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 growing up around volatility — both financial and emotional — and how it fuels her empathy-first approach to financial journalism today.

We talk about:

• Why everyone, even billionaires, fears losing everything
• How to actually make money content more fun and accessible
• What David Booth (yes, that billionaire) thinks you should do instead of stressing about a stock crash
• How her background in political reporting shaped her calm, clear-eyed view of financial chaos
• The most important account a woman can open (hint: it starts with “I” and ends with freedom)
• And the number one piece of advice for men in relationships—you’ll just have to listen and find out!

This is one of those rare conversations that gets behind the curtain of financial media and your own money story — and leaves you feeling a little smarter, a little braver, and a lot more equipped to have the hard conversations.

Interested in learning more about and/or following Mady Mills?

Instagram: @madymills

TikTok: @madymills

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 three investors—Chad, Nina, and Marge—each at very different life stages, each with a radically different approach to putting their wealth to work:

• Chad Slater, the thrill-seeking ex-startup bro who wants asymmetry, optionality, and upside. His portfolio is bold, volatile, and aggressive—global equities, venture capital, and yes, crypto.
• Nina Ellington, the grounded creative director turned Pilates instructor who wants growth without chaos. Her diversified, resilient mix of stocks, bonds, real estate, and alternatives prioritizes balance and autonomy over adrenaline.
• Marge Buttersworth, the sharp, independent retiree who wants reliability and peace of mind. Her income-focused portfolio features bond ladders, dividend stocks, and high-yield cash vehicles—designed to pay her, not stress her.

These are not just asset allocations. They are reflections of who these people are, what they value, and what they need their money to do for them.

💡 Along the way, we explore key questions:

• How soon will you need the money?
• How much risk can you stomach?
• Are you trying to grow, preserve, or withdraw from your portfolio?

And if you stick around until the end, I share exactly how I invest my own money—no hype, no secrets—just a simple, transparent walk through my personal allocation and why I chose it.

📌 In this episode, you’ll learn:

• 3 distinct investing strategies for $1M portfolios
• How risk tolerance, time horizon, and goals shape allocation
• The truth about fees, diversification, and asset class correlation
• Why your neighbor’s portfolio has nothing to do with yours
• How to evaluate your definition of enough

📬 Bonus: If this episode resonates, subscribe to my free weekly newsletter for deeper dives and personal stories at tylergardner.com

🎙️ Disclaimer: I’m not your financial advisor—I’m your guide on the side. Everything here is for educational purposes only. Always do your own research and consider working with a fiduciary advisor who understands your unique circumstances.

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 ever read, and it remains one of the few I return to over and over again—for its timeless principles, relatable tone, and surprising humor.

In this conversation, we cover:

• The unlikely path from Slavic literature major to bestselling financial writer
• Why “don’t be boring” might be the best writing advice you’ll ever get
• The epic laundry list of startup investments that went very sideways (and what he learned from each)
• The true cost of chasing returns vs. chasing happiness
• Why retirement isn't a finish line—but a lifestyle with the right people
• His most embarrassing investing losses—and how they became his favorite teaching tools

Andrew doesn’t just teach people how to manage money—he shows us how to think about it, with warmth, wit, and an honesty that’s rare in finance.

🎧 If you’ve ever wondered what makes financial advice stick—or how to build a life rich in meaning as well as money—this episode is for you.

🔗 Subscribe, rate, and share if it resonates. And thank you for joining me on Your Money Guide on the Side.

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 need an advisor—skill, will, and time—and then I’m sharing seven real-world filters for choosing the right one if you do.

Because the truth is:

• Working with a financial advisor might be one of the smartest moves you’ll ever make.
• Or it might be an expensive, unnecessary distraction.

The difference lies in what you need and who you choose.

We’ll talk about:

• The difference between CFP®, CFA®, CPA, and the rest of the alphabet soup
• What being a “fiduciary” really means (and doesn’t mean)
• The myth of market-beating promises (run from those)
• Fee models that make sense—and those that don’t
• Why credentials are clues, but not the whole story
• How investing is often more about behavior than brilliance
• The one question you must ask every advisor: “How do you invest your own money?”

And yes, I even compare hiring a financial advisor to dating—because, honestly, it is.
This episode won’t give you a rubber-stamped answer, but it will give you something far more valuable: a lens to look through so you can make the call yourself.

🎧 Whether you’re DIY-ing your financial life or just trying to figure out if the grass really is greener with professional help—this one’s for you.

If you enjoy the show, don’t forget to subscribe, leave a review, and share it with a friend who’s wondering if they should “talk to someone” about their money.

📩 And as always, you can sign up for the free newsletter at tylergardner.com for more clear, action-oriented financial education.

