The Scholar Wealth Podcast

How should families plan for the future when so much feels uncertain? In this episode, Stephan answers two listener questions that reflect real tradeoffs many high-income families are navigating right now. The first looks at how to approach 529 planning at a time when AI is reshaping education and the job market, and why flexibility matters as much as tax efficiency. The second explores a values-d...

In this episode of the Scholar Wealth Podcast, we work through two listener questions that reflect the financial and personal tradeoffs many high earners face as they approach retirement. We begin with a question about Social Security timing. A high-income listener wonders whether it makes sense to claim benefits early and invest them, rather than waiting until age 70, especially given concerns ab...

This week on the Scholar Wealth Podcast, we explore three topics that come up as wealth, assets, and complexity grow. We begin with a listener question from a business owner who recently realized a significant capital gain and is evaluating a Qualified Opportunity Zone investment. Stephan breaks down how QOZs actually work, why tax deferral is no longer the primary benefit, and why the underlying...

In this episode of the Scholar Wealth Podcast, we work through three business planning questions that touch on how assets, equipment, and employees are treated from a tax and benefits perspective. We start with a question about the tax treatment of working assets. Stephan walks through how the IRS distinguishes between a legitimate business activity and a hobby, why profit motive and documentation...

In this episode of the Scholar Wealth Podcast, we tackle three areas of planning that often intersect during major financial moments. We begin with a question from a tech professional whose company may be heading toward an AI-driven IPO. With valuations moving quickly and equity packages growing more complex, we walk through how to think about RSUs, ISOs, AMT exposure, and concentration risk witho...

This week on the Scholar Wealth Podcast, we look at three very different decisions that all require clear thinking and long-term planning. First, Stephan breaks down the financial and family considerations behind buying a €450,000 childhood home in Portugal, including how to separate emotion from economics and how to navigate cross-border tax and management issues. We then shift to carried interes...

This week on the Scholar Wealth Podcast, we look at three areas that matter for high-net-worth families. Stephan explains how exchange funds can reduce concentration risk for investors holding large amounts of appreciated stock, including the tradeoffs and IRS rules that determine when these structures make sense. Then we turn to IRMAA — how Medicare’s income-based surcharges are calculated, why t...

In this week’s Scholar Wealth Podcast, two listener questions that reflect the increasingly global and multi-generational nature of wealth management. First, how non-U.S. residents can access broad index-fund diversification without triggering unnecessary U.S. estate and withholding tax exposure, including how Irish-domiciled ETFs work, where they differ from U.S. funds, and what investors should...

This week, two listener questions that both center on how investors allocate capital — whether between homes, markets, or tax structures. First, how to evaluate the tradeoff between selling investments for cash versus taking on short-term debt when buying a new home before selling the old one — including how to model opportunity cost, liquidity, and market exposure. Next, a look at private market...

In this week’s Scholar Wealth Podcast, Stephan and Dr. Deon Strickland tackle two listener questions that both center on defining value. First, how to approach a wedding budget when affordability isn’t the issue — shifting the focus from numbers to meaning, and how family values shape financial decisions. Next, they revisit the Efficient Markets Hypothesis through the lens of the documentary Tune...

In this week’s Scholar Wealth Podcast, Stephan answers two listener questions that arise after major financial events. First, he explains how a charitable remainder unitrust (CRUT) can help real estate investors defer capital gains, create an income stream, and maintain flexibility in charitable giving. Next, he turns to a contingency attorney who just received a seven-figure payout and needs to b...

In this episode, we explore how financial decisions often bridge emotion, legacy, and precision. First, we answer a listener’s question about restoring a historic Virginia home and whether the available tax incentives justify the cost when renovations rival the purchase price. Next, we unpack how valuation discounts work for families transferring ownership of LLC interests — and why proper documen...

