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Gambling Man: The Wild Ride of Japan’s Masayoshi Son
Japan’s Masayoshi Son has made and lost several fortunes, investing or controlling assets worth $1trn in the past two decades through his media-tech giant, SoftBank. He bankrolled Alibaba, China’s internet colossus, before the world had heard about it; plotted with Steve Jobs to turn the iPhone into a wonder product; and financed hundreds of tech start-ups, fuelling the biggest boom Silicon Valley has ever seen.
This book takes you on Masa’s wild ride, from his birthplace in a Korean slum in post-war Japan to the modern-day temples of power. It speeds through Donald Trump’s golden skyscraper in Manhattan, the royal palaces of Riyadh and the throne rooms of China’s Marxist rulers; all places where Masa has deployed his unique blend of techno-optimism, financial engineering and insane risk-taking.
In his own Masa is the world’s craziest investor. He spent billions supporting the visions of founders like WeWork’s Adam Neumann only to lose everything. Yet, despite the reverses, he’s never abandoned his belief that technology, particularly artificial Intelligence, will change our lives for the better.
Masa’s story captures a 25 year-span of hyper-globalisation in which money, technologies and ideas flowed freely. He’s made billions and lost billions during the dot.com bust, the global financial crisis, and the Covid pandemic. His is a story of constant reinvention and perpetual motion, ever seeking the Next Big Thing.
As an ethnic Korean in Japan, Masa has overcome adversity and discrimination to become Japan’s best known businessman and empire-builder but he remains an elusive, intensely private figure, an enigma to the western world. This book reveals the man behind the money, what drives him, why he matters, and what he plans for his next act.
This book takes you on Masa’s wild ride, from his birthplace in a Korean slum in post-war Japan to the modern-day temples of power. It speeds through Donald Trump’s golden skyscraper in Manhattan, the royal palaces of Riyadh and the throne rooms of China’s Marxist rulers; all places where Masa has deployed his unique blend of techno-optimism, financial engineering and insane risk-taking.
In his own Masa is the world’s craziest investor. He spent billions supporting the visions of founders like WeWork’s Adam Neumann only to lose everything. Yet, despite the reverses, he’s never abandoned his belief that technology, particularly artificial Intelligence, will change our lives for the better.
Masa’s story captures a 25 year-span of hyper-globalisation in which money, technologies and ideas flowed freely. He’s made billions and lost billions during the dot.com bust, the global financial crisis, and the Covid pandemic. His is a story of constant reinvention and perpetual motion, ever seeking the Next Big Thing.
As an ethnic Korean in Japan, Masa has overcome adversity and discrimination to become Japan’s best known businessman and empire-builder but he remains an elusive, intensely private figure, an enigma to the western world. This book reveals the man behind the money, what drives him, why he matters, and what he plans for his next act.
386 pages, Kindle Edition
Published October 3, 2024
174 people are currently reading
1733 people want to read
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Displaying 1 - 30 of 48 reviews
July 31, 2025
A funny book…I can see why it got a lot of attention within its genre, but it becomes apparent that Masayoshi Son: (a) isn’t that interesting on a personal level - he just has a higher than usual risk appetite among the cohort of investor billionaires; and (b) Lionel Barber was a significantly better editor than he is a story-teller. There’s not even that much that could be generalisable from Masa’s career!
Mainly interesting it (like most FT readers) you see Masa’s name and biography pop up in lots of stories and you’re keen to understand more as to why.
Mainly interesting it (like most FT readers) you see Masa’s name and biography pop up in lots of stories and you’re keen to understand more as to why.
April 19, 2025
A well researched account of the life of arguably the most daring entrepreneur of his generation.
The book starts with Masa's beginnings, then on to his education in the United States, and then his incredible and often topsy turvy journey to the dizzying heights of the global tech world.
A great book if you're interested in the history of some of the most recognisable businesses in the world i.e Apple, Yahoo, Alibaba, T-Mobile, Sprint, Softbank etc.
The book starts with Masa's beginnings, then on to his education in the United States, and then his incredible and often topsy turvy journey to the dizzying heights of the global tech world.
A great book if you're interested in the history of some of the most recognisable businesses in the world i.e Apple, Yahoo, Alibaba, T-Mobile, Sprint, Softbank etc.
May 1, 2025
This book is a gripping biography of Masayoshi Son whose audacious bets and relentless ambition reshaped businesses around the globe. The book is a page-turner, so dense with information that blinking feels like a risk—you might miss a pivotal deal, a daring gamble, or a glimpse into Son’s complex psyche. Barber’s meticulous research and fast-paced narrative make it hard to put down, though at times the sheer volume of financial and corporate detail can feel overwhelming.
For the first 140 pages, Son comes across as a slick operator, possibly even a fraud, gaming the system with charm and audacity. His early ventures, marked by bold promises and risky loans, invite scepticism. But a pivotal quote shifts the narrative: “Masa saw things differently. If you are born in a slum with nothing, losing everything is relative. You just go back to square one. Then, like the Korean slum dwellers in Tosu, you build back up.” This perspective, rooted in Son’s humble origins as part of Japan’s marginalized Korean minority, bolsters his relentless risk-taking as a product of resilience rather than recklessness.
Son’s creation of a telecom empire through SoftBank serves as a testament to his legitimacy. Far from merely playing the system, he built a tangible, innovative business that disrupted Japan’s entrenched corporate landscape. His success in securing loans based on vision rather than collateral and launching a broadband and mobile phone business in Japan against fierce opposition underscores his ability to turn ambition into reality.
