Your Money Guide on the Side

4d ago

Here are a few helpful resources from the people who support this show and keep it free for you. Always. If you’ve ever wondered whether you’re doing “fine” with your money or just hoping future-you figures it out, Facet sets you up with a team of expert CFP® professionals who look at your entire financial life — not just your investments, and not just the parts that are fun to talk about at dinner parties. No commissions. No product pushing. Just real advice for one flat annual membership fee. If you're interested in heading into 2026 with a real financial plan from real experts, check out Facet today, here . -- Most people don’t lose money because they pick terrible investments. They lose money because they’re human . In Part 1 of this two-part series on behavioral economics , Tyler walks through the five most common psychological biases that quietly, systematically sabotage investment returns — even when you’re invested in low-cost index funds and “doing everything right.” This episode is about the stuff that happens between your ears . The mental shortcuts. The overreactions. The stories we tell ourselves after the fact. In this episode, we cover: Why overconfidence makes investors trade more and earn less How recency bias convinces us that whatever just happened will keep happening Why we overvalue the investments we already own (even when we shouldn’t) How loss aversion turns normal market volatility into bad decisions Why hindsight bias makes the past feel obvious and the future feel predictable (it isn’t) This isn’t about being smarter than the market. It’s about building systems that protect you from your own instincts — automation, diversification, fewer decisions, and a little less checking. If the show has helped you think differently about money — maybe even made you laugh while doing it — please take 30 seconds to leave a review on Apple or Spotify. It helps more than you think and keeps this whole experiment in free, digestible financial literacy alive and well.

Dec 8

Here are a few helpful resources, from those who continue to make this show possible for and accessible to you. Visit them today to learn more! To experience what you've been missing by paying rent without getting some amazing rewards along the way, check out how Bilt can help you, here . And if you're like me and have started a small business and don't want to make managing your taxes your SECOND business, explore Gelt today, here . There’s something oddly therapeutic about deciding what not to do with your money next year. Like a financial New Year’s resolution — but with fewer spreadsheets and way less kale. In this episode, Tyler flips the usual “5 things millionaires do” format on its head and shares the five things he refuses to do with his money in 2026. From why he won’t pay off his mortgage early to why high-yield savings accounts aren’t the financial flex you think they are, this episode is all about resisting motion for motion’s sake and reclaiming simplicity in a culture obsessed with doing more. You’ll learn: Why not paying off your mortgage early can actually make you money (hint: opportunity cost). Why high-yield savings accounts aren’t as “safe” or “smart” as they seem — and what to use instead. The trap of saving or investing just to feel responsible , and how to reconnect your money with purpose. Why spending for the sake of deductions is just expensive procrastination (and how to stop doing it). How to keep your portfolio simple — and why complexity almost always costs more than it earns. Tyler reminds listeners that real wealth isn’t about doing more — it’s about doing less, better. This is your invitation to create your own “Not To Do” list for 2026: the habits, purchases, and pressures you’re done with. If the show has helped you think differently about money — maybe even made you laugh while doing it — please take 30 seconds to leave a review on Apple or Spotify. It helps more than you think and keeps this whole experiment in free, digestible financial literacy alive and well.

Dec 1

If you’ve ever wondered how to invest $2 million—or any substantial portfolio—without losing sleep, this episode is for you. I break down a simple, historically backed approach: 90% in stocks (VOO/VTI), 10% in a money market fund (SPAXX). This allocation maximizes growth, keeps volatility manageable, and allows you to spend confidently. We challenge conventional wisdom: the 4% rule is too conservative for most retirees. With disciplined withdrawals of $120k–$200k per year, your portfolio can keep pace with inflation, fund meaningful experiences, and still grow over time. Think of it as the financial equivalent of having your cake, eating it, and watching it regenerate. We also tackle the psychology of spending: most retirees underspend, living smaller than necessary due to “consumption gap anxiety.” Intentional withdrawals for travel, family experiences, and “bucket list” adventures can bring more lasting happiness than accumulating wealth alone. Historical context matters: even through market crashes—2008, 2020—you can maintain your lifestyle using a 10% cash buffer. Percentages matter more than principal; the strategy scales from $500k to $20M. And if it's good enough for Buffett's estate...it's good enough for me. Key Highlights: Percentages over principal: 90/10 allocation works for nearly any portfolio size. Withdraw confidently: $120k–$200k/year supports lifestyle while portfolio grows. Spend for experiences: vacations, relationships, and quality of life matter more than hoarding. Liquidity is your friend: 10% in cash lets you ride out crashes without selling stocks. High-stakes bingo: later in retirement, increase withdrawals for “once-in-a-lifetime” experiences. Resources and research mentioned in this episode: William Bengen, 4% Rule (1994) Michael Kitces on dynamic withdrawals Wade Pfau, Safety-First Retirement Planning Bill Perkins, Die With Zero David Blanchett, Retirement Spending Smile If this episode helps you feel more confident about using your money to live well, consider leaving a review on Apple or Spotify. Your feedback helps keep this financial literacy experiment alive. And if you're still feeling stuck and are looking for expert advice for a flat annual membership fee, check out this episode's sponsor, Facet , by going to facet.com/tyler

