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In the year 2000 for 3 days, this man says he was the richest person on Earth. Within months, he had lost about 70 billion dollars. More money, by some counts, than almost anyone in history had ever lost. Most people would never gamble again. He did the opposite. He made bigger bets. He backed Alibaba.
He bought one of the world's most important chip designers. He built the largest tech fund ever created. And now, he's borrowing billions to bet his company on artificial intelligence. This is the story of Masayoshi Son. And this is the Outlier Era. Masayoshi Son was born in 1957 in Tosu, in southern Japan, to a family of Korean descent.
As a child, he was bullied for his background, but he had a hero, Den Fujita, the man who brought McDonald's to Japan. Son kept trying to meet him until finally Fujita gave him 15 minutes. His advice was simple, learn English, study computers, and go to America. So, at 16, Son moved to California. At university in Berkeley, he helped develop an electronic translator and sold it to Sharp for 1.7 million dollars.
He wasn't even out of college and he had already made his first big bet pay off. In 1981, back in Japan, he started a company called SoftBank. It began by selling software. Then, as the internet arrived, Son started investing in it. He bought into Yahoo and in 2000, he met a former English teacher from China who was trying to build an online marketplace.
His name was Jack Ma. Son wanted to invest more than Ma would accept. They settled on 20 million dollars. That 20 million dollars would one day be worth more than 100 billion. One of the greatest investments ever made. At the peak of the dot-com boom, Son's fortune was rising by billions every week.
For 3 days, he says, he was the richest person in the world. But that peak was about to become a cliff. Then the dot-com bubble burst. SoftBank's shares fell 75% in 2 months. By the end of 2000, they were down 93%. Son lost, by most estimates, around $70 billion. The company nearly went under. For most people, that would be the end of the story.
For Masayoshi Son, it was just the first chapter. Because the bets he made next were even bigger, and some of them went very, very wrong. In 2016, Son bought ARM, the British company whose chip designs are inside almost every smartphone, for about $32 billion. A year later, he launched the Vision Fund, around $100 billion to invest in technology, the largest tech fund the world had ever seen.
He handed out money faster than anyone in Silicon Valley. One of his biggest bets was on WeWork, the office-sharing company, which at its peak was valued at $47 billion. Then it fell apart. Its plan to go public collapsed, and in 2019, Son admitted, "My own investment judgment was really bad." Four years later, WeWork filed for bankruptcy.
SoftBank's losses on it are estimated at more than $11 billion, and there was another mistake, one that hurts even more today. In 2019, SoftBank sold its stake in a chip company for about $3.6 billion. That company was Nvidia. By some estimates, that stake would later be worth well over $150 billion.
He even tried to sell ARM to Nvidia for $40 billion. Regulators around the world pushed back, and in 2022, the deal collapsed. It turned out to be a lucky escape. ARM later went public and became one of the most valuable pieces of SoftBank's empire. By 2022, the Vision Fund had posted a record loss of more than $27 billion in a single year.
Once again, people said Masayoshi Son was finished. Once again, he wasn't. In January 2025, Son stood in the White House next to the president of the United States, Sam Altman of OpenAI, and Larry Ellison of Oracle. They announced Stargate, a plan to spend up to $500 billion on AI infrastructure. Son would be its chairman.
A few months later, back at the White House, he explained why. This the importance is this is the largest infrastructure for the AI, which is the future of mankind, I believe. Then he went all in on OpenAI, the company behind ChatGPT. To pay for it, he sold SoftBank's entire stake in Nvidia, again. He took out a $40 billion loan.
Later, SoftBank sold bonds at the highest interest rates it had ever paid. By 2026, SoftBank had committed about $65 billion to OpenAI. On paper, it's working. SoftBank has reported billions of dollars in gains on the investment. But according to Bloomberg, some people inside SoftBank are worried. Analysts estimate that OpenAI and ARM now make up about three-quarters of SoftBank's value.
If AI keeps booming, Son could look like a genius. If it stumbles, SoftBank is carrying an enormous amount of debt. And here is the strangest part. In October 2026, the man who bet everything on artificial intelligence stood on a stage in Kyoto and warned that superintelligence in the wrong hands could be super dangerous.
Just to be clear, this is a story, not investment advice. We're not telling anyone to buy or sell anything. So, what makes Masayoshi Son an outlier? It's not that he's always right. He's been wrong, spectacularly, more than once. It's that losing doesn't stop him. $70 billion gone, and he bet again.
WeWork collapsed, and he bet again. He sold Nvidia too early, and then he bet again. Most investors try to avoid big losses. Son seems to accept them as the price of being early to the next big thing. Is that vision, or is it gambling? The next few years may give us the answer, because this time he's betting on the biggest technology of our lifetime.
This is the outlier era. If you want more stories like this, subscribe, and I'll see you in the next one.
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