Your Money Guide on the Side

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.

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.

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.

A massive "thanks," as always, to this weeks's sponsors: Anthropic: I use Claude every hour of every day to optimize my life. If you haven't explored what Claude can do for you and your business, it's time. Check out Claude today at claude.ai/tyler LMNT: I drink LMNT before and after each workout, and I have never felt better. Mango Chili and Watermelon Salt are my go-tos, and take advantage of the sampler pack, so you can find yours today. Check out LMNT before your next workout at drinklmnt.com/tyler Facet: I continue to partner with Facet in 2026 because I have yet to find a financial planning resource more fitting and cost effective for my audience. Check them out today to see where you've been leaving money on the table. Go to facet.com/tyler to learn more. And now on to the show notes! At some point, the financial industry starts telling you that once you cross a certain number — $5 million, $10 million — you need something more sophisticated. In this episode, Tyler explains why that’s mostly nonsense. After his “How to Invest $2 Million” episode, the big follow-up question was whether wealth changes the strategy. The answer: it doesn’t. The fundamentals stay the same — time horizon, asset allocation, tax efficiency, fees, and real diversification. In this episode, Tyler breaks down five portfolio options: One fund (VTI or VOO) for maximum simplicity Two funds (stocks + bonds) for risk control Target date funds for true autopilot investing The three-fund portfolio for global diversification The five-fund “2.0” version for small allocations to real estate, gold, or crypto None require hedge funds. None require private equity. None require paying 1% for unnecessary complexity. Tyler also explains why “accredited investor” status often just means you’re being sold something expensive — and why many ultra-wealthy investors still stick with index funds. This episode isn’t about leveling up your portfolio. It’s about keeping it simple — no matter how much money you have. 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.

A massive thank you to those who make this show possible! Facet: Every January we obsess over physical health. But what about your financial health? If you're ready to actually get a plan instead of just hoping for the best, Facet pairs you with CFP® professionals who build personalized strategies for a flat fee. Head to facet.com/tyler to get $250 into your brokerage account when you invest $5,000 in your first 90 days, plus waived enrollment fees for new annual members. Fabric: If anyone relies on your paycheck, term life insurance isn't optional—it's the safety net that catches them if you're not there. Fabric by Gerber Life lets you apply online in ten minutes with no health exam, and a million dollars in coverage often costs less than a dollar a day. Head to meetfabric.com/tyler to get covered before you finish your coffee—policies issued by Western-Southern Life Assurance Company, not available in certain states, prices subject to underwriting. And now on to the show notes! Saving money for retirement gets all the attention. Spending that money intelligently is the hard part. In this episode, Tyler tackles the part of retirement no one really teaches: how to draw down your money without running out, losing sleep, or overpaying in taxes. Accumulation is mostly math and discipline. Decumulation is judgment, flexibility, and understanding tradeoffs. This is a practical walkthrough of dynamic retirement income strategies — not rigid rules — and why the approach your parents used probably doesn’t work anymore. In this episode, Tyler breaks down: Why retirement drawdown is harder than saving — and why there’s no single “right” rule The three main income strategies in retirement: selling growth assets, living off dividends, and fixed income How the 4% rule actually works — and why it shouldn’t be followed blindly The pros and cons of dividend-focused portfolios, including tax implications When bonds, ladders, and annuities can make sense as income stabilizers Why inflation is the silent risk most retirees underestimate The most tax-efficient order to withdraw from accounts How Roth conversions, low tax brackets, and timing can save real money Along the way, Tyler explains why flexibility beats optimization, why peace of mind matters as much as returns, and why most retirees end up using a blend of all three strategies, not just one. This episode isn’t about squeezing every last dollar out of your portfolio. It’s about making your money last long enough to enjoy it — and knowing how to adapt as markets, taxes, and life change. If you’re approaching retirement, thinking about early retirement, or just want to understand how the endgame actually works, this episode gives you a solid framework to start from. And if the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps. As always, hope this gives you something worth thinking about this week.

This week's endeavor in free financial literacy for all, brought to you by: LMNT: You can have all the money in the world, but if you don't feel good physically, none of it matters. For years, I'd finish my morning workout and be foggy-headed with a headache by 1 PM—turns out I was chronically under-hydrated and needed actual electrolytes, not just water. LMNT has 1,000mg sodium, 200mg potassium, 60mg magnesium, and zero sugar that keeps me sharp all day. My routine: one during my workout, then a Sparkling LMNT around 4 PM (Mango Chili is the move). Right now they're offering a free sample pack with any purchase at drinklmnt.com/tyler. Bilt: I spent my late 20s throwing thousands at rent in Vermont while maxing out retirement accounts, feeling like I was getting nothing back. ⁠Bilt⁠ fixes that by turning rent and mortgage payments into actual rewards—flights, hotels, fitness classes, or Amazon purchases. Join at ⁠joinbilt.com/Tyler⁠ and make money you're already spending work harder. Facet: Every January we prioritize physical health like it's the New Year's resolution Olympics, but why don't we give our financial health that same energy? I get hundreds of messages weekly asking for personalized advice, and while I want to help, I can't responsibly address your specific situation in a podcast. That's why I partner with ⁠Facet⁠: you get dedicated CFP® professionals who build actual financial plans tailored to your life, charging a flat fee instead of a percentage of assets. Connect with Facet at ⁠facet.com/tyler⁠ and start 2026 with both your health and your wealth dialed in. And on to the Show Notes! Somewhere between "retire at 30" and "work until 70," there's a middle path. Tyler talks with Andy Hill, host of Marriage, Kids and Money and author of Own Your Time, about how he and his wife reshaped their financial life to work 20–25 hours a week while staying financially secure—without winning the lottery or selling a tech company. This isn't a FIRE hype episode. It's a grounded conversation about tradeoffs, mistakes, marriage tension, and building a life that doesn't feel like a trap. Tyler and Andy discuss why extreme FIRE often breaks down in family life, how "Coast FIRE" creates a realistic middle ground, why income growth matters as much as cost-cutting, how money conversations can go wrong in marriage, and what it actually took to leave corporate work without blowing up financial security. Andy shares three concrete starting steps for anyone who feels stuck or burned out and wants to reclaim control over their time. This episode isn't about escaping work—it's about finding work you don't need to escape from. If the show has been helpful, leaving a quick review on Apple Podcasts or Spotify genuinely helps more people find it.

