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$70 billion gone in a single year. How did one man manage to lose that much money? And more importantly, how do you ever come back from it? He didn't just recover, he doubled down again and again. In this video, we're diving into the story of Masayoshi's son, the man who pulled off the impossible and built wealth that would last for centuries.
Born in Japan, Masayoshi's son belonged to a Korean family, making him an outsider from day one. His family wasn't exactly wealthy either. His parents were farming pigs and chickens for a living, barely surviving. All while Son had a burning passion in his heart. He doesn't think in years or decades, Sun was thinking centuries ahead.
Obsessed with western culture and the rising revolution of technology, Sun decided to move to California at just 16 years old, he landed at UC Berkeley. And while others chased a degree, Son was here to build a utopia capable of generating generational wealth. By 21, Sun was already a millionaire. He invented an electronic translator and sold it to Sharp for a breathtaking $1.7 million.
Then he made a fortune importing used Pac-Man and Space Invaders arcade machines from Japan and leasing them across California. His wealth grew, but so did his ambitions, something that would later lead him to the biggest mistake in his life. In 1981, Sun returned to Japan and founded SoftBank, a tiny software distributor with two part-time employees.
He told them the company would hit $75 million in sales within 5 years. They quit instantly, calling him delusional and crazy. But their doubts were quickly disproven soon after. In 1995, Sun dropped over $100 million on a scrappy American startup company called Yahoo. Insiders called him stupid, but Sun knew exactly what he was doing.
He launched Yahoo Japan, an empire that would later dominate the Japanese internet for decades. Sun wasn't exactly chasing quick wins. He believed in the technological revolution and saw potential in companies that others avoided at all cost. Sun wasn't just buying stocks. He was slowly funding his 300-year plan for Soft Bank.
The goal wasn't just profit. It was to lead the information revolution. But that same goal would later come crashing down as Sun got dragged into disaster by his own ambition. The '9s were coming to an end and the internet was slowly taking over. The dotcom fever was everywhere and stocks were climbing higher than ever before.
For Sun, this was validation, proof that he'd been right all along. SoftBank turned into a money printing machine with only one purpose in sight. pour large amounts of cash into hundreds of internet startups as fast as possible. Sun was throwing billions at e-commerce, online finance, and every digital niche with.com in its name.
At its peak, SoftBank held stakes in over 800 companies. Sun's plan was simple, bold, and clear. In the year 2000, Sun met Jack Ma, a Chinese charismatic English teacher turned entrepreneur. At the time, his startup company, Alibaba, was tiny. But Maya had big plans in mind. Plans that captivated Sun after just 30 minutes of talking.
The initial investment was set at $5 million, but Sun refused, insisting on donating $50 million. Me hesitated, worried he'd lose control. So, they decided to settle at $20 million, not knowing that this single bet would go down as one of the greatest venture investments in history. By February 2000, the market was on fire.
Soft Bank's market cap hit $180 billion. Sun's net worth soared past $78 billion. His net worth was so high he even managed to surpass Bill Gates for a few days, making Masayoshi's son the richest man in the world. But his greatest strength, the unshakable instinct, was also his biggest weakness. Son wasn't just investing.
He was actively gambling on a scale no one had ever seen before. Profits didn't matter, only growth did. Son was addicted to the thrill of the bet. And while a missionary, his addiction would soon lead him into making the biggest mistake of his life. March 2000, the dot bubble began to crack. At first, it looked like a simple correction.
Sun shrugged it off, thinking that a few stocks dipping wasn't a big deal. But this wasn't a dip. It was the edge of a cliff. The bubble burst faster than anyone expected. Companies worth billions one day were worthless the next. The market turned red and Soft Bank was the eye of the storm. Sun had bet on everything and lost.
Hundreds of internet startups collapsed. Erade fell from $400 million to just $22 million. SoftBank stock was obliterated. In just one year, its share price plunged 99%. Market cap went from nearly $200 billion to a pathetic $2 billion. Sun's $78 billion fortune came crashing down in an instant. Day after day, billions vanished.
Sun's $78 billion net worth was reduced to pocket change. Nearly $70 billion gone. This was the single largest personal wealth wipeout in history. He later said that losing 99% of his money taught him the value of cash. His dream of building a 300-year company now stood on the edge of collapse. And the worst part, it hasn't even been a decade.
For anyone else, it would have been the end. But for Sun, this was just the beginning. Years passed after the dot crash. Softbank was a shadow of its former self, losing a billion dollars every year. Son's name became a warning, but he wasn't broken, nor did he give up. Sun still believed in the digital future.
