Adam Neumann says a automotive journey with Masayoshi Son is when WeWork’s $47 billion collapse started

“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 with SoftBank founder Masayoshi Son in late 2016. The night before, Neumann said, WeWork’s board had agreed he would raise $300 million to $400 million, slow the company’s growth, turn a profit, and take it public. Son, pressed for time ahead of a meeting with then–President-elect Donald Trump, spent just 12 minutes in WeWork’s lobby before inviting Neumann to keep talking in his car. By the end of the ride, roughly half an hour all told, Son had offered about $4 billion—”$4.2 to be exact,” Neumann recalled—and both men signed the terms on an iPad. SoftBank’s investment, announced the following year, ultimately totaled $4.4 billion.

Son got out around 54th Street, and Neumann walked the 36 blocks back to WeWork’s headquarters.

“The guy that sat in the car was a mission-driven entrepreneur who really believed in creating a world where people make a life and not just a living,” Neumann said. “Every step that I take, it goes higher and higher. And by the time I walk into HQ, 18th Street, I forgot what we were all about.”

“It suddenly became about the money,” he said.

Neumann says the root problem was how he defined success. “If one of us defines success by making the most money and the other person defines success by being the most fulfilled, the most happy, the most light that they can be, then [we’re] playing two different games,” he said.

The 47-year-old now measures success by how he expects to feel at the end of his life. “In that last moment, right before you go, how do you feel? Do you feel full and surrounded by love, and like life has been this amazing journey? Or is there regret?” he said. As he put it, “the one thing that happens right before we pass away: the ego goes away completely.”

At the helm of WeWork, Neumann became known as a messianic leader whose company’s IPO prospectus declared a mission to “elevate the world’s consciousness.” Former employees told Business Insider he had a taste for $140 bottles of Don Julio tequila, and Neumann told Bartlett he worked 18- to 20-hour days, seven days a week, in WeWork’s early years.

The company also signed long-term leases in expensive cities around the world while renting space to members on short-term commitments, a mismatch Neumann acknowledged on the podcast. “We were taking long-term commitments against short-term commitments,” he said.

WeWork had disclosed a $1.9 billion net loss for 2018, and when it published its IPO prospectus in August 2019, investors balked at its mounting losses and Neumann’s outsize control. The offering was shelved, and Neumann stepped down as CEO that September. He told Bartlett he went “from 13,000 employees to 3 employees in 1 week.”

The pandemic, which emptied offices in 2020, deepened WeWork’s troubles. The company filed for Chapter 11 bankruptcy in November 2023 with nearly $19 billion in debt. Neumann tried to buy it back in early 2024, reportedly assembling a financing package of more than $500 million, but WeWork emerged from bankruptcy later that year without him.

Still, Neumann insists he has no regrets. “I am so much happier today,” he said. Of the hardest parts, he added, “I am so happy that they happened because they made me exactly who I’m meant to be.”

He’s bringing those lessons to Flow, the residential real estate startup he launched in 2022 with a $350 million investment from Andreessen Horowitz. “Falling is not bad,” he said. “The thing that’s bad is not when you fall, it’s how you get up.”

“If you fell, you look around, you’re like, ‘Wow, everybody saw.’ You clean up, you get up, and you say, ‘Let’s do it again.’ If you have that in you, nothing will stop you.”