A wave of money is about to move across generations, and Michael Gold has built his Westport practice to sit at the center of it.

The numbers behind that shift are striking. An estimated $84 to $120 trillion is projected to pass between generations over the next two decades, with the transfer expected to peak around 2026. Meanwhile, nearly three-quarters of privately held business owners plan to transition or exit their companies within ten years, a shift tied to $10 to $14 trillion in potential wealth from those sales. Gold, founder and CEO of Gold Family Wealth, calls this convergence a defining moment for his industry, one made more acute by the fact that close to half of financial advisors intend to retire by 2035.

Bridging Generations

To meet families where they are, Michael Gold Westport-based firm has focused on building teams that can speak to both the wealth creators and their heirs. Younger advisors are being brought in specifically to close cultural and communication gaps with Millennial and Gen Z beneficiaries, a pattern Gold sees playing out across the advisory world as firms try to retain relationships through generational handoffs.

Judgment Over Volume

Gold cautions that handling this much capital movement well requires more than adding staff. Ultra-high-net-worth families, he says, operate inside a complex web of legacy goals, family dynamics and multigenerational coordination that resists standardized solutions. “These are not transactional issues. They cannot be automated or managed through standardized models,” he said.

His answer has been to position his Westport office as what he calls the intellectual engine of the firm, developing frameworks for advanced modeling, contingency planning and multigenerational governance that then inform how the rest of the organization serves clients. As trillions of dollars begin changing hands, Gold argues that families who choose an advisor now, rather than waiting until a transition is underway, stand the best chance of avoiding costly missteps during the handoff. Refer to this article for related information.

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