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Your Money Guide on the Side

Your Money Guide on the Side

By: Tyler Gardner
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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.© 2025 Your Money Guide on the Side Economics Leadership Management & Leadership Personal Finance
Episodes
  • Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors

    Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors
    Jun 15 2026
    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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    34 mins
  • Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.

    Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.
    Jun 8 2026
    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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    31 mins
  • The 80% Problem: Why Wealthy People Don't Save for a Rainy Day

    The 80% Problem: Why Wealthy People Don't Save for a Rainy Day
    Jun 1 2026
    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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    30 mins
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