A little more than a year before Adam Neumann was ousted as WeWork's CEO and exited very, very rich, he thought he was about to become very, very, very rich. As Gabriel Sherman writes in a lengthy piece for Vanity Fair, Neumann had what Sherman terms an "escape plan": Though the company was expected to lose close to $2 billion, Softbank CEO Masayoshi Son agreed in the summer of 2018 to buy the bulk of the company for $16 billion. Neumann would become "insanely rich," and a former WeWork exec tells Sherman that Neumann behaved as if it was a done deal. It wasn't. On Christmas Eve, Masayoshi revised his offer way down: Softbank would instead sink another $2 billion into the company, giving it a $47 billion valuation, with the idea that Neumann would then take it public.
"Neumann was blindsided," writes Sherman. He headed to the Bay Area trying to secure deals. They didn't pan out, and when Neumann return to NYC, "he seemed desperate." Things wouldn't improve. In mid-September, the IPO was delayed amid investor concerns about both Neumann and the amount of cash the company was bleeding. He was out shortly thereafter. It was a stunning turn for a man whose driver ferried him around in a Maybach sedan worth six figures, a CEO who "controlled 65% of the stock and had the power to fire the board of directors if the board moved against him," writes Sherman. He adds: "So confident was Neumann of his job security that he once declared during a company meeting that his descendants would be running WeWork in 300 years." (Read the fascinating full story here.)