Hello, and welcome to Investor’s Bookshelf.Today I’d like to share with you Gambling Man: The Secret Story of the World's Greatest Disruptor, Masayoshi Son.
The author of this biography is Lionel Barber, former editor-in-chief of the Financial Times. The Financial Times is one of the most influential financial newspapers in the world, and Barber served as its editor-in-chief for more than a decade before retiring in 2019 to focus on writing. During his tenure, Barber interviewed Masayoshi Son multiple times, and after stepping down, he had the chance to hold long, in-depth conversations with Son for this book.
Masayoshi Son hardly needs an introduction. A Korean-Japanese entrepreneur, he first rose to fame through legendary early investments in Yahoo and Alibaba. A decade ago, he launched the $100 billion Vision Fund—the largest investment fund in the world—leveraging the immense wealth of Middle Eastern sovereign investors and reshaping the global financial landscape. His strategy of betting heavily on star entrepreneurs, burning cash for growth regardless of cost, became emblematic of the breakneck expansion of internet startups in the 2010s. The Vision Fund’s dramatic failure with WeWork, however, became a symbol of Son’s overreach.
The book’s title, Gambling Man, is telling—it conveys bold wagers, sky-high risk, and an almost reckless opportunism. Yet even as Barber likens Son to a gambler, he notes a crucial distinction: Son has an extraordinary capacity to stage repeated comebacks. In 2020, he suffered significant losses in the previous internet bubble, and the COVID-19 pandemic kept him from seizing the AI boom ignited by ChatGPT. But in 2025, shortly after Donald Trump’s second inauguration, Son joined OpenAI founder Sam Altman to announce the $100 billion Stargate initiative, marking the start of yet another audacious chapter in his career.
In the book, Barber aptly describes Son as a “middleman”—or, in less polite terms, a “broker.” Why so? Because Son is not a Silicon Valley-style technologist; rather, he excels at spotting trends, placing early bets on frontier technologies and high-potential founders, and arbitraging between different markets. In Barber’s eyes, the “gambler” is someone willing to commit earlier than anyone else to a major trend—sometimes too far ahead of the curve, and sometimes backing the wrong people. That, in essence, is what makes Masayoshi Son’s business saga one of dramatic rises and falls.
I. The Alibaba Curse
Let’s begin with SoftBank’s most famous investment—Alibaba.Masayoshi Son founded SoftBank in 1981. Yet, as he himself put it, SoftBank was neither a bank nor a software company. Over the years, it evolved into an increasingly complex investment platform.
SoftBank’s real connection to the internet boom of the 1990s began in 1995, when it became an early investor in Yahoo. Today, Yahoo has largely faded from public attention, but in the mid-1990s it was the hottest stock on the internet—the most widely used search engine (Google didn’t exist yet) and the leading web portal of the time.
Son’s successful bet on Yahoo made him famous, but his true arrival as a heavyweight internet investor came in 1999, when he invested in Alibaba.
That year, Son turned his eyes to China’s fast-emerging internet market. As a board member of Cisco—the global leader in internet hardware and network solutions—he saw firsthand the company’s rapid worldwide growth, with China as its fastest-growing market. He understood clearly that China’s internet industry was on the brink of explosive growth, and he needed to stake a claim. He instructed investment bankers to arrange meetings with Chinese internet-related startups—an arrangement that led to his first meeting with Jack Ma. In keeping with his consistent investment style, Son focused on two things: big trends and the founders driving them.
Shortly after meeting Ma, Son offered to invest $40 million in Alibaba for a 49% stake. Ma was not prepared to give up that much equity, but the two sides quickly reached an agreement: SoftBank would invest $20 million for a 30% stake.
It’s hard to imagine today, but that 1999 investment became the most successful deal in SoftBank’s history, generating more than a 1,000x return—some estimates put the total return above 3,000x. Yet lucky investments are double-edged swords. The Alibaba windfall drove Son to keep searching for the “next Alibaba,” but he never quite found it. Unless he could replicate that level of success, it would be difficult to prove to the world that SoftBank’s triumph was the result of his sharp foresight rather than sheer luck. In this sense, his Alibaba investment became a lifelong curse—a point we will explore in depth later.
