Episode Archive

55 episodes of The Scholar Wealth Podcast since the first episode, which aired on April 21st, 2025.

  • Episode 55: 529 Superfunding, Evaluating Memberships After a Liquidity Event, and Concierge Nursing

    May 4th, 2026  |  30 mins 28 secs
    529 planning, concierge healthcare, estate planning, financial independence, financial literacy, gifting strategies, liquidity event, private club memberships, retirement planning

    This week on the Scholar Wealth Podcast, Stephan walks through how 529 superfunding works, how it interacts with an existing annual gifting strategy, and whether it's actually the right estate planning tool for a family with a $40 million estate. He then breaks down a framework for evaluating the flood of pitches that follow a liquidity event — golf clubs, city clubs, private aviation cards, and family office intro services — and how to separate what's genuinely worth it from what just sounds like it should be. Finally, Jasmine Bhatti, founder and CEO of NaviNurses, joins to discuss the personalized healthcare landscape: from private duty nursing and post-surgical recovery care to concierge medicine, longevity practitioners, and integrative health.

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    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.

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    Episode 53: Structured Family Support, Cash Balance Plans, and Hiring a Private Chef

    April 20th, 2026  |  31 mins 52 secs
    adult child financial support, asset protection, business exit strategy, cash balance plan, charitable giving, defined benefit plan, domestic staff hiring, estate planning, family business, family gifting strategy, financial independence, gifting strategies, inheritance planning, private chef placement, retirement contribution stacking, retirement planning, solo 401k, tax planning

    A listener asks how to structure financial support for an adult child in a way that builds accountability rather than dependence. Then, a consultant explores whether layering a cash balance plan on top of a solo 401(k) makes sense, and what the long-term funding commitment actually looks like. Chris Demaillet, founder of Montclair Chef, joins From the Field to discuss what families need to know before hiring a private chef.

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    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.

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    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.

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    Episode 50: PE Exit Prep, Offshore Account Reporting, and Protecting Collector Vehicles with Hagerty's Trent Abbott

    March 30th, 2026  |  34 mins 50 secs
    asset protection, business exit strategy, car insurance, expat tax planning, family business, financial literacy, foreign account compliance, international planning, liquidity event, pe sale preparation, physician finance, private equity investment, specialty asset coverage, tax planning

    This week on the Scholar Wealth Podcast, Stephan walks through what a business owner should be doing in the years before entering a formal sale process, using the example of a regional physical therapy group fielding private equity interest. He then addresses the foreign account reporting obligations that can put returning expats out of compliance without realizing it. Finally, Trent Abbott, Vice President of Global Development at Hagerty, joins to discuss how families with significant vehicle collections should think about specialty insurance, agreed value coverage, and the unique risks that standard auto policies miss.

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    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.

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    Episode 48: Stock Compensation, Inherited IRA Taxes, and Documenting Family Legacy

    March 16th, 2026  |  36 mins 47 secs
    employee stock compensation, equity compensation, executive compensation, family legacy planning, financial literacy, inheritance planning, inherited ira, legacy storytelling, tax planning

    In this episode, we examine why publicly traded companies often compensate employees with stock instead of cash and how equity-based pay structures align incentives while creating new risks for employees. We then discuss the tax challenges of inheriting a large traditional IRA under the 10-year distribution rule and explore strategies for managing the resulting tax burden. Finally, in our From the Field segment, we speak with Susan Brody, founder of Family Legacy Videos, about preserving family stories, values, and history across generations.

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    Episode 47: AI Concentration Risk, Concierge Medicine, and Avoiding Trust Disputes

    March 9th, 2026  |  34 mins 22 secs
    concentration risk, concierge medicine, estate planning, fiduciary litigation, financial independence, healthcare planning, market timing, portfolio rebalancing, retirement planning, tech concentration, trust strategies

    In this episode, we discuss how to manage concentrated exposure to AI-driven tech gains without turning rebalancing into market timing, evaluate whether catastrophic coverage paired with concierge medicine is a rational strategy after financial independence, and speak with fiduciary litigator Ellen Morris about what families can do to proactively reduce trust and estate conflicts.

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    Episode 46: Evaluating PPLI, Investing in a Child’s Startup, and Cross-Border Tax Complexity

    March 2nd, 2026  |  37 mins 32 secs
    advanced tax strategies, complex wealth structures, cross-border planning, estate planning, family business, family capital decisions, international planning, private equity investment, tax planning, venture investing

    In this episode, we examine three sophisticated planning decisions that sit at the intersection of tax efficiency, family dynamics, and global mobility. We break down how affluent families should evaluate Private Placement Life Insurance beyond the marketing pitch, how to thoughtfully approach investing in a child’s venture-backed startup without distorting incentives or relationships, and close with a From the Field conversation on the real tax and structural complexities of building a life across borders.

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    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.

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    Episode 44: Oil Well Concentration Risk, Australian Superannuation, and Learning to Fly

    February 16th, 2026  |  27 mins 48 secs
    alternative investments, australian superannuation, concentration risk, cross-border tax planning, international planning, oil well investing, pilot licensing, private equity investment, tax planning

    In this episode, we answer two listener questions that highlight how complexity shows up in both private investments and cross-border planning. We discuss concentration risk in private oil well investments and how to think about projected IRRs and illiquidity within an alternatives allocation, then examine how dual U.S.–Australian families should approach Australian superannuation when retiring in the United States. We close with a From the Field conversation on what pilot licensing actually looks like for busy professionals, from training timelines to the real costs and lifestyle flexibility of aviation.