About the show

The Scholar Wealth Podcast delivers clear, expert insights into the financial decisions that shape the lives of successful individuals and families of significant means. Every Monday morning, our team of highly credentialed financial advisors brings clarity to complex wealth challenges—through listener questions, conversations with subject-matter experts, and real stories of financial journeys.

This isn’t generic guidance or mass-market advice. It’s financial clarity for people with more at stake: physicians navigating equity compensation, entrepreneurs preparing for business exits, and families stewarding multigenerational wealth. Each episode offers trusted guidance, grounded in experience and fiduciary care.

Disclaimer: The information provided in this podcast is for general informational and educational purposes only, and is not intended to constitute financial, investment, or other professional advice, the opinions. expressed are those of the hosts and guests and do not necessarily reflect the views of any affiliated organizations. Investing in financial markets involves risk, including the potential loss of principle, past performance is not indicative of future results. Before making any investment decisions, you should consult with a qualified financial advisor, who can assess your individual financial situation, objectives and risk tolerance.

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Episodes

  • 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.

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    Episode 43: Lean Family Office Builds, Trump Accounts, and Angel Investing

    February 9th, 2026  |  32 mins 8 secs
    angel investing, child savings, concentration risk, family business, family office, financial literacy, private equity investment, retirement planning, tax planning

    In this episode, we answer two listener questions that highlight common decisions families face as financial structures and options expand. We discuss how to build a family office without overbuilding too early, how new Trump Accounts fit alongside existing child savings options, and close with a From the Field conversation on how angel investors evaluate risk and judgment when outcomes are uncertain.

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    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.

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    Episode 41: Choosing Charitable Impact, Wash Sale Rules, and Business Valuation in Practice

    January 26th, 2026  |  38 mins 36 secs
    business exit strategy, business valuation, charitable giving, charitable impact, estate planning, family business, nonprofit evaluation, portfolio rebalancing, tax loss harvesting, tax planning, wash sale rules

    In this episode, we explore how financial decisions can still feel complicated even when the numbers clearly work. The conversation covers how to choose impactful charitable giving without an existing connection, how wash sale rules show up in real-world portfolios, and a practical discussion with Mike Blake on how business valuations actually work in practice.

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    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.