Gambling With the Future: What Founders Can Learn from Masayoshi Son’s Big Bets
A high-stakes story of vision, ego, and collapse—why Gambling Man is required reading for anyone building with other people’s money.
1. Introduction
If you’re a founder, product builder, or operator trying to understand the edge between brilliance and recklessness, Gambling Man is essential reading. It tells the story of Masayoshi Son, the SoftBank founder who reshaped global tech investing by betting bigger, faster, and more instinctively than anyone else—from Alibaba and the iPhone to WeWork and the Vision Fund.
The book is written by Lionel Barber, former editor of the Financial Times, whose access to boardrooms, political figures, and tech giants allows him to craft a story that’s both deeply sourced and sharply observed. Barber doesn’t just track Masa’s wins and wipeouts—he explores the psychology, ambition, and contradictions of a man who treats capital like narrative fuel and risk like an operating principle.
This review breaks the book down in five parts:
A quick summary of the full story arc
The pivotal bets that defined Son’s rise—and near-collapse
Lessons founders should take (and avoid)
A critical reflection on what went wrong
A final verdict on whether this book is worth your time
Because in the end, Son doesn’t just make you think about markets—he makes you question your own risk tolerance.
Would you bet everything on instinct? And could you survive if you were wrong?
2. High-Level Book Summary
Before we unpack the key lessons, it’s worth understanding the arc of this extraordinary story. Gambling Man follows Masayoshi Son’s life in five sweeping acts—from his outsider upbringing in Japan to his rise as the most aggressive tech investor on the planet, and the spectacular crashes that followed. What emerges is not just a biography, but a high-stakes narrative about vision, risk, and the thin line between genius and recklessness.
Part 1 Boy Genius: Humble Roots and Early Bets
Born in the Margins
Masayoshi Son was born in 1957 into a Korean-Japanese family in the dusty outskirts of Kyushu, Japan.
His parents, second-class citizens in a fiercely hierarchical society, lived on the literal and metaphorical margins:
Their neighborhood was unofficial and undocumented.
His father, Mitsunori Son, hustled to survive: brewing moonshine, dealing scrap, running pachinko arcades.
The family lived in constant legal and economic precarity.
Son witnessed all this as a child—not with resentment, but with an early understanding: society’s rules were negotiable, and sometimes, survivable only if you bent them.
“I started making moonshine when I was sixteen. I knew it was illegal… Then I stopped caring whether what I did was legal or not.”
—Mitsunori Son
Young Masa grows up internalizing two messages:
You don’t belong.
You don’t have to follow the same path.
A Fire to Prove Himself
At school, Masa is bullied—not just for being Korean, but for being different.
He retreats inward. But instead of folding, he forges something defiant: a self-image of genius.
He tells himself: “I’m not inferior. I’m exceptional.”
“If you truly believe you’re strong, you’re a genius, then failure just bounces off you.”
—Mitsunori Son
It’s the psychological operating system he carries for life: self-belief first, evidence later.
America: The Awakening
At 16, he leaves for California. It’s not just a physical move—it’s a philosophical break.
He arrives at UC Berkeley and is immediately struck by the culture:
People protest authority.
Mixed-race friendships are normal.
Success isn’t inherited—it’s built.
“I’m not gonna escape anymore. I’m gonna fight. I’m gonna prove that I’m an equally good man.”
—Masayoshi Son
This is where the idea crystallizes: technology is the tool to reshape status. If you control the future, you never have to beg for dignity.
The First Million-Dollar Move
Still in school, Son invents a speech translation device.
He licenses it to Sharp for $1 million.
It makes him rich—but more importantly, it makes him right.
His belief in asymmetric outcomes—one small bet, infinite upside—is now real.
He’s validated. But he doesn’t immediately scale. He pauses.
The Thinking Retreat
After that first win, Son does something unusual:
He disappears for three years, into near-total isolation.
He moves into a modest apartment in Fukuoka and reads. Obsessively.
Technology forecasts
Global infrastructure maps
Business history, psychology, science
He’s not building a product. He’s building a mental model of the future:
Information infrastructure will become essential.
Bandwidth, software, and chips will become the new oil.
Whoever controls the pipes, controls the flow.
This retreat becomes the intellectual seed of SoftBank.
No one sees it. That’s the point.
Return to Japan: Time to Build
Son comes back home not as a dropout or inventor—but as a strategist.
He founds a company with a name as bold as his ambitions: SoftBank—not a bank, but a software capital machine.
He tells two employees on day one:
“In five years, profits have to be 10 billion yen, then in ten years 50 billion. Eventually, I want to count profits in trillions.”