The epilogue’s summation captures Son’s essence: “Alongside the bravado, the extraordinary wealth and the manifest waste lie courage, creativity, and a capacity to effect change.” Barber paints a nuanced portrait of a man who rose from despised origins to challenge Japan’s corporate titans, pioneered software distribution, strategically invested in Chinese businesses that have since become global phenoms, acquired major American assets, and orchestrated the Sprint–T-Mobile merger, creating a telecom powerhouse and now trying to put his weight behind ARM Holdings. Despite hubris leading to spectacular falls—not once, but three times—Son’s refusal to surrender defines him.
For the first 140 pages, Son comes across as a slick operator, possibly even a fraud, gaming the system with charm and audacity. His early ventures, marked by bold promises and risky loans, invite scepticism. But a pivotal quote shifts the narrative: “Masa saw things differently. If you are born in a slum with nothing, losing everything is relative. You just go back to square one. Then, like the Korean slum dwellers in Tosu, you build back up.” This perspective, rooted in Son’s humble origins as part of Japan’s marginalized Korean minority, bolsters his relentless risk-taking as a product of resilience rather than recklessness.
Son’s creation of a telecom empire through SoftBank serves as a testament to his legitimacy. Far from merely playing the system, he built a tangible, innovative business that disrupted Japan’s entrenched corporate landscape. His success in securing loans based on vision rather than collateral and launching a broadband and mobile phone business in Japan against fierce opposition underscores his ability to turn ambition into reality.
The epilogue’s summation captures Son’s essence: “Alongside the bravado, the extraordinary wealth and the manifest waste lie courage, creativity, and a capacity to effect change.” Barber paints a nuanced portrait of a man who rose from despised origins to challenge Japan’s corporate titans, pioneered software distribution, strategically invested in Chinese businesses that have since become global phenoms, acquired major American assets, and orchestrated the Sprint–T-Mobile merger, creating a telecom powerhouse and now trying to put his weight behind ARM Holdings. Despite hubris leading to spectacular falls—not once, but three times—Son’s refusal to surrender defines him.
January 4, 2026
没读这本书前我真的以为软银是家银行，但又跟很多新闻报道的事件不符。
孙是韩裔日本人，从父亲这一代开始家族富有，卖猪肉赚了第一桶金后进军游戏机产业、房地产业，孙从小就志向远大本科就去了加州伯克利分校；
孙胆子非常大，为了发展事业和收购某公司杠杆借了很多钱，但都穿越了风暴，或许真的有看穿未来的本事，但你要看他从事的工作真的是太累了，赚钱也很累，冒很大的风险，现在身价还不到500亿美金，不过人家也不是为了钱。
孙是韩裔日本人，从父亲这一代开始家族富有，卖猪肉赚了第一桶金后进军游戏机产业、房地产业，孙从小就志向远大本科就去了加州伯克利分校；
孙胆子非常大，为了发展事业和收购某公司杠杆借了很多钱，但都穿越了风暴，或许真的有看穿未来的本事，但你要看他从事的工作真的是太累了，赚钱也很累，冒很大的风险，现在身价还不到500亿美金，不过人家也不是为了钱。
May 30, 2025
Loved this biography, Kinda a story of agency
February 21, 2025
An incredible well-written biography of the legendary Masayoshi Son. Previously not a public figure outside of Japan, he's become increasingly well known in the past 25 years for making and losing billions of dollars. Equal parts tech visionary, business titan, investor, con man -- he is above all a gambler.
The book does a great job to expand upon Masa's own public story of overcoming adversity and discrimination as an ethnic Korean in Japan to become a technology empire-builder. While at every turn looking deeper to better understand the man behind the money, what drives him, what rules did he break, why he matters, and what he plans for his next act (as his story isn't over yet). I particularly liked the decision to spend early chapters discussing his family's rise from poor immigrants to Pachinko empire and cross-referencing Masa's early story by interviewing his old business partners and mentors.
I've always been curious about why the Saudi's invested in Masa's vision fund, why Apple launched the IPhone exclusively in Japan through Softbank, how Masa ended up investing in Yahoo, Alibaba, Didi, Coupang, and other successful tech ventures. I also learned a lot I wasn't expecting -- like how
Sheldon Adelson (billionaire owner of Sands casinos, mega-political donor to Trump, Republicans and Israel) made a huge part of his fortune when Masa overpayed massively to buy COMDEX in 1995. Or how Masa's famous 4 min meeting with Adam Neuman where he agreed to invest $4.4 billion in WeWork was while Masa was in a car to visit Trump Tower. Or his involvement in 'doomed-to-fail' giant vanity project to build Nusantara in Indonesia (brand new capital city).
From an investor standpoint, Masa is probably best seen as the greatest fool repeatedly buying speculative assets at the very top of market bubbles and seeing them become worthless. His access to credit & investment (Japanese retail investors & banks, Oil sheiks) and his industry and political connections (it's easy to make friends when spending billions), and his own confidence (in himself and his vision for technology) makes him a huge force in the world -- distorting markets, inflating bubbles, and misallocating capital. He's made a few good bets over the year, but the evidence leans towards luck & connections rather than genius.
The book does a great job to expand upon Masa's own public story of overcoming adversity and discrimination as an ethnic Korean in Japan to become a technology empire-builder. While at every turn looking deeper to better understand the man behind the money, what drives him, what rules did he break, why he matters, and what he plans for his next act (as his story isn't over yet). I particularly liked the decision to spend early chapters discussing his family's rise from poor immigrants to Pachinko empire and cross-referencing Masa's early story by interviewing his old business partners and mentors.
