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Gambling With the Future: What Founders Can Learn from Masayoshi Son’s Big Bets

Gambling With the Future: What Founders Can Learn from Masayoshi Son’s Big Bets

A high-stakes story of vision, ego, and collapse—why Gambling Man is required reading for anyone building with other people’s money.

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Jack
May 02, 2025
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Gambling With the Future: What Founders Can Learn from Masayoshi Son’s Big Bets
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1. Introduction

If you’re a founder, product builder, or operator trying to understand the edge between brilliance and recklessness, Gambling Man is essential reading. It tells the story of Masayoshi Son, the SoftBank founder who reshaped global tech investing by betting bigger, faster, and more instinctively than anyone else—from Alibaba and the iPhone …

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