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.