Gambling Man

The Secret Story of the World's Greatest Disruptor, Masayoshi Son

By: Lionel Barber

Narrated by: Keong Sim

“The defining account of an era in business history.”—Evan Osnos, National Book Award-winning author of Age of Ambition

The binge-worthy first Western biography of SoftBank CEO Masayoshi Son, financial disruptor and personification of the 21st century’s addiction to instant wealth, from the former editor of the Financial Times.

As Wall Street swooned and boomed through the last decade, our livelihoods have—now more than ever—come to rely upon the good sense and risk appetites of a few standout investors. And amidst the BlackRocks, Vanguards, and Berkshire Hathaways stands arguably the most iconoclastic of them all: SoftBank’s Masayoshi Son.

In Gambling Man, the first Western biography of Son, the self-professed unicorn hunter, we go behind the scenes of the world’s most monied halls of power in New York, Tokyo, Silicon Valley, Saudi Arabia, and beyond to see how Son’s firm SoftBank has defied conventional wisdom and imposing odds to push global tech and commerce into the future.

From the dizzying highs of Uber, DoorDash, and Slack to the epic lows of WeWork and tech-infused dogwalking app Wag Son and SoftBank have been at the center of cutting-edge capitalism’s absolute peaks and valleys. In the process, Son, son of a pachinko kingpin who grew up in a slum in Japan, has been a hero, a villain, and even a meme-ified hero to the internet tech- and finance-bro set all at once.

Based on in-depth research and eye-opening interviews, Gambling Man is an unforgettable character study and alarming true story of twenty-first-century commerce that will stick with you long after you hear the final word.

©2025 Lionel Barber (P)2025 Simon & Schuster Audio

A deep look into the life of a man who doesn’t quit!

The cadence of the storytelling is perfect and provides more insight into a man who was secretive personally, but fearless publicly.

Degenerate Gambler

The book is really good and well written.

But the story of Son himself is not really that interesting from an entrepreneurial standpoint because he comes off as a degenerate gambler who’s black jack table are mega-billion dollar bets on companies. He also seems to surround himself with people that don’t seem to have many redeeming qualities. Some of his bets work, a lot don’t, and it just seems reckless as opposed to reading about a true innovator or investor (a la Warren Buffett) where there seems to be a real methodology to what they’re doing.

I’d still say it’s a good read because even today he’s still relevant but I came away honestly feeling like I was reading about a gambling addict.