Mr. Stillman's Opus

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:

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:

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:

For a lot of folks, retirement and travel go hand-in-hand, whether that’s taking a trip to Europe or rolling into every Cracker Barrel in the Southeast. But here’s the thing: dreaming is free, but the travel costs aren’t. In this episode, John shares how to build a realistic, flexible plan that supports your travel goals in retirement, whether it’s an RV road trip to national parks or annual international adventures with a passport in hand. We’ll also break down how to budget realistically for travel in retirement, including why we often recommend a dedicated travel account funded by interest and dividends, one that can also serve as a backup for long-term care. We’ll also help you define what “travel” really means to you so that you can build a plan flexible enough to match your lifestyle, not just your wish list Here’s what we discuss in this episode: ✈️ Two types of travel lifestyles

When the market takes a dive, most people panic. But the most successful investors often see downturns differently. Being able to recognize opportunity in the middle of market uncertainty can help you make critical decisions during difficult market environments. Let’s talk about what steps you can take to strengthen your plan while others sit on the sidelines. We'll cover four smart strategies that can work during volatile periods, including increasing savings, timing Roth conversions, reallocating investments, and using the experience as a wake-up call to build a more resilient plan. No matter what stage of life you’re in, taking the time to pause, think, and respond with purpose instead of fear will help you emerge stronger. Here’s what we discuss in this episode:

Tax season is here, but did you know that filing your 2024 return is only part of the equation? With the 2025 tax changes in place, John breaks down key areas where you may be able to reduce your tax bill. With increased standard deductions and higher retirement contribution limits, now is the time to evaluate how you can plan smarter and potentially put more money toward your future. In this episode, we dive into the major tax changes for 2025 and discuss how smart planning now may save you a lot of money and stress later. From updates to the standard deduction to misconceptions about catch-up contributions, John explains what really matters for pre-retirees and retirees. Here’s what we discuss in this episode:

Once you’re on a fixed income in retirement, it can be difficult to open the checkbook to pay for major expenses. Emotion and logic both play into the decision, and many spouses can feel apprehensive about spending large sums of money without a paycheck still coming in. So how do you determine if you can afford that home renovation you’ve always wanted and what’s the best way to convince your partner it’s going to be okay long-term? We’ll highlight three potential scenarios regarding that cause someone to have reluctance to spending: emotional resistance, logical miscalculations, or a valid conclusion that the expense isn’t feasible. We want to approach these discussions openly and honestly, ensuring that both partners feel heard and understood. So let’s walk through the process for determining whether the concern is justified and show how knowing the numbers can help alleviate fears and make informed decisions. Here’s what we discuss in this episode: 0:00 – Intro 2:51 – Logical reasons 4:53 – How we help   C

There’s a lot of anxiety out ​there ​right ​now ​about ​the ​market ​and ​the ​current ​economy ​that ​we're ​experiencing. ​People are concerned about the uncertainty surrounding Social Security, DOGE, tariffs, and more. So ​I ​wanted ​to ​get ​on ​here ​and ​try to ​dispel some of the ​myths, ​talk ​about ​what's ​actually ​happening, ​and ​then ​drill ​down ​specifically ​to ​what ​you ​should ​be ​doing ​yourself. Here’s some of the things we’ll cover:

What’s the average age that people retire? While that question can give you an idea of what most Americans do, it’s best to understand why people choose the specific ages they do. This video will explain the key ages that influence retirement decisions to help you identify the factors that might affect your timeline. We’ll tell you why the milestone ages begin at 59.5 and what ages are most important for Social Security and Medicare. Most of our clients at Rosewood Wealth Management tend to retire between the ages of 65 and 68, but there is a wide spectrum of retirement ages based on individual circumstances and goals. Plus, there’s a wildcard that you need to know about if you’re a state employee. Here’s what we discuss in this episode: 0:00 – Intro 0:56 – Age 59.5 1:52 – Age 62 2:44 – Age 65 4:20 – Age 66/67 5:52 – Wildcard for state employees 7:11 – Our clients’ retirement age   Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a Meeting: http://meetwithjohn.com Chec

