Masayoshi Son’s Biggest Gamble Yet May Finally Secure His Legacy

In Gambling Man, Lionel Barber charts the Softbank founder’s rollercoaster career and his persistent quest for acceptance. 

Illustration: Richard Chance for Bloomberg

Seven years ago, just before Masayoshi Son turned 60, a reporter asked how the tech investor graded himself on a scale of 1 to 100. The billionaire’s response: 28.

“What have I accomplished?” the founder of Japan’s SoftBank Group Corp. said. “There’s so much I would have done differently, and I feel so frustrated thinking back to all the times I fell short. But this is not the end.”