Mr. Stillman's Opus

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment ☎️ 919-391-3446 You inherit a home, and suddenly you’ve got options. In this episode, John walks through one of the most common questions people face in this situation: whether to turn it into an Airbnb or take a different path. It’s a decision that goes beyond potential income and touches on lifestyle, effort, and long-term strategy. Before you jump in, tune in to hear the practical reality of what this commitment would look like day-to-day. Here’s what we discuss in this episode: 🏠 Airbnb Opportunity: Short-term rentals may generate high income ⚠️ Workload Reality: Managing turnover and guests takes effort 📉 Property Wear: Short-term guests may not treat it carefully 📊 Tax Strategy: Step-up in basis can make selling attractive 🏛️ Zoning Risk: Local rules could impact your ability to rent 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

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

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

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

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

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

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

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

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

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

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

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

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 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

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

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

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

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

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

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? Focus on contribution, not chasing returns 📈 The power of compounding after the groundwork is done 🎯 The key lesson: patience multiplies payoff 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

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 it could impact your financial outlook. From a continued high standard deduction to a potential SALT cap increase, John lays out what’s worth your attention. He also covers proposed changes to healthcare subsidies and what they could mean for folks not yet on Medicare. If you’re wondering how this bill could affect your retirement plan, tune in for a clear, candid look at what we know so far. Here’s what we discuss in this episode: 🏛️ What’s really inside the “Big Beautiful Bill” 📉 How extended tax cuts might benefit (or hurt) you 💸 SALT cap tug-of-war: red vs. blue states 🧾 Standard deductions and estate tax updates 🚑 What could change for your healthcare subsidies 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