Westport advisor Michael Gold on educating the next generation before an exit

Michael Gold has spent more than 25 years working with business owners approaching exits. What strikes him most consistently centers on what they have overlooked rather than what they have assembled. Most of the readiness work has been focused on the transaction itself: valuation, deal structure, tax treatment at closing. What happens to the family after the wire transfer rarely receives the same attention. A JPMorgan Chase survey found that 70% of small business owners have no formal succession plan or are only in early-stage planning, and just 8% report being fully prepared to transition ownership. When asked in a recent interview, Michael Gold, founder and CEO of Gold Family Wealth in Westport, Connecticut, to name the single most common mistake, his answer was two words. “Lack of readiness,” Gold said. The readiness gap he describes runs deeper than the balance sheet. It lives in the people who will be responsible for the wealth after the exit, and whether they have been prepared for it. The proceeds transfer into families whose rising generation has never been asked what stewardship means, never participated in a structured governance framework, and never had a values conversation that happened before the wealth arrived rather than after it. The window that closes before the sale The pre-exit period is the only time preparation can happen without the distortions that newly arrived wealth introduces. After a sale, conversations about values are crowded out by questions of distribution. After a transfer, education happens under pressure. Before the LOI is signed, a family can explore what stewardship means in the context of earning and building, not receiving. The window is narrow, and most founders let it close. The consequences, at the extreme end, are clear. Joe Robbie built the Miami Dolphins from nothing. He died in 1990 without adequate estate planning, with the bulk of his assets in illiquid holdings. His family was forced to sell the franchise four years later for $109 million, with roughly $43 million absorbed by estate taxes, the remainder divided among heirs who had spent those years in litigation. The franchise is now worth $12.5 billion. The Robbie family’s name on the stadium was gone within a decade. Gold draws on a framework from Sun Tzu that he has read in more than 20 translations. “My favorite quote, Sun Tzu, The Art of War is, ‘The battles are won in the temples,'” he says. “It’s my favorite quote because that is a matter of being ready.” The battle for multigenerational wealth, in Gold’s view, is not won in the legal documents drafted after the LOI is signed. It is won in the preparation that happens years earlier, in the conversations and structures built before the transaction is even on the table. Preparing heirs for what they did not earn Gold’s Westport practice uses a Family Council structure as the mechanism through which next-generation preparation happens before a liquidity event: a formal governance body that functions as the board of directors of the family enterprise. Families that have built this kind of structure before a sale arrive with shared decision-making processes, a common vocabulary around wealth and responsibility, and some experience functioning as a collective. Those that have not often discover how little alignment actually existed once the money is real. In the forthcoming book, “The GoldPrint”, Gold writes directly to the children of exiting owners: “Your parents can leave you wealth, but the true gift is wisdom; that’s what sustains a family for generations.” A Dynasty Trust, properly designed, exists to create responsible stewards of what took a generation to build. Gold’s own discipline is instructive. He wakes at 4:35 every morning and maintains a written daily plan across every area of his life: career, finances, family, health, spouse, hobbies, and long-term goals in each. “I’m up at 4:35 every day. I don’t want to, like that alarm goes off,” he says. “By the time I get to the office, I’ve done more than 99% of the people.” The model he brings to clients is the same one he imposes on himself: preparation before the moment of decision, structure before the crisis arrives. Cerulli Associates projects $124 trillion will transfer between generations through 2048. Most of it will land in the hands of heirs whose preparation varied enormously. The families whose next generation has been educated for stewardship before the sale, rather than surprised by wealth after it, are the ones most likely to still be managing that wealth three generations from now. The pre-exit window is when that education can actually happen. Gold’s argument is that founders who spend years building something and then fail to prepare their heirs for it have answered only the easier half of the question. DISCLAIMER – “Views Expressed Disclaimer – The information provided in this content is intended for general informational purposes only and should not be considered financial, investment, legal, tax, or health advice, nor relied upon as a substitute for professional guidance tailored to your personal circumstances. The opinions expressed are solely those of the author and do not necessarily represent the views of any other individual, organization, agency, employer, or company, including NEO CYMED PUBLISHING LIMITED (operating under the name Cyprus-Mail).