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, and a contagious belief that you can take control of your money — excuses not included.

In this episode of Your Money Guide on the Side, we dive into the moments that shaped Dan’s mission, including his two-year journey out of over $100,000 in debt and why vulnerability—not credentials—is his currency of trust. We talk about his viral “Smart Guy vs. Dumb Guy” series, the backlash he gets over car payments (you’ve been warned), and why he thinks showing integrity is far more important than performing expertise.

You’ll also hear us unpack:

• What makes people defensive about money
• Why so many creators struggle with relevance and comparison
• How to stay grounded (literally and spiritually) when the work feels heavy
• The reality behind Austin’s finance/media scene
• And the books that actually changed our lives (spoiler: one’s still in print after 2,000 years)

If you’re tired of being yelled at by the financial internet or just want to hear two humans wrestle with what it means to help others and still help themselves—this one’s for you.

Listen wherever you get your podcasts. And don’t forget to subscribe if you’re into financial literacy, big questions, and small wins.

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 loans, or just debating whether to pay off your 3% mortgage early, this episode is your new north star for how to think clearly about debt. You’ll learn how to:

✅ Decide whether to pay off debt or invest
✅ Use a practical ranking system to tackle your debt (hello, Debt Emergency Scale!)
✅ Think about opportunity cost like an investor
✅ Understand the psychological weight of debt—and why some people sleep soundly with it while others spiral
✅ Use the avalanche or snowball method depending on your own wiring
✅ Flip the script: how leverage (yes, debt!) can be used strategically to build wealth the way entrepreneurs and investors do every day

Plus, Tyler shares a vulnerable reminder that debt isn't a moral failing—it's a part of modern life. The goal isn’t perfection. It’s clarity, action, and momentum.

This one is personal. And powerful. And might just change the way you think about debt forever.

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 teach (and don’t teach) about money.

Andy has worn a lot of hats—boarding school English teacher, PWC consultant, MBA grad, educational administrator—and he brings a rare combo of humility, humor, and clarity to the messy overlap between education, money, and life purpose.

You’ll hear:

• Why Andy left the classroom—and why he came back
• How business was “demystified” for him in the least expected way
• What actually drives the cost of college (and why some schools won’t survive)
• The myth of the “money expert”—and how to choose who you trust
• What a CFO wishes more teachers asked him (but never do)

🎙️ Plus:

• The uncomfortable truth about health insurance, school budgeting, and stock-picking competitions in high schools
• Why college needs a Julliard-style reset for the modern world
• And why Psychology of Money by Morgan Housel just might be the most important book you’ll ever read

This one’s for anyone navigating careers, family, and the growing pressure of financial decision-making in a world that feels increasingly complex and expensive. Whether you're saving for college or trying to explain your 401(k) to your teenager, this episode helps add clarity, confidence, and maybe even some joy to the process.

📚 Education, meet real-world finance.

🐶 Also: Tyler’s dogs make a guest appearance with some strong opinions on college tuition.

🔍 Highlights & Resources:

• Book: The Psychology of Money by Morgan Housel
• Concept: Education vs. College (yes, there’s a difference)
• Tool: Why every good CFO keeps a whiteboard in their office
• Framework: You don’t need to be a teacher to teach

📬 Subscribe to Tyler’s newsletter for 3 weekly money insights: tylergardner.com
🎧 More episodes at Your Money Guide on the Side

Have you ever said, “I’m just bad with money”?

Yeah—me too. But what if the real issue isn’t your spending or saving or investing strategy... but your ability to name the actual problem in the first place?

This solo episode is a follow-up to last week’s conversation with CFP® Victoria Ferguson, and it’s all about creating a personal framework that helps you stop spinning your wheels and finally make meaningful progress in your financial life.

You’ll learn:

• Why most people never get past step one in solving their money problems
• How to stop drowning in to-do lists and prioritize the right thing
• A new lens for filtering financial advice (and spotting BS in a sea of influencers)

🔍 Whether you’re overwhelmed by credit card debt, unsure how to retire, or simply tired of feeling like you’re doing everything but getting nowhere, this episode gives you the tools to:

✅ Name the problem
✅ Prioritize the problem
✅ Solve the problem—without getting lost in the noise

Plus:

• What Warren Buffett’s 25-5 Rule has to do with your finances
• The Latin origin of the word “priority” (spoiler: it was never meant to be plural)
• Why vague financial advice is like shopping at Costco while hungry
• And how smoke alarms at 2 a.m. taught me more about problem-solving than any spreadsheet ever did

If you want clarity, confidence, and a simple way to move forward in your financial life—this episode is for you.

🎯 Don’t just solve problems. Solve the right one.