A Curious Midlife Crisis for a Tech Entrepreneur

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A Curious Midlife Crisis for a Tech Entrepreneur

For a time, he lived on a 20-acre estate in Bedford, N.Y., overseen by a butler whom he paid $50,000 a year, and he hosted grand parties for 60 guests or more.

They swam in his pool, waged paintball wars in the woods and played padel tennis on his private court.

With no family or boss to answer to, he was able to go skiing in Utah on a whim, working whenever he wanted to, as long as he had decent Wi-Fi and a robust cell signal.

Sometimes, when he was restless, he would go for drives in his $300,000 McLaren sports car. On weekends he might crash at his $13,000-a-month Manhattan pied-à-terre near Madison Square Park. He booked late-night tables at chic restaurants and dined in the company of beautiful, intelligent women.


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