• May 30, 2026

Michael Gold of Westport on the $14 Trillion Wealth Transition

The numbers are difficult to ignore. Close to three-quarters of privately held business owners in the United States expect to transition or exit their businesses within the next decade. Analysts estimate this represents $10 to $14 trillion in wealth that will change hands over that period. For the families involved, the advisor they choose during this window may be the most important financial relationship of their lives.

Michael Gold, founder of Gold Family Wealth in Westport, Connecticut, has been preparing clients for exactly these kinds of transitions for more than 25 years. His perspective on selecting the right advisor is grounded in hard-won experience with the complexity these moments create.

Why the Wrong Advisor Can Be Costly

Selecting the wrong wealth manager during a business transition can cost families millions in unnecessary taxes and structural errors, Michael Gold Westport notes. Those aren’t recoverable losses. A poorly structured sale, a missed estate planning opportunity, or a tax strategy that conflicts with investment decisions can have lasting consequences across generations.

Gold holds a Certified Exit Planning Advisor designation specifically because exit planning requires a distinct set of skills beyond general wealth management. Understanding how to sequence a transition, structure proceeds, and immediately begin protecting newly liquid assets demands coordination that most advisors simply are not built to deliver.

What Trustworthiness Actually Means

Research consistently shows that investors prioritize trustworthiness above all other qualities when choosing an advisor. But Gold argues most families don’t know how to evaluate it beyond surface impressions. The answer, in his view, is process. Does the advisor conduct real discovery before recommending anything? Do they acknowledge tradeoffs, or does everything sound perfect? Do they ask who is coordinating the full picture across your specialists?

Gold’s Westport practice has positioned itself around what he calls orchestration. His firm’s goal is to ensure every advisory relationship a family holds works in concert. For families approaching a major liquidity event, that integration is not a luxury. It is the difference between protecting what they have built and leaving value on the table. Refer to this article for related information.

 

Watch for more information about Michael Gold Westport on https://www.youtube.com/@goldfamilywealth