Jonathan Crystal was dangling his legs from a Deer Valley ski lift alongside his teenage son when he realized that an imminent windfall was about to radically shift the futures of his three children.

His family had recently agreed to sell Crystal & Company, a Wall Street insurance brokerage his grandfather founded in 1933. Three generations had grown the risk-management firm to 11 offices nationwide until economics and technology combined in 2018 to create the right moment to sell. Crystal chose the solitude of the lift to tell his son, who replied, “Does that mean you and Uncle Jamie and Uncle Sandy and GPa aren’t going to work together anymore?” Then another repercussion dawned on him. “I guess I’m not going to have a chance to work with you.”

“And it really hit me hard,” Crystal says.

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