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Gambling Man: The Secret Story of the World's Greatest Disruptor, Masayoshi Son
The unputdownable 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 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 turn the final page.
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 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 turn the final page.
365 pages, Kindle Edition
Published January 21, 2025
275 people are currently reading
3835 people want to read
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Displaying 1 - 30 of 79 reviews
June 8, 2025
This was a fascinating read about SoftBank CEO Masayoshi Son. I did not know much, if anything, about him, and being in this industry, I wanted to read this one, and it did not disappoint. He came to the US with basically nothing, made a ton, lost it, and made it back. That’s summing it up very broadly, but this is a wild ride, and Barber did a great job at writing this in a way that kept me captivated the entire time. The audio for this was wonderful, and I recommend reading it this way if you can.
Thank you to Atria / Signal One Publishers for the digital copy to review.
Thank you to Atria / Signal One Publishers for the digital copy to review.
October 31, 2025
3.5 stars 🌟
Decent read and good to know the psyche of a person who once was the richest man in the world, lost everything and built it again.
He swings hard be it to bet on the future or technology trends. He collected his own shares of multi baggers but then many duds too.
He remains intriguing to many (including me) but this book helps to peel some of the layers. Worth reading once.
Decent read and good to know the psyche of a person who once was the richest man in the world, lost everything and built it again.
He swings hard be it to bet on the future or technology trends. He collected his own shares of multi baggers but then many duds too.
He remains intriguing to many (including me) but this book helps to peel some of the layers. Worth reading once.
April 27, 2025
A riveting and vivid storytelling of one of the most influential people of our time.
December 15, 2025
the story is good but the writing seems uneven. that may be expected as this book reads very much like the author’s other work "the powerful and the damned" which i really liked. the fast paced, jumpy style worked there, in this book it feels rushed. .
still i enjoyed the book and found it interesting to learn more about softbank and Masayoshi Son.
still i enjoyed the book and found it interesting to learn more about softbank and Masayoshi Son.
April 1, 2025
Gambling man covers the life story of Masayoshi Son, from his upbringing in a very unprivileged position in Japan to his huge ups and downs later in his career. He is the opposite of Buffet who is a very long-term focused calm investor. Masa is very impulse driven and has bet the house many times in his career on risky tech bets. He won the jackpot with Alibaba and Yahoo, but besides it, he has mostly lost a lot of money. One would wonder whether he would have ever had the opportunity to invest in his big home runs had he not been so reckless, but the jury stands that his strategy has yielded very mixed results. I wish the book would have covered more his personal life and personality, but I also thoroughly enjoyed learning about his business wins and losses. Both a lesson for others and inspiration for many future entrepreneurs. Recommended.
March 4, 2025
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.
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.
November 26, 2024
This book is most impressive of a philanthropist, risk taker and big investor: Masayoshi (Masa) Son. In 1981, he created SoftBank, Japan’s leading PC software distributor; a net worth of $82.77 billion (as of November 25, 2024). This book captures a vivid image of Masa and how he built a business like no other. He made it with impressive results and some would say he acquired a powerful sense of greatness.
Who is this man that benefitted from the fast-moving digital age? Masa somehow was able to find the profitable deals as if he was playing an advanced game of chess. He visualized the future and gambled with huge sums of money. He was right on top of the financial game with his private jets to meet with top tech leaders and potential start-up companies.
The book was engaging with conversations Lionel Barber tracked down from an extensive amount of research and interviews. He was able to get into the head of Masa and how he had a deep desire to be wealthy and more powerful than any other man. The book showcased the rapidly moving innovations in the tech world.
It’s well written and brings back memories of pinball machines, floppy discs, dial-up connections and the long lines for the first Apple iPhones. Barber ended the book with Masa’s imagination and thoughts on what’s next.