He sets up shop in a tin-roofed room with no product, no customers—just a vision of future dominance.
He’s not interested in gadgets. He’s interested in owning the rails on which future technologies will run.
📌 Part 1 in a Sentence:
Masayoshi Son begins not as a mogul—but as an outsider with nothing to lose, who turns exclusion into a blueprint for empire. His first billion-dollar bet was on himself.
Part 2 Rise and Fall: The First Empire, Yahoo, and the Dot-Com Collapse
From Illness to Insight
In the early 1990s, Masayoshi Son is diagnosed with chronic hepatitis.
He goes into a three-year physical and mental retreat—not unlike his earlier isolation phase.
But this time, the stakes are higher. SoftBank exists. Son is already an entrepreneur. Now he wants to become a visionary industrialist.
He doesn’t stop working. He just stops showing up. Behind closed doors, he obsesses over the coming wave of digitization—search engines, content distribution, digital commerce.
The message he tells himself:
“If technology can save me, it can save the world.”
The Gateway Strategy
As the internet gains traction, Son positions SoftBank not to build websites, but to own the gateways:
He secures distribution deals with CompuServe and Apple Japan.
He launches joint ventures with Ziff Davis (tech publishing) and Yahoo!.
He builds the pipes and platforms through which others operate.
Son doesn’t need to own the gold. He owns the shovels.
“I’m not interested in what’s hot. I’m interested in what’s inevitable.”
By 1996, SoftBank isn’t just a tech company—it’s a portfolio of bets on the future of attention.
The Yahoo! Moment
Son’s $100M investment in Yahoo! is a career-defining decision.
At the time, Yahoo is barely making revenue. But Son sees its potential as the global internet front door.
When Yahoo goes public, SoftBank’s stake explodes in value. Son becomes a billionaire—on paper.
His confidence soars. His playbook is validated: bet on infrastructure, and get in early.
“In Silicon Valley, we call Masa the information shogun.”
—Yahoo co-founder Jerry Yang
Paper Wealth, Real Risk
As the late ’90s heat up, Son starts making bigger, faster, more aggressive bets.
He invests in over 800 companies—including startups in telecom, fintech, and e-commerce—many of them pre-revenue.
SoftBank’s market cap soars. Son briefly becomes the richest man in the world—worth over $70 billion on paper.
But few of these investments generate cash. Many are overvalued. Some are outright vaporware.
“What does it take to win? A willingness to fail 9 times to get the 10x payoff once.”
—Son’s portfolio logic
He calls this the "Silicon Valley approach." Japanese investors call it reckless.
The Dot-Com Implosion
When the bubble bursts in 2000, everything unravels.
SoftBank’s stock plummets over 90%.
Son loses tens of billions in valuation in months.
Dozens of SoftBank-backed companies collapse.
Critics label him a fraud. Investors flee. His narrative—“information infrastructure will reshape society”—feels suddenly hollow.
“I wanted to change the world. I ended up broke, ashamed, and mocked.”
—Masayoshi Son
He’s no longer a tech prophet. He’s a cautionary tale.
After the Fall: A Flicker of Belief
And yet… Son doesn’t walk away.
Even in the rubble, he continues to believe in the thesis.
He cuts costs. Refocuses. Begins plotting the next layer: broadband.
He tells himself the collapse wasn’t proof the internet was wrong—just that the timing was early.
“I’m not done. The information revolution is still coming.”
The world sees a failure. Son sees a misfire.
📌 Part 2 in a Sentence:
Masayoshi Son builds a paper empire on the future of the internet, becomes the richest man in the world—then loses almost everything. But the fire doesn’t go out.
Part 3 The Operator: Rebuilding Through Infrastructure and the iPhone Bet
Picking Up the Pieces
After the dot-com crash, SoftBank is left battered.
Its market cap has evaporated, and Son is written off by investors and the media.
But instead of chasing new hype, he returns to first principles:
What is still inevitable?
His answer: the internet needs pipes. Fast ones. Cheap ones. For everyone.
He sets his sights on broadband—and on doing what Japan’s telecom incumbents won’t.
The Broadband Insurgency
In 2001, Son launches Yahoo! BB, an aggressive low-cost ADSL broadband service.
He offers free modems in subway stations.
He undercuts NTT’s pricing by more than half.
He bundles content with bandwidth to attract new users.
The strategy is pure Masa:
High burn
High scale
High faith in user behavior shift
Despite deep skepticism, Yahoo! BB takes off. Within two years, SoftBank becomes Japan’s leading broadband provider.
