The Boy Bosses of Silicon Valley Are on Their Way Out

Leaving as billionaires, they have emanated Silicon Valley’s relentless positivity. Pinterest “is just getting started,” Airbnb “is in the best hands it’s ever been in” and Instacart has a “enormous opportunity ahead,” the founders wrote. Both Mr. Mehta and Mr. Gebbia said they had plans for new projects.

Investors say they anticipate more of these resignations from founders who are realizing they now have to work harder for less (relatively speaking). “Now, they can let some executives step up, take over and grow it with different incentives,” Mr. Cohen said.

Last week, Brad Hargreaves, the founder of Common, a start-up that operates communal living spaces, announced he would step down as chief executive, becoming chief creative officer. The company’s head of property, Karlene Holloman, a hotel industry veteran, will take over as chief executive.

The market downturn factored into Mr. Hargreaves’s decision. In flush times, he said, it’s good to have a founder at the top of the company who can sell investors, employees and customers on a grand vision. “Operations don’t really matter that much,” he said. “No one’s really watching the bottom line.”

Today’s environment requires someone with Ms. Holloman’s extensive experience and operational skills, he said. “In a tighter time, when operations matter a lot and nobody’s buying into any grand visions, you want an operator in that seat,” he said.

“A lot of founder-C.E.O.s stick around too long,” he added.

The founders who have so far stayed on amid the downturn — and there are many, including at Stripe, Coinbase and Discord — can expect greater demands and more pressure. The stock trading app Robinhood has laid off more than 1,000 employees this year as it loses active customers. Dan Dolev, an analyst at Mizuho Securities, said several investors had privately suggested Robinhood bring in a more seasoned executive to help its co-founder, Vlad Tenev. Mr. Tenev cannot be forced out, since he and his co-founder, Baiju Bhatt, together hold a controlling stake in the company.

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