Adam Neumann and the Art of Failing Up

Last year, WeWork bought access to a Gulfstream G650 for $60 million, about the sum that the company was losing every two weeks. He installed an infrared sauna and a cold plunge pool in his Manhattan office. In a glaring conflict of interest, he made millions leasing buildings he partly owned back to WeWork. Indulging his penchant for mysticism, Mr. Neumann changed the company’s name to the We Company. Its I.P.O. filing, which included at least 150 references to the word “community,” noted that Mr. Neumann had acted to trademark “We” and extract a $5.9 million payment from the company for the use of the pronoun. He later returned the fee.

Some employees found his behavior noxious. In a federal complaint filed Thursday, Medina Bardhi, a former chief of staff to Mr. Neumann, accused him of retaliating against her for becoming pregnant and derided her maternity leave as a “vacation” and “retirement.” (She also said she had to stop traveling with Mr. Neumann while pregnant because he liked to hotbox the company jet. A WeWork spokeswoman said the company would “vigorously defend itself” and had “zero tolerance for discrimination.”)

Over the years, many on Wall Street and in the business press have scoffed openly at WeWork’s business model; last year, Vanity Fair questioned its “$20 billion house of cards.” And some came to wonder if Mr. Neumann had been wise to share, during a 2017 speech at Baruch College, a story from his first date with Rebekah. “She looked me straight in the eye and she said, ‘You, my friend, are full of” crap, Mr. Neumann recalled. “‘She then said, ‘Every single word that comes out of your mouth is fake.’”

No one disputes that Mr. Neumann had an uncommon vision. In nine years, WeWork grew from a single office to encompass more than 45 million square feet of real estate, with roughly 527,000 tenants — or “memberships” — in some 110 cities. WeWork became the single-largest private occupier of office space in London, New York and Washington. Its sleek quarters became synonymous with entrepreneurship in the gig economy and millennial hustle, complete with “Thank God It’s Monday!” T-shirts. Large corporations including IBM, Microsoft and Salesforce moved employees into WeWork spaces.

When luminaries like the JPMorgan Chase chief executive Jamie Dimon, the Microsoft chief executive Satya Nadella and the private-equity tycoon Henry R. Kravis came by WeWork offices, Mr. Neumann knew how to wow them. He might instruct his team to “activate the space,” with an enormous touch screen displaying WeWork’s premium locations, like London’s postmodern No. 1 Poultry building and an old opium factory in Shanghai with pastel terrazzo tiles. And Mr. Neumann made sure potential investors stopped by the desk of WeWork’s “head of visualization,” who handled virtual reality renderings. Suddenly, visitors could see themselves inside a future WeWork space in Paris or Tokyo. As Dave Fano, the company’s chief growth officer, told Forbes in 2017, “Landlords just sell aluminum. We make iPhones.”

For a long time, Mr. Son protected Mr. Neumann. In mid-September, as the I.P.O. effort was collapsing and Mr. Neumann was facing outside and board pressure to resign, Mr. Son invited him to sit at his table at the Langham Hotel in Pasadena, Calif., for a Vision Fund social gathering. John Legend would be playing. According to a person briefed on the conversations, SoftBank executives told Mr. Son that the optics of Mr. Neumann attending the event, much less joining him at the main table, would be awful.

Ultimately, Mr. Neumann did not appear — and pointedly, Mr. Son gave other attendees a stern reminder about the importance of profitability and strengthening corporate governance before a company attempts to go public.