Mr. Stillman's Opus

Hosted by John Stillman

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Nov 2026

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Financial and retirement guidance from John Stillman, founder of Rosewood Wealth Management. Serving Durham, Chapel Hill, and the rest of the Triangle. Make sure your finances are designed to deliver you a harmonious retirement.

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November 13, 2026Episode 16613 min

What the Midterms Mean to Your Retirement Plan: Investing & Markets (Part 1)

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Does the outcome of an election really matter for your investments? In part one of this two-part series, John and Jake look at how markets have tended to behave before and after elections, why uncertainty tends to rattle the market more than the result itself, and what gridlock can mean for day-to-day swings. Jake also shares how to filter the headlines down to what actually touches your plan. Whatever side of the aisle you’re on, your portfolio shouldn’t have to pick one. Here’s what we discuss in this episode: 🗳️ Before the Vote: Why volatility often comes first ❓ Uncertainty Stings: Markets dislike not knowing more than bad news 📊 The Long View: Party control has mattered less than you’d think 🚦 Gridlock: Why the market may not mind it 🎢 Volatility Isn’t a Crash: Brace for whiplash days 📰 Filter the Noise: Avoiding emotional decisions Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

November 6, 2026Episode 16510 min

Do I Need Life Insurance in Retirement?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Does retirement mean it’s time to drop your life insurance? John and Jake take a practical, case-by-case look at how coverage may help replace lost income, support loved ones, or provide liquidity for an estate. They explain why the right amount—and whether you need coverage at all—depends on your goals, finances, and family’s needs. Before you cancel that policy, tune in to see what it may still be doing for you. Here’s what we discuss in this episode: 🧾 Life Insurance Bias: Why opinions about life insurance vary 💵 Retirement Needs: When coverage may still matter 🧮 Work Backward: Use insurance to help fill an income gap your assets can’t cover 🧩 It’s Just Part of the Puzzle: Insurance is one tool—not the only answer Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

October 30, 2026Episode 16410 min

Can I Stop Chasing Investment Growth?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Plenty of retirees reach a point where they don’t care much about growth anymore. They just don’t want to lose what they’ve spent 30 or 40 years building. Is that foolish? John doesn’t think so. When a team is up by nine late in the game, nobody calls a deep pass. They line up in victory formation and protect the ball. But taking a knee too early is its own mistake. John explains why the right time to pull back isn’t about your age, or even your retirement date. It’s about when you’ll actually need the money for income. Here’s what we discuss in this episode: 🏈 Victory Formation: Protecting what you’ve built isn’t foolish ⏱️ Don’t Take a Knee Too Early: Pulling back too soon has a cost 📅 It’s Not Your Birthday: Timing depends on when you need income 🏛️ The Pension Factor: Steady income can change your risk needs 🧩 Not All or Nothing: Protect near-term money, invest the rest 🏍️ Plan to Stick Around: Your money likely needs to last decades Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

October 23, 2026Episode 16317 min

How Do You Plan for Long-Term Care?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Long-term care is one of those retirement expenses nobody exactly looks forward to planning for, but ignoring it can leave your nest egg exposed if the bill eventually lands in your lap. In this episode, John and Jake walk through the different ways retirees can prepare, and some strategies that may help keep a major care event from shipwrecking the rest of the plan. The right answer depends on how all the pieces of your retirement fit together and which financial levers you have available to pull. You may not need long-term care insurance, but you absolutely need a plan for how you’ll handle the cost if the need arises. Here’s what we discuss in this episode: 🏥 Care Planning: Prepare before the need 💰 Self-Insurance: Know what assets can cover 📄 Insurance Options: Compare different coverage types ⚖️ Tradeoffs: Understand costs and risks 🏡 Alternative Strategies: Use assets intentionally ✅ Bottom Line: Have a payment plan Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

October 16, 2026Episode 16214 min

What To Do NOW To Reduce Next Year's Tax Bill

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Most people don't think about taxes until they're sitting down to file, and by then, most of the best opportunities are gone. The moves that actually lower your tax bill usually have to happen before December 31. Here's what's worth tackling now. The best tax planning rarely happens in April. It happens months earlier, while there's still time to do something about it. If you haven't looked at this year's picture yet, now's the time. Here’s what we discuss in this episode: 🧾 Q4 Planning: Make decisions before deadlines arrive ❤️ Charitable Giving: Use generosity more strategically 💼 Self-Employment: Explore additional retirement plan options 🏥 Tax Tools: Take advantage of overlooked accounts 📅 Year-End Review: Adjust plans while there’s time Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

