The Scholar Wealth Podcast

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...

This week, Rachel Cruze — author, speaker, and co-host of The Ramsey Show — joins Stephan for a candid conversation about the third-generation wealth trap, the mistakes well-intentioned parents make, and how to raise kids who can actually handle money. Rachel shares what it was like growing up as Dave Ramsey's daughter, how she's navigating those same questions with her own three kids today, and t...

If you're thinking about selling your business in the next few years, the most important work happens before you ever hire a banker. Stephan breaks down how to reduce owner dependency, clean up financials, identify synergistic buyers, and position a business to command the highest possible multiple, using the example of a physical therapy group with 14 locations and growing PE interest. Next, Step...

In this episode, we begin with a listener looking to simplify a real estate portfolio in their early 60s. With multiple properties and significant appreciation, selling outright would trigger both capital gains and depreciation recapture. Stephan walks through how Delaware Statutory Trusts function within a 1031 exchange, the appeal of moving from active management to passive ownership, and the tr...

Why do companies sometimes pay employees with stock instead of cash? And what happens when you inherit a multi-million-dollar IRA under the 10-year rule? In this episode of the Scholar Wealth Podcast, we answer two listener questions that highlight how compensation structures and tax rules shape financial decisions. First, we examine why publicly traded companies use equity compensation for employ...

This week, we begin with a listener whose $6 million portfolio has drifted from 25% to 42% in large-cap tech following the AI-driven surge. Stephan reframes the issue as portfolio drift rather than a market call, and walks through how to think about concentration risk, disciplined rebalancing, and tax-aware trimming without reacting to headlines. Next, we examine healthcare planning after financia...

This week, we begin with a listener question about Private Placement Life Insurance. While the promise of tax-deferred growth and liquidity through policy loans can sound compelling, Stephan walks through the real tradeoffs: layered fees, insurance drag, liquidity constraints, and whether similar outcomes can be achieved more simply through traditional brokerage structures and securities-backed le...

This week: a family with three adult children is navigating an unexpected tension: two children still travel privately with their parents, while one prefers to fly commercial and would like the unused travel spend redirected toward charitable giving. We discuss the difference between gifting an experience and gifting cash, why fair does not always mean identical outcomes, and how families can use...

In this episode of the Scholar Wealth Podcast, we answer two listener questions that highlight how risk, complexity, and discipline show up in real financial decisions. First, a listener who recently sold part of a business and now has $12 million invested asks whether allocating $750,000, half of their alternatives bucket, to a single private oil well investment makes sense. We discuss concentrat...

How lean is too lean when building a family office, and when does early flexibility turn into future complexity? In this episode, we answer a listener question on scaling a family office thoughtfully, including the role of fractional CFOs and CIOs, outsourcing functions like cybersecurity and bookkeeping, and knowing when it makes sense to bring capabilities in-house. Next, we discuss Trump Accoun...

What should you do when a large portion of your wealth is tied up in illiquid or misunderstood assets? In this episode, we tackle a listener question from someone who inherited a substantial real estate portfolio, including a primary residence, a vacation home, and rental properties. He walks through how to separate emotional and economic decisions, evaluate real estate as an investment, and avoid...

This week, we begin with a listener question on charitable giving. When there is room in the plan to give meaningfully but no personal connection to a specific organization, Stephan discusses how to think about impact, why local giving can matter at this scale, and how to evaluate organizations without falling into decision paralysis. Next, a common tax planning concern around wash sale rules. Ste...

This week on the Scholar Wealth Podcast, we tackle two listener questions that highlight a common challenge for high-income investors: how to evaluate opportunities that come with compelling tax benefits or strong projected returns, but also meaningful risk. First, Stephan breaks down commercial solar investments that advertise large tax write-offs. We discuss how these tax benefits are generated,...