“You win not by fighting the old system. You win by bypassing it entirely.”
—Masayoshi Son
Back to Growth, But This Time as an Operator
For the first time, Son is not just investing in growth—he’s operating it.
He gets deeply involved in marketing, customer acquisition, and retention strategies.
This isn’t a portfolio play. It’s a platform.
And it’s profitable.
SoftBank transitions from being seen as a reckless investor to a national telecom challenger.
But Son is just getting started.
The Mobile Bet: Vodafone Japan
In 2006, Son makes his boldest move yet:
He acquires the failing Japanese division of Vodafone for $15 billion—nearly all SoftBank can afford.
At the time:
Vodafone Japan is bleeding money.
The mobile market is saturated.
Analysts say it’s corporate suicide.
But Son has a secret—he’s had a handshake deal with Steve Jobs to bring the iPhone to Japan.
No contract. No paperwork. Just Jobs’ word.
“I told my bankers: Trust me. Steve Jobs said yes. That’s enough.”
—Masayoshi Son
The iPhone Arrives—and Everything Changes
In 2008, SoftBank becomes the exclusive iPhone carrier in Japan.
The effect is immediate:
New subscribers flood in.
SoftBank’s brand transforms overnight—from underdog to innovation leader.
The iPhone becomes the ultimate distribution weapon.
Son’s gamble pays off—spectacularly.
SoftBank becomes the fastest-growing mobile operator in the country.
“The iPhone was the distribution platform. SoftBank was the pipe. That’s all we needed.”
The Platform Play Begins
With broadband and mobile under his control, Son starts thinking bigger again.
He now owns:
The infrastructure (broadband and mobile)
The content gateway (Yahoo Japan)
The attention channels (media + handset)
SoftBank is no longer a passive investor. It’s a tech-operating ecosystem.
The collapse is behind him. The next empire is forming.
📌 Part 3 in a Sentence:
Masayoshi Son rises from near-bankruptcy by going operational: building Japan’s broadband rails, acquiring a dying telecom, and riding the iPhone to resurgence—without a signed deal.
Part 4 The Empire Builder: The $100 Billion Fund and the Age of Exponential Bets
The Return of the Storyteller
By the early 2010s, Masayoshi Son is back on top.
SoftBank’s broadband and mobile businesses are thriving.
He’s no longer seen as a failed gambler—but as a visionary who came back stronger.
But Son isn’t content being a telecom mogul. He wants to shape the future of civilization.
He starts pitching a new idea:
“A 300-year vision for humanity’s evolution.”
It’s not a startup. It’s not a product.
It’s a global investment vehicle for building the future of intelligence.
The Birth of Vision Fund
In 2016, Son meets with Saudi Crown Prince Mohammed bin Salman (MBS).
In a 45-minute meeting, he lays out his case for a $100 billion tech investment fund.
“I have a crystal ball. I can see the future.”
MBS, seeking to transform Saudi Arabia’s oil-dependent economy, is intrigued.
He commits $45 billion to what becomes the SoftBank Vision Fund.
Other money flows in from Abu Dhabi and sovereign funds.
In months, Son controls more capital than the entire VC industry combined.
The Global Blitz Begins
Vision Fund starts deploying capital at a historic pace:
$9B into Uber
$4.4B into WeWork
Billions more into DoorDash, ARM, Slack, OYO, Grab, and dozens of others
The strategy: go big, go fast, and bet on category killers.
If you can control the market leader, you control the market.
Son doesn't care about modest wins. He wants monopolistic scale and data dominance.
“We invest in leaders, not learners.”
The Cult of the Founder (and the Cracks Beneath It)
Son’s style becomes mythic:
He bets based on instinct. On people. On energy.
“When I see the fire in their eyes, I know.”
But he often over-indexes on charisma, not control.
Nowhere is this clearer than in his backing of WeWork founder Adam Neumann.
Son invests over $10 billion in Neumann’s vision of “elevating consciousness.”
No clear governance. No profitability plan. No adult supervision.
Internally, SoftBank becomes chaotic too—rivalries flare between key lieutenants, including Rajeev Misra and Nikesh Arora.
The empire is getting too big, too fast.
Owning the Future: ARM and Platform Power
Not all of Vision Fund’s bets are reckless.
Son acquires ARM, a chip company that powers most of the world’s smartphones.
It’s a calculated move:
AI and IoT are coming.
Chips are the foundation.
ARM is the toll booth of the coming era.
This is Son’s deeper strategy at play: don’t just invest in apps—own the rails.
