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In the year 2000, one man was briefly the richest person on Earth. Months later, he had lost more money than almost anyone in history. Twenty years after that, he poured billions into WeWork, and watched it collapse into bankruptcy. Most people would quit. Masayoshi Son did the opposite. Today, his company has committed around sixty five billion dollars to OpenAI, the company behind ChatGPT.
He sold every share he owned in NVIDIA to help pay for it. And he borrowed tens of billions more. So is this the smartest bet of the AI era, or the biggest gamble in tech history? Let's break it down. Masayoshi Son was born in 1957 in Tosu, a small town in southern Japan. His family was ethnically Korean, and growing up, he faced discrimination because of it.
His father raised pigs and chickens to get by. At sixteen, Son moved to California with a simple plan. Get rich, and come back. He finished high school in about three weeks, then went to the University of California, Berkeley. While he was still a student, he worked with professors to build an electronic translator, and sold it to Sharp for about one point seven million dollars.
In 1981, back in Japan, he started a small software company. He called it SoftBank. Legend has it that on day one, he stood on a box and told his two part time employees that the company would one day be worth trillions. They both quit. In the 1990s, Son bet early on the internet. He backed Yahoo, and hundreds of other web companies.
When the dot com boom hit, SoftBank's stock exploded, and for a moment, Masayoshi Son was the richest person in the world. Then the bubble burst. He lost more than fifty nine billion dollars, at the time the biggest personal loss in recorded history. But in the middle of that chaos, he made one small bet.
In 2000, he invested twenty million dollars in a little Chinese company run by a former English teacher named Jack Ma. That company was Alibaba. By its stock market debut in 2014, his twenty million dollar stake was worth around seventy five billion dollars. It became one of the greatest investments ever made.
And it gave Son something dangerous. Proof that his gut could be right, even when everyone else said he was crazy. In 2016, he bought the British chip designer Arm for about thirty two billion dollars, whose designs sit inside almost every smartphone on the planet. A year later, in 2017, Son launched the biggest tech investment fund the world had ever seen.
The SoftBank Vision Fund, with nearly one hundred billion dollars, much of it from Saudi Arabia and Abu Dhabi. His plan was to own a piece of every company shaping the future. Early on, he bought about five percent of a chip maker called NVIDIA. Then, in late 2018, NVIDIA's stock crashed by about half.
Son sold the entire stake. By early 2019, it was gone, for around three point six billion dollars. A few years later, that same stake would have been worth around one hundred and sixty billion. Son later admitted he had to tearfully sell the shares, and said, the fish that got away was big. But NVIDIA wasn't even his worst mistake.
That was still coming. WeWork rented office space, split it into desks, and rented those desks out. Its founder, Adam Neumann, sold it as a tech company that would change how the world works. Son believed him. Reports say Son met Neumann for just a few minutes before agreeing to invest. SoftBank poured in billions, and by early 2019, WeWork was valued at around forty seven billion dollars.
Then WeWork tried to go public. Investors finally read the numbers, and they saw huge losses, and a business that looked a lot like a landlord. The IPO was pulled. Neumann was pushed out. SoftBank had to put together a rescue package worth about nine and a half billion dollars just to keep it alive.
In November 2023, WeWork filed for bankruptcy. SoftBank lost more than eleven billion dollars on it. Son told shareholders, I fell in love with WeWork. He even said he might be more at fault than Adam, for telling him to be more aggressive. After WeWork, Son went quiet. He stepped back from public events and said he was focused on one thing.
Artificial intelligence. Then, in January 2025, he stood at the White House next to Sam Altman, Larry Ellison and President Trump. They announced Stargate, a plan to spend up to five hundred billion dollars building AI data centers in the United States. Son was named chairman. And he didn't stop there.
SoftBank had already invested about thirty five billion dollars in OpenAI. In February 2026, it committed thirty billion more, paid in three ten billion dollar chunks through October. In total, about sixty five billion dollars, for roughly thirteen percent of OpenAI. It's one of the largest bets any company has ever made on a single startup.
And to pay for it, Son had to let go of the very thing that made the AI boom possible. In November 2025, SoftBank sold its entire stake in NVIDIA, about five point eight billion dollars worth. Yes, the same company he regretted selling years before. He sold billions of dollars of T Mobile shares too.
Then, in March 2026, SoftBank took out a forty billion dollar loan from banks including JPMorgan and Goldman Sachs, mainly to fund its OpenAI investment. That loan is due in March 2027. So here's the risk. OpenAI is valued at around seven hundred and thirty billion dollars. But it still spends enormous amounts on computing power, and it faces fierce competition.
And the clock is ticking. If AI keeps booming, Son could own a huge piece of the most important company of this decade. But if the AI bubble pops, SoftBank is holding a giant stake it paid top dollar for, and a pile of debt that still has to be paid back. So what does this tell us? Masayoshi Son's career is a pattern.
He sees the future early. He bets bigger than anyone else is willing to. Sometimes it's Alibaba, and he looks like a genius. Sometimes it's WeWork, and he looks like a fool. With OpenAI, he's making the biggest bet of his life, on the biggest technology of our lifetime. Maybe he finally caught the fish that got away.
Or maybe history is about to repeat itself. Either way, the next few years will decide how Masayoshi Son is remembered. If you want to know why one of the men who built AI is now afraid of it, watch our Geoffrey Hinton video next. And subscribe to Current Thesis for more stories on business, tech and money.
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