I've always been curious about why the Saudi's invested in Masa's vision fund, why Apple launched the IPhone exclusively in Japan through Softbank, how Masa ended up investing in Yahoo, Alibaba, Didi, Coupang, and other successful tech ventures. I also learned a lot I wasn't expecting -- like how
Sheldon Adelson (billionaire owner of Sands casinos, mega-political donor to Trump, Republicans and Israel) made a huge part of his fortune when Masa overpayed massively to buy COMDEX in 1995. Or how Masa's famous 4 min meeting with Adam Neuman where he agreed to invest $4.4 billion in WeWork was while Masa was in a car to visit Trump Tower. Or his involvement in 'doomed-to-fail' giant vanity project to build Nusantara in Indonesia (brand new capital city).
From an investor standpoint, Masa is probably best seen as the greatest fool repeatedly buying speculative assets at the very top of market bubbles and seeing them become worthless. His access to credit & investment (Japanese retail investors & banks, Oil sheiks) and his industry and political connections (it's easy to make friends when spending billions), and his own confidence (in himself and his vision for technology) makes him a huge force in the world -- distorting markets, inflating bubbles, and misallocating capital. He's made a few good bets over the year, but the evidence leans towards luck & connections rather than genius.
February 6, 2025
"The Gambling Man" is a compelling account of Masayoshi Son’s extraordinary life, definitely worth reading. Only downside: I felt the book could have better balanced his visionary outlook with the financial rollercoaster that defined his career. It leans too heavily into portraying Son as a gambler, emphasizing his high-risk bets and dramatic financial swings. Yet, he is far more than just a risk-taker—he is a visionary whose deep belief in technological transformation, connectivity, IoT, and AI has shaped entire industries.
Born in 1957 to a Korean family in Japan, Son faced discrimination as a Zainichi Korean. Supported by his entrepreneurial father, he studied economics and computer science at the University of California, Berkeley, where he was exposed to the nascent tech industry.
His first major breakthrough came in the early days of the internet when his 1995 investment in Yahoo secured a 35% stake for SoftBank—a masterstroke. As the internet boom accelerated, he pushed further, establishing Yahoo Japan in 1996, a joint venture that became one of the most successful internet businesses in Asia. At the peak of the dot-com bubble, Son’s net worth soared, and for a brief moment in early 2000, he was considered one of the richest men in the world, even surpassing Bill Gates. However, the bubble burst, wiping out nearly $70 billion of his wealth overnight.
Few could recover from such a blow, but Son proved a master of reinvention. In 2000, he met Jack Ma and invested $20 million in Alibaba, then a struggling e-commerce startup. That investment became one of the greatest in business history—by the time Alibaba went public in 2014, SoftBank’s stake was worth over $60 billion. This windfall cemented Son’s reputation as a master investor, giving him the confidence to make even bolder moves—some highly successful, others catastrophic.
His ambitions extended into telecom. In 2013, he acquired Sprint for $21.6 billion, betting he could turn the struggling U.S. carrier into a powerhouse through a merger with T-Mobile. However, Sprint’s heavy debt burden and inability to compete with AT&T and Verizon led to years of financial struggles. Finally, in 2020, Sprint merged with T-Mobile, salvaging what could have been a disastrous investment.
Always dreaming big, Son launched the SoftBank Vision Fund in 2017, raising an unprecedented $100 billion with backing from Saudi Arabia’s Public Investment Fund and the UAE’s Mubadala. The fund aimed to invest in transformative technologies such as AI, robotics, and fintech.
His massive investment in WeWork proved costly for SoftBank. He committed over $10 billion to Adam Neumann’s co-working startup, valuing it at $47 billion before its ill-fated IPO attempt in 2019. The IPO exposed WeWork’s financial instability and governance issues, forcing SoftBank to write down billions in losses. Son was overly optimistic about Neumann’s leadership and failed to exercise sufficient oversight. The debacle damaged his reputation and raised concerns about the Vision Fund’s investment strategy.
In 2016, he made one of his largest acquisitions, purchasing ARM Holdings for $32 billion, believing its chip architecture would dominate mobile and IoT markets. Son opted to take ARM public in 2023, positioning it as a key player in AI and semiconductors. The investment proved successful, with ARM now valued at more than $160 billion.
However, Son missed a major opportunity to maximize his stake in Nvidia. While SoftBank did invest in the AI chip giant, he sold its shares too soon, failing to capitalize on Nvidia’s meteoric rise amid the AI boom.
Throughout his career, Son aggressively leveraged debt to fuel his investments. By 2020, SoftBank’s debt had swelled to over $160 billion, making it one of the most indebted companies in the world. He often made billion-dollar commitments within minutes of meeting a founder, guided by an almost mystical belief in his ability to foresee the future. His high-risk, high-reward strategy led to extreme volatility—one moment, he was hailed as a genius investor; the next, he was scrambling to reassure shareholders. The WeWork failure and market downturns forced SoftBank to sell parts of its Alibaba stake and undertake share buybacks to stabilize investor confidence.
Beyond his investments, Son’s vision for the future revolves around the transformative power of AI, robotics, and the Internet of Things (IoT). He believes AI will surpass human intelligence, revolutionizing industries such as healthcare, finance, and transportation. His long-term outlook drives his aggressive investment strategy, prioritizing disruptive companies that could define the next century. This conviction has led to some of the biggest successes in tech history—Alibaba being a prime example—but also costly missteps, such as WeWork, where optimism overrode business fundamentals.