From Investment Firm to Infrastructure Force
Vision Fund becomes more than a financial entity—it starts to function like a sovereign tech allocator.
Its presence shifts entire industries:
Founders tailor their pitch decks to SoftBank’s preferences.
Competitors fear being outspent if a rival gets SoftBank money.
Governments begin to question whether Vision Fund is a neutral player—or geopolitical leverage.
Son doesn’t care. He believes he’s doing what others are too cautious to try.
“Only those who see what others cannot, will do what others will not.”
📌 Part 4 in a Sentence:
Masayoshi Son builds the largest tech fund in history by convincing sovereign wealth leaders that he can see the future—and spends it shaping a world dominated by AI, data, and founder charisma.
Part 5 Hubris: WeWork, Collapse, and AI Reawakening
The Empire Wobbles
At first, Vision Fund’s sheer size keeps the dream alive.
But cracks are forming beneath the surface:
Startups burn cash recklessly.
Unit economics are ignored.
SoftBank boardrooms become arenas of political tension.
Even internally, power struggles break out.
Rajeev Misra launches a covert smear campaign against rival executives.
Son is no longer leading an empire—he’s presiding over a court in crisis.
The financial world begins to whisper:
“Is this man a visionary—or a delusional gambler?”
The WeWork Disaster
The collapse begins with the most high-profile bet of all: WeWork.
Adam Neumann, once celebrated by Son as a messianic figure, is exposed:
Lavish personal spending
Failed IPO
Corporate governance chaos
Son had poured $10+ billion into Neumann’s dream.
He now has to bail out the company, fire its founder, and rescue what’s left.
The press turns on him.
The markets punish him.
SoftBank loses tens of billions in value.
“This is a shit year. I am ashamed.”
—Masayoshi Son, 2019
From Vision to Villain
Publicly, Son becomes a cautionary tale.
Privately, he’s unraveling:
Longtime allies leave the firm.
Investors question his judgment.
He cancels press briefings.
He retreats into silence, visibly shaken.
At one point, a founder tells him to his face:
“I hope you go bust.”
This is the inverse of belief: when the charisma fades, when the narrative breaks, and the crowd walks away.
Grief Behind the Numbers
The business is hurting—but so is Son.
In the same period:
His beloved dog Marie dies.
His father is diagnosed with cancer.
He begins to question his legacy.
He speaks less about wealth, more about meaning.
In one meeting, he reportedly weeps at the table.
“This has been a shitty, shitty year. I lost money, I lost people, and I lost face.”
For the first time in decades, Masayoshi Son sounds unsure.
The Whale Is Still Hungry
And yet… he doesn’t quit.
Even after the WeWork catastrophe, Son continues to believe in technology’s long arc.
He pulls back from aggressive investing—but shifts his focus to something deeper:
AI.
He starts meeting with AI founders.
In 2023, he quietly joins OpenAI’s funding round.
He begins reassembling his strategic vision—not for attention, but for relevance.
“The whale is still hungry.”
The vision is smaller, quieter, but still alive.
From Fireworks to Flickers
Son is no longer the emperor on magazine covers.
He is, instead, a founder again: bruised, rebuilding, and looking for the next inevitability.
The man who once declared a 300-year vision now rarely speaks publicly.
But behind the scenes, he is betting that AI is the next frontier—and this time, he doesn’t want to miss it.
📌 Part 5 in a Sentence:
Masayoshi Son’s empire collapses under the weight of overconfidence and under-governed bets—but in the wreckage, he quietly returns to his core belief: that the future still belongs to those who see further.
3. Key Stories + Lessons
Behind Masayoshi Son’s towering vision are a series of defining bets—some brilliant, some catastrophic, all revealing. This section dives into the most pivotal stories from Gambling Man that shaped SoftBank’s rise, near-collapse, and ongoing reinvention. More than dealmaking, each story captures a hard-earned lesson about conviction, control, founder psychology, and the cost of believing too much—or too little. For founders and builders, these aren’t just case studies—they’re cautionary tales and sources of strategic clarity.
The Deal That Launched SoftBank into the Internet Era
Story: Masa’s aggressive investment in Yahoo! and the birth of Yahoo! Japan
In 1995, Yahoo! was a quirky little search directory run by two Stanford grads—Jerry Yang and David Filo—with a name even they joked about: “Yet Another Hierarchical Officious Oracle.” Most investors didn’t take it seriously. But Masayoshi Son did.
After Sequoia’s Mike Moritz put in the first check, Masa flew straight to San Jose, met Yang and Filo, and declared he wanted in. When Yang floated a valuation of $40 million (much higher than what Sequoia had paid the day before), Masa didn’t flinch.
