“All of that changed in the last 90 days, and it’s not coming back anytime soon,” said Wil Schroter, founder of Start-ups.com, an accelerator program for young companies. The “we’ll figure it out later” story is no longer attractive to investors, he added.

In addition to Silbermann, Gebbia and Mehta, founders at the top of Twitter, Peloton, Medium and MicroStrategy have all resigned over the past year.

They’re not leaving on a high note. Shares of Pinterest are down 60 per cent from a year ago. Elliott Management, an activist shareholder known for pressuring companies to make big changes, recently took a stake in the company. Airbnb shares are down 25 per cent from a year ago. And Instacart lowered its internal valuation almost 40 per cent in March, as it prepares to go public in a hostile market.

‘If you’re as already rich, famous and successful as these guys, there usually comes a point where staying in the saddle is less appealing than riding off into the sunset.’

University of Pennsylvania’s Kevin Werbach

“It’s surely less fun being a CEO when markets are down, the economy is trending negative and regulation is increasing,” said Kevin Werbach, a professor of business at the Wharton School of the University of Pennsylvania. “If you’re as already rich, famous and successful as these guys, there usually comes a point where staying in the saddle is less appealing than riding off into the sunset.”

‘I’m CEO, bitch’

In start-up lore, Mark Zuckerberg pioneered the modern boy boss. Carrying business cards that read, “I’m CEO, bitch” and ruffling Wall Street feathers with his “disrespectful” hoodie, he demanded investors let him keep a controlling interest in Facebook as it grew, ushering in today’s era of “founder-friendly” deal-making.

Young, ambitious men like Zuckerberg received similar protections and leeway as venture capital firms rushed to appear as accommodating as possible, lavishing the entrepreneurs with perks (dinners, jets, celebrities) and services (recruiting, public relations, design).

One firm even publicly pledged to never vote against a founder on company matters.

“It inspired our whole generation to believe in the impossible that they could start companies,” said Trace Cohen, 34, an investor in very young start-ups.

Founders took advantage of their upper hands. They stayed in the top jobs, even when the companies outgrew their skills as managers. And they kept their companies private for as long as possible, avoiding pesky business realities like turning a profit. They were given the benefit of the doubt — something female founders rarely got.

As the tech sector became a dominant force in our economy, the cult of the start-up founder made its way into popular culture via celebrities like Ashton Kutcher and TV shows like HBO satire “Silicon Valley.

Some founders of this era took their latitude too far. Adam Neumann’s spending and partying got him forced out of WeWork in 2018, even though he held a controlling stake in the company. And Travis Kalanick’s aggressive tactics at Uber resulted in his ouster in 2017, despite his super-voting shares.

The rest mostly held on through the companies’ initial public offerings. But it turns out that running a publicly traded company, with its attendant fiduciary duties, analyst calls and slog of quarterly earnings, is a far cry from the hustle and thrill of start-up life. Now, as troubles mount amid a market meltdown, they’re giving up the power and control they once fought for.

Losing their halo

In his announcement, Silbermann said that running Pinterest had been “the gift of a lifetime.” Gebbia, who will become an adviser to Airbnb, posted an effusive reminiscence of the company’s early days, alongside photos, nicknames of his co-founders and lessons about the goodness of humanity. Mehta tweeted that he “cared deeply” about Instacart — the “one thing I have thought about for every waking minute of the last decade.”

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. Mehta and Gebbia said they had plans for new projects.

Investors say they anticipate more of these resignations from founders who are realising 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,” Cohen said.

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. Stock trading app Robinhood has laid off more than 1,000 employees this year as it loses active customers.

Making matters worse, start-up founders have lost their halo of positive cultural cachet — a trend that began during the tech backlash of 2017 and that has grown with the release of devastating books and TV shows about WeWork, Uber and other tech darlings.

“Once you’ve made a certain amount of money, you’re playing for status, and the status isn’t there,” Hargreaves said.

Still, there’s always the comeback story. If the market gets worse and companies start seriously tanking, we could see the reverse dynamic of founders returning to right the ship, said Werbach, the business professor.

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It would be a throwback to the original cult hero founder, who commanded admiration long before unicorns roamed the Valley and who even inspired Zuckerberg’s swaggering business cards.

He was, perhaps, the original boy boss: Steve Jobs.

This article originally appeared in The New York Times.

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