Your Money Guide on the Side

Why the S&P 500 is the Best (And Worst) Thing to Ever Happen to Investors

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠⁠tyler.gardner.com/book⁠⁠⁠⁠ [https://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: * ⁠⁠⁠⁠ [https://facet.com/tyler]⁠ [https://square.com/go/tyler]Superpower [superpower.com]: → superpower.com [superpower.com]⁠ Use code Tyler for $20 off your membership! And remember, wealth means nothing without your health. * Facet⁠ [facet.com/tyler]: → ⁠⁠facet.com/tyler [facet.com/tyler]⁠ for an exclusive $550 kickstart offer! * ⁠ [https://livemomentous.com]⁠Copilot Money [www.copilot.money/tyler]⁠: → ⁠www.copilot.money/tyler [www.copilot.money/tyler]⁠ — use code TYLER2 for two free months.⁠ * ⁠Fabric⁠ [meetfabric.com/tyler]: → ⁠meetfabric.com/tyler [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.

Why I Will Never Retire. And Why the Premise Itself Might Be Wrong.

Pre-order Tyler's book, Real Wealth, at ⁠⁠⁠tyler.gardner.com/book⁠⁠⁠ [https://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: * ⁠⁠ [https://facet.com/tyler]Square [square.com/go/tyler]⁠⁠⁠: → ⁠⁠⁠⁠⁠ [https://facet.com/tyler]⁠square.com/go/tyler [square.com/go/tyler]⁠ Get up to $200 off Square hardware and run your business smarter today. * ⁠ [https://drinklmnt.com/tyler%E2%81%A0%E2%81%A0]Wispr Flow: [wisprflow.ai/tyler%E2%81%A0] → wisprflow.ai/tyler [http://wisprflow.ai/tyler] for one free month of Wispr Flow Pro free! * Momentous [livemomentous.com]⁠: → ⁠⁠livemomentous.com [livemomentous.com]⁠ Use code Tyler for up to 35% off your first order!⁠ * ⁠ [http://keepersecurity.com/tyler]Anthropic [claude.ai/tyler%20]⁠: → ⁠⁠claude.ai/tyler [claude.ai/tyler%20] ⁠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.

The 80% Problem: Why Wealthy People Don't Save for a Rainy Day

Pre-order Tyler's book, Real Wealth, at ⁠⁠tyler.gardner.com/book⁠⁠ [https://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: * ⁠Facet⁠ [facet.com/tyler]: → ⁠⁠facet.com/tyler⁠ [facet.com/tyler] for an exclusive $550 kickstart offer! * LMNT⁠ [drinklmnt.com/tyler%E2%81%A0%E2%81%A0]: → drinklmnt.com/tyler [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: [https://joingelt.com/tyler]→ ⁠⁠joingelt.com/tyler [https://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 [http://keepersecurity.com/tyler]: → keepersecurity.com/tyler [http://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.

The 5 Best (And Worst) Cars You Could Ever Buy (Financially Speaking, Of Course)

Pre-order Tyler's book, Real Wealth, at ⁠tyler.gardner.com/book⁠ [https://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: * ⁠⁠ [https://joingelt.com/tyler]Wispr Flow [https://wisprflow.ai/tyler]: → wisprflow.ai/tyler [https://wisprflow.ai/tyler] for one free month of Wispr Flow Pro free! (And to make your life immensely more efficient.) * ⁠ [https://livemomentous.com]⁠Copilot Money [https://www.copilot.money/tyler]⁠: → ⁠www.copilot.money/tyler⁠ [https://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 [https://joinbilt.com/tyler]⁠: → joinbilt.com/tyler [https://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 [https://meetfabric.com/tyler]: → ⁠meetfabric.com/tyler⁠ [https://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.

How to Divorce-Proof Your Finances (Whether You're Married, Divorced, or Somewhere In Between)

Pre-order Tyler's book, Real Wealth, at tyler.gardner.com/book [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]⁠: → ⁠joingelt.com/tyler [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]⁠: → ⁠⁠livemomentous.com [livemomentous.com]⁠ Use code Tyler for 35% for up to 35% off your first order! * Facet⁠ [facet.com/tyler]: → ⁠⁠facet.com/tyler [facet.com/tyler]⁠ for an exclusive $550 kickstart offer! * LMNT [drinklmnt.com/tyler]⁠: → drinklmnt.com/tyler [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.