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 34: Buying a €450K Home Abroad, Planning Around Carried Interest, and Building a Wine Collection That Lasts

December 8th, 2025  |  34 mins 34 secs

carried interest, concentration risk, cross-border real estate, deferred compensation, estate planning, inheritance planning, international planning, legacy assets, private equity compensation, private equity investment, real estate investing, tax planning, vacation rental, wine collecting

Buying a €450K family home in Portugal often involves emotion, complex tax rules, and long-term management considerations.

Carried interest can be valuable, but payouts are uncertain. Planning should assume a base case of no carry and treat future distributions as upside.

Wine expert Walker Strangis explains how families can build and maintain collections with both personal meaning and financial value.