“It’s a deal,” he said on the spot—no hesitation, no due diligence.
He wanted more than equity. He wanted a gateway into the U.S. internet—and eventually, to bring it back home to Japan.
Going All-In (and Then Some)
Three months later, Masa returned with a far bolder offer:
**$100 million for a third of Yahoo!**—a record-setting bet for a minority stake at the time.
Yang hesitated. So Masa played hardball.
“If I don’t invest in Yahoo!, I’ll fund your biggest rival and kill you.”
That got Yang’s attention.
But Masa wasn’t done. He added a new condition:
Yahoo! had to launch a Japan joint venture, with SoftBank owning 60%. Masa would provide the engineers, $2 million in startup capital, and handle the localization.
Yang agreed.
Yahoo! Japan launched April 1, 1996.
The Instant Payoff
When Yahoo! went public just days later, SoftBank’s stake jumped in value, netting Masa a $150 million paper gain almost overnight.
It wasn’t just a financial win—it was strategic leverage.
Masa now had:
An appreciating U.S. internet asset
A fast-scaling Japanese consumer brand
A blueprint for bringing U.S. innovation to Asia
*“From now on,” Masa decided, “we replicate this formula.”
Founder Lesson: Own the Localization Layer
Masa didn’t just invest in Yahoo!—he repackaged it for Japan.
He saw early that copying tech was easy—translating culture was hard. That was SoftBank’s superpower: bridge U.S. product innovation with Asian market dominance.
By 1999, Yahoo! Japan was one of the most profitable internet businesses in the world. It would later become central to:
Yahoo! BB: Japan’s fastest-growing broadband service
The strategic triangle between Yahoo, Alibaba, and SoftBank
SoftBank’s IPO, credit profile, and borrowing power
At times, the Yahoo! stake was more valuable than SoftBank’s operating business itself.
The Bet of a Lifetime: $20M on Jack Ma
Story: Masa’s instinctive investment in Alibaba that returned over $100 billion
On October 31, 1999, in a Beijing “speed-dating” session for startups, Masayoshi Son met a wiry, fast-talking entrepreneur named Jack Ma. Ma had no revenue, a clunky website, and an idea he likened to the Arabian Nights: a digital Yellow Pages connecting Chinese buyers and sellers. What Ma did have was presence. He spoke fluent English, pitched with energy, and, in Son’s words, had an “animal smell”—the scent of a fellow underdog.
Masa offered $40 million on the spot for nearly half of Alibaba. Ma turned it down. “It’s too much,” he said. Alibaba was still a baby. They eventually agreed on $20 million for a 30% stake—a deal that valued the scrappy startup at over $60 million despite no profits and little infrastructure.
SoftBank’s own VC partners were skeptical. Ma wasn’t technical. He couldn’t predict profitability. But Masa overruled them. He didn’t see a spreadsheet. He saw himself.
“I invest in people who can’t be stopped.”
What followed was not just an investment—it was a 20-year partnership in building one of the most dominant tech companies on earth.
The Domino Effect: From Yahoo! to Alibaba
In 2005, Masa used his position in Yahoo! and Yahoo! Japan to broker the historic triangle deal:
Yahoo! invested $1B in Alibaba and handed over Yahoo! China.
SoftBank folded its Taobao stake into Alibaba, receiving cash and equity.
SoftBank retained a 30% economic stake in Alibaba.
“Masa made out like a bandit,” said Joe Tsai.
“I feel like your ATM machine,” joked Jerry Yang.
But the outcome was clear:
Yahoo! made Alibaba possible.
Alibaba made SoftBank unshakable.
Founder Lesson: Vision > Metrics
Masa didn’t invest in margins or traction. He invested in unreasonable belief. Ma’s conviction was irrational, his ambition outsized—and that was the point. This wasn’t a deal based on today’s numbers. It was a bet on who would own the future.
When eBay entered China with 90% market share, Masa doubled down. He backed Alibaba’s launch of Taobao—funded the losses, absorbed the risk, and pushed for a 10x product catalog. Jack Ma responded not with legal assurances, but with a handwritten promise to try. Masa called it a “Man’s pride” letter—and it was enough.
SoftBank’s $20M initial investment eventually became worth over $100 billion, and at one point made up more than half of SoftBank’s total asset value. Even Jack Ma would later admit:
“In the beginning, SoftBank made Alibaba. But in the end, Alibaba made SoftBank.”
For founders, the lesson is stark: when you meet someone who believes before the world does—hold on. That relationship might shape your entire company.
