Mr. Stillman's Opus

Hosted by John Stillman

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Oct 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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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

August 28, 2026Episode 15610 min

Millions Are Retiring Earlier Than Planned — Are You Ready If You're Next?

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment ☎️ 919-391-3446 Many people plan to retire around 65, but new research shows a large percentage are leaving the workforce several years earlier—and often not by choice. Health problems, job loss, and rising healthcare expenses can suddenly force a retirement timeline to change. In this episode, Jake explains why those extra few years matter so much and how better planning can make an unexpected early retirement more manageable. Here’s what we discuss in this episode: 📉 Early Retirement: Many leave sooner than planned ⚠️ Unexpected Exits: Health and jobs drive change 👨‍👩‍👦 Real-Life Impact: Family circumstances alter timing 💰 Income Differences: Flexibility varies by resources 🧮 Scenario Planning: Test earlier retirement dates 🔄 Flexible Plans: Adapt without losing direction Resources for this episode: Millions Are Retiring Earlier Than Planned. Do Advisors Need To Rethink Planning? https://www.fa-mag.com/news/most-americans-retire-earlier-than-planned--here-are-the-top-reasons-87149.html Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

August 21, 2026Episode 15513 min

High Expectations, High Support: The Relationship Your Money Deserves Too

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment ☎️ 919-391-3446 A simple parenting moment might be the clearest picture of what real financial advice should look like. Jake unpacks the “High Shoulders Theory” and how expectations and support shape your relationship with money and your advisor. You’ll see why “you’re fine” and “you’re doing it all wrong” both miss the mark, and what a true partner in your financial life actually does for you. Stick around to find out which quadrant your advisor falls into… and where you really want to be. Here’s what we discuss in this episode: 🚫 Low Support: Little guidance or accountability 😌 Too Comfortable: Support without meaningful challenge ⚠️ High Pressure: Expectations without a plan 🤝 Ideal Relationship: Accountability backed by support 📋 Clear Plan: Priorities with specific actions ✅ Ongoing Support: Regular check-ins and follow-through Resources for this episode: The High Shoulders Theory https://www.sahilbloom.com/newsletter/the-high-shoulders-theory 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

August 14, 2026Episode 15415 min

Why Are You Still Working? The Real Reasons People Delay Retirement

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment ☎️ 919-391-3446 Some people keep working because they love what they do. Others stay because retirement feels financially, socially, or emotionally uncertain. In this episode, Jake explores the different forces that can keep someone in the workforce longer than expected and why the real goal is understanding whether work is a choice or a necessity. A retirement plan should do more than tell you when you can stop working; it should help you prepare for what comes next. Here’s what we discuss in this episode: 💼 Working Longer: People remain in the workforce for many different reasons 🤝 Social Connection: Leaving work can mean losing relationships, routine, and part of your identity 💵 Financial Necessity: A retirement income plan can help determine whether working longer is truly required 😟 Retirement Fears: Uncertainty can keep people working even when the numbers may support retirement 🏃 Semi-Retirement: Cutting back hours or changing careers can provide a middle ground 🗺️ Retirement Phases: A plan needs to account for decades of changing needs after work ends Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://meetwithrosewood.com Check us out on YouTube: https://bit.ly/46RaLvL

July 31, 2026Episode 15321 min

Trump Accounts: What Parents and Grandparents Need to Know

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment ☎️ 919-391-3446 Trump Accounts may offer families a valuable new way to save, but they are not automatically the right solution for every goal. In this episode, John and Jake explain how these accounts work, where they may fit, and why careful planning still matters. Tune in to find out whether this new account type deserves a spot in your financial toolbox or should be left on the shelf. Here’s what we discuss in this episode: 🆕 How It Works: Understand how Trump Accounts work ⚠️ Use Caution: Outdated information can create confusion 🎯 Start With Goals: Match each account to its purpose 🧾 Tax Considerations: Different accounts carry different tax treatment 📲 Getting Started: Setup is easier than expected Resources for this episode: https://trumpaccounts.gov Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: https://www.rosewoodwealthmanagement.com/schedule-an-appointment Check us out on YouTube: https://bit.ly/46RaLvL