Adam Neumann says a half-hour car ride with Masayoshi Son is when his ego took over—and WeWork’s $47 billion collapse began

Billionaire WeWork cofounder Adam Neumann is back in the entrepreneurship game with Flow, and he says he’s determined not to repeat the mistakes that led to the coworking startup’s monumental $47 billion collapse. This time, he says, he knows exactly why he failed.

“I think society has taught us that once we gain that success, once we gain those material things, we get to this number, suddenly that hole that we all feel inside of us will be full,” Neumann said on The Diary of a CEO podcast in an episode released Sept. 28. Of the most successful people he knows, he added, “I have not seen one that got happy or fulfilled from attaining a number or a material thing.”

At WeWork’s height, Neumann lived large. The company peaked at a $47 billion valuation after SoftBank invested $2 billion in January 2019, and Forbes estimated Neumann’s net worth at $4.1 billion that March. WeWork bought a roughly $60 million Gulfstream G650ER that Neumann used extensively, and he and his wife, Rebekah Neumann, amassed a residential real estate portfolio the Wall Street Journal valued at around $90 million. WeWork also launched WeGrow, a for-profit private school led by Rebekah Neumann. Meanwhile, the company was losing billions.

Neumann now says he can pinpoint the moment he lost his way: a meeting........

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