The fall from fame and business grace came hard for WeWork co-founder Adam Neumann. Investors pressured him out in 2019 after hyper growth, a dizzying $47 billion valuation, and a failed IPO after financial details in the S-1 revealed, among other things, a $900 million loss on $1.5 billion in revenue, as CNBC reported. 

In November, Neumann publicly aired some of his regrets. However, the massive severance agreement that neared $1.7 billion, according to the Wall Street Journal, apparently offered a soft cushion. As the Journal also reported in 2019, he also sold some holdings and borrowed against others to cash out an estimated $700 million that went into a family office.

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