The Alibaba story did not end with that first check. In the early 2000s, Alibaba went head-to-head with eBay in China, launching Taobao to compete. SoftBank ultimately invested in Taobao as well, taking its total investment in Alibaba above $100 million. Son provided more than capital: SoftBank’s experience in mobile networks, fiber-optic services, and marketing in Japan gave him deep consumer insight. He even brought in Tadashi Yanai, founder of Uniqlo, to join SoftBank’s board—someone with a sharp understanding of consumer needs and trends. This allowed Son to advise Alibaba in its early days on both consumer psychology and the operation of online marketplaces.
The most significant binding of SoftBank and Alibaba came in 2005, when Son orchestrated a deal between Yahoo and Alibaba. Yahoo invested $1 billion for a 40% stake in Alibaba and handed over control of Yahoo China to Alibaba. SoftBank sold part of its stake for $360 million in cash but, thanks to its cross-holding in Yahoo, still retained 30% of Alibaba’s equity. After the deal, Yahoo founder Jerry Yang quipped to Son: “We’ve become your ATM.” The next decade of Alibaba’s rapid growth rewarded both SoftBank and Yang far beyond expectations.
From his Yahoo and Alibaba deals, Son’s investment philosophy can be summed up in three points:
1. Seeing the future earlier—and betting big.
He foresaw the coming digital revolution of the internet well before his rivals and dared to commit heavily. Yahoo represented the earliest wave of internet startups; Alibaba was the rising star of China’s internet scene.
2. Once the trend is clear, price is secondary.
Unlike Warren Buffett, whose craft is finding undervalued blue chips, Son focuses on companies with explosive growth potential, regardless of valuation. For him, growth potential is the true north; short-term profits or losses are distractions. His logic: if you’re right about the trend, any company within that trend is “cheap” in hindsight. Early-stage valuation hardly matters because the long-term payoff can be exponential. Offering Jack Ma $40 million on their first meeting is a prime example.
3. Once you find the right target, invest by any means necessary.
In 1995, Son missed Yahoo’s Series A but relentlessly pursued a stake—pressuring Sequoia Capital and Jerry Yang with the threat that, if SoftBank wasn’t allowed in, he’d back Yahoo’s biggest search rival, Excite. Eventually, they relented, and SoftBank led Yahoo’s $4.8 million Series B.
This tactic resurfaced in 2018 when Son targeted Uber. He threatened that if SoftBank couldn’t invest, he’d back Lyft instead. Uber CEO Dara Khosrowshahi later explained why he accepted: “I know Son’s money is rocket fuel—it’s hot, and he has an unrelenting appetite for growth. I’d rather have that fuel powering me than blasting me out of the sky.”
These principles helped Son land two of the most successful investments in tech history. But in the smartphone and mobile app boom of the 2010s, they also morphed into something else: Son became the biggest driver of the mobile-internet investment bubble, fueling aggressive, unsustainable startup growth. The most famous example was WeWork.
In December 2016, after visiting President-elect Donald Trump in Trump Tower, Son headed straight to WeWork’s headquarters for the first time. Founder Adam Neumann had prepared a two-hour tour; Son, who rarely spent more than 15 minutes on a pitch, showed up late, cutting the meeting to 12 minutes. Neumann emphasized WeWork’s “tech-driven” vision, but SoftBank staff saw little actual technology. Son invited Neumann to continue the conversation in his car, where he pulled out an iPad and drafted a term sheet for over $4 billion.
The story quickly became tech-industry lore. At the time, Son was launching his $100 billion Vision Fund, $45 billion of which came from Saudi Crown Prince Mohammed bin Salman. Press reports claimed their meeting took an hour; Son corrected them: “It was 45 minutes—$1 billion per minute.” Neumann, in turn, bragged that securing $4 billion from Son took him barely half an hour—$100 million a minute.
The episode captured the excess of the bubble era. Son still adhered to his principles—industry conviction, indifference to high prices, and falling for visionary founders—but his belief in growth had hardened into an almost militant “growth at all costs” mindset. To longtime Alibaba veterans, his nickname was “Add a Zero,” because he would urge founders to multiply their targets by ten.
