SoftBank's Masa Son Called WeWork 'the Next Alibaba.' It Filed for Bankruptcy.

Masayoshi Son bet $18.5 billion on WeWork, a company that rented office space with ping pong tables and free beer. He was so enchanted by founder Adam Neumann's charisma that he reportedly committed $4.4 billion in just 28 minutes during a meeting. Son believed WeWork would be his next Alibaba — the 2000 investment that turned $20 million into $100+ billion.

Reality had other plans. WeWork's IPO attempt in 2019 revealed that the "tech company" was actually just an overleveraged real estate firm burning through cash faster than a WeWork member burns through La Croix. The valuation collapsed from $47 billion to $8 billion almost overnight. Adam Neumann got a $1.7 billion golden parachute while employees got pink slips.

WeWork eventually went public via SPAC in 2021 at a $9 billion valuation, then filed for Chapter 11 bankruptcy in November 2023. SoftBank's total losses? Roughly $14 billion. Son later admitted the investment was "foolish" — which is one way to describe paying $47 billion for a company that couldn't figure out how to make renting desks profitable.