While reading about the billions of funds controlled by people like Masayoshi Son, Jeff Bezos, Bill Gates, Elon Musk and others, it’s a natural response to think of what more they could be doing for climate change, poverty and peace in our world. Much of the book reminds readers of what has happened with technology and misleading information. It makes us wonder if it has made our world a better place. This book would make an excellent one for discussions.
My thanks to Atria and NetGalley for allowing me to read an advanced copy of this book with an expected release date of January 21, 2025.
Who is this man that benefitted from the fast-moving digital age? Masa somehow was able to find the profitable deals as if he was playing an advanced game of chess. He visualized the future and gambled with huge sums of money. He was right on top of the financial game with his private jets to meet with top tech leaders and potential start-up companies.
The book was engaging with conversations Lionel Barber tracked down from an extensive amount of research and interviews. He was able to get into the head of Masa and how he had a deep desire to be wealthy and more powerful than any other man. The book showcased the rapidly moving innovations in the tech world.
It’s well written and brings back memories of pinball machines, floppy discs, dial-up connections and the long lines for the first Apple iPhones. Barber ended the book with Masa’s imagination and thoughts on what’s next.
While reading about the billions of funds controlled by people like Masayoshi Son, Jeff Bezos, Bill Gates, Elon Musk and others, it’s a natural response to think of what more they could be doing for climate change, poverty and peace in our world. Much of the book reminds readers of what has happened with technology and misleading information. It makes us wonder if it has made our world a better place. This book would make an excellent one for discussions.
My thanks to Atria and NetGalley for allowing me to read an advanced copy of this book with an expected release date of January 21, 2025.
Want to read
October 29, 2025The mystery of Masayoshi Son, SoftBank’s great disrupter - https://on.ft.com/4gtRWTz via @FT
FT review
Gambling Man — the remarkable, rollercoaster story of SoftBank’s Masayoshi Son - https://on.ft.com/3YmbWAx via @FT
Masayoshi Son may be the oddest of the oddball billionaires
https://www.businesstimes.com.sg/opin...
Masayoshi Son becomes Japan’s richest with US$55 billion fortune -BT 30 Dec 2025
https://bt.sg/tq7k
FT review
Gambling Man — the remarkable, rollercoaster story of SoftBank’s Masayoshi Son - https://on.ft.com/3YmbWAx via @FT
Masayoshi Son may be the oddest of the oddball billionaires
https://www.businesstimes.com.sg/opin...
Masayoshi Son becomes Japan’s richest with US$55 billion fortune -BT 30 Dec 2025
https://bt.sg/tq7k
September 30, 2025
Well crafted biography of a fascinating man, Masa. His rise, fall, rise, fall, and potential rise again is a tale you have to read to believe. He has a Forrest Gump-level ability to be at the right or wrong place at the wrong or right time.
January 1, 2026
Wonderful read.
February 4, 2025
Great biography of Masayoshi Son, the Korean-Japanese founder of SoftBank, the man who lost the most wealth (and then remade it!)
November 26, 2025
Possibly the best book I've read this year
August 22, 2025
Chaotic writing
Trading with debt is okay?
Not the right reader.
Trading with debt is okay?
Not the right reader.
May 12, 2025
Lionel Barber’s Gambling Man is an electrifying and deeply researched portrait of Masayoshi Son, the enigmatic founder of SoftBank and one of the most daring figures in global finance and technology. Barber takes readers on a whirlwind journey through Son’s extraordinary career, from his humble beginnings as the son of a pachinko parlor owner in Japan to his outsized influence in Silicon Valley and beyond.
The book excels at capturing Son’s relentless ambition and high-stakes, risk-taking approach to business, chronicling his early bets on the PC revolution, his prescient investments in Alibaba and ARM, and his audacious creation of the Vision Fund, which reshaped the world of tech investing. Barber’s sharp, cinematic prose brings to life both the dizzying highs-like SoftBank’s triumphs with Uber and DoorDash-and the spectacular lows, most notably the WeWork debacle.
