Nearly 200,000 UHNW families are in the U.S., a 20.5% increase from 2023. Globally, the ultra-high-net-worth population has grown 12.4%, pushing the total to over 484,000 individuals. Heading into 2026, these families face the largest intergenerational wealth transfer in history, with $84 to $120 trillion projected to move between generations over the next two decades.
Yet most families are unprepared. Michael Gold, founder and CEO of Gold Family Wealth in Westport, Connecticut, says the single most common mistake he sees comes down to one word: readiness.
“Lack of readiness and fragmented advice,” he says. “Most people, when they get referred to us, say they just signed an LOI. Can you help us now?”
The problem is that arriving late to the planning process can leave families vulnerable to gaps that can cost millions or destroy legacies entirely.
The $8 Billion Mistake
Michael Gold uses a case study that drives the point home. Joe Robbie, owner of the Miami Dolphins in the 1980s, died in 1990 without proper planning. The estate tax bill came due, but his assets were illiquid, tied up in real estate and the team itself. After four years of fighting, his family sold the Dolphins for roughly $109 million. $47 million went to the IRS. The rest was divided among heirs.
The Miami Dolphins are worth approximately $7.5 billion today.
“That’s why we don’t hear about the Robbie dynasty like we hear about the Rockefeller dynasty,” Michael Gold says. “Not being ready can cost not only a legacy, but forget about just the impact every generation of your family will have forever. If there were philanthropic causes somebody in the family cared about, how much of an impact could that money have made beyond just the family? All because somebody didn’t take the time to plan in advance.”
Where Readiness Fails
The Westport advisor says readiness failures happen across three layers: business, financial, and personal.
On the business side, families fail to address structural issues years before an exit. Some need to re-characterize their business structure, which means waiting 12 months to sell because the tax drag would be too severe. Others face customer concentration issues. “If I’m buying somebody and the customers only like the owner, what am I buying?” he says.
There is often no management succession, no sales force depth, and no buy-sell agreements among partners. These gaps can reduce enterprise value or derail exits entirely.
The financial layer is just as problematic. Families have assets spread across jurisdictions and entities, but no coordinated view of how everything fits together. Michael Gold compares his approach to a neurosurgeon, not a salesperson. “I had three spine surgeries. Not at one point was the surgeon like, so what do you think about this or that?” he says. “They did a suite of tests, laid out all the options from conservative to aggressive, and almost tried to push off surgery in every case.”
Wealth advisors should operate the same way. “We need to really understand the client’s business, their family, what’s going on on their net worth statement, their risk management, their kids, their professional life, all the things. Then we can see what gaps and/or missed opportunities exist and lay them out in priority order,” he says.
Looking Under the Hood
The personal layer is where planning often becomes emotional. Blended families, outdated estate documents, and beneficiary designations that no longer reflect current relationships can create unnecessary conflict. Even successful advisors can overlook details in their own planning when life circumstances change.
The solution is comprehensive. “You have to look under the hood. You have to look at every aspect to see, are there any gaps? And if so, how severe they are, what are the solutions to address them, and what should you address first, second, third,” Michael Gold says.
Readiness is not analysis paralysis. Gold references Sun Tzu’s The Art of War: “The battles are won in the temples.” That means doing the homework, but then taking action. “Too many people will do the research and do everything, but they won’t move. You gotta do your homework, but you gotta move. And if you’re wrong, you’ll know you’re wrong quickly, and you can pivot.”
For ultra-high-net-worth families navigating exits, transitions, or wealth transfer, the cost of unreadiness is measured not just in dollars, but in lost legacy, fractured relationships, and opportunities that will never return.
Contact information:
Gold Family Wealth
257 Riverside Ave., 1st Floor
Westport, CT 06880
646-844-2533
Investment advisory services offered through CWM, LLC, an SEC Registered Investment Advisor.
