A version of this article first appeared in CNBC's Inside Wealth newsletter with Robert Frank, a weekly guide to the high-net-worth investor and consumer. Sign up to receive future editions, straight to your inbox.

In 1989, Byron Trott was working at Goldman Sachs in the private wealth management division when he paid a visit to Jack Taylor, founder of Enterprise Rent-A-Car Co.

"Jack was there with his son, Andy, who was running the company," Trott said. "And they said to me, 'Sport, I don't know who told you we have any money, but we are 10 to 1 levered on our business.' Now, 36 years later, they are one of the model companies of the world, with significant excess cash. And the next generation will not only be maintaining the legacy of Enterprise, Alamo, National Enter

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