an exclusive $550 kickstart offer! Schedule your intro call today! Fabric → ⁠⁠meetfabric.com/tyler⁠⁠ because if someone depends on your income, term life insurance is the next item on your financial agenda! ⁠⁠⁠⁠⁠⁠⁠⁠⁠Thrive Market⁠ → ⁠⁠thrivemarket.com/tyler⁠ for $20 off your first three orders plus you’ll get a FREE $60 gift! And On To the Show Notes! A traditional IRA can look like your money. But part of it belongs to the IRS. In Part 3 of the Art of Decumulation series, Tyler tackles three of the most important—and expensive—pieces of retirement tax planning: Roth conversions, RMDs, and IRMAA. Because the goal isn’t to avoid taxes entirely. It’s to control when you pay them and at what rate. In this episode, Tyler covers: Why the years between retirement and RMDs can be your biggest tax-planning opportunity How Roth conversions work—and when they can save significant money Why filling lower tax brackets deliberately can matter more than minimizing income How required minimum distributions (RMDs) can push retirees into higher brackets later Why IRMAA is a cliff, not a normal marginal tax bracket The importance of planning for the widow’s penalty Why retirement tax planning should become an annual practice, not a one-time decision The core idea: Your traditional IRA is a future tax bill. The question is whether you choose when to pay it—or let the IRS choose for you. This is Part 3 of the Art of Decumulation series. Next week: market downturns, sequence-of-returns risk, and when to actually change the plan. 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.

  4. Jul 27

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

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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.

  5. Jul 20

    The 6 Money Moves to Make Before You Retire

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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.

  6. Jul 13

    The $2 Million Portfolio: Two Funds, Three Funds, or Five?

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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.

  7. Jul 6

    5 Money Milestones and the Lie Each One Tells

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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.

  8. Jun 29

    How to Build an Inflation-Proof Portfolio (And 3 Mistakes to Avoid)

    Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠⁠tylergardner.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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Hosts & Guests

4.9
out of 5
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About

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 4M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be. 

Information

  • Creator
    Tyler Gardner
  • Years Active
    2025 - 2026
  • Episodes
    81
  • Rating
    Clean
  • Copyright
    © 2025 Your Money Guide on the Side
  • Show Website
    Your Money Guide on the Side

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