Neumann retained lawyers from the white-shoe firm Paul, Weiss and P.R. advisers from Edelman to set up a war room. On Friday, September 20, Neumann arrived at WeWork’s headquarters vowing to fight for his job. “I’m never not going to be CEO,” he told a colleague. One of Neumann’s favorite words is optionality, but he was rapidly running out of them. In the wake of the Journal exposé, investor Michael Eisenberg and WeWork CFO Artie Minson held a conference call with WeWork’s directors and argued that Neumann had to step down, two people briefed on the call said. On Sunday afternoon, he met with Dimon at JPMorgan’s headquarters. Dimon made it clear that WeWork would never be able to secure fresh capital as long as Neumann remained CEO. And while Dimon didn’t say it, the subtext was clear: WeWork was barreling toward bankruptcy, and Neumann would be unable to repay the $380 million he borrowed against the value of his now potentially worthless stock. Two days later, Neumann resigned.

Neumann’s fall is one of the most spectacular flameouts in recent corporate history, an Icarus story for its time. Though in Neumann’s case, he floated down under a golden parachute. When SoftBank bailed out WeWork on October 22 for $9.5 billion, Neumann walked away with a package that included $1 billion in stock, $500 million in credit to pay back loans, and a $185 million consulting fee. The money, though, didn’t blunt the confusion and anger he was experiencing, people who spoke with Neumann said.

In the weeks after losing control of his company, he became paranoid that he was being followed. He heard a rumor from a reporter that one of his investors hired the Israeli private intelligence firm Black Cube—the same firm Harvey Weinstein used to track Ronan Farrow—to dig up dirt on him to force him out as CEO. Mainly, he holed up in his Gramercy condo, trying to piece together what had gone so disastrously wrong.

Not long after Neumann started WeWork in 2010, the then-31-year-old Israeli entrepreneur showed up at a real estate industry conference on Park Avenue wearing his now-familiar uniform, T-shirt and jeans, with shoulder-length surfer hair that looked like it hadn’t been washed in days. Neumann, who is six-foot-five and shares model good looks with his sister, a former Miss Teen Israel, was an instant object of fascination among the suit-clad executives, many of whom were twice his age. They were taken with his exotic backstory (he was raised on a kibbutz in southern Israel, not far from the Gaza Strip). But it was his hyper-confidence that one attendee most recalled. “I remember Adam asked me what company leases the most office space in New York. I told him JPMorgan. They have about 3.5 million square feet. And he said, ‘Well, I’m going to lease more than they do.’ ”

It was a delusional idea at the time. Neumann was a college dropout with no commercial real estate experience and a business track record of having launched two failed start-ups: a company that sold women’s shoes with a collapsible heel and a line of baby clothes called Krawlers that featured pants with kneepads sewn into the legs. When the financial crisis hit in 2008, Neumann had burned through an investment from his grandmother of nearly $100,000 and scrambled to hire a lawyer to renew his visa to stay in the country. To help pay rent, he let another company sublet space in Krawlers’s Brooklyn loft.

It was the genesis of the WeWork idea: In the postcrash recession, Neumann had the foresight to bet landlords would need tenants, and that legions of underemployed professionals would pay for an appealing alternative to working from a Starbucks while they got back on their feet. Neumann partnered with a laconic 34-year-old architect named Miguel McKelvey, who grew up on an Oregon commune, and together they convinced Krawlers’s landlord to let them convert an unused floor into a shared workspace called Green Desk. The concept did well. A little over a year later, they sold it to the landlord at a reported $3 million valuation and struck out on their own.