Son also broke cultural barriers by openly using his Korean name in traditionalist Japan, imposing himself in elite circles and meeting presidents, princes, and business tycoons as an equal. He maintained an extravagant lifestyle, owning opulent residences in Tokyo and Silicon Valley, a multi-million-dollar wine collection, and traveling by private jets and yachts. While befitting his immense wealth, his lavish spending has drawn scrutiny, particularly during SoftBank’s financial struggles.
His life could be the subject of a captivating movie—and the last chapter is yet to be written.
Born in 1957 to a Korean family in Japan, Son faced discrimination as a Zainichi Korean. Supported by his entrepreneurial father, he studied economics and computer science at the University of California, Berkeley, where he was exposed to the nascent tech industry.
His first major breakthrough came in the early days of the internet when his 1995 investment in Yahoo secured a 35% stake for SoftBank—a masterstroke. As the internet boom accelerated, he pushed further, establishing Yahoo Japan in 1996, a joint venture that became one of the most successful internet businesses in Asia. At the peak of the dot-com bubble, Son’s net worth soared, and for a brief moment in early 2000, he was considered one of the richest men in the world, even surpassing Bill Gates. However, the bubble burst, wiping out nearly $70 billion of his wealth overnight.
Few could recover from such a blow, but Son proved a master of reinvention. In 2000, he met Jack Ma and invested $20 million in Alibaba, then a struggling e-commerce startup. That investment became one of the greatest in business history—by the time Alibaba went public in 2014, SoftBank’s stake was worth over $60 billion. This windfall cemented Son’s reputation as a master investor, giving him the confidence to make even bolder moves—some highly successful, others catastrophic.
His ambitions extended into telecom. In 2013, he acquired Sprint for $21.6 billion, betting he could turn the struggling U.S. carrier into a powerhouse through a merger with T-Mobile. However, Sprint’s heavy debt burden and inability to compete with AT&T and Verizon led to years of financial struggles. Finally, in 2020, Sprint merged with T-Mobile, salvaging what could have been a disastrous investment.
Always dreaming big, Son launched the SoftBank Vision Fund in 2017, raising an unprecedented $100 billion with backing from Saudi Arabia’s Public Investment Fund and the UAE’s Mubadala. The fund aimed to invest in transformative technologies such as AI, robotics, and fintech.
His massive investment in WeWork proved costly for SoftBank. He committed over $10 billion to Adam Neumann’s co-working startup, valuing it at $47 billion before its ill-fated IPO attempt in 2019. The IPO exposed WeWork’s financial instability and governance issues, forcing SoftBank to write down billions in losses. Son was overly optimistic about Neumann’s leadership and failed to exercise sufficient oversight. The debacle damaged his reputation and raised concerns about the Vision Fund’s investment strategy.
In 2016, he made one of his largest acquisitions, purchasing ARM Holdings for $32 billion, believing its chip architecture would dominate mobile and IoT markets. Son opted to take ARM public in 2023, positioning it as a key player in AI and semiconductors. The investment proved successful, with ARM now valued at more than $160 billion.
However, Son missed a major opportunity to maximize his stake in Nvidia. While SoftBank did invest in the AI chip giant, he sold its shares too soon, failing to capitalize on Nvidia’s meteoric rise amid the AI boom.
Throughout his career, Son aggressively leveraged debt to fuel his investments. By 2020, SoftBank’s debt had swelled to over $160 billion, making it one of the most indebted companies in the world. He often made billion-dollar commitments within minutes of meeting a founder, guided by an almost mystical belief in his ability to foresee the future. His high-risk, high-reward strategy led to extreme volatility—one moment, he was hailed as a genius investor; the next, he was scrambling to reassure shareholders. The WeWork failure and market downturns forced SoftBank to sell parts of its Alibaba stake and undertake share buybacks to stabilize investor confidence.
Beyond his investments, Son’s vision for the future revolves around the transformative power of AI, robotics, and the Internet of Things (IoT). He believes AI will surpass human intelligence, revolutionizing industries such as healthcare, finance, and transportation. His long-term outlook drives his aggressive investment strategy, prioritizing disruptive companies that could define the next century. This conviction has led to some of the biggest successes in tech history—Alibaba being a prime example—but also costly missteps, such as WeWork, where optimism overrode business fundamentals.
Son also broke cultural barriers by openly using his Korean name in traditionalist Japan, imposing himself in elite circles and meeting presidents, princes, and business tycoons as an equal. He maintained an extravagant lifestyle, owning opulent residences in Tokyo and Silicon Valley, a multi-million-dollar wine collection, and traveling by private jets and yachts. While befitting his immense wealth, his lavish spending has drawn scrutiny, particularly during SoftBank’s financial struggles.
His life could be the subject of a captivating movie—and the last chapter is yet to be written.
March 3, 2025
There’s been a surge of biographies lately, and I’ve been particularly drawn to the stories of Asian entrepreneurs, such as Morris Chang from TSMC, Jensen Huang from Nvidia, and Masayoshi Son from SoftBank. These three men are connected through business but have drastically different approaches and leadership styles. Masayoshi Son: The Founding Father of SoftBank is the first of the three biographies I’m reading, and I found Son’s story to be particularly fascinating.