A famous exchange from the book illustrates the mentality:
Son: “In a fight, who wins—the smart one or the crazy one?”
Neumann: “The crazy one.”
Son: “Correct. But…” (with a trace of concern) “you’re not crazy enough.”
Son’s outsized funding fueled Neumann’s hubris and reckless expansion. By 2019, WeWork’s IPO collapsed, Neumann was ousted, and SoftBank’s $4 billion investment was nearly wiped out—the largest single loss in its history.
So why can’t Son escape the “Alibaba curse”? Barber’s explanation:
The Alibaba investment was almost accidental—purely the product of Son’s original philosophy: spot a sector on the verge of explosion and invest in several leading companies, rather than backing a single founder. In 1999, besides Alibaba, Son also invested in several other Chinese internet startups introduced by bankers. But a market like China in 1999—an economy of a billion people growing at double digits for years, while its internet sector leapt to parity with the West in record time—is nearly impossible to replicate.
Another reason is the sheer scale of Son’s empire. In the early days, $4.8 million for Yahoo or $20 million for Alibaba were early-stage venture bets that naturally reaped extraordinary returns as those companies entered hypergrowth. By the 2010s, with $100+ billion at his disposal, Son could hardly look at anything under $100 million, meaning targets were already mature and opportunities fewer. Moreover, Son had reshaped the VC/PE industry—his rivals all suffered the same FOMO (“fear of missing out”) and chased the next Google or Facebook, driving valuations up and making good opportunities scarce.
In short, Son’s early success came from seeing the internet’s potential more clearly than others, betting big on innovators, and ignoring short-term valuation noise in favor of long-term growth. By the 2010s, as his war chest grew exponentially, that philosophy morphed into fueling growth with vast sums of money, often backing founders as aggressive—and as reckless—as himself. The result was often the opposite of his early triumphs.
Does this mean Son’s investment model is obsolete? Not necessarily.
In 2016, just after Trump’s first election victory, Son raced to Trump Tower to pay his respects, then promised $50 billion in U.S. investment and 50,000 jobs. Eight years later, he was at Mar-a-Lago—the so-called “Winter White House”—pledging $100 billion over four years to create 100,000 jobs. The day after Trump’s second inauguration, he joined OpenAI’s Sam Altman and Oracle’s founder at the White House to unveil the $100 billion Stargate AI infrastructure plan.
The tides rise and fall, but Son’s appetite for future-facing investments—and for making grand promises—has only grown. How does he manage it? Barber’s answer: Son’s core strength is as a middleman—or, less politely, a broker—one with many layers of brokerage skill across multiple domains.
II. Masayoshi Son, the “Broker”
What kind of middleman is Masayoshi Son?
Barber believes that, first and foremost, he is a capital broker. For the past 30 years, Japan’s economy has been in prolonged stagnation, with near-zero interest rates. This created extremely low borrowing costs and fueled a popular investment strategy among Japanese retail investors known as carry trade—borrowing yen at negligible rates to invest in higher-yielding currencies. If exchange rates stayed stable, it was almost a guaranteed profit.
Son took carry trade to an entirely new level. He once remarked publicly that borrowing money in Japan was “like getting it for free—why wouldn’t you take it?” His rise began in the 1990s, precisely when Japan entered its “lost decades” of zero interest rates. He tapped heavily into the domestic credit market and funneled that capital into overseas ventures—a windfall he saw as the era’s greatest gift to him.
Cheap money, however, is not enough—you still have to pry it loose. Japan’s banking sector is notoriously conservative, and traditional banks were reluctant to lend to a maverick like Son. His ability to mobilize financial resources depended heavily on a capable CFO. This CFO seized the opportunity presented by regulators eager to push reforms, bypassing the banks entirely by issuing corporate bonds through securities firms. At the time, banks dominated corporate bond issuance in Japan. Son became an early beneficiary of this reform wave—slashing underwriting fees by half, securing longer-term financing at lower rates, and effectively forcing the banks to dance to his tune.
By the 2010s, Son’s ability to bankroll aggressive “growth-at-all-costs” strategies for startups was again rooted in cheap capital. After the 2008 financial crisis, Western central banks cut rates sharply. Global capital hunted for higher returns, and SoftBank thrived in this environment.
