The Scholar Wealth Podcast

A listener writes in after reading about a new insurance product that covers trustee theft, with up to ten million in coverage. He's weighing whether to add it as protection for his children when the trust eventually passes to them. Stephan works through why the insurance itself isn't the first question to answer, how single-trustee structures create the underlying risk, what a corporate co-truste...

A listener preparing to sell his business writes in after our earlier episode on earnouts. He now understands that piece of the deal, but wants to know what else could cost him at close. Stephan walks through the parts of a transaction that get less attention than the headline number: rollover equity, escrow holdbacks, working capital true-ups, and reps and warranties. Each one moves the number th...

A high-earning locums anesthesiologist wants to know whether stacking a $200K cash balance plan on top of a maxed solo 401(k) is worth the added complexity. Stephan works through when it makes sense, when it doesn't, and why a taxable brokerage should probably come first. A plaintiff's attorney whose income swings from $380K to $2.1M year to year, with no plans to retire, wants a real system inste...

A listener was asked to serve as executor of a close friend's estate: fifteen million dollars, three properties, a business, and two adult children who don't speak to each other. She said yes and is now second-guessing it. We walk through what the executor role actually involves, why illiquid assets and family dynamics make this kind of estate particularly risky to take on, and how a corporate co-...

A self-managed investor with a $13 million portfolio is thinking about suggesting a wealth manager to his 28-year-old son. His son isn't reckless, but he's not interested in investing either, and the gifts they make just sit in his checking account. Stephan walks through why the real question isn't the fee, why five minutes a year in one or two index funds often solves the immediate problem, and w...

This week we're dedicating the full episode to a conversation with Anthony Bolognese, founder of Capitol Hill Clothiers . Anthony is a DC-based custom clothier who works with attorneys, lobbyists, business owners, and a handful of clients whose day-to-day requires more than a nice fabric. Stephan and Anthony get into the real differences between off-the-rack, made-to-measure, and true bespoke, and...

A couple planning to buy a $2.8 million second home in Boulder is weighing three ways to fund the purchase: pay cash, put 25 percent down and finance the rest with a jumbo mortgage, or open a securities-based line of credit against the portfolio. She does not want to disrupt the tax picture by selling; he is opposed to the SBLOC. Stephan walks through the two questions that actually determine the...

A listener with a significant concentrated stock position asks whether he should enroll in Vanguard's Fully Paid Lending Program to earn extra income on the shares he already owns. On paper it looks like free income. Stephan walks through how fully paid securities lending actually works, why the economics rarely justify it for a retail investor, how substitute dividend payments change the tax trea...

This week Noah Lewis and Evan Mills take the mic for another speed round, running through seven of your shorter questions in quick succession. The conversation ranges from the mechanics of individual bonds versus bond index funds at a $5M portfolio scale, to whether adding QQQ or MAGS actually diversifies an already tech-heavy IRA, to how to evaluate a multi-manager private credit fund pitched as...

Two locum tenens physicians spent years grinding to reach financial independence at 45. Three years in, the portfolio is fine, but they're spending closer to $100,000 against a plan that said $200,000, and one spouse can't get past the saving habit long enough to trust the number they built. Stephan walks through why post-FIRE underspending is more common than overspending, and the double-brokerag...

At $800K of income, a listener realizes his CPA is filing history rather than shaping strategy — great in March, invisible the other eleven months. Stephan digs into why the accounting business is structured that way, how it changes as income climbs past $500K to $800K and beyond, and what real proactive planning actually looks like at that level. Entity structure, retirement plan design, charitab...

We open with a tech executive in the Bay Area, mid-forties, around $18M invested, trying to be more strategic about IPO access after landing only 13% of his SpaceX allocation through Schwab. Stephan walks through how the offer process actually works, why IPO underpricing makes the first-day pop where the real return lives, and why the brokerage relationship matters more than the size of your balan...