A $17 Billion iPhone Handshake
Story: Betting everything on a verbal promise from Steve Jobs
In 2005, Masayoshi Son flew to California to meet Steve Jobs—not to ask for a partnership, but to preempt one. Jobs was famously secretive, but Son pressed him with a sketch: a mobile iPod with a large screen running Apple’s OS. Jobs reportedly scoffed:
“Don’t give me your shitty drawing, Masa. I’ve got my own.”
But then he paused. And smiled.
“You’re the first to ask. When I’m ready, it’s yours for Japan.”
No term sheet. No timeline. No product name.
Just a gentleman’s agreement.
And with that flicker of trust, Son did something insane:
He borrowed billions to buy Vodafone Japan for $17 billion, gambling everything on a product he hadn’t seen, from a company that hadn’t yet entered the phone business.
“You didn’t give me anything in writing,” Son told Jobs later. “But I made a $17 billion bet on your word.”
Jobs laughed: “Masa, you are a crazy guy. But yes—we’ll do what we said.”
From Underdog to Market Shaker
In Japan, Son was facing enormous pressure. Mobile number portability laws were about to take effect, letting users easily switch carriers. Without a killer product, SoftBank would hemorrhage subscribers to giants like NTT Docomo and KDDI.
But Son had a weapon: the iPhone.
When it finally launched in Japan in July 2008, SoftBank was the exclusive carrier.
At first, critics were skeptical.
The iPhone lacked features prized by Japanese consumers (like emoji and mobile payments).
Apple was seen as a music player company, not a telecom disruptor.
But Son saw what others missed: Jobs wasn’t selling hardware—he was changing consumer behavior.
Founder Chemistry as a Competitive Moat
What sealed the deal wasn’t spectrum charts or carrier logistics. It was chemistry.
Jobs and Son understood each other:
Maverick visionaries
Obsessed with product and design
Comfortable making billion-dollar decisions without contracts
SoftBank’s network wasn’t technically superior—but it was simpler, more rollout-friendly, and backed by a founder who would push it at all costs.
“Japan needs a maverick,” Jobs reportedly said. “Masa’s the guy.”
The Payoff
When SoftBank launched the iPhone, it didn’t just gain users—it redefined the market.
In 2006, SoftBank’s mobile share was 17%.
By 2011, it had climbed to 23%, even after losing iPhone exclusivity.
The iPhone became the ultimate growth engine—and a brand transformator.
This wasn’t just product-market fit. It was founder-founder fit—and Masa knew how to scale a moment into a movement.
Founder Lesson: Conviction Outranks Contracts
Son made a $17 billion decision on a wink. It could have ended in disaster.
But what he saw—before others—was that the iPhone wasn’t a phone. It was a platform shift, and SoftBank could own its entry point in Japan.
Would your investors let you bet the company on a sketch and a smile?
Son did. And he won.
The Fantasy That Cost $10 Billion
Story: Masa Son backs Adam Neumann’s vision of a $10 trillion real estate empire—and watches it collapse
When Masayoshi Son met Adam Neumann, the charismatic founder of WeWork, he saw more than a CEO—he saw a messianic energy that reminded him of a young Jack Ma. Neumann pitched a new category: not real estate, not coworking, but a global movement. A place where people didn’t just rent desks—they belonged.
Masa was sold.
In 2017, he committed $4.4 billion—co-financed by SoftBank and the Vision Fund—with the vision of turning WeWork into “Alibaba for space.” The funding implied a $20 billion valuation, a number bigger than Hilton Hotels.
The pitch? World domination.
Neumann promised to expand to one billion square feet, generate $101 billion in revenue, and reach a $10 trillion valuation by 2028. Masa sketched the numbers himself—on an iPad—like a digital fever dream.
“Only he looks like Alibaba today,” Masa reportedly told a colleague.
“But you’re not crazy enough,” he told Neumann later.
Founder Lesson: Vision without brakes becomes delusion
Behind the scenes, cracks formed fast.
Neumann was elusive, demanded more money constantly, and showed little interest in governance. He personally sold stock worth hundreds of millions while WeWork burned cash.
SoftBank insiders tried to rein him in.
He acted like a union leader among founders.
He ghosted meetings.
He reportedly staged an “incipient insurrection” to renegotiate his investor terms.
Still, Masa believed—_too much_.
The Collapse
By mid-2019, the company unraveled:
IPO paperwork revealed massive losses and erratic leadership.
The public turned on Neumann.
Valuation plunged from 8 billion.
Neumann was ousted.