This week: the tradeoffs in triple net lease investing — comparing three smaller Starbucks properties to a single Walgreens location — and how to think about diversification, stability, and timing when committing $5 million to real estate. Then, a question from a family whose net worth now exceeds the estate tax threshold: what’s the smartest way to begin gifting to children through irrevocable tr...

This week, Stephan breaks down what to consider before converting a 401(k) to a Roth — from comparing current and future tax brackets to using partial conversions and asset location to minimize taxes. Next, he turns to the headlines about gold hitting record highs and explains how investors should think about gold’s role in a portfolio without getting caught up in short-term performance. And in ou...

This week: two listener questions that highlight the tension between family, finances, and legacy. First, we explore how couples can approach disagreements over whether to spend more now or preserve more wealth for their children. Next, we break down the risks of concentration when a large share of net worth is tied up in a family business, and how to weigh reinvesting versus diversifying. In our...

This week, we take on three listener questions that reveal the real-life complexity of wealth planning. First, how should parents handle fairness in gifting when one child values a large family wedding and another prefers a smaller celebration but asks for the same amount in cash? Next, a tech executive with most of his $6 million net worth tied up in stock options faces the uncertainty of an upco...

We start with a question from a couple who each set up SLATs during the high exemption years. With inflation and rising living costs, they’re now wondering whether to adjust trust distributions with cost-of-living increases or more flexible payout provisions. Stephan explains the options for modifying SLATs, the role of HEMS standards, and the trade-offs between flexibility, asset protection, and...

This week’s episode starts with a question from a couple who inherited complications after their parents passed with wills only. Now that their own estate is $5 million, they want to avoid the same outcome for their kids. Stephan explains when it makes sense to move from wills to a trust and the benefits of control, protection, and probate avoidance. Next, we hear from an investor pitched on a pri...

Is keeping all your cash and investments at one major bank simply convenient, or a hidden risk? Stephan explains the differences between FDIC and SIPC insurance, what each actually protects, and if splitting accounts across banks and custodians can provide a valuable safeguard for liquidity and access. Next, we explore how to select a distribution schedule for a nonqualified deferred compensation...

In this episode of the Scholar Wealth Podcast, Stephan Shipe answers three listener questions that highlight the real-world decisions families face at different stages of wealth. First, we look at a parent’s dilemma when their 23-year-old daughter wants to invest $50,000 in crypto. How can families encourage curiosity and independence in investing while setting guardrails to protect long-term weal...

This week’s episode opens with a listener wondering whether to help their brother with a down payment on a new home. The brother plans to repay the funds after selling his current house, but how do you balance protecting your wealth with supporting family? Stephan breaks down the risks, protections, and alternatives to consider. Next, we hear from an attorney preparing to make partner at their law...

In this episode of the Scholar Wealth Podcast, we tackle big wealth strategy questions. First, Stephan answers whether now is the right time to sell a gold coin collection worth $250,000, with gold prices at record highs. We cover how to value a gold collection, when to sell gold coins, and how to identify a fair auction house commission versus being taken advantage of. Next, we explore currency d...

This week’s episode starts with a question from a business owner preparing for a future liquidity event, with about $20 million currently tied up in private company stock. Stephan walks through how to manage the risk of overconcentration, ways to diversify before the sale, and how to preserve your business legacy through thoughtful planning. Next, we hear from a listener deciding whether to join a...

This week’s episode starts with a question from an executive who has about half of their net worth tied up in company stock. Stephan walks through why that level of concentration can be risky, how a 10b5-1 plan works, and the tax and compliance considerations that come with diversifying. Next, we hear from a parent who has been funding their kids’ 529 plans for years and is close to fully funded....

This week’s episode starts with a question from a family debating whether to keep their fractional jet ownership or buy a midsize jet outright. Stephan walks through the tax benefits, depreciation rules, and hidden costs that factor into the decision—and why the math isn’t as simple as cost per hour. Next, we hear from an executive with a large stock option package who wants to exercise wisely wit...