What happens when you get remarried and want to create a new will and estate plan with your new spouse? Do you have to change all of your previous beneficiaries or will the new will override those existing designations? That’s the question we’re answering in this week's show.    Here’s what we discuss in this episode: 0:00 – Intro 0:51 – Beneficiaries override the will 2:32 – Estate planning challenges with second marriages   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

With Halloween on the horizon, we’re rolling out a themed edition of the show today by tackling some of the trick or treat decisions of the financial planning world. We’re going to present John with four different products that have risen in popularity recently and find out whether he would characterize them as tricks or treats.   Here’s what we discuss in this episode: 0:00 – Intro 1:20 – Home equity line of credit 5:18 – Infinite banking 8:12 – Buying gold 10:17 – No closing cost mortgage   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

Getting laid off or forced into retirement earlier than expected can be a big blow emotionally and financially, but it’s a life event that many people will have to navigate. If you find yourself in this position of no longer having a job before you were prepared to retire, should you go find another job or can you find a way to retire without it? Today we’re answering a question we received recently from someone who is 61 and trying to determine if they need to go back to work. John will walk you through the factors that will impact this decision, like financial readiness and health insurance needs. Covering that gap until Medicare kicks in is often one of the biggest financial challenges for retiring early so we’ll share some options you could consider. This is one of those situations where planning is critical for getting a clear answer that will allow you to move forward confidently, and we’ll give you a better understanding of the process we work through to help you develop that plan.     Here’s what we d

Social Security timing is one of the most crucial decisions you’ll make in your retirement planning journey. Should you wait until 70 to claim your benefits, or is it better to start earlier? Today we’re going to answer a question from someone who planned to wait until 70 for Social Security so they didn’t leave money on the table, but now that they’re approaching age 68, they’re having second thoughts about waiting. So what’s the best path forward? John breaks down the pros and cons of taking Social Security at different ages and why there’s never one answer that applies to every situation. He’ll also share practical examples of how Rosewood Wealth Management has helped clients make the best decision about Social Security within their overall income plan. You want a well-thought-out retirement plan that takes your entire financial picture into account because Social Security is a decision need to get right.   Here’s what we discuss in this episode: 0:00 – Intro 0:44 – When to start taking Social Security ben

As we age, one of the most pressing questions we face is how to manage long-term care expenses. What coverage will you need and what’s the best way to pay for that coverage? Today we answer a question about purchasing LTC insurance and whether it’s worth doing while you’re in your 50s. John will discuss whether it is a necessary investment for those nearing retirement age and examine alternative options such as self-insuring and leveraging life insurance policies with accelerated death benefits. One significant drawback of insurance is the potential for premiums to increase over time, potentially pricing policyholders out just when they might need the coverage the most, which is why you want to know all of the options available. Join us as we break down the pros and cons of different strategies to address long-term care expenses.   Here’s what we discuss in this episode: 0:00 – Intro 0:39 – LTC insurance at an earlier age can be a mixed bag 2:50 – Can you self-insure? 6:45 – Life insurance to pay for long-ter

It can be challenging for a lot of folks to think about legacy planning because it takes a lot of forward thinking. Not everyone wants to plan that far ahead, but for some, it’s incredibly important to leave their loved ones with an inheritance.   Today we are answering a question from someone who wants to leave money for their children and grandchildren but also wants to ensure that they’re not paying more in taxes on that money than they need to. John will examine some common thoughts and concerns that revolve around legacy planning and discuss some better ways to think about the answer to this question.   This video focuses on how to ensure your legacy is as tax-efficient as possible. Whether you are a parent or grandparent, understanding how to structure your inheritance can make a significant difference in the amount of money your heirs will receive. This is the final part of a four-part series where we’ve been looking into how children and grandchildren fit into financial planning, as we take a holistic

