Volatile Investor Goaded WeWork Entrepreneur “to Think Bigger”

(p. B1) Adam Neumann and Masayoshi Son were negotiating a possible $20 billion check when Mr. Son pulled up an image of Yoda on his iPad.

It was summer 2018 and Mr. Son’s tech conglomerate, SoftBank Group Corp., had already pumped over $4 billion into WeWork, the shared office space startup Mr. Neumann co-founded eight years earlier. Now Mr. Neumann was trying to get Mr. Son to buy a majority stake in WeWork. It would have been the largest acquisition ever of a startup, part of a bid to turbocharge a three-pronged strategy to dominate global real estate.

Mr. Son, a risk-taking investor who likened his gut-based strategy of “use the force” to that of the bat-eared Star Wars Jedi, was visibly excited that his new disciple was pushing for such an ambitious plan. Mr. Neumann, more than 20 years younger than Mr. Son and roughly a foot taller, charted out (p. B6) gargantuan growth projections in presentation after presentation throughout the summer. Mr. Son, scribbling on his iPad, calculated WeWork would be worth $10 trillion in a decade, more than 10 times the price tag of Apple at the time, the world’s most valuable company.

Still, Mr. Son kept urging Mr. Neumann to think bigger.

WeWork’s salespeople, real estate professionals and buildings numbered in the low hundreds. Mr. Son, though, told Mr. Neumann each category needed to grow—to 10,000. On his iPad, he commemorated the dictate.

“10k, 10k, 10k!” Mr. Son wrote in yellow, above Yoda grasping a green lightsaber. He signed below: “Masa.”

Fourteen months later, WeWork underwent one of the most spectacular corporate meltdowns of the decade.

. . .

Mr. Neumann, a long-haired, energetic entrepreneur, started WeWork after struggling to build a baby-clothes business in New York, where he moved from Israel in 2001.

. . .

Following a dinner with Walter Isaacson, biographer of Steve Jobs, he gathered staff around to read a complimentary email from the author. He told his employees he wanted Mr. Isaacson to write a biography about him.

. . .

Playing a role in Mr. Neumann’s growing ambitions was Mr. Son, who was frequently needling Mr. Neumann to think bigger.

At a meal in Tokyo with Mr. Son and Cheng Wei, CEO of Chinese ridehail giant Didi Global Inc., Mr. Son told Mr. Neumann that the Didi CEO beat out Uber Technologies Inc. in China not because he was smarter than Uber CEO Travis Kalanick. Mr. Cheng was crazier, Mr. Son said.

On the same Tokyo trip, Mr. Son asked Mr. Neumann who would win a fight between a smart guy and a crazy guy, according to people familiar with the conversation. He told Mr. Neumann that being crazy is how you win and that Mr. Neumann was not crazy enough, according to these people.

Roughly a year later at another meeting in Tokyo, Mr. Son clicked on a promotional video of SoftBank-backed Oyo Hotels & Homes, led by the then 24-year-old Ritesh Agarwal. Oyo was growing far faster than WeWork, Mr. Son told Mr. Neumann, ribbing him about lagging behind his SoftBank-backed counterpart, whom Mr. Son equated with a sibling.

“Your little brother is going to beat you,” Mr. Son told Mr. Neumann, according to people familiar with the conversation. “He is being bolder than you.”

Following meetings like this, Mr. Neumann often pushed for bigger ideas, aides said.

For the full commentary, see:

Eliot Brown and Maureen Farrell. “The We That Didn’t Work.” The Wall Street Journal (Saturday, July 17, 2021): B1 & B6.

(Note: ellipses added.)

(Note: the online version of the commentary has the same date as the print version, and has the title “The We That Didn’t Work at WeWork.”)

The commentary quoted above is based on the authors’ book:

Brown, Eliot, and Maureen Farrell. The Cult of We: WeWork, Adam Neumann, and the Great Startup Delusion. New York: Crown, 2021.

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