Here are some truly helpful resources from this week's sponsors: First, the ONLY way I am able to make this much content, day in day out, is by feeling my best. Always. And that starts with my working out each morning and needing something that doesn't leave me feeling like I just ate four pounds of candy. Enter LMNT. It is literally the product designed for people like me: need the fuel, don't need the crash, game on. Check out LMNT today here. And if you're looking to start 2026 with a bang, like, a "get my act together financially once and for all" type bang, check out Facet. They continue to practice what I preach, and they provide real advice from real experts for real people. Check them out today here. And now on to this week's the show notes! Most people say they believe in long-term investing. Far fewer people actually behave like it — especially when markets are at all-time highs. In this episode, Tyler tackles one of the most common (and expensive) investing mistakes there is: sitting in cash while waiting for the “right time” to invest. The twist? That “right time” almost never shows up, and the data is brutally clear about what it costs. Despite how uncomfortable it feels, buying stocks at all-time highs has historically been a perfectly reasonable — and often superior — strategy compared to waiting on the sidelines. In this episode, Tyler walks through five reasons why staying in cash is costing you a fortune: All-time highs are normal — markets hit them far more often than most people realize Even terrible timing beats no timing — buying at the worst possible moments still outperforms sitting in cash “This time is different” almost never is, no matter how convincing the headlines sound Missing the best days destroys long-term returns, and those days often arrive during chaos Doing nothing is still a decision — and it carries real risk Along the way, Tyler breaks down decades of market history, real return data, and behavioral traps that convince smart people they’re being cautious when they’re actually sabotaging themselves. This episode isn’t about ignoring risk or investing recklessly. It’s about recognizing that waiting for certainty is just another way to lose money. Markets go up. Markets go down. But sitting in cash while hoping to outsmart two centuries of economic progress has never been a winning strategy. If you’ve ever told yourself you’re “just waiting for a pullback,” this episode is for you. And if this helped you rethink your approach — or finally get out of your own way — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole thing moving. As always, hope this gives you something useful to think about this week.

This week's helpful resources: Fabric (term life) and Gelt (small business taxes). Term life insurance sits at step three in my financial order of operations—before your emergency fund—because if something happens to you, it becomes the emergency fund for everyone you leave behind. Get covered in ten minutes at meetfabric.com/tyler. If you're a small business owner or high net worth individual, finding the right tax partner isn't optional—it's the first domino that determines whether you keep your money or hand it to the IRS. Start with a free consultation at joingelt.com/tyler. And now back to the show(notes!) :) Most investing mistakes don’t feel like mistakes while you’re making them. They feel reasonable. Sometimes they even feel responsible. In Part 2 of this behavioral economics series, Tyler moves past the “greatest hits” and into the deeper, quieter biases that don’t get talked about as much — but are still quietly wrecking portfolios day after day. Think album tracks, not radio singles. If Part 1 was Madison Square Garden, this episode is the smaller venue where the real damage happens. In this episode, Tyler breaks down five lesser-known behavioral biases: The Disposition Effect — why we sell winners too early and cling to losers too long The Ostrich Effect — how avoiding uncomfortable information can sabotage your plan Mental Accounting — why treating dollars differently based on where they came from is costing you real returns The Gambler’s Fallacy — how seeing patterns in randomness leads to terrible timing The Action Bias — why doing something often feels better than doing the right thing (which is usually nothing) Along the way, Tyler explains why these behaviors feel correct in the moment, why willpower doesn’t fix them, and why most investors don’t need better predictions — they need better systems. Automation. Rules. Fewer decisions. Less fiddling. This episode isn’t about becoming more active or more sophisticated. It’s about accepting a hard truth: successful investing is supposed to be boring. If it’s exciting, you’re probably paying for that excitement with your returns. If this episode helped you recognize one habit you need to break — or one urge you need to stop indulging — leaving a quick review on Apple Podcasts or Spotify genuinely helps. It helps other people find the show and keeps this whole experiment going. Until next time, remember: the best investors aren’t the smartest. They’re the ones who do the least amount of dumb stuff.