Instilling good financial habits in children starts at a young age, but that doesn’t mean that every lesson will stick in adulthood. Once your kids start working and earning significant money for the first time, it’s pretty common to put spending ahead of saving. As parents, we want to help them establish good financial habits but what’s the best approach to do that? In this video, John will address a question we received from a parent who wants to make sure their kid is doing more than just getting by financially. Join us as we discuss strategies you can use to get those messages across. It all begins with solid communication, but we’ll also share some ways to help motivate your kids to grasp these financial concepts that will help them work toward financial independence. Financial literacy is a vital component of a strong financial legacy. By communicating effectively, using incentives, and finding the right balance between help and independence, parents can equip their children with the skills they need to

With college costs continuing to rise, some grandparents wonder if there’s anything they can do to help ease the burden of college expenses for their grandchildren. Today we’ll explore the best strategies for those who want to support their grandchildren’s college education without compromising their own financial stability.   The 529 plan gets most of the attention when it comes to college savings, but we’ll share a few more options that are worth considering. All of these could work for you but the best approach depends on your family’s unique situation and goals. Whether you prioritize the tax advantages of a 529 plan or the flexibility of a brokerage account, the key is to start planning early and consider all available options.   Here’s what we discuss in this episode: 0:00 – Intro 1:43 – The pros and cons of a 529 plan.  5:14 – Transferring 529 funds into a Roth IRA.   8:18 – Other savings options for college.   Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446 Schedule a

It’s not uncommon for children to stay on their parent’s payroll in some capacity when they’re adults, but that could end up impacting the parent’s ability to retire. At what point do you move your kids off of the payroll and what’s the best way to handle that conversation? In this episode, we’re going to address this situation and talk about how it ends up happening for parents. John sheds light on this issue, sharing his own experiences and those of his clients. He also emphasizes the importance of setting boundaries and understanding the long-term implications of continued financial support. If you’re in this situation or feel like the time is coming soon, we hope this conversation will help prepare you for ripping that band-aid off. This is part one of a four-part series where we’ll explore how your kids and grandkids fit into your overall financial plan and discuss how to work through some of the key areas that children impact you financially.   Here’s what we discuss in this episode: 0:00 – Intro 1:43 –

When you have multiple IRAs, managing them across different platforms and figuring out your RMDs for each account can be a little bit tricky. So what’s the best way to manage these accounts? Should you consider consolidating your IRAs? Today’s featured question comes from a comment left on one of our previous videos so thank you for the contribution. Here is the question John will answer: We have multiple IRAs set up over the years as different approaches appealed each year. Would you recommend consolidating all those IRAs to one account? Would it matter if we were taking RMDs or not in your answer? Join us to hear strategies for consolidating IRAs, some benefits to simplifying your accounts, and best practices for navigating your RMDs. By simplifying your accounts and understanding the true nature of diversification, you can streamline your retirement planning and make informed decisions.   Here’s what we discuss in this episode: 0:00 - Intro 1:24 - Consolidating IRAs 8:27 – Old IRAs and 401(k)s   Connect wi

Inheriting assets can be a life-changing financial boost, but it often comes with a maze of tax implications and decisions. In this episode, we will answer a question about an inheritance and lay out the tax considerations for a variety of assets to help you better understand what you might owe.   Discover how to navigate the tax implications of IRAs, annuities, bank accounts, real estate, and stocks to make the most of your inheritance. Even with this information, you still want to plan ahead as much as possible. If you know an inheritance is coming, or if you've just received one, it's crucial to sit down with a financial advisor to put a comprehensive plan in place. This will help you make the most of your inheritance, ensuring that you are as tax-efficient as possible.   Here’s what we discuss in this episode: 0:00 – Intro 1:06 – Today’s question 2:17 – IRA 4:41 – Annuities 5:45 – Bank account 6:50 – Home and stock   Connect with us: Web: https://rosewoodwealthmanagement.com/ Phone: 919-391-3446