Your Money Guide on the Side

EXPLORE

Society & Culture

© 2024 PodJoint

https://is1-ssl.mzstatic.com/image/thumb/Podcasts221/v4/b5/36/9b/b5369b95-5f13-5017-87fa-1b0b02eadc8b/mza_1534959554785771025.jpg/600x600bb.jpg

Your Money Guide on the Side

Tyler Gardner

42 episodes

1 week ago

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 IR...

Show more...

Entrepreneurship,

All content for Your Money Guide on the Side is the property of Tyler Gardner and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

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 IR...

Show more...

Entrepreneurship,

Episodes (20/42)

Your Money Guide on the Side

Why Retiring in Iowa Might Make You Richer Than Florida (Seriously) - Part 1 of 2

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 IR...

1 week ago

27 minutes

Your Money Guide on the Side

The Real Financial Order of Operations - Part 2 of 2

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...

2 weeks ago

28 minutes

Your Money Guide on the Side

The Real Financial Order of Operations - Part 1 of 2

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...

3 weeks ago

31 minutes

Your Money Guide on the Side

The DIY Investor's Guide to Building Your Own Index Fund (And Why It's a Terrible Idea)

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 ...

4 weeks ago

37 minutes

Your Money Guide on the Side

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

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...

1 month ago

28 minutes

Your Money Guide on the Side

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

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...

1 month ago

26 minutes

Your Money Guide on the Side

10 Ways Investors Lose Money Without Knowing It

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...

1 month ago

29 minutes

Your Money Guide on the Side

The Only Asset Allocation Guide You’ll Ever Need

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...

1 month ago

29 minutes

Your Money Guide on the Side

The Secret Art of Finding Work You Love and Funding the Life You Want | Chris Hutchins

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 ...

2 months ago

40 minutes

Your Money Guide on the Side

How I Invest My Own Money in 2025

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. ...

2 months ago

25 minutes

Your Money Guide on the Side

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

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...

2 months ago

28 minutes

Your Money Guide on the Side

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

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...

2 months ago

28 minutes

Your Money Guide on the Side

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

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...

3 months ago

25 minutes

Your Money Guide on the Side

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

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 ...

3 months ago

28 minutes

Your Money Guide on the Side

When Should I Take Social Security? | Taylor Sohns

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 Street’s biggest investment shops — the ones that build the ETFs, mutual funds, and hedge funds ...

3 months ago

41 minutes

Your Money Guide on the Side

How do I Make ChatGPT My New (Free) Financial Advisor?

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 emotionally-stable, algorithmic thought partner. One that can help you think better about mo...

3 months ago

32 minutes

Your Money Guide on the Side

3 Silent Wealth Killers Hiding in Fine Print | Tess Waresmith

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. Tess has been featured by CNBC, Business Insider, and Fox 5 NY, and is a self-made millionaire ...

3 months ago

42 minutes

Your Money Guide on the Side

The ONLY 6 Accounts You Will Ever Need

And in case you missed it, check out last week's episode of Your Money Guide on the Side where Bill Perkins and I answered the question, How Do I Die With Zero? In this solo episode, Tyler breaks down the only six financial accounts you’ll ever truly need—and more importantly, how to actually use them. Whether you’re just getting started or managing a more complex portfolio, this is your streamlined, nonsense-free guide to designing a system that works. No more chasing every new fi...

4 months ago

33 minutes

Your Money Guide on the Side

How to Die With Zero | Bill Perkins

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 do I beat the stock market? Is Future Planning Ruining Your Future? What if your financial advisor told you to spend your money now? To give away your inheritance early? To go on more vacations? To prioritize experience over investment? What if they told you the only inflation-protected asset is experience? Bill Perkins is a hedge fund manager, poker playe...

4 months ago

33 minutes

Your Money Guide on the Side

3 Reasons You’ll Never Beat the Stock Market

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 do Billion Dollar Portfolios Look Like? Let’s be honest: you’re not going to beat the stock market. And that’s not an insult — it’s a liberation. In this episode of Your Money Guide on the Side, Tyler Gardner unpacks one of the most misunderstood goals in investing: trying to “win” against the market. Drawing on decades of investing experience (and more than a few...

4 months ago

31 minutes