The IPO was scrapped.
WeWork was bleeding.
And here’s the twist: the Vision Fund didn’t bail it out. SoftBank did—breaking every VC convention.
Masa poured in $9.5 billion more to rescue the company, including a $3 billion tender offer to buy out Neumann and other investors. SoftBank ended up with 80% ownership of a deeply flawed business model.
It wasn’t an investment anymore. It was triage.
The Aftermath
What started as Masa’s next “Alibaba” became his most painful and public failure.
The Saudis were furious.
SoftBank’s share price wobbled.
Neumann walked away with nearly $1 billion.
The Vision Fund’s credibility took a beating.
SoftBank eventually installed new leadership, slashed costs, and tried to position WeWork within its tech ecosystem—but the damage was done.
Lesson: Don’t confuse founder charisma with founder discipline
Neumann could raise money. But he couldn’t build systems.
He sold culture when he needed margin. He cast vision when he owed operations.
Masa bet on a story—and lost billions.
For founders: big vision wins attention, but structure earns trust.
For investors: know when you’re backing a prophet—and when you’re following a mirage.
The $32 Billion Bet on the Brains of the Future
Story: Masa Son acquires ARM to become the foundation layer of the AI era
In 2016, while Silicon Valley chased software unicorns, Masayoshi Son made a quieter—but bolder—move. He bought a company most consumers had never heard of: ARM Holdings, a UK-based microchip designer.
ARM doesn’t build chips. It designs them—super-efficient blueprints that power 95% of the world’s mobile devices, and increasingly, everything from smart speakers to self-driving cars. Apple, Amazon, Google—they all license ARM’s architecture. In Masa’s mind, ARM wasn’t just a chip company. It was “the central nervous system of the future.”
“In the age of a trillion connected devices, ARM will be the brain.”
Masa had admired the company for years. When he finally moved, he moved fast.
The Smash-and-Grab Deal
In July 2016, Masa flew to London, handed over a one-page letter, and offered $21.4 billion to ARM’s chairman. A few days later, he upped it to $32 billion in all-cash, a staggering 40% premium over ARM’s all-time high.
The ARM board was stunned. One banker called it a “smash-and-grab”. In just under two weeks, the deal was done.
While critics fumed over the sale of a UK tech crown jewel, Masa promised:
To double the workforce from 3,000 to 6,000
To keep the HQ in Cambridge
To invest in R&D for the AI era
UK regulators, reeling from Brexit, approved the deal with minimal resistance.
Founder Lesson: Infrastructure is the ultimate power play
Unlike his headline-grabbing WeWork or Uber bets, ARM was pure strategy. Masa wasn’t buying flash—he was buying the foundation. Where most investors chased apps, he bought the substrate beneath them.
Internally, not everyone agreed.
SoftBank’s then-COO Nikesh Arora reportedly said:
“Over my dead body.”
He was worried about the Sprint debt load and questioned the $600 billion valuation Masa claimed ARM could reach.
The friction helped push Arora out. Masa didn’t blink.
After the Deal: Promises Kept, Plans Blocked
To his credit, Masa kept his word:
Jobs were doubled
R&D expanded
ARM thrived as a key pillar of SoftBank’s ecosystem
Masa later tried to sell ARM to Nvidia in a mega-merger, hoping to create the “Intel of the AI era.” But regulators shut it down. Still, ARM remained central to Masa’s long game—fueling his Neom City ambitions and forming part of SoftBank’s long-term bet on deep tech.
Lesson: Long-term plays take more than vision—they take patience
ARM wasn’t about momentum or blitzscaling. It was about control, timing, and deep infrastructure.
For founders and investors alike, the ARM story is a masterclass in thinking 10 years ahead, even when the world is chasing trends.
Masa didn’t buy ARM to win headlines.
He bought it to own the layer no one could afford to ignore.
Becoming the Capital Market: Inside the Vision Fund Gamble
Story: Masa raises $100 billion to reshape the tech world—and nearly loses everything
In 2016, Masayoshi Son didn’t just want to invest in the future—he wanted to own it. His answer: the SoftBank Vision Fund, the most audacious capital vehicle in venture history. The target? $100 billion. The pitch? Forget traditional VC. This was a global empire of AI-driven businesses, each backed with enough capital to overwhelm competitors. Masa didn’t want to be in the market—he wanted to be the market.
He raised $45 billion from Saudi Arabia in 45 minutes (a comment that later offended his investors), secured billions more from the UAE, and even approached Bill Gates. The Vision Fund ultimately launched at 500M, 4B at a time.
