Son overrode his own team to pour $16B into WeWork — and lost $11.5B of it

SoftBank first invested $4.4 billion in WeWork in August 2017, and Masayoshi Son kept adding to the position, overriding internal objections to hand founder Adam Neumann another $2 billion in January 2019 and push the company's valuation to $47 billion — on par with Hilton Hotels, for a business that leased office space and sublet desks. When WeWork filed for its IPO in August 2019, the prospectus revealed $1.9 billion in annual losses and governance red flags around Neumann; investors balked, the IPO was withdrawn, and Neumann was pushed out as CEO.

With the company it had spent two years inflating suddenly near insolvency, SoftBank assembled a $9.5 billion rescue package in October 2019 — including $1.7 billion to buy out Neumann's control — that valued WeWork at just $8 billion, a sixth of its peak. By Reuters' count, SoftBank's cumulative equity and debt commitments to WeWork totaled roughly $16 billion. WeWork went public a second time via a SPAC merger in 2021 at a $9 billion valuation, but never turned its business around.

WeWork filed for Chapter 11 bankruptcy on 6 November 2023, listing almost $19 billion in debts. SoftBank's own accounting put its equity losses at an estimated $11.5 billion, with another $2.2 billion of debt exposure still outstanding. Son told shareholders in June 2023, before the bankruptcy, 'I may be more at fault than Adam, for telling him to be more aggressive' — an admission the losses traced to his own judgment, not just Neumann's management.