Mr. Stillman's Opus

Should You Roll Over Your 401(k)?

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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 somewhere else entirely? The answer isn’t always obvious, and like most financial decisions, the right move depends on your unique situation. Today, John walks through the real-world considerations behind a 401(k) rollover and helps simplify a decision that often gets overcomplicated.
 
Here’s what we discuss in this episode:
 
🔄 Rollover Benefits and Flexibility
📋 Conditions for Rolling Over 401(k) to an IRA
💵 Comparing Costs and Administrative Fees
🧭 Planning and Investment Strategies

Is a Swimming Pool a Bad Investment?

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☎️ 919-391-3446
 
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: does every dollar you spend have to be an “investment?” In this episode, John unpacks the difference between financial ROI and life ROI. Because sometimes the value of something isn’t measured in resale price, it’s measured in memories, convenience, and the kind of home environment you want to create.
 
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

Inherited a House — Are the Taxes Really That Bad?

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☎️ 919-391-3446
 
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 other. John tackles a listener question about whether selling an inherited home really triggers some monster tax bill, or if that worry’s been blown a little out of proportion.
But more importantly, he highlights why communication matters just as much as calculation. When everyone understands the rules — and talks openly about goals and concerns — decisions stop being driven by fear and start being guided by clarity.
 
Here’s what we discuss in this episode:
🏠 Inherited Home Concerns: Tax fears and stalled decisions
🗣 Family Communication: Conversations before emotions rise
📊 Property Value Growth: Step-up basis and appraisal timing
👨‍👩‍👧 Multiple Heirs: Buyouts, tension, and coordination
 
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
 

Think Living Off Interest Sounds Smart? Think Again.

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☎️ 919-391-3446
 
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 analogy to explain why relying solely on dividends and interest can sabotage your financial future. If you’ve ever said, “I’ll never touch principal,” this conversation may change your mind before reality does.
 
Here’s what we discuss in this episode:
 
💸 Dividend Trap: Why “interest only” sounds smarter than it is
🧯 Portfolio Buffer: Planning for surprises (because life happens)
⚠️ Hard Truth: Why this strategy fails and what to do instead
 
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
 

Spotting Hidden Fees (And Where You'll Find Them)

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☎️ 919-391-3446
 
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 same way. If you know where to look and ask the right questions, you’ll uncover those hidden fees sneaking by unnoticed. Tune in and let’s make sure you’re collecting all your eggs, and every dollar that belongs to you.
 
Here’s what we discuss in this episode:
🥚 Egg Routine: Knowing the right spots
💸 Hidden Fees: What statements don’t show
🎯 Better Questions: How clarity is uncovered
 
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

Why Slow Growth Wins (Even if It’s Boring)

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
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 “fake growth” never lasts and why mastering money in small doses matters far more than sudden windfalls. If you’ve ever wished your wealth would grow overnight, this episode politely reminds you it won’t.
 
Here’s what we discuss in this episode:
🌧️ The Rainwater Analogy: real growth vs. the stuff that just “looks” like growth
🪣 Collecting the Good Stuff: why shortcuts don’t deliver the nutrients your finances need
💸 Wealth Lessons Hidden in Gardening: real wealth, the slow kind, is what actually lasts
 
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

Mailbag: Big Raises, Gifting Rules & Social Security Timing

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
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 simple questions deserve careful thinking and a strategy built around your unique situation. Good planning is always personal, never one-size-fits-all.
Here’s what we discuss in this episode:
💸 Managing a big income jump: avoiding lifestyle creep and planning for taxes
🎁 Gifting to adult children: understanding annual limits and estate rules
🧓 Social Security timing: why “wait until 70” isn’t always the right advice
 
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

Why You Shouldn’t Bet Everything on One Investment

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
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