WeWork

WeWork's $47 billion valuation collapse is the defining startup cautionary tale of the 2010s. The co-working company raised $12.8 billion from SoftBank, then saw its IPO fail amid $1.9 billion in annual losses and founder Adam Neumann's erratic self-dealing, including leasing buildings he personally owned. By 2023, it filed for bankruptcy, ending with a market cap near zero; Neumann received a $1.7 billion golden parachute. That payout is 3.3 times larger than the $5.3 billion debt load that doomed Toys "R" Us (#8), highlighting how founder enrichment outpaced creditor recovery.