‘Billion Dollar Loser’ Recounts WeWork’s Big Dreams and Its Harsh Wake-Up Call

‘Billion Dollar Loser’ Recounts WeWork’s Big Dreams and Its Harsh Wake-Up Call

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Emerging in the wake of the 2008 financial crisis, WeWork took advantage of distressed building rents and essentially engaged in a simple arbitrage: taking out long-term leases, subdividing spaces and renting them out to short-term tenants at a markup. It was a model that could be profitable — and in fact, competitors to WeWork already existed, though none of them were run by anyone with Neumann’s market-dominating ambitions. He wasn’t content for WeWork to be another office leasing company, and looked enviously at the technology companies that were able to scale without incurring the unavoidable costs of real estate expansion. WeWork would be a “tech-enabled physical social network,” Wiedeman writes of Neumann’s goal. “He was a community builder, not a landlord.”

Credit…Makayla Booker

From the beginning, Neumann was a “deal guy” who loved to schmooze while other people sorted out the details. His co-founder, an architect named Miguel McKelvey, was tasked with translating Neumann’s high-flown dreams into tangible reality. It was a division of labor that suited the media-shy McKelvey, depicted in this book as hard-working but managerially useless, doing nothing to shield the growing staff from Neumann’s extreme demands.

WeWork pulled the classic new-economy maneuver of hiring idealistic young people, deploying them to the point of exhaustion and paying them peanuts while telling them that they were part of a revolution — what Neumann called “the ‘We’ decade.” Eventually, WeWork offered stock options, though Neumann would be the one to cash out hundreds of millions in stock in order to fund an escalating lifestyle that had grown to include five children, several houses, a penchant for $200 T-shirts and lots of pot.

Throughout it all, Wiedeman is an appropriately understated guide, aware that his subject is so laden with self-regard that it only takes a deadpan clause to convey the absurdity of it all. “From prison, McFarland told me …” Wiedeman writes, describing an exchange with Billy McFarland, the grifter impresario of the Fyre Festival, who of course crossed paths with Neumann. Another sentence pivots around a pointed discretionary comma. Writing about Neumann’s wife, Rebekah, who started a short-lived private school called WeGrow despite having no experience in education, Wiedeman describes the admissions certificates she sent to the students: “Rebekah signed the certificate with her name, and a heart.”

“Billion Dollar Loser” would be absorbing enough were it just about one man’s grandiosity, but Wiedeman has a larger argument to make about what Neumann represents. Neumann finagled funding not only from SoftBank, the Japanese conglomerate led by the billionaire-entrepreneur Masayoshi Son, who liked to say that “feeling is more important than numbers,” but also from the venerable venture capital firm Benchmark. Neumann had passed himself off as a tech visionary, even though he rarely used a computer and WeWork’s IT department was once run by a high school student from Queens.

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