Mr. Stillman's Opus

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When you leave a job, one of the biggest financial questions you face is what to do with your old 401(k). Should you roll it into an IRA? Leave it where it is? Or move it somewhe...

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You’ve probably had this conversation. The family wants a pool, but you’re wondering if it makes financial sense.

But here’s the bigger question: doe...

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When a parent dies, it’s not just the photo albums and memories that get unpacked. The house usually comes with it. And that’s where feelings and finances start bumping into each...

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Living off interest sounds great, until you realize you’ve built a retirement plan that can easily collapse the moment life hits. In this episode, John uses a chicken-and-egg ana...

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Ever feel like you’re missing something right under your nose? On the farm, knowing all the hidden spots for eggs means a bigger haul every day, and your investments work the sam...

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John takes an everyday problem—keeping plants alive—and uses it to explain why slow, steady wealth building actually works better than chasing quick wins. He breaks down why “fak...

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What should you do first when your income suddenly skyrockets? Is waiting until age 70 for Social Security always worth it? In this episode, John answers a fresh round of listener questions, each one highlighting the real-life financial decisions people wrestle with every day. The truth is, even...

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John’s okra plants usually thrive, but this year nearly every seed failed to sprout. In this short episode, John shares how his gardening mishap illustrates one of the most important principles in investing — diversification. Whether it’s okra or your portfolio, balance and variety are what he...

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Medicare can feel like alphabet soup—Part A, Part B, Part D, Advantage, Supplement—how do you make sense of it all? John talks with Ryan Nutter of Cornerstone Senior Advisors, one of the most knowledgeable Medicare specialists in the country. Together, they cut through the confusion to explain how the system re...

Sometimes the best lessons come from the most ordinary places, like the chicken coop. A simple thing like farm-fresh eggs can teach a powerful lesson about investing. Here’s the scoop: farm-fresh eggs can sit safely on your counter for weeks because of a natural protective coating called a “bloom.” But wash that coating off, and suddenly they spoil fast and need to be refrigerated.

Your investments are a lot like those eggs. Over-h...

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For decades, families have been told college is the only ticket to success. But with skyrocketing costs, shifting job markets, and the rise of AI, the economics of higher education are more complicated than ever. Career and college coach Kristin Heimstra joins John to break down how parents and ...

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Deciding where to live in retirement is about more than just money; it’s about lifestyle, family, and long-term comfort. In this episode, John explores the often-emotional decision of keeping the family home, downsizing, or relocating entirely. He shares real examples of weighing the memories ti...

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If you’ve ever dabbled in gardening, you know that some plants thrive together while others fight for resources. Tomatoes and potatoes? Terrible neighbors. But tomatoes and basil? That’s a match made in salad heaven. The same principle applies to your money. Certain accounts and investments simp...

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📕 Download our free Eat Smart, Spend Less guide: https://thirdwheelmedia.com/wp-content/uploads/2025/08/Eat-Smart-Spend-Less-PDF.pdf

Feeling like your grocery bill needs its own 401(k)? You're not alone. In this episode, John sits down with Functional Medicine Nutritionist Katie Garrott to unpa...

This week, we're back on the farm with another hands-on financial lesson, because sometimes the best way to understand money is to get your boots dirty. In part two of our Finance Lessons from the Farm series, John breaks out a literal toolbox and a little dirt to teach a big concept: using the right financial tool for the right job. He walks through common missteps, explains how these mismatches happen, and shares how to rethink y...

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Congress has passed and President Trump has signed the Big Beautiful Bill, which is our new tax code (along with a bunch of other things). While you might have a strong opinion on different aspects of this legislation, all we care about today is how it will impact tax planning and financial pl...

If you're only using your Health Savings Account (HSA) to pay for co-pays and prescriptions today, you’re missing out on its biggest superpower. In this episode, John reveals how to “hack” your HSA and turn it into a tax-free retirement goldmine. He also shares tips on contribution strategy, the portability of HSAs, what qualifies as a medical expense, and how to retroactively reimburse yourself in retirement.

Here’s what we discus...

Bees might not seem like financial gurus, but when it comes to patience, long-term planning, and compound growth, they might just outsmart most investors. In this episode, John teaches on what his personal beekeeping hobby taught him about investing, and why the early years of building wealth often feel frustrating or futile.

Here’s what we discuss in this episode:

🕰️ Why early returns often look discouraging

💸 Feeling behind? Fo...

A new tax proposal, referred to as “The Big Beautiful Bill,” has officially passed the House. But before anything’s set in stone, it has to make it through the Senate, where revisions are all but guaranteed. The bill’s main goal? To extend several provisions of the 2018 tax code, with a few adjustments and updates along the way. In this episode, John breaks down what’s currently in the bill, what might shift in the Senate, and how ...