October 9, 2026Episode 16114 min

What Scares Investors More Than Halloween?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 It's spooky season. And while most people are thinking about haunted houses and horror movies, a lot of pre-retirees have scarier things on their minds: running out of money, or a market crash at exactly the wrong time. Today, Jake shines a flashlight on five of the biggest financial frights and how to prepare for them. Most of what scares people about retirement isn't the event itself. It's not knowing what happens next. A plan won't make the unknowns disappear, but it can make them a lot less frightening. Happy Halloween. Here’s what we discuss in this episode: 💸 Running Out: Know what you can safely spend 📉 Market Risk: Match investments to actual needs 🏥 Healthcare: Prepare for rising medical expenses 🩺 Long-Term Care: Discuss difficult possibilities early ❤️ Losing Spouse: Prepare for life-changing transitions 🧭 Clarity: Replace uncertainty with informed planning Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

October 2, 2026Episode 16013 min

These 5 Questions Reveal A Lot About Your Financial Plan

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Talking about money can be hard for some people, and sometimes it just takes the right question to get things rolling. Jake goes over a few today that he thinks are worth asking. None of these questions are really about money. That's kind of the point. Sometimes the best way into a financial conversation is to start somewhere else entirely. Here’s what we discuss in this episode: 🧞 Financial Constraints: Identify worries holding you back ❤️ Purpose: Define what matters beyond money 🔙 Past Regrets: Learn from previous financial choices 🧠 Money Mindset: Recognize habits shaping retirement decisions 🪣 Bucket List: Turn future dreams into goals 📅 Retirement Stages: Plan around changing life seasons Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

September 28, 2026Episode 15914 min

Are Roth Conversions Right for Me?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Roth conversions can sound simple on the surface, but the decision can become much more nuanced once you look at the full picture. In this episode, John and Jake explain why the bigger issue is not simply whether to convert, but how taxes, family goals, flexibility, and timing all fit together. They also explore why the answer can change depending on what the money is ultimately meant to accomplish. The best Roth conversion strategy is the one that makes sense within the entire financial plan. Here’s what we discuss in this episode: 👨‍👩‍👧 Generational Wealth: Considering heirs in the strategy 🛡️ Tax Defense: Creating flexibility against future changes 🏥 Medicare Costs: Watching income-related premium impacts 💍 Surviving Spouse: Preparing for future filing changes ⏱️ Conversion Timing: Why age and timing matter ⚠️ Implementation Risk: Avoiding costly conversion mistakes Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

September 18, 2026Episode 15813 min

When is the Best Time to Start Social Security?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 Spoiler Alert: There’s no single “best” age to claim Social Security because the right answer depends on far more than the size of the monthly check. In this episode, John and Jake explain why Social Security should be viewed as one piece of a larger retirement plan, with other key factors all influencing the decision. They also unpack several common misconceptions that can push people toward claiming too early or waiting too long. Here’s what we discuss in this episode: ⏳ Claiming Age: Why there isn’t one universally correct time to start Social Security 🧩 Bigger Picture: How Social Security fits into income, taxes, investments, healthcare, and legacy planning 🧾 Tax Strategy: Why delaying benefits can sometimes create room for Roth conversions or IRA withdrawals 💵 Income Needs: When taking Social Security earlier may help preserve other assets 📈 Delayed Benefits: Understanding the difference between a larger future benefit and an investment return ⚖️ Balancing Act: Avoiding the mistake of draining liquid assets simply to delay Social Security Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

September 4, 2026Episode 15711 min

What Does "Safe Money" Actually Mean?

Ready to grow your wealth with confidence? Let’s talk! 👉 http://www.meetwithrosewood.com ☎️ 919-391-3446 “Safe” sounds simple, but in retirement planning, it can mean very different things to different people. Jake explains why feeling comfortable with your portfolio isn’t the same as having the right amount of risk for your actual financial situation. The goal isn’t to avoid risk altogether, it’s to make sure the risk you’re taking actually fits the life your money needs to support. Here’s what we discuss in this episode: 💬 Client Perceptions: What people usually mean by “safe money” ⚖️ Risk Capacity: How much risk your plan can actually support 😴 Risk Tolerance: How much volatility you can emotionally handle 📈 Market Influence: Why strong markets can distort perception 🔍 Portfolio Reality: Why people often underestimate their risk 💵 Income Protection: Keeping retirement spending on track Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://www.meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL