Episode 54: Mortgages, Trusts, Hedge Funds, and More: Live Q&A from Our Annual Conference

April 27th, 2026  |  35 mins 10 secs

estate planning, financial literacy, gifting strategies, incentive stock options, inheritance planning, live q&a, real estate investing, real estate syndication, retirement planning, stock option exercise, talking to kids about money, tax planning, trust distribution, trust strategies

This week, we're bringing you something a little different. This episode was recorded live at our 2026 annual personal wealth conference at the Grove Park Inn in Asheville, North Carolina. Stephan is joined by Deon Strickland, Ph.D. and Derek Cheshire, CFP®, EA for a live Q&A panel, fielding questions submitted on the spot by conference attendees. Topics include the pros and cons of paying cash for a home, annual gift tax exclusion strategies for large families, structuring inheritances for young adults, trust disputes between beneficiaries, troubled real estate syndications, ISO exercises and AMT credits, talking to your kids about money, evaluating a hedge fund, and navigating a parent's estate after a spouse passes.

Episode 52: Self-Directed IRAs, EU Citizenship, and the K-Shaped Economy - Scholar Big Picture with Dr. Deon Strickland

April 13th, 2026  |  36 mins 10 secs

asset protection, fbar reporting, foreign bank accounts, international planning, k-shaped economy, market timing, portfolio rebalancing, prohibited transactions, real estate investing, self-directed ira, tax planning

Stephan breaks down why splitting a private real estate loan between a Roth IRA and non-qualified funds at different interest rates is a prohibited transaction risk — and what to do instead. Then, a listener with newly obtained EU citizenship wants to know what U.S. tax and reporting obligations come with foreign bank accounts. To close, Dr. Deon Strickland joins for the quarterly Scholar Big Picture conversation on the K-shaped economy, what AI means for labor versus equity returns, and why industrial metals may be worth watching.

Episode 51: Rachel Cruze of The Ramsey Show on Raising Money-Smart Kids, DAFs vs. Private Foundations, and Getting Into Alternatives

April 6th, 2026  |  36 mins 25 secs

alternative investments, charitable giving, donor-advised funds, estate planning, family business, family philanthropy, financial literacy, generational wealth transfer, gifting strategies, inheritance planning, parenting and money, private equity investment, private foundations, real estate investing, rental property, tax planning, third-generation wealth, trust strategies

Rachel Cruze, author and co-host of The Ramsey Show, joins us to talk about how financial values are formed, passed down, and sometimes lost across generations. We also look at when a private foundation makes more sense than a donor-advised fund for a family giving $200,000 a year, and whether rental real estate is a smart entry point into alternatives — or just trading one set of risks for another.

Episode 49: Delaware Statutory Trusts, Illiquid Business Wealth, and Designing Legacy Homes

March 23rd, 2026  |  29 mins 19 secs

1031 exchanges, business exit strategy, business owner retirement strategy, concentration risk, delaware statutory trusts, illiquid wealth planning, liquidity event, luxury home design, real estate investing, retirement planning, tax planning

In this episode, we explore how to exit appreciated rental real estate without triggering unnecessary taxes, how entrepreneurs can rebalance wealth away from an illiquid business ahead of a future sale, and in our From the Field segment, what truly distinguishes exceptional luxury residences designed to endure across generations.

Episode 45: Family Travel Fairness, STR Bonus Depreciation, and Digital Risk Management

February 23rd, 2026  |  37 mins 26 secs

asset protection, bonus depreciation, charitable giving, cybersecurity, family dynamics, financial literacy, gifting strategies, intergenerational wealth, real estate investing, short-term rentals, tax planning, vacation rental

In this episode, we explore how complexity shows up in family dynamics, tax strategy, and digital risk. We discuss how parents can navigate lifestyle differences among adult children without falling into the reallocation trap, unpack how bonus depreciation for short-term rentals actually works under the One Big Beautiful Bill, and close with a From the Field conversation on modern cybersecurity risks facing high-profile families and family offices.

Episode 42: Managing Inherited Property, Protecting Physician Wealth, and Inside the Bourbon Market

February 2nd, 2026  |  42 mins 57 secs

asset protection, bourbon collecting, concentration risk, estate planning, financial literacy, inheritance planning, inherited property, legal exposure, ownership tradeoffs, passion investing, physician finance, real estate investing, tax planning, trust strategies, vacation rental

In this episode, we answer two listener questions that highlight common tradeoffs as wealth and complexity grow. We discuss how to approach inherited real estate when illiquidity and emotional attachment are involved, how high-net-worth physicians can think about asset protection as income and exposure rise together, and close with a From the Field conversation on what actually drives quality and value in the bourbon market.

Episode 40: Solar Tax Write-Offs, Franchise Investment Decisions, and the Scholar Big Picture

January 19th, 2026  |  38 mins 1 sec

commercial solar investing, concentration risk, financial literacy, franchise investing, inflation planning, investment due diligence, market timing, passive investment myths, private equity investment, real estate investing, tax driven investments, tax planning

In this episode of the Scholar Wealth Podcast, Stephan answers two listener questions focused on evaluating investments that look attractive on paper but require deeper analysis. We start with commercial solar investments and large tax write-offs, then turn to franchising and what investors should consider before committing meaningful capital. The episode closes with the Scholar Big Picture, a quarterly conversation with Dr. Deon Strickland on market behavior, economic uncertainty, and what to watch right now.

Episode 39: 529 Planning in an AI World, Raising Grounded Kids, and Understanding REITs

January 12th, 2026  |  28 mins 51 secs

529 plans, financial literacy, higher education, inheritance planning, lifestyle inflation, raising grounded kids, real estate investing, reits, tax planning

In this episode of the Scholar Wealth Podcast, we start with two listener questions facing many high-income families today. First, we discuss how to think about funding a 529 plan when AI is rapidly changing education, careers, and credentialing, and how to plan for college without overcommitting to a single path. We then turn to a lifestyle question about enjoying financial success while raising kids who stay grounded and understand the value of money. In the second half of the episode, we’re joined by Dr. Stace Sirmans, Professor of Finance at Auburn University, for a clear, academic explanation of how REITs work and how they’re structured.

Episode 38: Social Security Timing, Home Sale Capital Gains, and Educational Travel with Road Scholar

January 5th, 2026  |  31 mins 12 secs

capital gains tax, estate planning, financial independence, inflation planning, inheritance planning, longevity planning, multigenerational travel planning, primary residence sale, real estate investing, retirement planning, social security timing, tax planning

In this episode, we answer two listener questions that highlight common retirement planning tradeoffs. We discuss Social Security timing for high earners, capital gains considerations when selling a long-held primary residence, and how families think about prioritizing meaningful experiences through educational travel with Road Scholar.

Episode 37: Qualified Opportunity Zones, IDGTs, and Modern Estate Management

December 29th, 2025  |  38 mins 25 secs

business exit strategy, business sale planning, estate management, estate planning, family business, high-net-worth home management, inheritance planning, intentionally defective grantor trust, liquidity event, qualified opportunity zones, real estate investing, tax planning, trust strategies

Evaluating Qualified Opportunity Zone investments after a large business sale requires balancing tax incentives with risk and liquidity.

IDGTs can help transfer future business growth, but they introduce meaningful cash flow and complexity considerations.

In our From the Field conversation, Peter Hansen explains what modern estate management looks like and how staffing and systems help homes run smoothly.