Episode 61: Preparing the Spouse Who Doesn't Manage the Money, When Vacation Rental Income Disappears, and Preparing Heirs with Jessica McGawley

June 15th, 2026  |  29 mins 9 secs

asset protection, estate planning, family business, family governance, family wealth transfer, financial literacy, gifting strategies, inheritance planning, real estate investing, retirement planning, spousal financial planning, trust strategies, vacation rental

A wife who has managed every dollar of her family's $19 million for thirty years faces the reality that her husband doesn't know where any of it is. A couple at 63 lose their beach house rental income overnight when a zoning change kills VRBO on their street. And in From the Field, Jessica McGawley of Dallington joins us on preparing the next generation for wealth, not just preparing the wealth for them.

Episode 60: Buying a Business in the Era of Mass Retirement

June 8th, 2026  |  42 mins 42 secs

asset protection, business acquisitions, business exit strategy, business valuation, due diligence, family business, financial independence, mass retirement, private equity investment, seller discretionary earnings

Brandon Mendez, Ph.D., CPA, Professor of Finance at the Darla Moore School of Business and U.S. Navy veteran, joins Stephan in the studio for a full-episode conversation on what it actually takes to buy a business today. They cover how to read multiples and seller discretionary earnings, why private equity has a structural edge over individual buyers, what AI is doing to the talent side of acquisitions, and where the real red flags hide in a set of financial statements.

Episode 56: $200K a Year in AUM Fees, Buying Your Nanny a Car, and Education with Lindsay Tanne Howe

May 11th, 2026  |  38 mins 23 secs

asset protection, aum fees, education planning, estate planning, family business, family relocation strategy, financial independence, financial literacy, higher education, household employee planning, international planning, liquidity event, tax planning

This week on the Scholar Wealth Podcast, Stephan tackles a listener paying his wirehouse advisor over $200,000 a year on $18 million in AUM and wondering whether self-management really has the threshold his advisor claims. He then walks through the right way for a family to provide a vehicle for their full-time nanny, covering insurance, title, and the cleanest structures for everyone involved. Finally, Lindsay Tanne Howe, founder and CEO of LogicPrep, returns to the show for a conversation on how education is increasingly driving where families choose to live, the rise of new global hubs from Lisbon to South Florida, and how AI is reshaping both the college admissions process and the curriculum on the other side of it.

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.

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 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.

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.

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.

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.

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.