Episode 75: Selling Your Business Beyond the Earnout, Family Loans and the IRS, Counterfeit Wine

September 21st, 2026  |  40 mins 43 secs

asset protection, business exit strategy, business sale deal structure, collectibles authentication, family gifting strategies, gifting strategies, inheritance planning, intrafamily loans, liquidity event, tax planning, wine collecting

This week on the Scholar Wealth Podcast, Stephan takes on two listener questions and is joined in From the Field by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. The first listener is preparing to sell his business and, after hearing our earlier earnout episode, wants to know what else in a deal structure can cost sellers at close. The second is a set of parents hoping to help their son and daughter-in-law buy their first home in an expensive market through a below-market family loan, and wants to understand what the IRS actually allows. Maureen walks through how fake wine ends up in top cellars, why an estimated one in five bottles of fine wine on the secondary market is counterfeit, and how The Chai Method authentication process works.

Episode 72: The Uninterested Heir, Earnout Reality Check, and Hiring a Nanny

August 31st, 2026  |  28 mins 42 secs

business exit strategy, business sale earnout planning, financial literacy, gifting strategies, gifting to adult children, household staff, inheritance planning, liquidity event, nanny, tax planning

A self-managed investor asks whether his 28-year-old son should use a wealth manager. A business owner selling on an earnout tries to figure out how much of it to plan around. And Stephanie Fornaro of Hello Nanny on the mistakes families make when they hire household support.

Episode 63: Partner Buyouts, the Surgeon's Retirement Cliff, and Executive Protection

June 29th, 2026  |  31 mins 4 secs

asset protection, business exit strategy, business valuation, estate planning, executive compensation, executive protection, income cliff planning, partnership buyout, physician finance, retirement planning, surgeon retirement

A founder with an $18M medical staffing business wants to buy out his 22% minority partner before selling in five to seven years, an orthopedic surgeon at 58 plans a retirement around a hard physical expiration date on his hands, and Brendan Weed of Arux Group walks through what personal security and executive protection actually look like for families with significant wealth and visibility.

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 59: Family Property Tax Traps, I Bonds vs. Treasury Ladders, and Rethinking the Prenup with Aaron Thomas

June 1st, 2026  |  40 mins 33 secs

asset protection, business exit strategy, cash management, corporate cash strategy, estate planning, family property tax, gifting strategies, i bonds, inflation planning, liquidity event, prenuptial agreements, real estate investing, tax planning, treasury laddering, vacation rental

Three properties, family use, and a CPA raising tax flags. Twelve million in cash and the I bonds versus Treasury ladder debate. Then Aaron Thomas, founder of Prenups.com and one of the country's leading family law attorneys, joins Stephan to reframe prenuptial agreements as foundational tools for clarity and alignment, not defensive instruments.

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 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 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 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.