SoftBank's Masayoshi Son Called WeWork "The Next Alibaba." He Invested $18.5 Billion. It Went Bankrupt.

Son overrode his own lieutenants' objections to pour billions into the co-working startup, pushing its valuation to a preposterous $47 billion. He was so confident he compared Adam Neumann—a man who cashed out $700 million before the IPO even happened—to Jack Ma, the greatest investment of his career. But WeWork wasn't building e-commerce infrastructure for a billion Chinese consumers. It was subletting office space with beer taps. When WeWork filed its S-1, investors actually read the financials and recoiled in horror. The IPO collapsed within six weeks. By 2020, Son publicly admitted he was "foolish." By November 2023, WeWork filed for bankruptcy. SoftBank's total write-down: over $14 billion. The "next Alibaba" became the next cautionary tale in every business school textbook.