Mr. Stillman's Opus

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
 

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

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
 

Ready to grow your wealth with confidence? Let’s talk! 👉 https://www.rosewoodwealthmanagement.com/schedule-an-appointment
☎️ 919-391-3446
 
John addresses the obvious right away: it’s not just him anymore, and everyone should get used to seeing Jake because he isn’t going anywhere. In this episode, John welcomes longtime friend Jake Doser as the newest partner and Financial Advisor at Rosewood Wealth Management. They share how the partnership came together and how the move creates new opportunities without changing the personal experience clients have come to expect. Plus, Jake offers an update on the whirlwind family journey from Connecticut to North Carolina.
 
Here’s what we discuss in this episode:
 
🛣️ Jake’s Journey and Background
🏀 Jake learns quickly about Carolina’s “different shades of blue”
🤝 Client Interaction and Team Dynamics
👶 Personal Updates and Family News
 
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
 
After 40+ years in the same home, the idea of packing up and moving somewhere new—like Florida—can feel both exciting and overwhelming. The tax savings might look great on paper, but there’s a lot more to consider than just the financial side. Today, John walks through the real questions you should be asking before making a move in early retirement. It’s all about making a decision that works not just financially, but for your day-to-day life.
 
Here’s what we discuss in this episode:
 
🌴 Tax Savings: No income tax has advantages
🌦️ Weather Reality: Florida summers hit different
📦 The Big Move: Downsizing takes time and effort
🏡 Housing Tradeoffs: Size, price, and location shift
🧭 Lifestyle Fit: Daily life may change more than expected
⚖️ Whole Picture: Money is only part of the decision
 
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
 
You can’t go back and fix the past, but you can make smarter decisions moving forward. John tackles a question a lot of people quietly wrestle with: how do you catch up after years of not saving? This isn’t about chasing quick wins or risky bets. It’s about using the position you’re in right now to make meaningful progress. The opportunity you have today might be bigger than you think.
 
Here’s what we discuss in this episode:
⚠️ Avoid Big Bets: Chasing “home runs” can backfire
📈 Prime Earning Years: Your 50s can be your strongest saving window
💸 Lower Expenses: Fewer obligations create opportunity
📊 Know Your Numbers: Understand what it costs to live
🧾 Use Tax Advantages: Catch-up contributions can help
 
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
 
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