Your Money Guide on the Side

A massive thank you, as always, to this week's sponsors: ⁠Copilot Money⁠: Want to actually see where your money goes without judgment or manual spreadsheets? ⁠Copilot Money⁠ connects all your accounts in one place, tracks subscriptions automatically (no more surprise renewals), and uses AI to categorize spending so you're not tagging transactions like a digital archaeologist. It's privacy-first (t...

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 ne...

For those of you looking for more helpful resources, check out the amazing companies that make this endeavor in free financial literacy possible: 1) If you are running small business and DON'T want to make your taxes yet ANOTHER small business, check out Gelt today. They can help small business owners and high net worth individuals who are looking for strategy beyond filing. 2) And if you are tire...

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, fi...

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 dinn...

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...

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 conserva...

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...

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 fleei...

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 MythYou’ve heard it before: “Keep six months of...

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...

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 ed...

Your 50s are a tax-planning sweet spot—a decade when smart strategies can save you tens or even hundreds of thousands over the course of retirement. In this episode, Part Two of our two-part series, we explore four advanced but practical moves to keep more of your money compounding where it belongs. Here’s what we cover in this episode: The HSA Triple Play: Why this account is the most underrated...

Taxes in your 50s may not be cocktail party conversation, but they can make or break your retirement plan. In this episode, I kick off a two-part series on the smartest tax moves to make once the kids are (hopefully) off your payroll and you’re staring down retirement. In Part One, we cover four essential strategies: Roth Conversions: Why your 50s and early 60s may be the perfect window to pay tax...

Most portfolios don’t implode in one dramatic crash; they leak slowly. A percent here, a hidden fee there, and before you know it, your retirement fund has been funding someone else’s yacht. (Cough, cough...your advisor's...) In this episode, I shine a light on ten common wealth leaks that quietly drain portfolios, plus practical fixes for each one. We’ll cover: How a “tiny” 1% fee can cost you a...

Your portfolio’s performance isn’t about finding the next hot stock; it’s about how you slice the pie. In this episode, I break down the real math behind compounding, why losses hurt more than wins help, and three simple allocation models you can actually follow without losing sleep. We’ll cover: Why “average returns” are misleading and compounding is what matters. How diversification really works...

Guest: Chris Hutchins, host of All the Hacks Episode theme: Building wealth with meaning—how to design a career (and life) you actually want, while optimizing the money side. What we cover: Meaning > money-first: Chris didn’t start out chasing wealth; he chased options. Early jobs in consulting/banking felt misaligned (little meritocracy, lots of “performance”). That tension pushed him toward work...

Please take a moment to complete this brief survey so I can learn more about YOU and what it is YOU want from this show! I promise, it will take no longer than 97 seconds, and it will help me continue to make the show better for you.  There’s a strange YouTube genre called “What’s in My Bag?” where people pull out chapstick like it’s a state secret. This episode is basically that…except the bag is...

Before you hit play: I’ve put a quick listener survey together for listeners. It takes less time than finding your password for your old 401(k), and it helps me shape future episodes around what you actually care about. Please take a moment to fill out this 3 minute listener survey here. This week I’m wading into a swamp I usually avoid like lukewarm gas-station sushi: money and politics. Talking...

What if the biggest financial surprise in your life isn’t running out of money—but realizing that “having enough” doesn’t feel anything like you thought it would? In this episode, I explore the hidden side of wealth: the regrets, letdowns, and quiet disappointments that often surface after you’ve hit your financial goals. From savers who can’t spend, to retirees who waited too long for joy, to hig...

In case you missed it, check out last week's episode of Your Money Guide on the Side that answers the question How Do I Manage My Own Investments? This Week...Your kid thinks money comes from your phone. Or maybe a magical debit card named Mom. Taxes? Rent? The economics of movie popcorn? Foreign concepts. This episode isn’t about turning your child into a trust fund caricature. It’s about giving...

In case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question: When Should I take Social Security? This week on Your Money Guide on the Side, we’re tackling one of the questions I used to get more than any other—right after “Should I buy gold?” and “Is my advisor secretly bad at this?” We’re talking about how to vet your own portfolio. Not how...

In case you missed it, check out last week's episode of Your Money Guide on the Side answered the question: How do I Make ChatGPT My New Financial Advisor? How secure is your future benefit and what should you actually do about it? Taylor Sohns is a Certified Financial Planner™ and co-founder of Life Goal Wealth Advisors. Before starting his own firm, Taylor spent over a decade inside some of Wall...

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question How Much Does a Financial Advisor Actually Cost? What if your smartest financial sidekick never sleeps, never judges, and doesn’t charge 1% AUM? In this episode of Your Money Guide on the Side, Tyler Gardner explores how to use ChatGPT—not as your stock-picking guru, but as your...

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, What Accounts do I Actually Need? Tess Waresmith is a financial educator, speaker, and investor known for helping people reach financial independence with simple investing. She’s the founder of Wealth With Tess, where she helps women build wealth and confidence through investing...