Imagine losing $70B almost overnight, then rallying to chase even bigger dreams. That’s Masayoshi Son. He briefly topped the rich list (surpassing Bill Gates), but the 2000 dot‑com bust erased 97% of his wealth. 

In the same era, he pulled in $45B in a 45‑minute meeting (literally $1B per minute). He backed visionaries like Yahoo’s founders and Jack Ma – his $20M Alibaba gamble would later be worth over $70B. 

Now, Son is waging a $500B AI bet with OpenAI and Oracle (the “Stargate” project) to build new AI super‑infrastructure. 

His saga, from bullied outsider to bold tech investor, feels almost fictional. But every crazy claim is true: a Japanese kid from poverty who became a Gambler Extraordinaire.

From “Dirt Track” Kid to Rebel

Son’s early life reads like a movie script. He was born in 1957 on a “dirt track with no name” in Kyushu to Korean parents struggling in postwar Japan. 

His grandfather was a miner from Daegu, and his father raised pigs and illegally brewed sake just to make ends meet. 

The family even hid their Korean identity to escape prejudice, but once his classmates found out, Son endured bullying and stones thrown at him for being a “Zainichi” outsider. 

The cruelty hit him hard at one point, and he even contemplated suicide, but it also stoked a fierce resolve. By middle school, he had made a vow: he would become Japan’s most successful businessman. 

That chip on his shoulder led him to idolize Den Fujita, the McDonald’s Japan founder. As a determined teenager, he repeatedly called Fujita’s office, even flying to Tokyo in person to secure a 15‑minute meeting. 

Den’s advice was simple but life-changing: “Computers.” And, he said, “Go to America.” Son took it to heart.

The American Hustle: $10,000/month Working 5 Minutes/day

At 16, armed with Fujita’s advice, Son moved to California. He sped through high school by convincing administrators to let him take the college exam early. At UC Berkeley, he studied economics and computer science, but even as a freshman, he was obsessed with making money. 

He challenged friends to suggest a way to earn $10,000 a month by doing five minutes of work a day. 

The answer he landed on was invention. 

Each night, he set an alarm for five minutes of creative brainstorming, amassing 250 ideas in a notebook by year’s end. His best one was a pocket translator device. 

He and a physics professor built a prototype and pitched it to electronics firms. In 1976, Sharp paid $1.7M for the patent. Son was 19 and technically a millionaire.

But that was just side quest one. On another front, Son saw a chance with arcade games. In the mid-1970s, Space Invaders was a huge hit in Japan but was new to the U.S. 

So Son imported over 350 Space Invader machines, leasing them to bars and restaurants. It paid off quickly. Within six months, he’d cleared more than $1M in profit. 

Son famously financed the imports by putting the machines on credit and flying them in by plane, fast but expensive, so he often recouped his money before the supplier was paid. 

Clearly, the young Masayoshi had a nose for opportunity. He worked relentlessly, seven days a week, with minimal sleep, simply because he loved it.

SoftBank: A Billion‑Dollar Dream

After graduating, he returned to Japan as promised. He mapped out 40 possible business ideas and ranked them. The winner was computer software distribution. 

In 1981, he founded SoftBank as a floppy disk distributor. On day one, he even stood on a crate to declare to his two employees, “SoftBank will be a billion‑dollar company.” 

They quit, thinking he was crazy. 

The early days were lean, SoftBank struggled, and many told Son to stop burning his life’s savings. But he ignored them, pumping every penny back in. 

By the early ’90s, Japan’s personal-computer boom hit, and SoftBank finally rode the wave.

But, as fate would have it… a health scare nearly derailed everything. In the mid-1990s, Son was diagnosed with chronic hepatitis and was bedridden. He hid the illness to keep bank funding, sneaking out of the hospital for meetings. 

After recovery, the scare crystallized his mindset. Life was short, so he needed to get even bigger, even faster, even crazier. 

By 1995, SoftBank had 800 employees and $1B in annual sales. Son took it public. With healthy cash flow from software distribution, he began to branch out into aggressive tech investments.

Big Bets: Yahoo, Alibaba, and the Internet Goldrush

Son had a knack for wild pitches. In 1998, he poured $40M into a small startup called Yahoo! when its IPO was imminent. A few months later, Yahoo’s stock pop meant SoftBank’s stake was suddenly worth $808M, an INSANE 18x return in no time. 

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SoftBank by then was acting like a venture firm, putting $3B into roughly 800 startups by 2000. Son met hundreds of founders each quarter, knowing most ideas would fail, but a few monsters could cover a hundred losers.

His all‑in attitude led him to Alibaba in 2000. Son heard founder Jack Ma’s vision and was relentless, even as Ma initially said he had enough money. 

Son sensed a giant potential and invested $20M into Alibaba, a minuscule sum at the time. That stake, years later, exploded in value. By 2014, it was worth around $70B.

Losing $70B Overnight 

In that era, Son raised the largest fund ever seen in Japan and was nicknamed “the Bill Gates of Japan.” In fact, for a few dizzy days in 2000, Son briefly overtook Gates on the billionaires list.

Then reality hit. The dot-com bubble burst by March 2000. SoftBank’s stock crashed, vaporizing Son’s fortune. 