Barber’s research is impressive, offering behind-the-scenes insights into Son’s deals and the broader forces driving tech capitalism. The book also explores the cultural and historical context of Son’s identity as a zainichi (ethnic Korean in Japan), adding depth to his outsider status and maverick mindset.
While Gambling Man is a gripping read, it sometimes overwhelms with dense financial detail and business jargon, which may challenge readers less familiar with the intricacies of high finance. The narrative occasionally leans more toward dramatization than strict fact, and some may wish for a deeper exploration of Son’s personal life beyond the boardroom.
Overall, Gambling Man is an engaging, thought-provoking biography of a true disruptor. Highly recommended for anyone fascinated by the intersection of technology, global finance, and the personalities who shape the modern world
The book excels at capturing Son’s relentless ambition and high-stakes, risk-taking approach to business, chronicling his early bets on the PC revolution, his prescient investments in Alibaba and ARM, and his audacious creation of the Vision Fund, which reshaped the world of tech investing. Barber’s sharp, cinematic prose brings to life both the dizzying highs-like SoftBank’s triumphs with Uber and DoorDash-and the spectacular lows, most notably the WeWork debacle.
Barber’s research is impressive, offering behind-the-scenes insights into Son’s deals and the broader forces driving tech capitalism. The book also explores the cultural and historical context of Son’s identity as a zainichi (ethnic Korean in Japan), adding depth to his outsider status and maverick mindset.
While Gambling Man is a gripping read, it sometimes overwhelms with dense financial detail and business jargon, which may challenge readers less familiar with the intricacies of high finance. The narrative occasionally leans more toward dramatization than strict fact, and some may wish for a deeper exploration of Son’s personal life beyond the boardroom.
Overall, Gambling Man is an engaging, thought-provoking biography of a true disruptor. Highly recommended for anyone fascinated by the intersection of technology, global finance, and the personalities who shape the modern world
April 24, 2025
Japanese business, entrepreneurship, history, etc. very interesting
March 22, 2025
The Gambling Man - The secret story of the World’s greatest disruptor - Masayoshi Son. The boom depicts the story of the Forrest Gump in the financial and tech world. Masa is an important character in the most pivotal moments in technology since the 70’s. He was there interacting and investing with Steve Jobs and Bill Gates in the early days of the PC era.
He was there investing in the dot com era and later backing Jack Ma before anyone knew Alibaba. He invested early in microchips backing up ARM which turned up to be a great bet. He later invested in the telecom era in Sprint, turned it around and converted it in the 3rd largest telecom in the US.
He was there in the VC era creating Vision Fund 1 and Vision Fund 2 to disrupt the world of investment in startups. That proved to be a great bet but for a impulsive investor like him, his greatest weakness.
He invested early in the sharing economy: DoorDash, Lyft and Uber.
He made his greatest mistake investing in WeWork.
He is an early investor in Open AI.
Masa pops up in every important time in innovations in the past 50 years.
What makes this book fascinating is not just the timeline of Masa’s deals, but his fearless, almost childlike vision combined with an appetite for risk that borders on reckless. You get the sense that he operates on instinct, guided by a long-term belief in technology’s power to reshape the world.
It’s not a clean, polished success story; it’s messy, unpredictable, and full of lessons about vision, resilience, and the price of ambition.
If you’re into stories of bold moves, big swings, and the kind of thinking that doesn’t fit inside the box, this one is definitely worth the read.
Masa and SoftBank shaped innovation and technology in the past 50 years and apparently he will continue to do so
#mdbookreview
He was there investing in the dot com era and later backing Jack Ma before anyone knew Alibaba. He invested early in microchips backing up ARM which turned up to be a great bet. He later invested in the telecom era in Sprint, turned it around and converted it in the 3rd largest telecom in the US.
He was there in the VC era creating Vision Fund 1 and Vision Fund 2 to disrupt the world of investment in startups. That proved to be a great bet but for a impulsive investor like him, his greatest weakness.
