The We That Didn’t Work at WeWork


Adam Neumann


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.

9984 -0.70%

, 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 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.”

Mr. Son left a signature and evidence of his WeWork optimism next to an image of Yoda.

Fourteen months later, WeWork underwent one of the most spectacular corporate meltdowns of the decade. It aborted an initial public offering, Mr. Neumann was ousted as chief executive, the company’s valuation tumbled by nearly $40 billion and Mr. Son—having never completed the $20 billion deal—saw his tech-oracle image become fodder for jokes. This account is based on interviews with numerous former and current employees at both WeWork and


as well as friends of Mr. Neumann and WeWork investors. WeWork declined to comment, a SoftBank spokesman for Mr. Son declined to comment and Mr. Neumann didn’t respond to a request for comment through a spokesman.

The high profile immolation of the country’s most valuable startup was caused by an array of factors including loose corporate governance, loose money and a financial sector thirsty for founders promising vision and innovation.

But playing a starring role in WeWork’s rise and fall was the relationship between the two entrepreneurs, Mr. Son and Mr. Neumann. The pair often relied on erratic decision making as they made highly consequential decisions with billions of dollars—decisions that ultimately paved the way for WeWork’s implosion.

It was a mix of mentor and disciple, competitive rivalry, and some father-and-son dynamics—resulting in a battle of one upmanship that left both men humiliated and furious with each other, said former and current employees of WeWork and SoftBank.

Today, the company is still grappling with the hangover. Now worth $8 billion, down from $47 billion, WeWork is on track to go public, this time through a merger with a special-purpose acquisition company. It exited some leases taken on by Mr. Neumann with SoftBank’s money but must still absorb an enormous amount of office space. Occupancy is at a once-unthinkable 53%.

Burning hot

The union of Mr. Son and Mr. Neumann came about largely as a result of geopolitical luck that married two unflinching techno-optimists with extraordinary ambition at the exact right time.

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. He proved a gifted fundraiser, positioning the office-space company first as a social network, then as a product of the sharing economy—and raised $1.7 billion from a top roster of the world’s investors.

Mr. Neumann moved to New York City from Israel in 2001 and started WeWork after struggling to build a baby clothes business. He proved a gifted fundraiser.


Mark Lennihan/Associated Press

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