He went from the world’s richest to crushing losses, roughly $70 billion disappeared in months. It was, as one source puts it, “the biggest personal loss in history.” Yet Son would not stay down.

Risk‑Crazy Tactics: Broadband and iPhones

Instead of yielding, Son started running at the next curve. 

In 2001, he stormed into Japan’s telecom ministry, even threatening to set himself on fire with gasoline unless the government approved a new broadband network. 

He launched SoftBank’s broadband service at extremely low prices. It ran at a loss for years by design. Son was focused on market share and growth, convinced that profits would come later with add-on services. 

“We thought we would make money eventually,” SoftBank told investors, as customers snapped up its half-price connection plans.

He had a similar hunger for mobile phones. In 2007, Son had a call with Steve Jobs in the garage. He wanted the exclusive rights to sell the iPhone in Japan. 

Jobs laughed, saying SoftBank didn’t even own a carrier, but Son was undeterred. He promptly took on more debt and bought Vodafone Japan for $20B, effectively buying a phone company so he could carry the iPhone. 

It worked. SoftBank became Japan’s iPhone carrier, selling countless contracts at razor‑thin margins to build share.

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All these moves had one thing in common: vision-first. He drew up a “300-year vision,” talking publicly about telepathy networks and talking-to-dogs technology. 

Co-workers said Son truly believed SoftBank might one day help people literally talk to their pets. It sounds wild, but it underscores his mindset that he was playing the very long game.

The $100B Vision Fund: Loosing It All Again

By the late 2010s, Son was known as a tech gambler with some hits and some horror stories. In 2017, he launched the SoftBank Vision Fund, then the world’s largest tech investment fund, with $100B in capital. 

It was backstopped by Saudi Arabia’s Public Investment Fund ($45B), SoftBank itself ($28B), Abu Dhabi’s Mubadala ($15B), and others. 

Son’s mission was blunt: fund “the next age of innovation.” He openly said it, they would invest in anything at the frontiers of artificial intelligence and the internet.

The Vision Fund poured insane sums into global tech unicorns. It bought big pieces of Uber and WeWork, backed India’s Flipkart, robotics firms, health startups, SpaceX, and dozens more. 

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It even doubled down on Arm (the British chip designer) and Grindr. Son’s strategy was to be the biggest fish in every tank. 

He believed that being the best‑funded startup often scares off rivals.

Yet with scale came risk. By 2019, cracks were showing. 

A botched plan to IPO WeWork revealed its woes, forcing SoftBank to prop it up.

 Other portfolio companies hit headwinds, e.g., SAAS company Katerra and co-working space Ucommune stumbled. SoftBank’s official filings by spring 2020 were bleak. The Vision Fund had reported a ¥1.9 trillion loss (around $18B) for fiscal 2020, one of the worst annual losses ever recorded. Much of that loss came from WeWork and Uber. 

Together, they accounted for almost $10B in write‑downs. Even ride-hailing app Getaround and Indian hotel chain Oyo cut thousands of jobs under pressure.

When Elliott Management, an activist investor, took a stake in SoftBank in 2020, it blasted the fund’s lack of transparency and poor results. 

But Son retained the faith in his vision. He accepted responsibility, quipping, “Too much guts, I lose a lot of money,” but refused to change course. 

As SoftBank’s own documents noted, Son had learned that one big winner could mask all the other failures combined. Indeed, Alibaba’s windfall was making that point.

From Riches to Ruin and Back

Masayoshi Son has lived through extremes. He was once officially the richest man on Earth, yet for years he held the title of “the person who lost the most money in history” (about $59B in 2000 alone). 

By early 2025, he’s back on billionaire lists (around $17B net worth), but SoftBank’s stock has swooned and recovered with every market turn. 

The dot-com wipeout took 93% of SoftBank’s value, and Vision Fund losses almost wiped out its own capital for a time. 

Yet Son has always bounced back. Each bust taught him to double down on resilience.

Now, in the AI age, Son is charging ahead with what might be his biggest bet yet. He is co-leading OpenAI’s new Stargate project, a $500B plan to build AI computing centers in the U.S. 

Lessons for Entrepreneurs: Dream Big, Grow Faster

So, what does the Son saga teach us? First, vision trumps convention. Son famously invested in Alibaba and others, backing founders with a “sparkle in their eyes” rather than rigid plans. 

He even laughed that he had listened to cautious advisers, he would never have done the Alibaba deal. 

Indeed, his former CFO quipped that everything Son did is a warm-up act because Son has always been willing to jump first and fix things later. 

For founders, that’s a green light to think big. If Son had asked the room for permission, we might never have had Alibaba or SoftBank’s smartphone era.

Second, growth often beats profits in the beginning. Son’s broadband and mobile moves were loss‑making at first, but they grabbed market share. 

Third, resilience is everything. Losing $70B would crush most people, but Son treated every blow as fuel. Entrepreneurs can take heart that one implosion doesn’t end the story. As Son has proved, a few big wins, like Alibaba, can mask dozens of failures.

Finally, intensity and passion. Son slept little, worked hard, and filled a 50-year plan since his teens. He speaks simply and energetically. 

Masayoshi Son’s next chapter, an AI infrastructure boom funded by a $500B plan, will affect us all. Whether he succeeds or not, we’ve already seen how his bets ripple across industries.