He invested early in the sharing economy: DoorDash, Lyft and Uber.
He made his greatest mistake investing in WeWork.
He is an early investor in Open AI.
Masa pops up in every important time in innovations in the past 50 years.
What makes this book fascinating is not just the timeline of Masa’s deals, but his fearless, almost childlike vision combined with an appetite for risk that borders on reckless. You get the sense that he operates on instinct, guided by a long-term belief in technology’s power to reshape the world.
It’s not a clean, polished success story; it’s messy, unpredictable, and full of lessons about vision, resilience, and the price of ambition.
If you’re into stories of bold moves, big swings, and the kind of thinking that doesn’t fit inside the box, this one is definitely worth the read.
Masa and SoftBank shaped innovation and technology in the past 50 years and apparently he will continue to do so
#mdbookreview
April 20, 2025
Son is fun to learn about. His ability to see the future and adjust is fantastic. His appetite for risk, especially in regards to borrowing money, is terrifying. I wish there was more information on his personal life.
did-not-finish
January 1, 2025DNFed at... 17%? 18%? Oof. Marketers, I beg of you: please don't sell a book as being "unputdownable," as it's soooo subjective and creates unrealistic expectations that are often dashed. Because I picked this up and read a bit of it a few times, but every time I put down my Kindle, I never felt the urge to pick it back up again... until, one day, that stuck.
Oh, it's not a bad book. Barber's prose is very stylish, sometimes unbelievably so; at times I wondered if he wasn't perhaps taking TOO many creative liberties with assuming that he knew what people were thinking or feeling.
I was okay with this at first, especially coupled with learning that Son's family are zainichi--ethnic Koreans living in Japan--who I first learned about in Min Jin Lee's Pachinko. It added a layer of intrigue to Son that I hadn't expected.
But when the business stuff started, the more I tried to read, the more confused I got. The book never really seemed to adequately explain what, exactly, Son's business is in. Software? Just... making money? I don't have a head for any of these things, and I wished the book had stepped back from its stylistic choices a bit to give readers a bit more straightforward information about what it is that Son did to make money.
After the book started to move into Son's cycles of making maverick amounts of money and then losing almost the same amount due to risky (stupid?) business behavior, I felt lost and disinterested. I wanted more of the "human" side and less of the "business".
Thank you to Atria and NetGalley for the free e-ARC in exchange for an honest review
Oh, it's not a bad book. Barber's prose is very stylish, sometimes unbelievably so; at times I wondered if he wasn't perhaps taking TOO many creative liberties with assuming that he knew what people were thinking or feeling.
I was okay with this at first, especially coupled with learning that Son's family are zainichi--ethnic Koreans living in Japan--who I first learned about in Min Jin Lee's Pachinko. It added a layer of intrigue to Son that I hadn't expected.
But when the business stuff started, the more I tried to read, the more confused I got. The book never really seemed to adequately explain what, exactly, Son's business is in. Software? Just... making money? I don't have a head for any of these things, and I wished the book had stepped back from its stylistic choices a bit to give readers a bit more straightforward information about what it is that Son did to make money.
After the book started to move into Son's cycles of making maverick amounts of money and then losing almost the same amount due to risky (stupid?) business behavior, I felt lost and disinterested. I wanted more of the "human" side and less of the "business".
Thank you to Atria and NetGalley for the free e-ARC in exchange for an honest review
April 20, 2025
Great insights into the life and working of Mr Son and his wild ride with softbank
January 20, 2025
Gambling Man is the first Western biography of SoftBank CEO Masayoshi Son. This book goes back a couple generations so we can learn what world Son comes from. He is the son of a pachinko kingpin who grew up in a slum in Japan.
Honestly, I didn’t know who Masayoshi Son and reading a biography on him was a complete learning experience. Thank you Atria and NetGalley for an ARC. #NetGalley #GamblingMan
Honestly, I didn’t know who Masayoshi Son and reading a biography on him was a complete learning experience. Thank you Atria and NetGalley for an ARC. #NetGalley #GamblingMan
March 8, 2025
Another entry in the: books about profoundly evil people with sad origins.