A few fun facts of Masayoshi Son - I didn’t know was the pivotal influence of Den Fujita, the founder of McDonald’s Japan, who advised Son to study in the United States and pursue a career in technology. Son made his first fortune while still a student at UC Berkeley, collaborating with Berkeley professor Forrest Mozer to create an electronic translator, which he sold to Sharp. After graduating, he immediately returned to Japan and launched SoftBank. In the early 2000s, he suffered a massive financial loss of $70 billion during the dot-com bust. Despite this setback, he came back and eventually raised several vision funds to invest in the new wave of tech & tech-enabled companies like Uber, doordash, and OpenAI. His involvement in high-profile deals such as the acquisition of Sprint and the merger of Sprint and T-Mobile stands as a testament to his influence in the tech world. Interestingly, he was once the largest shareholder of Nvidia stock but sold his position in 2018, just before the company’s stock skyrocketed a few years later.
Son’s story resonates with me in many ways. As an immigrant, his drive to succeed and his optimism mirror my own aspirations. However, as the title suggests, he is undeniably a “gambling man.” He has a tendency to go all-in on his ideas, even when they may not always be grounded in reality. While he’s had some extraordinary successes—such as his investments in Yahoo, Alibaba, and more recently ARM—he’s also faced his share of significant failures, which have deeply affected SoftBank. The book paints a picture of a man who, despite losing billions of dollars, has demonstrated remarkable resilience and the ability to bounce back. His ability to recover from setbacks and pull off the unthinkable is truly inspiring.
I’m not sure I would follow Son’s high-risk, high-reward path. Nevertheless, this biography provides a great understanding of one of the most iconic investors of our time. His story is a testament to the power of perseverance, bold vision, and the ability to rise from failure—qualities that continue to define his career and legacy.
A few fun facts of Masayoshi Son - I didn’t know was the pivotal influence of Den Fujita, the founder of McDonald’s Japan, who advised Son to study in the United States and pursue a career in technology. Son made his first fortune while still a student at UC Berkeley, collaborating with Berkeley professor Forrest Mozer to create an electronic translator, which he sold to Sharp. After graduating, he immediately returned to Japan and launched SoftBank. In the early 2000s, he suffered a massive financial loss of $70 billion during the dot-com bust. Despite this setback, he came back and eventually raised several vision funds to invest in the new wave of tech & tech-enabled companies like Uber, doordash, and OpenAI. His involvement in high-profile deals such as the acquisition of Sprint and the merger of Sprint and T-Mobile stands as a testament to his influence in the tech world. Interestingly, he was once the largest shareholder of Nvidia stock but sold his position in 2018, just before the company’s stock skyrocketed a few years later.
Son’s story resonates with me in many ways. As an immigrant, his drive to succeed and his optimism mirror my own aspirations. However, as the title suggests, he is undeniably a “gambling man.” He has a tendency to go all-in on his ideas, even when they may not always be grounded in reality. While he’s had some extraordinary successes—such as his investments in Yahoo, Alibaba, and more recently ARM—he’s also faced his share of significant failures, which have deeply affected SoftBank. The book paints a picture of a man who, despite losing billions of dollars, has demonstrated remarkable resilience and the ability to bounce back. His ability to recover from setbacks and pull off the unthinkable is truly inspiring.
I’m not sure I would follow Son’s high-risk, high-reward path. Nevertheless, this biography provides a great understanding of one of the most iconic investors of our time. His story is a testament to the power of perseverance, bold vision, and the ability to rise from failure—qualities that continue to define his career and legacy.
December 21, 2024
Not the very best written biography but the subject of the book is my point of interest. Ever since I was in my college years, I used to read about Masayoshi Son and his billion dollar bets on Indian Startups from Flipkart, Oyo, Ola and Snapdeal. He is one of the most influential mogul who has influenced the tech startup in India. Granted, that many of the unicorns later on proved to be dud but some endured the ups and downs and now successfully listed on Public market.
Then back in 2017-18, the business news was incomplete without the Vision Fund- a $100 bn tech startup fund which to date has never been matched by any of the venture capitalists. So I always had this grandiose image of Masa and when a month ago I came across an article that this book had come out profiling his life, I had to get my hands on it and devour it!
Boy oh boy! I didn’t disappoint. I never knew that Masa came from a poor background living in a slum as a Zainichi Korean in Japan. The journey from there to becoming one of the most consequential tech investors in the world is quite fascinating with plenty of ups and down. What I liked about him is that after almost losing everything (once losing 97 percent of his net worth after the dot com bubble crash) he bounced back. This is weirdly the pattern of his life and his tenacious approach to life shows.
Then back in 2017-18, the business news was incomplete without the Vision Fund- a $100 bn tech startup fund which to date has never been matched by any of the venture capitalists. So I always had this grandiose image of Masa and when a month ago I came across an article that this book had come out profiling his life, I had to get my hands on it and devour it!
Boy oh boy! I didn’t disappoint. I never knew that Masa came from a poor background living in a slum as a Zainichi Korean in Japan. The journey from there to becoming one of the most consequential tech investors in the world is quite fascinating with plenty of ups and down. What I liked about him is that after almost losing everything (once losing 97 percent of his net worth after the dot com bubble crash) he bounced back. This is weirdly the pattern of his life and his tenacious approach to life shows.