Nov 24

Not all “no-income-tax” states are created equal—and some of the states you’ve been avoiding might actually be financial hidden gems. In this second installment of our two-part series on retirement locations, we dive deep into the numbers behind effective tax rates, deductions, and exemptions, revealing which states quietly reward retirees and which can quietly drain your life savings. Highlights from this episode include: The Unexpected Winners: Iowa, Pennsylvania, and New Jersey come out on top for tax efficiency. Yes, New Jersey can be a retirement hero under the right circumstances. The Surprising Losers: Oregon, Minnesota, Hawaii, and New Mexico might make your retirement dream feel expensive, despite gorgeous scenery or “low-tax” branding. Marriage Matters: Married couples can save up to six percentage points in taxes—enough to turn a modest nest egg into a significantly more comfortable retirement. Why Effective Tax Rate is King: Forget slogans and state income tax lists. The only number that really matters is what you actually pay after all deductions, exemptions, and costs are considered. But beyond taxes, and this is primarily why I made this a two-parter, we explore why happiness, community, and lifestyle often matter more than the spreadsheets. Retiring in a state just because it looks cheap might save you a few dollars but cost you your sense of home. The best retirement state balances financial security with quality of life. If you enjoyed this episode, leave a review on Apple Podcasts or Spotify, or share it with a friend planning their retirement. And if you missed Part 1, we highly recommend listening to last week’s episode to get the full story on The Great Tax Mirage and why “no state income tax” can be misleading. And if you're interested in learning more about this week's sponsors, the amazing companies who allow this free content to get to you week after week after week, check them out here: For the single best electrolytes drink I have found to drive and sustain my energy on a daily basis: drinklmnt.com/tyler And for those small business owners who are as overwhelmed as I am about learning the ins and outs of optimizing our taxes: joingelt.com/tyler

Nov 17

Everyone will tell you to move to Florida or Texas to retire tax-free. But the truth? Taxes are more complicated than a “No State Income Tax” billboard. In this first part of a two-part series, we unpack The Great Tax Mirage and reveal why some so-called high-tax states like New Jersey, Pennsylvania, and Iowa may leave retirees with more money in their pocket than the sunny paradises they’re fleeing. We dive into Fidelity’s latest study modeling retirees withdrawing $100,000 a year from an IRA and show how effective tax rates—what you actually pay after exemptions and deductions—can dramatically flip conventional wisdom on its head. For example, a couple retiring in Oregon might pay close to 13% in effective taxes, while a move to Iowa could drop that number to 7.5%, potentially growing tens of thousands of dollars over a decade. We also explore the underrated power of marriage in retirement planning. Married couples filing jointly can save around six percentage points on combined federal and state taxes versus singles—enough to add tens of thousands of dollars to a nest egg over ten years. Key takeaways from this episode include: No state income tax doesn’t automatically mean you keep more money. Certain high-tax states offer exemptions and deductions that outperform so-called tax havens. Marriage can be one of the most powerful retirement tax strategies. Your effective tax rate—not the headline rate—determines what you actually keep. Planning where to retire is about life satisfaction as much as taxes. Whether you’re dreaming of beaches, cornfields, or just a comfortable, worry-free retirement, this episode will change the way you think about where your money—and your life—goes next. Part Two drops next week, where we’ll rank the best and worst states for retirees, explore the real impact of marital magic, and dig into other often-overlooked factors that matter more than taxes when choosing where to spend your golden years. If you enjoy the show, please leave a review on Apple Podcasts or Spotify and share it with a friend who’s plotting their retirement escape. It helps more than you know—and makes sure that no one accidentally retires somewhere that quietly nibbles their nest egg.

