Mr. Stillman's Opus

Why You Shouldn’t Bet Everything on One Investment

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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 help you grow something that lasts.
Here’s what we discuss in this episode:
📉 Overconfidence Risk: The danger of assuming past success guarantees future results
🏢 Company Stock Trap: Why loading up on your employer’s stock can backfire
📊 Diversification: How spreading risk helps protect your long-term financial goals
💬 Simple Advice: Don’t go all in on one seed—or one stock
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

(Almost) Everything You Need to Know About Medicare + a FREE Guide

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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 really works, what each part covers, and how to choose between Advantage and Supplement plans. Medicare doesn’t have to be overwhelming if you understand how the pieces fit together.
Get your free 2026 Medicare Guide here: https://tinyurl.com/4zy3w35n
Here’s what we discuss in this episode:
🧩 Breaking Down Medicare: the difference between Parts A, B, C, and D
💸 “Free” Isn’t Free: why you’ve already paid for Part A
🧾 Supplement vs. Advantage: which plan design fits your lifestyle
💊 Drug Coverage Details: understanding Part D and the Inflation Reduction Act changes
📈 Rate Increases Explained: why premiums are rising and what to expect in 2026
 
Get in touch with Ryan at Cornerstone Senior Advisors:
Website: https://advisemedicare.net
Email: office@advisemedicare.net
Phone: 316-260-3331
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

Take Your Hands Off Your Nest Egg

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-handling can shorten their shelf life and hurt long-term growth. Instead, patience and restraint usually pay off. Just like eggs last if you leave them alone, your portfolio can thrive if you trust the protective power of time, diversification, and sound strategy. Pre-retirees and retirees, take note: sometimes the smartest move is knowing when to do absolutely nothing.
Here’s what we discuss in this episode:
🚫 The financial danger of over-handling investments
📉 Why market dips rarely need a panic response
🥚 What farm-fresh eggs can teach us about financial planning
⏳ How time and patience protect growth
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

The Economics of College with Kristin Heimstra

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☎️ 919-391-3446
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 students can navigate these choices with clarity and confidence.
Kristin shares her perspective on when a private school may be worth the price, why community colleges are an overlooked gem, and how to think critically about degrees, ROI, and career fit. She also explores the growing role of trade schools and hands-on careers that AI can’t replace. If you’ve ever wondered how to balance cost, value, and opportunity when it comes to higher education—or how to help your kids or grandkids make smarter choices—this conversation is for you. The bottom line: it’s not just about where you go, it’s about knowing yourself, your goals, and the return on your investment.
Here’s what we discuss in this episode:
🎓 Rethinking the “college or bust” mindset
💰 When private education can be worth the cost
🔧 Trade school opportunities in an AI-driven world
🏫 Community college as a launchpad for success
🤝 Building networks and connections that matter
 
Get in touch with Kristin:
Art of Potential website: https://www.artofpotential.com/
Email: Kristin@artofpotential.com
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

Should You Downsize in Retirement? The Emotional Vs. Financial Debate

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☎️ 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 tied to a house against the reality of upkeep, property taxes, and shifting housing markets.
John explains why there’s no “one-size-fits-all” answer. For some, hiring help for maintenance makes more sense than selling. For others, equity in a large home is essential to funding their retirement income plan. And sometimes, the desire to live near children and grandchildren trumps both cost and convenience. With rising interest rates and changing property values, the math isn’t always straightforward. This conversation will help you think about both the numbers and your emotions, so you can feel confident about your next move.
 