December 21, 2025
Masa has a pretty wild story, and that makes the book just about interesting enough to not ditch it. He's been involved in, if not central to, many of the craziest stories in tech history. His sheer willpower is also inspiring, even if a lot of his behaviors are rather questionable. In general, it seems as Masa is just riding the most extreme, max bull, max leverage playbook, and somehow has gotten away with it. Why? Because of his unrelenting belief in technology? Because he was able to identify and get into the top 1% of deals? Because he's operating at a larger scale than anyone else, which opens entirely different doors? I'm not quite sure, I am certain thought that most of what he has done is not to be emulated and probably wouldn't have worked in a high % of alternative worlds. Nevertheless, impressive what he has built.
Unfortunately the book isn't well written. There's no clear hero's journey or story arc to it, it more or less feels like a chronology of Masa's life. I think it's also unbalanced in how deep / shallow it goes into different topics. Sometimes it tells the background of a character for a page, only for that character to disappear shortly after, but then skims over other seemingly quite relevant sections very quickly. I'd only advise for anyone that's specifically interested in Softbank / Masa Son.
Unfortunately the book isn't well written. There's no clear hero's journey or story arc to it, it more or less feels like a chronology of Masa's life. I think it's also unbalanced in how deep / shallow it goes into different topics. Sometimes it tells the background of a character for a page, only for that character to disappear shortly after, but then skims over other seemingly quite relevant sections very quickly. I'd only advise for anyone that's specifically interested in Softbank / Masa Son.
June 22, 2025
Anyone interested in Softbank after reading this book will be satisfied. A book made from quite complete and reasonable research about SBG and Masa.
It's hard to imagine, Japan's lost decade was actually a diamond land for Masa. He skillfully used the Japanese "fear of falling behind" psychology combined with the FOMO psychology of American entrepreneurs during global investment expansion so well that his "huge leverage" strategy in most of his M&A deals kept repeating. Innovative financial products always had special backing.
80% of his success in his investment career probably focused on two names: Yahoo and Alibaba. They erased most of the serious mistakes he made in the past like JSkyB, Jiff, E-trade, WebVan... He understood how he bought something was not about valuation, but what he bought was its unlimited potential, not steady cash flow, but the opportunity to "inflate" in the future. But being stuck with Sprint and T-Mobile during restructuring and the WeWork mistake in 2018 poured cold water on Son after the peak of raising the Vision Fund $98.5 billion from the Middle East.
Future strategies with ARM or OpenAI will still repeat. He is also over 70 years old. Will it be another Alibaba/Yahoo or a total loss like WeWork? So excited to observe.
It's hard to imagine, Japan's lost decade was actually a diamond land for Masa. He skillfully used the Japanese "fear of falling behind" psychology combined with the FOMO psychology of American entrepreneurs during global investment expansion so well that his "huge leverage" strategy in most of his M&A deals kept repeating. Innovative financial products always had special backing.
80% of his success in his investment career probably focused on two names: Yahoo and Alibaba. They erased most of the serious mistakes he made in the past like JSkyB, Jiff, E-trade, WebVan... He understood how he bought something was not about valuation, but what he bought was its unlimited potential, not steady cash flow, but the opportunity to "inflate" in the future. But being stuck with Sprint and T-Mobile during restructuring and the WeWork mistake in 2018 poured cold water on Son after the peak of raising the Vision Fund $98.5 billion from the Middle East.
Future strategies with ARM or OpenAI will still repeat. He is also over 70 years old. Will it be another Alibaba/Yahoo or a total loss like WeWork? So excited to observe.
November 30, 2024
"Breathless." There is no better word to sum up the life that is lived by legendary Softbank founder Masayoshi Son. Every single person in the startup and venture capital ecosystem have heard the tales about the mighty rollercoaster that his professional life has been! Masa's mega venture hits - identifying the potential of Yahoo and Alibaba early on - cemented his legacy, which was promptly disrupted by the excesses of the Vision Fund, particularly the WeWork debacle. However, no one can argue about his impact - he has irrevocably changed the venture landscape globally.
I truly enjoyed this book because it was not only able to shed some light on the mystery around Masa, but also unemotionally dive deep into his journey. Other accounts of his journey have been via colored lenses - people either worship or despise him. The pacing was excellent, and the accounts were well balanced. I couldn't put this book down, and think it has been one of the better biographies on a tech sector (or adjacent industry) titan I've read of late.
I truly enjoyed this book because it was not only able to shed some light on the mystery around Masa, but also unemotionally dive deep into his journey. Other accounts of his journey have been via colored lenses - people either worship or despise him. The pacing was excellent, and the accounts were well balanced. I couldn't put this book down, and think it has been one of the better biographies on a tech sector (or adjacent industry) titan I've read of late.
June 8, 2025
Just before SoftBank's stock-market debut, Masa received an urgent fax that Ziff Communications puslishing empire was up for sale. He'd long coveted Ziff, the largest computer magazine publisher in the US with $1B in revenue. A full ownership would give him a swanky office on Manhattan's Fifth Avenue and an entree' into the top tech companies in the US.
Neither Steve Rattner nor Peter Ezersky, the two lead advisers to Ziff, had heard of Masayoshi Son. Neither would forget their first encounter. Masa presented each banker with a pair of exquisitely engraved chopsticks. Then came his life-story, delivered with his now trademark blend of innocence and bravado: growing up dirt poor, going to study in America, making a fortune with his pocket speech translator, returning to Japan, becoming number-one software distributor. No detail was spared.
'What does it take to win?' Masa asked his investment banking adviser, Morgan Stanley's Jeff Sine. 'You have to bid,' replied Sine, a laconic lawyer from New Jersey, who went on to be Masa's personal banker.
