Gambling Man: The Wild Ride of Japan’s Masayoshi Son

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“Gambling Man” details SoftBank founder Masayoshi Son’s rise from humble beginnings to briefly become the world’s richest person in 2000 at the height of the dotcom bubble. While he presciently invested in Yahoo!, Alibaba and Arm he also started the $100 billion SoftBank Vision Fund to invest in startups with mixed results. Success stories included DoorDash and Coupang while WeWork, Greensill Capital, Wag and Zume were among the blow ups. To get a glimpse inside Son’s world is to relive Japan’s asset bubble, the U.S. dotcom bubble and tech bubble all in one. Former Financial Times editor Lionel Barber writes the first Western biography of Son and it contains a lot of tidbits readers may not have heard about Son before. At the heart of it he is a gambling man and his latest bet is on artificial intelligence. How that turns out is anybody’s guess.

I. BOTTOM LINE: Read Gambling Man. Read Gambling Man if you care about venture capital, startups, or tech. Masa didn’t just play the game — he rewrote the rules. II. BOOK vs. ARTICLE: Read the Book. Read the book. No article could capture Masa’s impact. Lionel does — and does it right. My reasoning. For decades, journalists parroted Masa’s Myth without scrutiny. Lionel doesn’t. He broke the mold and wrote an authentic, credible, and reliable piece of biographical journalism that earned a spot on history’s bookshelf. III. IS THE BOOK READABLE: Absolutely. Absolutely. Lionel wrote the right book in the right way about Masa, one that doubles as an ode to the best of journalism. The Good. Lionel writes fluidly — no pretension, no pandering.. He paced the book just right and met my definition of good writing: Choose the right words, write tight sentences of varying length, and arrange and sequence them inside properly ordered paragraphs. I was also impressed by two stylistic techniques that more non-fiction writers should adopt. First, Lionel kept the chapters short — I’m always grateful for writers who make the journey enjoyable versus endurable. Readers want to feel progress and long chapters make it too hard to do so. And second, he wrote among the best end-of-chapter concluding paragraphs I’ve seen in years. Lionel captured the essence of each chapter in a brief yet powerful punch of a paragraph. They’re so good that I’m going to mimic his style as I shape my own approach. The Bad. Pay attention when you read. Lionel’s pacing is quick, and every idea builds on the last. The book is deceptively dense and demands your attention if you want to draw subtle yet powerful insights. IV. WILL I LEARN SOMETHING: Definitely. Ask yourself these questions as you read: - Is he crazy? - What’s his edge? - Did he help or hurt us? - What lessons can we learn? - Is he an entrepreneur, financier, or something else? - Is he a historical figure? IV. CAN YOU SHARE YOUR THOUGHTS: Of course. - Is he Crazy? Yes. But, so what? Every elite performer is crazy. - What’s his edge? Son’s superpower? A Napoleonic belief in his own destiny. He plays as if he can’t lose because he believes he won’t. As a result, Masa plans decades into the future and is firmly consistent, persistent, disciplined, focused, and relentless in his actions. - Did he help or hurt us? Masa’s boundless ambition and self-belief reshaped venture capital, startups, and tech— but not without collateral damage. - What lessons can we learn? Lessons: self-belief precedes ability. Decide who you want to be, then become it. - Is he an entrepreneur, financier, or something else? Masa’s genius isn’t in building but in selling — he mastered the art of optimism, aspiration, and expectation. - Is he a historical figure Maybe. He’s more of a cautionary character versus a model to emulate — a reminder that vision without discipline is as destructive as transformative. V. DID YOU FORM AN OPINION OF MASA: Yes; as will you. Masa’s financial engineering altered venture capital, startups, and tech in ways we may never fully untangle. The man literally rewrote the DNA of our global startup economy — and not in a good way. (Read the book and you’ll appreciate my claim.) All that aside, Masa’s possesses the same qualities as any elite entrepreneur: irrepressible, indefatigable, relentless, optimistic, joyful, determined, persistent, Napoleonic, and iconoclastic. What sets Masa’s apart from his peers is an extraordinary sense of self-belief, unassailable conviction, and a walk with destiny. VI. HOW DOES HE LEARN: He asks questions. Masa doesn’t read. Not one bit. He prefers image-laden, word-free PowerPoints. And he learns through rapid-fire questioning. Some insiders see him as a visionary. Others call him a dilettante — or worse, a charlatan. VII. ONE FASCINATING FACTOID: Reverence. Masa isn’t just building the future—he’s safeguarding Japan’s past. Unlike most disruptors, he reveres tradition while reshaping the present. VIII. FINAL VERDICT: Read the book. Read Gambling Man. If you’re a VC or an entrepreneur, it’s essential. If not, buckle up — this one’s pure Hollywood.

The amazing story of Masayoshi Son, a Korean refugee in Japan and his amazing rise to power via Softbank. Highlights the story of Softbank and its aggressive risk activities in acquiring technology companies across the globe. It also relates the story of how Arm holdings, a great British company was handed over to the Japanese company Softbank at an absurdly low valuation. Well written and well researched. Great read. Really enjoyed it.

Terrific book . Finished it in two sittings