• I Moved to Arizona for the Winter: The 5 Things Nobody Tells You About Snowbirding
    Apr 20 2026
    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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    47 mins
  • 5 Hard Truths About Investing From 26 Years at Motley Fool | Chris Hill
    Apr 13 2026
    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: 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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    42 mins
  • The $172,000 Retirement Surprise (And Exactly How to Avoid It)
    Apr 6 2026
    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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    Not Yet Known
  • The Only Investing Rule You Will Ever Need
    Mar 2 2026
    As always, a MASSIVE thank you to this week's partners: Fabric: if anybody relies on your income, you need to consider term life insurance asap. Check out meetfabric.com/tyler to find out the right coverage for you and your loved ones. Facet: and even though I WANT to offer you all direct advice, I can't, as I don't know you. But Facet can, and they continue to practice exactly what I preach. Check out joinfacet.com/tyler today. And on to the show notes! “How should a 60-year-old invest?” It sounds like a reasonable question. It’s also the wrong one. In this episode, Tyler dismantles the idea that your age should determine your portfolio — and replaces it with a framework that actually works: invest based on when you need the money, not how many birthdays you’ve had. Because two people the same age can — and often should — invest completely differently. Instead of age-based formulas like “110 minus your age,” Tyler introduces a simpler system: The Three Bucket Framework Bucket 1 (0–2 years): Cash, money markets, short-term treasuries. Zero stock exposure. Bucket 2 (2–10 years): A glide path. Years until goal = % in stocks. Bucket 3 (10+ years): 100% stocks in low-cost index funds. That’s it. This episode walks through real examples — retirees, early retirees, 30-year-olds saving for houses, 70-year-olds investing for grandkids — to show why timeline beats age every time. Tyler also explains: Why sequence-of-returns risk matters more than age How to structure withdrawals using the bucket system Why most “conservative by default” advice is lazy The 10 investing terms you actually need to understand How to match allocation to goals without overcomplicating it The core idea is simple: Your timeline is your allocation. Stop asking how a 60-year-old should invest. Start asking when the money will be spent. If this framework changes how you think about your portfolio, leaving a quick review on Apple or Spotify genuinely helps. Hope this gives you something to think about this week.
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    35 mins