Neither Steve Rattner nor Peter Ezersky, the two lead advisers to Ziff, had heard of Masayoshi Son. Neither would forget their first encounter. Masa presented each banker with a pair of exquisitely engraved chopsticks. Then came his life-story, delivered with his now trademark blend of innocence and bravado: growing up dirt poor, going to study in America, making a fortune with his pocket speech translator, returning to Japan, becoming number-one software distributor. No detail was spared.
'What does it take to win?' Masa asked his investment banking adviser, Morgan Stanley's Jeff Sine. 'You have to bid,' replied Sine, a laconic lawyer from New Jersey, who went on to be Masa's personal banker.
October 14, 2024
Kenny Rogers' famous song The Gambler has a lyric which provides a recipe for gambling success: "You've got to know when to hold 'em, Know when to fold 'em, Know when to walk away", one which Masayoshi Son ignored time and time again, though remarkably not to his own major detriment. Lionel Barber's "Gambling Man" is a fascinating biography of one of modern investing's unique figures. From growing up as an outsider in Japan to making (and then losing) more money than anyone else, Barber charts Son's most peripatetic of existences. Through Barber's writing, Son appears a multipolar man of contradictions - at once naive but also possessing great wisdom and vision, capable of great kindness and great harm. Barber contrasts the two elements of his professional self quite neatly, showing great respect for Son the operator and some bemusement at Son the investor.
In all, a wonderful read and a good insight into a man who has helped shape the technology ecosystem like few others.
In all, a wonderful read and a good insight into a man who has helped shape the technology ecosystem like few others.
January 13, 2025
This is the first biographay I have read that was not written by an academic/scholar and my expections were more-or-less met. The journalist author does a useful job of piecing together the background, meetings, and key events/transactions of Masayoshi Son. "Gambling Man" is an appropriate title, for what comes across to me from the narration is precisely this - somebody who bets big without much due dilgence. Some "bets" come off, such as Alibaba and Yahoo! but others are lost, such as Softbanks' disastrous involvement with the failed WeWork. I think it is useful as a historical matter to have a record of these transactions and that's probably the best thing I can say about the book. Son is not portrayed in a flattering light, but I do sympathize with his challenges from being of Korean ancestry in Japan and was inspired by the fighter instinct in him that pushed him forwards. This is motivating.
December 30, 2025
Gambling Man is the biography of Masayoshi Son (Masa), one of the most consequential tech investors of our time. The book reads like a cautionary thriller, chronicling a life that fuses several personalities at once: the megalomania of a nation builder à la Napoleon, the instinctive genius of a market maker, the recklessness of a risk-hungry adventurer — and the lingering bitterness of a Japan-born, ostracised Korean.
Barber paints these personalities through Masa’s business ventures. On one side sit the legendary hits: the early Alibaba investment (the kind of bet that rewrites a life), the ARM acquisition, telecom empire-building via Vodafone Japan / SoftBank Mobile, and the Yahoo Japan era. On the other are the spectacular face-plants — WeWork’s implosion, the chaos of the nearly $100B Vision Fund, and the quiet failure to capitalise on the NVIDIA rocketship.
A rare, insider view into the dazzling riches, non-stop dealmaking, and recklessness of big tech.
Barber paints these personalities through Masa’s business ventures. On one side sit the legendary hits: the early Alibaba investment (the kind of bet that rewrites a life), the ARM acquisition, telecom empire-building via Vodafone Japan / SoftBank Mobile, and the Yahoo Japan era. On the other are the spectacular face-plants — WeWork’s implosion, the chaos of the nearly $100B Vision Fund, and the quiet failure to capitalise on the NVIDIA rocketship.
A rare, insider view into the dazzling riches, non-stop dealmaking, and recklessness of big tech.
June 3, 2025
Just finished reading Gambling Man by Lionel Barber—and thoroughly enjoyed it.
What really stood out for me was the lucid, engaging writing. Barber has a knack for breaking down complex ideas without losing their depth. The book does a fantastic job of setting the scene—whether it's the chaos of the dotcom bust or the current buzz around AI, the context is always rich and well-crafted.
I especially appreciated how vividly it captures the world of venture capital. It’s not just about the deals or the money, but the personalities, the calculated risks, and the constant reinvention that defines the tech ecosystem.
More than anything, Gambling Man offers a front-row seat to how the tech world has evolved—from the early 2000s crash to the AI spring of 2024. If you're into tech, startups, or just enjoy a well-told business story, this one's definitely worth a read.
What really stood out for me was the lucid, engaging writing. Barber has a knack for breaking down complex ideas without losing their depth. The book does a fantastic job of setting the scene—whether it's the chaos of the dotcom bust or the current buzz around AI, the context is always rich and well-crafted.
I especially appreciated how vividly it captures the world of venture capital. It’s not just about the deals or the money, but the personalities, the calculated risks, and the constant reinvention that defines the tech ecosystem.
More than anything, Gambling Man offers a front-row seat to how the tech world has evolved—from the early 2000s crash to the AI spring of 2024. If you're into tech, startups, or just enjoy a well-told business story, this one's definitely worth a read.
May 17, 2025
A very thorough autobiography. Masa continues to play pachinko with high stakes. His knowledge of technology is limited and he relies on others to run his businesses, such as ARM and SoftBank Telecom. Who says that gambling never pays off. The last 30 years has been a high stakes gambler’s paradise, but will the music stop? Keep an eye on the Japanese interest rate. The last bastion of cheap money.
