Mr. Stillman's Opus

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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 ...

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment

☎️ 919-391-3446

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...

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment

☎️ 919-391-3446

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...

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment

☎️ 919-391-3446

📕 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...

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment

☎️ 919-391-3446

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 ...

For a lot of folks, retirement and travel go hand-in-hand, whether that’s taking a trip to Europe or rolling into every Cracker Barrel in the Southeast. But here’s the thing: dreaming is free, but the travel costs aren’t. In this episode, John shares how to build a realistic, flexible plan that supports your travel goals in retirement, whether it’s an RV road trip to national parks or annual international adventures with a passport...

When the market takes a dive, most people panic. But the most successful investors often see downturns differently. Being able to recognize opportunity in the middle of market uncertainty can help you make critical decisions during difficult market environments. Let’s talk about what steps you can take to strengthen your plan while others sit on the sidelines.

We'll cover four smart strategies that can work during volatile periods,...

Tax season is here, but did you know that filing your 2024 return is only part of the equation? With the 2025 tax changes in place, John breaks down key areas where you may be able to reduce your tax bill. With increased standard deductions and higher retirement contribution limits, now is the time to evaluate how you can plan smarter and potentially put more money toward your future.

In this episode, we dive into the major tax cha...

Once you’re on a fixed income in retirement, it can be difficult to open the checkbook to pay for major expenses. Emotion and logic both play into the decision, and many spouses can feel apprehensive about spending large sums of money without a paycheck still coming in. So how do you determine if you can afford that home renovation you’ve always wanted and what’s the best way to convince your partner it’s going to be okay long-term...

There’s a lot of anxiety out ​there ​right ​now ​about ​the ​market ​and ​the ​current ​economy ​that ​we're ​experiencing. ​People are concerned about the uncertainty surrounding Social Security, DOGE, tariffs, and more. So ​I ​wanted ​to ​get ​on ​here ​and ​try to ​dispel some of the ​myths, ​talk ​about ​what's ​actually ​happening, ​and ​then ​drill ​down ​specifically ​to ​what ​you ​should ​be ​doing ​yourself.

Here’s some o...

What’s the average age that people retire? While that question can give you an idea of what most Americans do, it’s best to understand why people choose the specific ages they do. This video will explain the key ages that influence retirement decisions to help you identify the factors that might affect your timeline.

We’ll tell you why the milestone ages begin at 59.5 and what ages are most important for Social Security and Medicar...

What happens when you get remarried and want to create a new will and estate plan with your new spouse? Do you have to change all of your previous beneficiaries or will the new will override those existing designations? That’s the question we’re answering in this week's show. 

Here’s what we discuss in this episode:

0:00 – Intro

0:51 – Beneficiaries override the will

2:32 – Estate planning challenges with second marriages

Conne...

With Halloween on the horizon, we’re rolling out a themed edition of the show today by tackling some of the trick or treat decisions of the financial planning world. We’re going to present John with four different products that have risen in popularity recently and find out whether he would characterize them as tricks or treats.

Here’s what we discuss in this episode:

0:00 – Intro

1:20 – Home equity line of credit

5:18 – Infinite...

Getting laid off or forced into retirement earlier than expected can be a big blow emotionally and financially, but it’s a life event that many people will have to navigate. If you find yourself in this position of no longer having a job before you were prepared to retire, should you go find another job or can you find a way to retire without it?

Today we’re answering a question we received recently from someone who is 61 and tryin...

Social Security timing is one of the most crucial decisions you’ll make in your retirement planning journey. Should you wait until 70 to claim your benefits, or is it better to start earlier?

Today we’re going to answer a question from someone who planned to wait until 70 for Social Security so they didn’t leave money on the table, but now that they’re approaching age 68, they’re having second thoughts about waiting. So what’s the ...