Masayoshi Son, the founder of SoftBank, is perhaps the most audacious gambler in financial history. His biography is one of extreme peaks and valleys. He famously turned a $20 million investment in Alibaba into over $60 billion—one of the greatest trades of all time. This “visionary” success gave him the leverage to launch the $100 billion Vision Fund.
Son’s philosophy is “investing in the future of AI,” but his execution has often been criticized as “capital destruction.” By flooding startups like WeWork and Katerra with more cash than they could effectively spend, he inadvertently encouraged reckless growth over profitability.
By 2026, Son’s legacy is a polarizing one. On one hand, he funded the infrastructure of the mobile and AI eras; on the other, he presided over some of the largest write-downs in venture capital history. He remains the ultimate “high-beta” figure: a m