September 21, 2025
Interesting read - more so due to Son having been involved across several key moments in the tech and telecom historical, as the storytelling could have been more colourful.
I thought the author portrayed Masa too negatively, highlighting any shortcomings (impulsive risk taker, indecisive manager, megalomaniac) but not giving enough credit to somebody who against all odds became Japan’s richest man though vision, charm, and persistence.
I thought the author portrayed Masa too negatively, highlighting any shortcomings (impulsive risk taker, indecisive manager, megalomaniac) but not giving enough credit to somebody who against all odds became Japan’s richest man though vision, charm, and persistence.
October 24, 2024
Excellent book - not necessarily the best written but interesting for those in tech. Not always easy to follow the many Asian names. Truly gives you perspective on the Masa and his risk on approach. Would’ve loved to see more from his perspective though - feels a lot of the material was gathered through 3rd party interviews.
March 26, 2025
An Authorative Insight into How the .0001% actually live and operate
There are many speculative and fanciful books and films about the super-rich risk-takers who shape our lives, for good or bad. This book, however, is the real deal, by an author who truly knows what goes on behind the closed doors of the world’s super-elite.
There are many speculative and fanciful books and films about the super-rich risk-takers who shape our lives, for good or bad. This book, however, is the real deal, by an author who truly knows what goes on behind the closed doors of the world’s super-elite.
April 13, 2025
Success comes from stumbling onto something; but you can only stumble if you are moving. Masa is always on the move. His borderline erratic self-belief and conviction in pursuing a goal are inspiring, to say the least. If you are into commerce, high-stakes negotiations, and generally a compelling story, this is a must-read...
October 30, 2024
Enjoyed reading this book. At times hard to follow with all the Japanese names and all the technical money talk. Masayoshi Son has lead a stressful life. Talk about a risk taker and someone always optimistic.
November 28, 2024
Fantastic story, extremely well told. What a maverick and a madman. Totally wild ride, unlike anyone else in the word perhaps other than Musk. The writing often lacked a bit of pace otherwise it would be five stars but it’s definitely worth 4 and a half stars.
January 11, 2025
A rollercoaster ride on top of barbaric sums of cash. Take a risk if you can afford the downside is worth it for the learning but perhaps more the story as inked by this book. A man on a mission with a vision.
March 18, 2025
Loved the background of Son. This along with Alok Sama”s Money Trap paints Masa”s winning streak in new light. The whole thing is just one big gamble thematically but he had the right ones that mattered. Beyond a certain point no one knows anything.
This was a great read on the Enigmatic Masa Son
This was a great read on the Enigmatic Masa Son
May 18, 2025
A winding and eccentric retelling of one of the most winding and eccentric figures in finance of our time. Masayoshi Son and SoftBank have a wild history I’m not sure I fully appreciated beyond the doomed over-investment in WeWork. Great read.
July 18, 2025
Masayoshi Son biografija nuo pat pradžios iki tada, kada dauguma jį sužinojo, kai su Vision Fund investavo milijardus į Uber, wework ir krūvą kitų tech įmonių praeitam dešimtmetyje. Įdomu, bet kiek per ilga, vietomis kai kuriuos etapus labai giliai kapsto.
July 28, 2025
A well researched documentation of the life of a serial entrepreneur. The sheer pace and scale of Masayoshi‘s deals and his penchant for leverage and risk-taking renders the story repetitive, somewhat less interesting from a literary perspective, though fast-moving throughout.
August 28, 2025
The Gambling Man by Lionel Barber offers a fascinating glimpse into the life and career of Masayoshi Son, the visionary founder and driving force behind SoftBank. Before reading this book, I knew little about the man behind the company, and I came away with a much deeper appreciation for his story.
Born into a humble background and facing discrimination as a Korean immigrant in Japan, Son broke through the rigid, insular structures of Japanese corporate culture. His resilience and determination allowed him to build an empire in an environment that often resisted outsiders.
What struck me most was his extraordinary tolerance for risk—and his ability to recover from failure. The book describes how Son lost much of his fortune on two separate occasions, only to rebuild with remarkable persistence and optimism. Rather than shy away from adversity, he embraced it with a challenger’s mindset.
I particularly loved this passage: “Time and again, he ventured where others feared to tread... He bought valuable assets in America. He launched his own broadband and mobile-phone business in Japan in the teeth of opposition. Against all odds, he brought off the Sprint–T-Mobile merger... he never gave up.”
This is a story not only about business gambles but about resilience, reinvention, risk taking, and the belief that setbacks are stepping stones to even greater ambition.
Born into a humble background and facing discrimination as a Korean immigrant in Japan, Son broke through the rigid, insular structures of Japanese corporate culture. His resilience and determination allowed him to build an empire in an environment that often resisted outsiders.
What struck me most was his extraordinary tolerance for risk—and his ability to recover from failure. The book describes how Son lost much of his fortune on two separate occasions, only to rebuild with remarkable persistence and optimism. Rather than shy away from adversity, he embraced it with a challenger’s mindset.
I particularly loved this passage: “Time and again, he ventured where others feared to tread... He bought valuable assets in America. He launched his own broadband and mobile-phone business in Japan in the teeth of opposition. Against all odds, he brought off the Sprint–T-Mobile merger... he never gave up.”
This is a story not only about business gambles but about resilience, reinvention, risk taking, and the belief that setbacks are stepping stones to even greater ambition.
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