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PODCAST

Your Money Guide on the Side

Your go-to podcast for mastering money and investing. Hosted by Tyler Gardner, a trusted influencer with over 3M followers, Your Money Guide on the Side simplifies the complex, adds nuance to what seems simple, and connects you with the brightest minds in finance, investing, and business. Whether you’re just starting or leveling up, this is your one-stop resource to navigate your own finances with clarity, confidence, and a bit of fun. Let’s get you one step closer to where you need to be.

business investing

All Episodes

43:27

How to Save $50,000 in Taxes by Moving Your...

Your Money Guide on the Side ·

2025/12/29

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 tired (as I was for WAY too many years) of paying rent and feeling as if you were getting nothing in

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31:39

Why Men Are Terrible Investors (And Lose 1% More Than...

Your Money Guide on the Side ·

2025/12/22

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

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49:40

Your Brain Is Stealing $245,000 From Your Retirement...

Your Money Guide on the Side ·

2025/12/15

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

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33:19

5 Things I Won't Do With My Money in 2026

Your Money Guide on the Side ·

2025/12/08

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

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37:27

The $2 Million Portfolio Plan No Advisor Wants You to...

Your Money Guide on the Side ·

2025/12/01

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

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28:38

The Best (And Worst) States to Retire To - Part 2 of 2

Your Money Guide on the Side ·

2025/11/24

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

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27:23

Why Retiring in Iowa Might Make You Richer Than...

Your Money Guide on the Side ·

2025/11/17

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

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28:10

The Real Financial Order of Operations - Part 2 of 2

Your Money Guide on the Side ·

2025/11/10

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 d...

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31:08

The Real Financial Order of Operations - Part 1 of 2

Your Money Guide on the Side ·

2025/11/03

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 $400,00...

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37:45

The DIY Investor's Guide to Building Your Own Index...

Your Money Guide on the Side ·

2025/10/27

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 ...

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28:48

4 Tax Moves That Can Save You 6 Figures - Part 2 of 2

Your Money Guide on the Side ·

2025/10/20

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 retirement tool, and how to turn it into a stealth IRA with triple tax benefits.Social Security T...

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26:18

4 Tax Moves That Can Save You 6 Figures - Part 1 of 2

Your Money Guide on the Side ·

2025/10/13

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 taxes on your terms, not Uncle Sam’s.Withdrawal Sequencing: The order in which you raid your taxable...

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29:27

10 Ways Investors Lose Money Without Knowing It

Your Money Guide on the Side ·

2025/10/06

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 third of your returns.Why overtrading turns your portfolio into Swiss cheese.The real silent kill...

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29:21

The Only Asset Allocation Guide You’ll Ever Need

Your Money Guide on the Side ·

2025/09/29

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 (hint: it’s not about guessing winners).Three practical allocation strategies for different level...

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40:55

The Secret Art of Finding Work You Love and Funding...

Your Money Guide on the Side ·

2025/09/22

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 that creates—startups, product, and eventually a podcast. From layoff to leverage: A 2008 ...

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25:05

How I Invest My Own Money in 2025

Your Money Guide on the Side ·

2025/09/15

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 my financial life. And instead of chapstick, it’s index funds and money markets. Not sexy. ...

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28:04

Trump vs. Obama: Whose 401(k) Made You Richer?

Your Money Guide on the Side ·

2025/09/08

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 about 401(k) policy across administrations feels like trying to explain cricket at Thanksgiv...

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28:59

What If More Money Still Doesn’t Feel Like Enough?

Your Money Guide on the Side ·

2025/09/01

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 high achievers who retired from something but not to something, we unpack why reaching your number d...

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25:09

How Do I Make My Kid Filthy Rich (Without Going Broke)?

Your Money Guide on the Side ·

2025/08/25

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 them the tools, education, and compounding head start so they have choices—whether that’s ta...

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28:51

How Do I Manage My Own Portfolio? 7 Steps to Start

Your Money Guide on the Side ·

2025/08/18

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 to invest—that’s for another episode. This is about taking the pulse of your current investments ...

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48 results

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