Beyond tapping low-cost yen and post-crisis cheap U.S. dollars, Son unlocked another source of mega-capital—the oil wealth of the Middle East. As noted earlier, in 2016 he met Saudi Crown Prince Mohammed bin Salman (MBS) and, in less than an hour, secured a pledge of $45 billion for the Vision Fund—boasting later that it was “$1 billion a minute.” MBS, irritated by the remark, felt it reinforced the stereotype of Middle Eastern money as abundant but naïve. Still, the Saudi Public Investment Fund ultimately committed $30 billion, becoming SoftBank’s largest single backer.
Are Gulf sovereign funds really “rich and foolish”? Not exactly. For instance, the Saudi investment in the Vision Fund was structured between equity and debt, with Son guaranteeing a fixed 7% annual return—a heavy burden that put most of the risk squarely on SoftBank. With a $100 billion fund and a minimum investment size of $100 million per deal, Son would have needed to find 1,000 such projects—an impossible task. In reality, only investments of $500 million or more could move the needle on the fund’s returns.
The Vision Fund’s deeper problems will be analyzed later. But the fact remains: raising capital at that scale is Son’s unique talent—the very thing he could flaunt in front of Trump, and the reason he could share a stage with Sam Altman at the height of the AI boom.
Son’s role as a broker began more simply—as a cultural bridge, bringing Silicon Valley innovation to Japan and other Asian markets. In Silicon Valley, there’s a saying: “The this for the that”—a copycat model that takes a proven startup idea and adapts it to a local market. For years, China’s internet industry was a paradise for this approach: Baidu was “China’s Google,” QQ traced its origins to Israel’s ICQ, and during the mobile internet era, Groupon’s group-buying model spawned countless imitators, including the early Meituan. Uber, likewise, faced homegrown competition from Didi.
Son’s copycat game predated China’s. Bill Gates once praised him for precisely this: in Japan, business trips often involve days of polite but unproductive formalities. Then, suddenly, an English-fluent insider who knows the ropes appears—how could you not be pleased?
Son’s first real fortune came from acting as that bridge for U.S. companies expanding into Japan. In the early 1990s, whenever he spotted a promising innovation in Silicon Valley, he would bring it back to Japan as a joint venture—usually with SoftBank holding the controlling stake. Leveraging Japan’s appetite for Western brands, he pushed these ventures forward. One landmark example was Yahoo Japan. After investing in Yahoo, Son brokered a joint venture between Yahoo and SoftBank to create the country’s first major portal site, with SoftBank owning 60%. In its scrappy early days, Son’s younger brother, then a third-year student at the University of Tokyo, rallied over 100 students to categorize Japanese websites and fill out Yahoo Japan’s directory.
The third layer of Son’s brokerage skill is his ability to spot potential arbitrage in acquisition targets. If there was integration potential, he didn’t mind overpaying, because he played the long game—a long-line fisherman willing to wait years for a massive catch.
How did a Japanese student in America, not a coder and a foreigner to boot, gain entry into Silicon Valley’s inner circle? Without that access, it’s hard to imagine how he could have invested in Yahoo in 1995. The answer: Son bought his way in.
In 1993, he paid $842 million for Comdex, the high-tech trade show that was, at the time, the CES of its era—the premier global showcase for the latest in computer hardware, software, peripherals, networking, and emerging technologies, drawing thousands of industry players each year.
Others valued Comdex by its direct earnings, and thought Son overpaid—especially as founder Sheldon Adelson had already been “milking” the event, prompting industry giants like Bill Gates to grumble about the high fees and consider starting a rival show. But Son saw something different: a ticket to stand shoulder to shoulder with Gates, Jobs, and other U.S. tech titans; a backstage pass to Silicon Valley’s innovation pipeline; and a platform for future arbitrage. From that perspective, the high price was not tuition—it was a bargain.
After selling Comdex, Adelson used the $842 million to focus on building casinos in Las Vegas and expanding the Sands brand into Macau and Singapore. He never forgot Son’s generosity. In 2016, when Son sought an introduction to President-elect Trump, Adelson was the one who made it happen.