Here’s what we discuss in this episode:
🏠 The emotional vs. financial sides of deciding where to live in retirement
📉 Why “downsizing” doesn’t always save you money
👨‍👩‍👧 Lifestyle questions to ask before making a move
💵 How property taxes and interest rates factor into your decision
🔑 Balance lifestyle with financial security
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

Don’t Plant Your Tomatoes Next to Your Potatoes (or Your Roth Next to a CD)

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 simply don’t belong side by side. In this episode, John explains how the concept of companion planting—pairing crops that help each other grow—mirrors smart financial strategies. Just like tomatoes thrive when planted near basil, your retirement plan flourishes when your investments, tax strategies, and income sources are designed to work together instead of competing for resources.
Here’s what we discuss in this episode:
🪴 Gardening wisdom for retirement planning
🥔 Why “taters and maters” don’t mix in finance
🚀 Roth IRAs need growth, not safety
🌿 Designing a healthy, balanced financial garden
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

Eat Smart & Spend Less with Katie Garrott

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 unpack one of the biggest myths in the wellness world: that healthy eating and saving money are mutually exclusive. Today, Katie offers our listeners simple, research-backed ways to eat nutrient-dense meals without destroying your financial goals.
Katie explains how focusing on nutrient density rather than calorie count can transform your meals and your budget, and how frozen foods, bulk bins, and lean proteins can help you eat clean without breaking the bank. They also dig into how processed foods, dyes, and preservatives can fuel inflammation, mood issues, and brain fog, quietly draining both your energy and your wallet. Plus, you’ll learn which parts of the animal store toxins so you can shop smarter. Tune in and learn how to make your pantry pull double duty, fueling your health and protecting your wallet.
Here’s what we discuss in this episode:
🛒 Why planning meals beats winging it (every time)
🧠 Decision fatigue, grocery store edition
🥜 How bulk nuts might just save your health and your wallet
💸 The real cost of cheap food (spoiler: it's not cheap)
💡 Meal templates = time and money saved
 
0:00 – Intro
0:52 – Katie’s Personal Journey into Functional Medicine
2:35 – Planning Meals like a Pro
5:12 – Eat Cheap or Eat Healthy? (The False Choice)
7:32 – Processed Foods: The Real Long-Term Cost
11:25 – Nutrient Density vs. Calorie Count
13:31 – Bulk Shopping Tips
16:16 – Frozen Food Hacks and Lean Protein Choices
18:29 – Shopping Tips & Meal Templates
22:45 – Where to Learn More from Katie
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

Using the Wrong Tools May Costs You

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 your approach so every tool in your financial plan is aligned with its intended purpose.
Just like you wouldn’t dig a hole with a four-foot level (seriously, don’t try it), you shouldn’t use life insurance as a long-term investment or stash your Roth IRA in bank CDs. These tools aren’t inherently bad, but they’re often wildly mismatched to the goals people expect them to accomplish. Tune in to make sure you’re using the right tools for the job.
Here’s what we discuss in this episode:
🛠️ Using life insurance the wrong way
🚜 The shovel-to-level investment analogy
🌳 Investing for long-term growth the right way
📦 Don’t let a product define your strategy
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

The New Tax Code is Here

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 planning for people preparing for retirement.
We’re going to run through all of the major provisions in the new bill, along with some of the items that might need your attention this year. These changes, among others, highlight the importance of staying informed and adapting financial strategies to align with the new tax landscape. As we move forward, it's crucial for individuals and families to reassess their tax plans to take full advantage of the benefits available under the new code.
Here’s what we discuss in this episode:
📉 Tax brackets made permanent (no more 2025 cliff!)
🧾 New $12K deduction for couples over 65
🏡 SALT deduction cap raised from $10K to $40K
🚗 Deduct car loan interest (yes, really)
⚠️ Trump Accounts, student loan limits & EV credit phase-out
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL

HSA Hacking: The One Account With Triple Tax Wins

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 discuss in this episode:
💡 Triple tax benefits in one account
🛠️ HSA vs. FSA—know the difference
💸 Why you should not swipe your HSA card
📈 Grow it now, spend it later
📁 Yes, receipts matter, retroactive hacks explained
 
Connect with us:
Web: https://rosewoodwealthmanagement.com/
Phone: 919-391-3446
Schedule a Meeting: http://meetwithjohn.com
Check us out on YouTube: https://bit.ly/46RaLvL