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

A listener preparing to sell his business writes in after our earlier episode on earnouts. He now understands that piece of the deal, but wants to know what else could cost him at close. Stephan walks through the parts of a transaction that get less attention than the headline number: rollover equity, escrow holdbacks, working capital true-ups, and reps and warranties. Each one moves the number the seller actually keeps, and each one is negotiable if you know it's there before you sign the LOI.

Next, a set of parents wants to help their son and daughter-in-law buy their first home in a market where the math no longer works on a conventional mortgage. They're considering a family loan at a rate well below what the bank would offer. Stephan covers what the IRS requires to keep a family loan from being reclassified as a gift, how the Applicable Federal Rate sets the floor, and the family dynamics worth thinking through before the money moves, especially when a spouse is on the other side of the note.

Then, in our From the Field segment, we're joined by Maureen Downey, founder of Chai Consulting and one of the foremost independent authorities on counterfeit wine. Maureen has advised the FBI and DOJ on major wine fraud cases and developed The Chai Method, the authentication process used by top auction houses, insurers, and private collectors. She explains why an estimated 20 percent of fine wine on the secondary market is counterfeit, how fakes end up in some of the most respected cellars in the world, and what collectors and their advisors should be doing before writing the next check.

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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 principal. 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. Thanks for listening!