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.

Some details are now leaking out, suggesting that Neumann is going old school through his family office, 166 2nd Financial Services. "Entities tied to Mr. Neumann have been quietly acquiring majority stakes in more than 4,000 apartments valued at more than $1 billion in Miami, Atlanta, Nashville, Tenn., Fort Lauderdale, Fla., and other US cities, according to court, property and corporate records and people familiar with the transactions," as the Journal reported on Tuesday. "Many of these investments occurred within the past year."