For a few days in the early 2000s, Masayoshi Son — nicknamed Masa — was the richest man in the world. A few days later, it all came tumbling down. The founder and CEO of the Japanese investment conglomerate SoftBank had failed to predict the future — an intuitive gift that first made his name as an investor, and his first billions. But even the most catastrophic losses wouldn’t stop his gambling habits, betting big on start-ups from Alibaba to WeWork over the next 20 years — all on a journey to becoming one of the most controversial venture capitalists of all time. In this week’s episode of Whale Hunting, Bradley sits down with the former Financial Times editor Lionel Barber to discuss Masa: the man behind the billions, how he calculates his bets, and why he likes to compare himself to Napoleon.

Mentioned in this week’s episode:

Lionel’s new biography of Masa: Gambling Man: The Wild Ride of Japan’s Masayoshi Son

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