Masayoshi Son is the $100 billion gambler who went from dirt track to tech titan — and he isn’t done betting yet

Softbank CEO Masayoshi Son has had a dizzying career betting big on technology.

On an evening at the turn of the millennium, Masayoshi Son had a rousing message for the entrepreneurs who flocked to Tokyo’s Roppongi district.

“Japan is going through its biggest social upheaval since the Meiji Restoration,” he said with characteristic grandiosity. “Let’s make it so that a millennium from now, people will look back on our time and remember that the kind of society they’re living in was created by us today.”

SoftBank, the media-technology conglomerate Son founded two decades prior, was riding high on the glory it attained in the dot-com boom. Son himself had briefly seen his wealth surpass that of Bill Gates in the era’s frenzy; he was the world’s richest person for three days. Now, he was ready to see a new generation emulate his success.

It’s a story that Lionel Barber, the former editor of The Financial Times, recounts in his new book “Gambling Man: The Wild Ride of Japan’s Masayoshi Son.” Over 335 pages, he charts the journey of the 67-year-old — known to many as Masa — from a life in poverty to a dizzying career betting it all on technology.

From his early years distributing software, he would go on to build a telecoms empire and mint a near-$100 billion investment fund that would splash money on everything from Uber to WeWork.

For Barber, who has stood face-to-face with leaders like Vladimir Putin at the Kremlin and Barack Obama in Washington, the allure of Son was simple. “This is a story of our times,” he told B-17. “The cheap money, leverage, technology — he’s ridden this wave right from when he started with software distribution, which has penetrated every aspect of society.”

As history shows, the hopes and dreams the SoftBank founder shared for the future that evening 24 years ago would crash back to reality days later. Having made a killing from an early $20 million bet on Jack Ma’s Alibaba and taking a share in Yahoo, Son was about to see an abrupt change in fortune as SoftBank’s stock crashed.

By March 2000, the dot-com bubble would burst altogether.

Masayoshi Son was an early investor in Jack Ma’s Alibaba. 

That said, Son’s humiliation at that moment would not stop him from chasing visions of extraordinary scope again and again, even if it meant hard falls were to come once more. This is the career of a man whose ambition has taken him to the brink and back.

And signs suggest he’s not done just yet.

Social pariah to technology visionary

Son’s rise to what Barber describes as a “place at the very pinnacle of the global plutocracy” was hardly guaranteed.

Though he’s now worth almost $17 billion, owns a mansion likened to Batman’s Wayne Manor, and places himself among a peer group of Napoleon Bonaparte, Genghis Khan, and Qin Shi Huang, the first Emperor of China, Son was born in August 1957 to Koreans “on a dirt track with no name” on the Japanese island of Kyushu, according to the book. It recounts that “Masa’s earliest memories were the smell of pigs and the sound of steam trains belching soot and smoke which filled his makeshift home.”

Discrimination was a part of his childhood, too, with postwar Koreans living in Japan labeled “Zainichi” — a term used as a pejorative to categorize the ethnic minority as second-class citizens. For Son, being born in poverty meant his early years involved a pariah-like experience.

However, as Barber notes, the younger Son would go on to enjoy a future audience with the 45th President of the United States and court royals in Riyadh. He would, more importantly, play a pivotal role in transforming the technology sector from a niche interest of computer obsessives into a global force that turns the world economy.

In Barber’s telling, a few key factors drove Son down this path. His inaugural visit to the US, where he attended Berkeley, coincided with the microprocessor revolution. Like Microsoft’s Gates, he claims to have had an epiphany after seeing the Intel 8080 microprocessor for the first time in a copy of the Popular Electronics magazine; he foresaw a future in which the world could one day be powered by silicon.

Masayoshi Son found early inspiration in Bill Gates.

However, self-conviction in his own “genius” appears to be first and foremost. Combined with his outsider status, Son was a young man with a chip on his shoulder. Visiting Son’s father, Mitsunori Son — creator of a gambling business built on arcade pachinko machines — at their family home, Barber recalled how it felt like a shrine devoted to their son. “He was treated like a princeling from day one and behaved like a princeling. He was told he was special,” Barber told B-17.

The early years are key to understanding how Son became preoccupied with unwieldy ambition that would take him too close to the sun time and again. He made his first major bet on his own genius when he founded SoftBank in 1981. It was the start of a two-decade chapter defined by high-profile encounters with the likes of Rupert Murdoch, Larry Ellison, and Jack Welch, acquisitions totaling billions of dollars, and an all-or-nothing attitude toward innovation.

At that time, Son was akin to an “arm-waving internet prophet,” Barber said, who devised the idea of distributing software. Years later, when Japan’s economy began to collapse, he quickly maneuvered a return to the US, where he bought big assets such as the then-popular tech trade show Comdex, gaining access to the deep Silicon Valley networks that came with it.

Though it ended with a spectacular crash, Son offset the damage that left SoftBank “virtually broke” by working 18-hour days, seven days a week, to bring the high-speed broadband revolution to Japan in the 2000s.

