Your Money Guide on the Side

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Your Money Guide on the Side

Tyler Gardner

31 episodes

22 hours ago

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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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.

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...

Show more...

Entrepreneurship,

Episodes (20/31)

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...

22 hours 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...

1 week 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 ...

2 weeks 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 weeks 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...

4 weeks 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 ...

1 month 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...

1 month 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...

1 month 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...

1 month ago

31 minutes

Your Money Guide on the Side

The Secret Strategies of Billion-Dollar Portfolios | Wendy Li

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, How Much Can I Spend in Retirement? Wendy Li managed billions for New York’s top institutions — here’s what she thinks individual investors can (and should) steal from the pros. After leading portfolios for the Met Museum, UJA-Federation, and the Mother Cabrini Health Foundation, Wendy now serves as CIO at Ivy Invest. She’s spent decades on the inside — and in this...

2 months ago

45 minutes

Your Money Guide on the Side

How Much Can I Spend in Retirement?

And in case you missed it, check out last week's episode of Your Money Guide on the Side with JL Collins where we answer the question, How do I get F-You Money? What if the most common retirement rule was never meant to be a rule at all? In this episode, we unpack the origins, flaws, and overlooked nuances of the 4% rule—and why it might not be the best way to plan your financial future. From its fear-based beginnings to its rigid application in a dynamic world, Tyler breaks down 5 key ...

2 months ago

27 minutes

Your Money Guide on the Side

The Simple Path to F-You Money | JL Collins

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 Buy a New Car Without Getting Screwed? Today’s guest is someone whose work has quietly and profoundly shaped how a generation thinks about money. JL Collins is the author of The Simple Path to Wealth, a personal finance classic that has empowered hundreds of thousands to think differently about investing, independence, and freedom. In this conversation, JL and...

2 months ago

45 minutes

Your Money Guide on the Side

10 Rules of Buying a New Car Without Getting Screwed

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Mady Mills where we answered the question, Why do Billionaires Still Panic? Car buying has become one of the most financially dangerous consumer experiences in modern life. In today’s episode, we’re flipping the script. Whether you’re buying or leasing, trading in or paying cash, I’ll walk you through the 10 timeless rules you must follow if you want to avoid getting taken for a ride—financiall...

2 months ago

34 minutes

Your Money Guide on the Side

What Men Need to Hear About Money | Mady Mills

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 Invest $1,000,000? She’s been on Bloomberg. The New York Times. Yahoo Finance. But Mady’s real talent? Translating the chaos of markets and money into stories that make you feel seen. In this episode, we dive into everything from surviving the 2016 election newsroom to navigating the terrifyingly personal world of money and relationships. Mady opens up about g...

3 months ago

40 minutes

Your Money Guide on the Side

3 Ways to Invest $1,000,000

And in case you missed it, check out last week's episode of Your Money Guide on the Side with Andrew Tobias where we answer the question, What is the easiest way to become wealthy? You've hit the million-dollar mark—now what? In this episode of Your Money Guide on the Side, we tackle the deceptively simple question: how should you invest a million dollars? This isn’t about theoretical asset allocation or textbook strategies. It’s about real lives, real goals, and real risk tolerance. We meet ...

3 months ago

33 minutes

Your Money Guide on the Side

The Only Investment Guide You Will Ever Need | Andrew Tobias

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, Should I Hire a Financial Advisor? What if the only investment guide you ever needed... actually was? This week, I sit down with personal finance legend Andrew Tobias—bestselling author, Harvard Business School grad, long-time political advocate, and the brilliant mind behind The Only Investment Guide You’ll Ever Need. His book was literally the first financial text I ev...

3 months ago

37 minutes

Your Money Guide on the Side

Should I Hire a 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 do I talk to Others About Money? This might be the most common money question I get, and maybe even the most important: Should I hire a financial advisor? And right behind it: If so, how do I find a good one? In today’s episode, I’m not giving you a yes or no answer (sorry, not sorry). Instead, I’m walking you through a three-part framework to decide if you ...

3 months ago

29 minutes

Your Money Guide on the Side

On Faith, Finance, and First Principles | Dan Brigham

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 Debt and Use Debt? He paid off $100K in debt and isn’t trying to sell you a thing — meet Dan the Budget Man. In a financial world cluttered with gurus, grifters, and gatekeepers, Dan Brigham (@budgeters_anonymous) is a breath of fresh air. No paywalls. No “six-figure side hustle” webinars. Just brutally honest content, bite-sized math on notecards, ...

3 months ago

30 minutes

Your Money Guide on the Side

The Truth About Debt: How to Use It (And Beat It)

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, How do I afford college for my kid?!? Is All Debt Bad? What the Wealthy Know That Most People Don’t Debt doesn’t have to be your enemy—and in this solo episode, Tyler Gardner breaks down how to make smarter decisions about debt, ditch shame, and leverage it as a tool for long-term wealth. Whether you’re currently drowning in high-interest credit cards, juggling student l...

4 months ago

28 minutes

Your Money Guide on the Side

The Educator’s Guide to Money & College | Andy Schneider

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, How do I solve any Financial Problem? What happens when a former English teacher becomes a CFO—and decides to teach everyone around him how money actually works? In this episode, Tyler sits down with longtime friend and campmate Andy Schneider, a career educator and current CFO at an independent school, for a wide-ranging and deeply honest conversation about what we teac...

4 months ago

30 minutes

Your Money Guide on the Side

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...