Nov 10

This is part two of our financial order of operations series. In part one, we covered the non-negotiables—the oxygen mask, debt payoff, insurance, and the foundation of every real financial plan. This week, we get into the gray areas. The places where conventional wisdom isn’t just outdated—it’s expensive. Here’s what we cover: 7️⃣ The Emergency Fund Myth You’ve heard it before: “Keep six months of expenses in cash.” The problem? That advice was built for a world where savings accounts paid double-digit interest. Today, it’s fear-based and mathematically backward. Most people will go years without a true financial emergency, and keeping $20,000 in cash for a maybe costs far more than it saves. Learn how to balance liquidity with growth without putting your future on pause. 8️⃣ The Taxable Brokerage Account Advantage Once you’ve maxed your Roth IRA, captured your 401(k) match, and funded your HSA, it’s time to open a taxable brokerage account. This is your flexibility play—your bridge between today and retirement. Access your money anytime, invest in low-cost index funds, and take advantage of long-term capital gains rates that beat most income taxes. 9️⃣ The Right Way to Think About Debt Debt isn’t moral—it’s mathematical. If your rate is above 5%, pay it off first. If it’s below 5%, investing probably wins over time. But if it’s keeping you up at night, pay it off anyway. Personal finance is personal—and peace of mind compounds, too. 🎯 Bonus: The 20-Minute “Tiered Pricing” Hack Call your phone, internet, and streaming companies once a year. Tell them you’re considering canceling. Decline their first “special offer,” and watch the discounts appear. It’s the modern coupon—no scissors required—and it can save you $1,000+ a year to redirect into your investments. At the end of the day, this two-part series gives you a complete, math-first roadmap for building wealth that lasts. It works whether you’re starting out or managing seven figures. And if you're interested in learning more about this week's show sponsor, Facet, check out facet.com/tyler today to learn more! 🎧 Listen now wherever you get your podcasts. 💌 Join the newsletter for weekly financial clarity (and the occasional heretical take): https://socialcapconnect.substack.com/subscribe

Nov 3

This week we’re tearing apart one of personal finance’s most overused frameworks: the “financial order of operations.” You’ve heard a version of it before—pay this, save that, sacrifice now, maybe retire someday. The problem? Most of those systems were built by people who either (a) never had real financial stress, or (b) have spent too long in the Dave Ramsey cinematic universe. So, I rebuilt the order from scratch. And it actually works in the real world, whether you make $40,000 or $400,000. Here’s what we cover: 1️⃣ Put your own oxygen mask on first. Take care of yourself before your kids. Financial stability isn’t selfish—it’s responsible. 2️⃣ Obliterate credit card debt. The “snowball method” is financial astrology. Attack the highest-interest balance first. 3️⃣ Get insurance. If someone depends on your income, you need term life and long-term disability. No gimmicks. 4️⃣ Max out your Roth IRA. It’s flexible, tax-free, and doubles as a stealth emergency fund. 5️⃣ Grab your 401(k) match. A 50% employer match is the only free lunch on Wall Street. 6️⃣ Max out your HSA (if you can). The triple tax advantage—deductible going in, tax-free growth, tax-free withdrawals—is unbeatable. We’ll go deeper into emergency funds, taxable brokerage accounts, and smart debt strategies in Part 2 next week. And a MASSIVE thank you to this episode's sponsor, Facet. If you are tired of paying more to an advisor simply because you make more, check out facet.com/tyler today to learn more. 👉 PLUS: stick around until the end of the episode for a modern trick that helps you find the money to do all of this in under 20 minutes—without canceling Netflix or giving up your morning coffee. If this episode helps you—or if you simply enjoy hearing someone roast bad financial advice with love—please consider leaving a review on Apple or Spotify or share this with a friend who still believes paying off a $200 credit card before a $20,000 one is “confidence building.” 🎧 Listen now wherever you get your podcasts. 📩 Join my newsletter for weekly financial philosophy that treats you like an adult: https://socialcapconnect.substack.com/subscribe

Oct 27

What if you could skip the index fund and build your own? In theory, you can. In practice…well, it’s a bit like building your own refrigerator. You’ll learn a lot, and maybe even get a working model, but you’ll also discover why the factory-made version is so efficient in the first place. In this episode, we dive into the peculiar urge to “DIY” the market, and why the exercise can be incredibly educational—even if you never actually follow through. Along the way, you’ll learn: The 11 Sectors of the Market: From flashy Tech to steady Utilities, every portfolio starts with understanding the cast of characters. How Benchmarks Really Work: Why the S&P 500 is more active (and more tax-efficient) than most people realize. The Temptation of Tilts: When to add seasoning like value or small-cap, and when ego is just disguising speculation. Building Your Own Fund: How to use sector ETFs to replicate the market—and why rebalancing can become a full-time job. Keeping Costs and Ego Down: The S&P’s hidden advantages in cost and tax efficiency, and why humility may be the cheapest asset in your portfolio. The takeaway? You can build your own index fund. You might even enjoy the process. But the real lesson is what it reveals: index funds are masterpieces of design, combining diversification, tax efficiency, and ruthless discipline—all while letting you spend your time on things that matter more than spreadsheets. And if you are interested in learning more about those who support this content and make the show possible, visit facet.com/tyler today! And see why they're the only partner I've brought to you thus far as a resource. 👉 If you found this episode useful (or at least more entertaining than quarterly earnings reports), please leave a review on Apple Podcasts or share it with a friend. It’s the best way to help the show grow—and keeps me from muttering about sector weights to myself in the Vermont woods.