Alan Tinsmon: What Wealthy Families Get Wrong About Happiness

In this episode, Pat sits down with a longtime friend, Alan Tinsmon - someone he's known since they were twelve-year-old wrestlers riding a bus together to summer camp at St. Lawrence University. Alan grew up in the Albany area after an early childhood in Rochester, New York, and shares how a middle school gym teacher first pointed him toward wrestling - a sport neither Pat nor Alan competes in anymore, but one they both still follow obsessively (the NCAA wrestling tournament remains, hands down, their Super Bowl).The conversation traces Alan's career from SUNY Oswego to Barnett Bank in Florida, then into the chaos of the savings and loan crisis working bank closures for the FDIC in his early twenties - including getting called "an arrogant young punk wielding imaginary powers" in a letter to a U.S. congressman. From there, Alan spent a decade at Serta Mattress Company moving across the country through a wave of acquisitions, before landing in a family office role he's now held for over 30 years, coordinating investment, estate, and philanthropic strategy for a family spanning five generations.The back half of the conversation turns reflective, with Pat and Alan digging into what actually makes wealthy families happy and functional (hint: it starts with health, not money), the challenge, and quiet burden, facing next-generation heirs of family businesses, the discipline required to avoid emotional investing, and the value of long-term, trust-based relationships built over decades rather than transactions.