I do wonder how his marriage looks like. the book desribes Masayoshi son as someone that is married to making money. His daughters are probably 40 now but hey if you want to fund a fella to make the worst art in history hit me up i can be a sugar baby
I do wonder how his marriage looks like. the book desribes Masayoshi son as someone that is married to making money. His daughters are probably 40 now but hey if you want to fund a fella to make the worst art in history hit me up i can be a sugar baby
April 3, 2025
very enjoyable
Easy to read account of a real gambler. Humble origins but massive aspirations and goals. Good on the guy. Unfortunately for him, he will always be remembered for WeWork.
Easy to read account of a real gambler. Humble origins but massive aspirations and goals. Good on the guy. Unfortunately for him, he will always be remembered for WeWork.
July 15, 2025
What a wild business ride into a high-stakes drama, equal parts of a visionary genius and delusional gambler. Masayoshi's bets swing between brilliance and madness, making for a spectacle more entertaining than enlightening. It's a fun, baffling read.
March 24, 2025
Relatable…
May 27, 2025
He must be the greatest social engineer in fundraising; otherwise, you cannot gamble for so long without going broke.
May 28, 2025
Gets a bit too nitty gritty into the details for my taste. Wish I got to know more about the man -- the surprising stuff one would not expect.
May 31, 2025
The title is a good summary
July 29, 2025
Disappointing. Text-book like. Only act 4 Hubris brings excitement.
August 29, 2025
SoftBank is a company that I've seen crop up in random places over the past fifteen or so years. They have always seemed a bit of a wildcard. Their purchase of ARM always sturck me as strange - why was this Japanese company specifically interested in a chip design firm here in the UK?
With this book, SoftBank starts to be a bit more explicable. I almost said "it makes more sense" but I think what I've really taken away from this is that my previous impression of the company being strange and not making much sense, was an accurate one. And the life and guidance of Masayoshi Son, SoftBank's founder and CEO, the guiding force for the company for most of its life, has a direct cause and effect relationship with that strangeness.
The book makes clear that even though today he's one of the richest people in the world, Masayoshi Son came from a destitute background. The stories of racism against him, of hiding his identity as an ethnic Korean, of the slums he lived in, are all enormous challenges in his early life, that you wouldn't wish on anyone. That he overcame them is both incredibly impressive and unfortunate that he'd had to at all. Contrast that to his later life in SoftBank, with the underground Tokyo apartment complex that houses a custom built indoor golf course designed to mimic famous courses from around the world, the jet-setting life that circled the globe every few days, and the hundreds of billions of dollars that he wielded through SoftBank. As the book's subtitle says, it's a wild ride.
Over the course of the story, Masayoshi Son's story manages to tip a bit, from eminently empathetic and well deserved success over adversity, to a level of wanton maverick that seems to be something of a danger to the markets SoftBank interacts with. I can't help but think that the tilt toward financialization of everything, which SoftBank embraces, ends up defeating the actual purpose of money and society. That after a certain layer of derivatives and accounting tomfoolery, the folks involved have forgotten that the purpose of a business should be to do something, not to exploit the mathematical properties of the concept of money to create larger numbers.
But that's more about the story of the man. The story of this book does a good job of covering a lot of ground in Masayoshi Son's life and affect on the world. I feel like a lot of pieces slot together of where I've seen SoftBank now that I read this in more detail. Lionel Barber doesn't idealize his protagonist, has some criticism for him, but is overall I think on Masayoshi's side. It's an interesting take that largely casts Masayoshi Son as an aspirational technologist. With the actions described in the book, I could believe it. Certainly it would explain some of the wackier choices.
