Softbank founder and CEO Masayoshi Son is Japan’s undisputed king of tech VC, but his personality contrasts sharply with the image you probably have of U.S. based tech investors. Descriptions from people who know him make him sound gentle and soft. He talks often about being sad and crying when things aren’t going well. Judging from a new report from Bloomberg, it sounds like insiders at Softbank are worried he’s about to do some of his worst crying in years. Recent turbulence at OpenAI has stakeholders apparently telling Bloomberg that Son may have been too trusting of OpenAI CEO Sam Altman, just as he was once too trusting of WeWork’s disgraced founder Adam Neumann. That would not be good, because Softbank’s stake in OpenAI totals about $60 billion. The story goes that Masayoshi Son was the world’s richest man for three days in 1999 or possibly 2000, and then the Dot-Com Bubble burst and he had to build fresh from a measly low-ten-figure net worth. Some of this may be apocryphal, but it’s important to Son’s personal mythology.
The next chapter in the Son story is that a wise investment of Son’s from around the time of the Dot-Com Crash would vindicate him. Son gambled on Chinese tech conglomerate Alibaba—and its charismatic founder, Jack Ma, and that bet eventually paid off enormously—described as a 4,000-fold increase shortly after Alibaba’s IPO in 2014. This second triumph made Son look like a prophet once again.