To truly understand Son’s role as a broker, we must see the three critical resources he’s mastered for doing global business:
Cheap capital—from zero-interest yen, to post-crisis low-interest U.S. dollars, to Middle Eastern petrodollars.
Global tech arbitrage—bridging business cultures, transplanting proven models into emerging markets, and executing “copycat” localization.
Access to exclusive circles—buying his way in, building relationships, and monetizing those networks.
It is this combination that transformed an unknown foreigner into a guest at the U.S. president’s table and a confidant to Silicon Valley’s elite.
Barber concludes that Son is not only a broker, but also a reckless gambler. The difference is that, although he cycles from one success to the next failure, he is unlike most gamblers in one crucial respect—he keeps coming back.
III. Masayoshi Son the Gambler: From One Success to the Next Failure—Yet Always Rising Again
Viewed over the long arc of his career, it’s not hard to see why Lionel Barber calls Masayoshi Son a gambler. He is indeed a wave rider—often wading in before the tide has fully risen. In the 1990s, he surfed the internet boom, but when the dot-com bubble burst in 2001, he was left the proverbial “last fool,” his net worth nearly wiped out. In the 2010s, he rode the mobile-internet wave, only to suffer a crushing loss on WeWork, at one point halting new investments entirely. When the current AI boom began, he was early once again—acquiring chip designer ARM in 2016 and even holding a 5% stake in Nvidia—yet exited too soon, missing the hundredfold rally in Nvidia’s valuation.
And yet, like an indestructible cockroach, Son resurfaced in 2025, returning to the AI stage—not only standing at the White House alongside Sam Altman to announce the $100 billion Stargate project, but also ambitiously positioning ARM at the heart of an AI infrastructure platform, with bigger dreams than ever.
In my view, three traits define Son’s gambler’s nature. Whether they are strengths or weaknesses is debatable—but they are undeniably, quintessentially his.
1. An Intuition-Driven Investor
Son’s intuition is not mere whim. Colleagues marvel at his ability to absorb vast amounts of data and information, which gives him a finely tuned sense for major waves before they crest. He trusts that if he can imagine something, it must be real. That conviction led him to bet correctly on Jack Ma—and disastrously on Adam Neumann of WeWork. More often, his problem is not that his intuition is wrong, but that his timing is: selling Nvidia too early cost him tens of billions.
Critics dismiss intuition-driven investing as a one-man show. They ask: “If you can go from hero to zero and back to hero, how do we know you won’t return to zero again? Is your track record just a handful of lucky bets?” Indeed, Son’s chronic delays in naming a successor, and his entanglement with the “Alibaba curse,” are closely tied to this trait.
The Achilles’ heel of intuition is focus. The world offers Son too many temptations, too many opportunities. Lose focus, and trouble follows. His investment career has been a roller-coaster not just because markets rise and fall, but because he struggles to sustain focus over the long term. His pattern is cyclical: a burst of creativity, intense passion, and concentration leads to overexpansion, failure, regret, and retreat—until the cycle begins anew.
The COVID-19 pandemic is a case in point. It cost him the chance to invest in OpenAI early; until Japan reopened in 2022, his ties to Silicon Valley had grown tenuous. That year could have been the perfect moment to buy AI-related companies before prices surged, but wary from past losses, he held back. Those earlier losses stemmed largely from the 2019 WeWork fiasco, after which he steered SoftBank toward hedge-fund-style trading. The problem was that he measured himself against the 40%+ annualized returns he had earned from Alibaba, and applied that yardstick to public-market trades. Lacking the patience to hold large-cap tech stocks long term, he ended up burned. In August 2022, when markets discovered that SoftBank was behind a run-up in big-tech shares, a short-squeeze reversal swung the firm from a $2 billion profit to a $7 billion loss—a $9 billion whiplash.
That’s why, in 2024, when he shared the stage with Jensen Huang, Son could ruefully admit that in 2019 he had bought over $200 million worth of Nvidia stock, only to sell quickly for a 40% annualized gain—avoiding volatility, but missing nearly a 100-fold return over the next five years.