The risk with this kind of book, even with an exciting main character, is that it becomes a bit of drudgery. Real life rarely stacks up a neatly arranged narrative like fiction does, but Lionel Barber puts one together here. The arc of Masayoshi Son over the course of the not-quite-chronological story of his life is clear - meteoric rises punctuated by precipitous falls, but in the long arc his life trends upwards.
With this book, SoftBank starts to be a bit more explicable. I almost said "it makes more sense" but I think what I've really taken away from this is that my previous impression of the company being strange and not making much sense, was an accurate one. And the life and guidance of Masayoshi Son, SoftBank's founder and CEO, the guiding force for the company for most of its life, has a direct cause and effect relationship with that strangeness.
The book makes clear that even though today he's one of the richest people in the world, Masayoshi Son came from a destitute background. The stories of racism against him, of hiding his identity as an ethnic Korean, of the slums he lived in, are all enormous challenges in his early life, that you wouldn't wish on anyone. That he overcame them is both incredibly impressive and unfortunate that he'd had to at all. Contrast that to his later life in SoftBank, with the underground Tokyo apartment complex that houses a custom built indoor golf course designed to mimic famous courses from around the world, the jet-setting life that circled the globe every few days, and the hundreds of billions of dollars that he wielded through SoftBank. As the book's subtitle says, it's a wild ride.
Over the course of the story, Masayoshi Son's story manages to tip a bit, from eminently empathetic and well deserved success over adversity, to a level of wanton maverick that seems to be something of a danger to the markets SoftBank interacts with. I can't help but think that the tilt toward financialization of everything, which SoftBank embraces, ends up defeating the actual purpose of money and society. That after a certain layer of derivatives and accounting tomfoolery, the folks involved have forgotten that the purpose of a business should be to do something, not to exploit the mathematical properties of the concept of money to create larger numbers.
But that's more about the story of the man. The story of this book does a good job of covering a lot of ground in Masayoshi Son's life and affect on the world. I feel like a lot of pieces slot together of where I've seen SoftBank now that I read this in more detail. Lionel Barber doesn't idealize his protagonist, has some criticism for him, but is overall I think on Masayoshi's side. It's an interesting take that largely casts Masayoshi Son as an aspirational technologist. With the actions described in the book, I could believe it. Certainly it would explain some of the wackier choices.
The risk with this kind of book, even with an exciting main character, is that it becomes a bit of drudgery. Real life rarely stacks up a neatly arranged narrative like fiction does, but Lionel Barber puts one together here. The arc of Masayoshi Son over the course of the not-quite-chronological story of his life is clear - meteoric rises punctuated by precipitous falls, but in the long arc his life trends upwards.
February 19, 2025
Thank you to Atria Books for this ARC!
Masayoshi Son is one of the most fascinating figures in modern finance—part visionary, part gambler, and entirely unpredictable. In Gambling Man, Lionel Barber delivers the first Western biography of the SoftBank CEO, offering an in-depth look at the man who has reshaped global tech investment with both dazzling successes and catastrophic failures.
This book is as much about Son as it is about the fast-moving digital economy, the rise of venture capital, and the forces shaping 21st-century commerce. Barber’s meticulous research and engaging storytelling bring Son’s journey to life, from his childhood as the son of a pachinko kingpin in Japan to becoming a billionaire tech investor navigating the financial highs and lows of companies like Uber, WeWork, and Slack.
____________________________________________________________
🔥 What Worked
✔ A gripping character study – Son is a complex and compelling figure, and Barber captures his relentless ambition and high-risk approach to business.
✔ Extensive research – The book is packed with insights from interviews, financial history, and behind-the-scenes moments in tech's biggest deals.
✔ Stylish prose – Barber’s writing is sharp, almost cinematic at times, making dense financial topics feel dynamic and engaging.
✔ Historical & cultural depth – Son’s background as a zainichi (ethnic Korean in Japan) adds an unexpected and intriguing layer to his story.