An 88-year-old mother wants to start gifting to her grandchildren now, while she's still around to see it. The complication is fifty years of embedded gains in one brokerage account, and a question about whether lifetime gifting quietly sacrifices the step-up at death. Stephan works through the textbook answer, the realistic answer, and where the two diverge. A 51-year-old executive has been defau...

This week on the Scholar Wealth Podcast, we open with a founder who built a regional medical staffing company to roughly $20 million in revenue and brought on a minority partner three years ago when he was burning out. The partnership delivered, but their visions for the next five years have split, the buyout clause in their operating agreement leaves the valuation methodology open to interpretati...

This quarter's Scholar Big Picture conversation runs the full episode. Deon Strickland, financial advisor at Scholar Advising, in-house economist, and finance professor at Wake Forest University, joins Stephan to work through the most consequential shift in public markets right now: the SpaceX IPO and what its $2.5 trillion valuation says about how investors are pricing the tail scenarios on AI. F...

This week we open with a listener in her early sixties who has managed every dollar of her family's nineteen-million-dollar balance sheet for thirty years, while her husband has never opened a statement. A recent health scare has forced the question of what happens when the spouse who runs everything is suddenly out of the picture. Stephan walks through the operational knowledge gap that shows up...

Brandon Mendez, Ph. D., CPA, Professor of Finance at the Darla Moore School of Business at the University of South Carolina, joins Stephan in the studio for a conversation on the wave of business acquisitions reshaping private markets right now. With a generation of business owners hitting retirement age at the same time, private equity firms are moving fast, and individual buyers are competing in...

A couple owns three properties across two states and has been letting their adult children and grandchildren use them freely. Their CPA recently raised concerns about imputed rental income and gift tax. Stephan walks through where the real risk actually sits, why personal use among family typically doesn't trigger imputed income rules, and when the picture genuinely changes — namely, when a proper...

"In this episode, we hear from a business owner in his mid-forties with around ten million saved who has noticed that every financial milestone, hitting his first million, paying off the house, watching the number keep climbing, has failed to bring the sense of arrival he expected. Stephan walks through why the pattern is so common, how the marginal value of every additional dollar changes once ba...

This week we're doing something a little different. Instead of the usual two-question format with a guest interview, we're handing the mic over to Associate Financial Advisors Noah Lewis and Evan Mills for a Q&A speed round covering eight shorter questions from listeners. The first half focuses on investing. Noah and Evan discuss how to think about AI as a structural shift without taking on ou...

A listener with $18 million at a wirehouse advisor is paying just over $200,000 a year in AUM fees and was told by his advisor that there's no way he could handle a portfolio that size on his own. Stephan separates the management of money from the advice on money, walks through why the AUM model scales well for advisors but poorly for clients, and gives a real answer on where the threshold for sel...

When you have a $40 million estate and four grandchildren, superfunding 529s can feel like an obvious estate planning move — but the math isn't always as clean as it looks. Stephan explains how the five-year election works, how it interacts with your annual gifting strategy, and why at this level of wealth, 529s may be the wrong vehicle entirely when compared to trusts, GRATs, or direct giving. Ne...

This episode was recorded live at our 2026 annual personal wealth conference at the Grove Park Inn in Asheville, North Carolina, where about 60 investors, business owners, and successful families gathered for two days of focused conversations on markets, strategy, and long-term wealth planning. Stephan is joined by Deon Strickland, Ph. D. and Derek Cheshire, CFP®, EA to answer questions submitted...

A listener shares that they've given their adult son roughly $180,000 informally over the years and it hasn't solved anything. Stephan walks through how to shift from reactive giving to intentional structure, including savings match programs, conditional support tied to milestones, and when a discretionary trust makes sense. Then, a consultant asks about layering a cash balance plan on top of a ma...

A listener wants to split a $250,000 private real estate loan between a Roth IRA and non-qualified funds — and charge each portion a different interest rate to maximize tax-free growth. Stephan breaks down why that structure raises serious prohibited transaction red flags, what the IRS is actually looking for, and why the risk-reward calculus may not add up. Then, a listener with newly obtained EU...