Selling a business is not a finish line. For most owners, it is the moment when years of deferred planning arrive all at once, and the gaps that were manageable inside a running company become deal-breakers, tax liabilities, or family disputes. Only 6% of business owners fully maximize the wealth they take from a sale. The other 94% leave money and, in many cases, legacy on the table. Michael Gold, founder and CEO of Gold Family Wealth in Westport, Connecticut, says the reason is almost always the same. “Lack of readiness,” he says. “People do not think about the end in mind early enough.”
The Joe Robbie Lesson No One Forgets
Gold reaches for history to make the point concrete. Joe Robbie built the Miami Dolphins into a franchise powerhouse during the Dan Marino era and privately funded the construction of his own stadium. When he died in 1990, his estate was asset-rich and liquidity-poor. Most of his wealth sat in real estate and the team itself, neither of which could be quickly converted to cash. After four years of legal fighting, his family was forced to sell the franchise for approximately $109 million. The IRS collected $43 million in estate taxes, and the remainder was disputed among heirs. The Dolphins are worth an estimated $12.5 billion today.
“Not being ready cost not only a legacy, but the impact to every generation of that family, forever,” Gold says. “How many causes could that money have supported? How many businesses could it have started? All because somebody didn’t take the time to plan in advance.” Gold describes the Robbie story as the extreme version of a pattern he sees constantly in his Westport practice: successful owners who spend decades building something valuable and almost no time preparing the structures that would protect it at transfer.
The consequences compound. A business worth $80 million with no liquidity plan leaves a family nine months to cover an estate tax bill that can run into the tens of millions. An owner who never separated personal finances from the business may have no income if the company is frozen in a legal dispute. The exit looks like freedom. Without preparation, it can become the opposite.
Three Categories of Gaps That Kill Deals and Destroy Value
Michael Gold organizes exit readiness failures into three distinct categories. Business gaps are the most visible to buyers. A company where all customer relationships run through the founder has a key person problem. The buyer is not acquiring a business; they are acquiring the owner’s Rolodex, and when the owner walks out, the value walks out with them. “If the customer only likes the owner, what am I buying?” Gold says. “There’s no management succession, no sales force, nothing like that.” A missing buy-sell agreement among partners creates another class of risk that surfaces only at the moment a deal needs to close.
Financial gaps are subtler but often more damaging. Gold cites a current client situation where the original business structure requires the owners to recharacterize their entity type and wait 12 months before selling, because executing the transaction now would generate a tax drag that would erode too much of the proceeds. “People do not think about the end in mind early enough,” he says. “So they restructure, or these things come up, and it kind of derails everything.” Tax structuring that would have taken months to implement years before the sale now requires a costly delay or a permanent reduction in what the family keeps.
Personal gaps are the third category, and Gold says they are the most frequently ignored. The question at the center of this category is straightforward: if you sold tomorrow, or were forced out suddenly, would your family be financially stable? Would there be continuity for employees and customers? Would the estate be structured to preserve wealth across generations, rather than funnel it to the IRS? As complexity grows, with real estate in multiple locations, blended families, business interests across entities, these questions become harder to answer without deliberate work done well in advance.
Battles Are Won Before They Are Fought
The moment Gold describes as the clearest sign that an owner needed to start planning years earlier is a phrase he hears too often: “We just signed an LOI, can you help us now?” A letter of intent begins the clock on a transaction. Tax structures cannot be put in place retroactively. Governance documents that should have been drafted over years cannot be assembled in weeks. The diagnostic work that would have identified gaps and addressed them systematically now has to happen under deal pressure, with limited options and limited time.
Gold’s process centers on what he calls “looking under the hood,” a systematic review of every aspect of a client’s financial architecture before any recommendation is made. “You have to look under every aspect to see if there are any gaps,” he says, “and if so, how severe they are, what the solutions are to address them, and what should you address first, second, third.” That sequence matters. Exit planning is not a checklist event. It is a continuous process that works best when it begins years before a transaction.
Gold closes with a principle drawn from Sun Tzu’s Art of War, a text he says he has read in more than 20 translations. His favorite line: “The battles are won in the temples.” The meaning, for Gold, is that preparation before the moment of action determines the outcome of that moment. Owners who treat an exit as the day they finally stop working are confusing liquidity with readiness. The two are not the same. Liquidity without structure, he argues, leads to fragility. What endures is what was built before the pressure arrived. “Wealth fades. Titles fade. But readiness endures.”
Investment advisory services offered through CWM, LLC, an SEC Registered Investment Advisor.