____________________________________________________________
🤔 What Didn't Quite Land
🔹 Business jargon overload – At times, the book assumes a level of financial knowledge that might leave general readers struggling. A bit more clarity on Son’s actual business dealings would have helped.
🔹 Style over substance? – Barber’s flair for dramatization sometimes makes it feel like he’s assuming what people were thinking rather than presenting solid facts.
🔹 Less business, more human – The book shines in exploring Son’s personality but can feel bogged down when cycling through the endless deals, risks, and financial swings.
____________________________________________________________
📌 TROPES & THEMES
💰 High-stakes finance & investment
📈 Boom-and-bust cycles
🛫 Jet-setting billionaire lifestyle
🧩 Maverick entrepreneur vs. the system
🎭 Visionary or reckless gambler?
🌎 Global impact of tech capitalism
____________________________________________________________
Final Thoughts
Gambling Man is an insightful and well-researched deep dive into one of tech’s most influential and enigmatic figures. If you're fascinated by high-stakes investing, the evolution of Silicon Valley, and the personalities shaping the future, this book is a must-read.
However, if you’re looking for a more balanced exploration of Son’s human side beyond his business moves, you may find the financial deep dives overwhelming. Still, Barber’s sharp storytelling makes this an engaging, thought-provoking read.
⭐⭐⭐⭐ Four stars! A fascinating, if occasionally overwhelming, portrait of a financial disruptor.
Masayoshi Son is one of the most fascinating figures in modern finance—part visionary, part gambler, and entirely unpredictable. In Gambling Man, Lionel Barber delivers the first Western biography of the SoftBank CEO, offering an in-depth look at the man who has reshaped global tech investment with both dazzling successes and catastrophic failures.
This book is as much about Son as it is about the fast-moving digital economy, the rise of venture capital, and the forces shaping 21st-century commerce. Barber’s meticulous research and engaging storytelling bring Son’s journey to life, from his childhood as the son of a pachinko kingpin in Japan to becoming a billionaire tech investor navigating the financial highs and lows of companies like Uber, WeWork, and Slack.
____________________________________________________________
🔥 What Worked
✔ A gripping character study – Son is a complex and compelling figure, and Barber captures his relentless ambition and high-risk approach to business.
✔ Extensive research – The book is packed with insights from interviews, financial history, and behind-the-scenes moments in tech's biggest deals.
✔ Stylish prose – Barber’s writing is sharp, almost cinematic at times, making dense financial topics feel dynamic and engaging.
✔ Historical & cultural depth – Son’s background as a zainichi (ethnic Korean in Japan) adds an unexpected and intriguing layer to his story.
____________________________________________________________
🤔 What Didn't Quite Land
🔹 Business jargon overload – At times, the book assumes a level of financial knowledge that might leave general readers struggling. A bit more clarity on Son’s actual business dealings would have helped.
🔹 Style over substance? – Barber’s flair for dramatization sometimes makes it feel like he’s assuming what people were thinking rather than presenting solid facts.
🔹 Less business, more human – The book shines in exploring Son’s personality but can feel bogged down when cycling through the endless deals, risks, and financial swings.
____________________________________________________________
📌 TROPES & THEMES
💰 High-stakes finance & investment
📈 Boom-and-bust cycles
🛫 Jet-setting billionaire lifestyle
🧩 Maverick entrepreneur vs. the system
🎭 Visionary or reckless gambler?
🌎 Global impact of tech capitalism
____________________________________________________________
Final Thoughts
Gambling Man is an insightful and well-researched deep dive into one of tech’s most influential and enigmatic figures. If you're fascinated by high-stakes investing, the evolution of Silicon Valley, and the personalities shaping the future, this book is a must-read.
However, if you’re looking for a more balanced exploration of Son’s human side beyond his business moves, you may find the financial deep dives overwhelming. Still, Barber’s sharp storytelling makes this an engaging, thought-provoking read.
⭐⭐⭐⭐ Four stars! A fascinating, if occasionally overwhelming, portrait of a financial disruptor.
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