A helping hand from Steve Jobs, who he first met at the Comdex trade fair in Las Vegas in the 1980s, also came as SoftBank struck an exclusive carrier deal in Japan for the iPhone from 2008 to 2011. It gave him a front seat to the smartphone boom.

Steve Jobs and Masayoshi Son first met in the 1980s. 

This cycle of rise and fall has made a curious reappearance throughout Son’s career. As Barber puts it, Son is a gambler, which means his life has followed a familiar pattern that goes something like this: “A blizzard of ideas followed by intense enthusiasm and focus, leading to overreach, failure, and repentance — until the whole process started over again.”

He is also someone Barber deems ruthless, a fighter with a penchant for the “crazy” that sits at odds with the portrait of a more shy and self-conscious leader that the billionaire has often presented to the public.

Nowhere have these elements shown themselves more than they have done in Son’s leadership over SoftBank 2.0.

A gambling man with $100 billion to play with

In 2010, as the world was picking itself up from the financial crash, Son spent a lot of time thinking about 2040. He wanted to know how technology would shape society in 30 years’ time.

He concluded that the tech-enabled information revolution should mean “happiness for everyone.” At that time, though, Son was getting bored of being an operator — it was time to be a “grand investor.” In Barber’s assessment, this is a period in Son’s life that shows how he’s “quite capable of serious hardball” to get what he wants while leaving himself entirely vulnerable to those who might dare to dream as big as he does.

Enter the Vision Fund. Rajeev Misra, a former trader at Deutsche Bank who profited from a huge short bet against the subprime mortgages at the center of 2008’s financial meltdown, was brought in to help lead Son’s investment charge. So, too, was Nikesh Arora, a “fast-talking” former Google executive pulled away from a $50 million-a-year package.

Rajeev Misra ran SoftBank’s Vision Fund.

In the context of traditional Japanese corporate life, these hires were total anomalies. But Son’s decision to bring them on board signaled the bold push he was ready to make. Buoyed by the credibility attained from the 2014 IPO of Chinese e-commerce giant Alibaba, Son tapped Misra’s ties to wealth funds in the Middle East to raise a combined $60 billion from Saudi Arabia’s Public Investment Fund and Abu Dhabi’s Mubadala.

In particular, for Mohammed bin Salman, Saudi Arabia’s ruler-in-waiting who led talks with SoftBank, Son’s proposition gave him the opportunity he sought to present himself at home as a prince with a bold plan for the future. “He wants to be seen as the great modernizer transforming this petrostate into a truly modern economy where technology is at the forefront,” Barber told B-17.

Eventually, almost $100 billion was raised for a startup investing vehicle known as the Vision Fund, which brought untold chaos to the technology sector. Silicon Valley’s biggest funds before then were no bigger than a few billion dollars, and SoftBank was ready to outbid them all to lead blockbuster investment rounds. Michael Moritz, lead partner at Sequoia Capital at the time, likened Son’s arsenal of capital to Kim Jong Un’s intercontinental ballistic missiles. Did Son care? Barber thinks not.

But as previous cycles in Son’s life dictate, the flurry of enthusiasm is typically followed by failure. Though he proved himself to be ruthless in the $32 billion acquisition of chip designer Arm in 2016 — its shares are up almost 200% since being re-listed last year — he would fall prey to the charms of WeWork cofounder Adam Neumann.

The Israeli entrepreneur, who Son invited into the back of a taxi while en route to see Donald Trump, would eventually cause him trouble. Billions of dollars of investment were burned as the office space company masquerading as a tech one fell apart. A SoftBank bailout of WeWork cost $9.5 billion in 2019.

It wasn’t the only blunder. SoftBank-backed Wirecard imploded after the Financial Times exposed large-scale fraud at the German payments provider. Greensill Capital, a supply chain finance firm that fell apart, forced the Vision Fund to write down a $1.5 billion investment.

Defending his track record in 2020, Son said Jesus was misunderstood.

Masayoshi Son has battled ups and downs in his career.

As the misfires have mounted, critics have put Son’s successful bets over the years down to luck. In Barber’s view, the picture is more complicated. He told B-17 that he sees an “intelligent brain thinking ahead, anticipating,” but also a reckless impulse to “put a chip on every board.” There is a visionary that co-exists with a “gambling addict.”

Barber’s book comes at a critical juncture. Since the launch of ChatGPT, the technology industry has made artificial intelligence its central focus, with an arms race underway among global companies wanting to make smarter versions of the technology. For Son, an AI obsessive long before the current era of generative AI chatbots, it’s a moment that seems tailor-made to his desires. But he has been slow to match that with the bold bets he has become known for.

While SoftBank oversaw Arm’s IPO in September 2023 and acquired chip firm Graphcore in July, it has not yet invested in companies developing the large language models powering the current boom, such as OpenAI or Anthropic. In 2019, it dumped its nearly 5% stake in Nvidia, the chip giant now worth over $3 trillion.

Still, it’s hard not to see a splurge coming soon. In June, the SoftBank boss told shareholders past investments were “just a warm-up” for the AI era. It’s no surprise to Barber, who sees Son as never satisfied.

“He’s definitely got another act,” Barber said. “There’s no question.”