It’s little wonder some observers call him an ordinary investor but a poor trader.
2. An Embrace of the “Great Man” Theory—and of Himself as One
Son has said more than once: “Don’t compare me to people like Zuckerberg or Gates. They run a business; I am building an empire. My peers are Napoleon, Genghis Khan, Qin Shi Huang.” He has also quipped, “I am not a CEO; I am building my own (business) empire.”
On the positive side, this imperial mindset allows him to spot connections between disparate assets. For example, his costly acquisition of the Comdex tech expo was meant not for profit from the event itself, but as an entrée into the Silicon Valley elite. Empire thinking keeps him focused on entire industries, not just individual companies.
It also sharpens his eye for foundational opportunities during major shifts. All empires, he believes, rest on infrastructure—just as “all roads lead to Rome” in the ancient world. This explains SoftBank’s early investments in Japanese mobile and broadband networks, its purchase of Vodafone Japan, and its acquisition of Sprint in the U.S., which was later merged with T-Mobile to form one of America’s top three telecom operators. In the AI era, this logic underpins Stargate—and his vision for ARM.
ARM sits at the center of Son’s plan for a vast AI infrastructure network, part of a push to transform SoftBank into an AI superpower. The scope includes AI chip design, data-center operations, industrial robotics, and power generation—a vertically integrated AI ecosystem. Recently, ARM announced its own chip-manufacturing plans, firing the first shot at Nvidia.
ARM is perhaps the closest Son has come to finding another “Alibaba.” He recognized early the importance of the Internet of Things and that ARM’s chips were its backbone. That’s why he paid $32 billion for ARM in 2016; eight years later, it is valued at $140 billion.
But imperial thinking has its flaws—chiefly in governance. SoftBank’s corporate governance is notoriously poor, with blurred lines between the company’s and Son’s personal interests. It is also among the ten most indebted companies in the world. Son’s dream empire rests on leveraging other people’s money—and after 30 years of cheap and plentiful capital, the return of inflation poses an existential challenge to his debt-driven, acquisition-heavy growth strategy.
3. Sustained Foresight
As early as the late 1990s, Son predicted the death of traditional television and the rise of desktop video-on-demand—five years ahead of the world, and a decade ahead of Netflix’s streaming pivot. Many see this foresight—grasping the contours of the digital revolution long before rivals—as his greatest gift.
How does he do it? One glimpse comes from a strategic discussion he led at SoftBank’s Tokyo headquarters in 2010, imagining the world 30 years hence, in 2040. He asked his top executives to tackle four questions:
What will computer chips look like?
- What applications and solutions will those chips make possible?
- How will people’s lifestyles change?
- What will business and competitive landscapes look like?
- These are, in essence, the same questions we now ask about AI and its infrastructure—especially chips. Son urged his team to “start from the conclusion,” because the destination matters most. “When you are lost,” he advised, “look further ahead.” His own destination for SoftBank: to build a company that lasts 300 years.
IV. Conclusion
To conclude, let’s briefly sum up Masayoshi Son’s defining traits.
Son’s intuition enables him to spot major trends earlier than most—whether it was backing Alibaba, acquiring ARM, or once envisioning a mega-ecosystem linking AI and mobile chips through a merger of ARM and Nvidia. Yet he is easily swayed by new trends, quick to chase the next big thing. In the early phase of a frenzied expansion, he often lands high-quality assets—like Nvidia—but in the later phase, he is forced to pull back, sometimes even vowing publicly to stop investing. Inevitably, it isn’t long before he returns to form, deciding his ambitions weren’t big enough after all. This cycle repeats itself, but his remarkable quality is that he always seems to catch the next wave.
Son has foresight—sometimes truly ahead of its time, sometimes a lucky accident. But it is precisely this combination of serendipity and prescience that keeps him from developing a fixed set of guiding principles, or from moving steadily from one victory to the next in the manner of Warren Buffett. At the same time, it ensures that he never leaves the table entirely; even after coming close to losing it all more than once, he strives to join the next big boom.
His stated goal is to build a company that will last 300 years, and to live to 120. By that measure, at 68 years old, he’s only halfway through his life—so it would be unwise ever to count him out.
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