“I will be the emperor of a trillion-dollar AI kingdom.”
Founder Lesson: Scale amplifies everything—including your blind spots
Unlike traditional VCs who nurture startups, Vision Fund operated like a hybrid hedge fund—using term sheets as suggestions, pushing valuations aggressively, and rewarding individual dealmakers over team collaboration. Governance collapsed into internal power games. Rajeev Misra, a credit trader with no VC experience, built an internal fiefdom while SoftBank’s COO Marcelo Claure was blocked from oversight.
The fund’s biggest bets revealed the cracks:
WeWork: Masa called Adam Neumann the next Jack Ma—then watched 8B. SoftBank had to bail it out, breaking all VC norms.
OYO, Greensill, and Light: Overhyped, overvalued, and imploded.
ARM was a rare strategic gem.
Coupang and Didi returned well—but couldn’t outweigh the carnage.
Masa backed founders who echoed his scale obsession, but many lacked discipline or unit economics. With a $7B annual obligation to investors just for the preferred return, the pressure to create paper gains led to “unicorn inflation” and misaligned incentives.
“We needed home runs. Instead, we stacked too many shitburgers,” a former adviser admitted.
The Fall: Margin Calls, Fake MOUs, and Fire Drills
After the WeWork disaster, SoftBank’s credibility cratered. Vision Fund 2 was announced with “38B down payment from the balance sheet**. Meanwhile, SoftBank’s own debt ballooned to $177 billion. Masa had borrowed personally against shares and began facing margin calls.
“I was peering over a cliff,” he admitted.
SoftBank's structure grew opaque. Investors complained of poor disclosure. Even loyal partners, like Saudi PIF’s Al-Rumayyan, felt alienated—told they were “back-seat LPs.” By 2022, Masa’s own stake in Vision Fund 2 was wiped out. He owed SoftBank billions.
Legacy: The Vision Fund Changed the Game—But at a Price
Despite its flaws, the Vision Fund reshaped venture capital. It forced top-tier firms like Sequoia to raise multi-billion-dollar war chests in response. It changed expectations around startup scale, speed, and globalization. It also proved that unbounded capital without discipline is just chaos with a logo.
“Masa turned SoftBank into the capital market itself. But in doing so, he lost control of what made him great: clarity.”
For founders, the Vision Fund is a cautionary tale: don’t let capital outrun conviction—and never mistake speed for certainty.
4. Critical Reflection – Not Just Praise
It’s easy to admire Masayoshi Son’s boldness. He made the biggest tech bets in history, saw trends years ahead of others, and played the game at a scale few would dare. But Gambling Man also makes one thing clear: vision without discipline can become a liability—to companies, to partners, and even to the visionary himself.
Masa’s greatest strength—his belief in the improbable—was also his greatest vulnerability. He was drawn to “fellow dreamers” like Adam Neumann and Ritesh Agarwal, who talked about changing the world but couldn’t operate within its constraints. In the Vision Fund years especially, he stopped acting like a strategist and started behaving like a myth-maker. Valuations ballooned. Governance decayed. His obsession with scale began to overshadow fundamentals like product truth, team execution, and timing.
What’s more, SoftBank's internal chaos—the “empire within an empire” culture of the Vision Fund, the lack of accountability, the margin calls and convoluted structures—revealed a founder who could see the future, but didn’t always manage the present.
And yet, it's hard not to respect the raw energy of someone who keeps playing after losing billions. There’s a difference between recklessness and resilience—and Gambling Man walks that line unflinchingly. The book doesn’t ask us to worship Masa. It asks us to study him. Learn from his conviction. Be warned by his blind spots.
Because in the end, Masa Son isn’t a hero or a villain. He’s a founder like the rest of us: prone to overreach, desperate to matter, and still chasing the next great bet.
5. Conclusion – Final Verdict
Gambling Man is more than a biography—it’s a window into how conviction, capital, and chaos collide at the highest levels of tech. Masayoshi Son doesn’t follow a roadmap. He writes his own gravity. And sometimes, it works spectacularly. Other times, it detonates.
For founders, the book is a rare study in scale psychology. It reminds us that the line between visionary and delusional is measured not by ideas, but by timing, governance, and execution. Son’s story isn’t one you copy. It’s one you extract principles from carefully.
Would I recommend this book? Absolutely—especially to those building in AI, infrastructure, or global markets. But don’t read it for inspiration alone. Read it like a founder’s field manual—full of high-stakes plays, hard lessons, and the cost of betting everything on belief.
Because as Gambling Man shows: anyone can place a bet. Few survive the consequences.