The vision wasn't wrong. It was the timing. With a new set of goals in mind, Sun's focus was now shifted on survival. This meant making brutal choices, selling assets, cutting ties, and protecting the crown jewels. Yahoo. Japan was a prime example. So was Alibaba. At the time, the investment looked like a long shot.
High risk, low reward. But Sun's conviction never wavered. With a steady cash flow, he prepared for the next wave. And just like before, his next move would be as bold and reckless as the last. In 2006, Sun pulled off a $15 billion deal by purchasing Vodafone Japan, a company that was barely recovering from a near-death experience.
Insiders thought he'd lost it, but Sun had an ace up his sleeve. Before the first iPhone was even announced, he flew to California and met Steve Jobs. With a handdrawn sketch, Sun managed to convince Jobs to give SoftBank exclusive rights to sell the iPhone in Japan. When the phone hit the market, SoftBank's network became the exclusive carrier.
One phone plan after another, SoftBank managed to fully rebuild itself. The wilderness years were finally over. Son had survived and he was hungry. Even after everything he went through, Sun was ready to go allin again. And his next move would be bigger than anything he had done before. The dot fever was just a warm-up.
It wasn't just the obsession. It was his vast skill set and sheer knowledge that helped with decision-making. Masayoshi's son knew the market because he was actively subscribed to our channel and he learned from others mistakes by watching the Quebe, something you can do as well for 0. By 2016, SoftBank had fully recovered and Sun was chasing his next thrill.
At 60, most founders think about legacy retirement, but not Sun. The next storm was approaching and Sun was ready to go allin. AI, robotics, mobile apps. This was bigger than the PC, bigger than the internet. And to win, Sun needed more money than ever before. This was no longer a venture fund. This was a financial superpower.
In 2017, he pulled the trigger. $100 billion, the largest venture fund in human history, bigger than every US venture fund of 2016 combined, backed by Apple and Saudi Arabia's public investment fund. The mission was bold yet simple. Fuel the AI revolution and build an ecosystem of AI powered giants.
Sun wrote checks at lightning speed, hundreds of millions, Uber, Door Dash, the list goes on. 30 Minutes with Sun could change a founders's life. He didn't just invest. He actively force-fed capital, insisting that founders take more than they ask for, pushing them to grow faster, burn brighter, and crush the competition.
Sun wasn't riding waves anymore. He was making them, betting on his foresight instead of the companies themselves. You'd think losing $70 billion would teach Sunaution. But no, he doubled down. creating a machine so massive it generated influence on the market. Yet behind it all, one fatal flaw was lurking in the shadows.
Pumping that much cash into dozens of companies created insane valuations. Insiders called it growth at all costs mania. All repercussions were ignored and no company proved this better than Wei Work. We work was a company that rented office space, slapped on a millennial friendly aesthetic and sublet.
But Sun didn't see real estate. He saw a techpowered revolution. Adam Newman, the charismatic founder, captivated Sun with his vision and received $4.4 billion. As a result, Sun pushed Noman to expand faster, burn more money, and grow bigger. As a result, Wei Work hit a staggering 47 billion valuation.
But in 2019, the IPO filings told an entirely different story. huge losses, empty promises, and marketing fluff. The IPO imploded. Valuations collapsed. Soft Bank scrambled for a multi-billion dollar bailout. Humiliation followed. We work became the poster child of reckless hubris and critics cheered as other bad bets piled on.
By 2023, a total net loss of $32 billion was revealed. It was a chilling echo from the past. The same wild optimism, the same obsession, and the same billions burned. Only one question remained. Could Masayoshi's son ever learn from his mistakes? Just when the world was ready to write him off once more, Sun did what he always does.
He pivoted. But instead of transitioning to a new industry, he decided to double down on artificial intelligence. In 2016, SoftBank spent $ 32 billion on purchasing ARM, a British company specializing in chip design. Sun believed in AI, and he knew that ARM's hyperefficient chips would serve as the backbone for the upcoming revolution.
This was a massive win. Furthermore, it was a credibility injection the world couldn't ignore. For years, the investment looks like a costly gamble. But in 2023, everything changed. Generative AI exploded. Suddenly, every company wanted ARM's chips. And that's when SoftBank took the company public. Valuations skyrocketed.
Numbers climbed faster than ever before. This was exactly the type of win Sun needed. Flushed with cash and confidence, he flipped Soft Bank from defense to offense. He wasn't just investing. He was going allin. By August 2025, the AI surge was delivered. Billions poured in week after week, and Sun was back to being Japan's richest man once more.
Some call him a visionary genius, others a reckless gambler who got lucky. But no matter what you choose to believe, one thing is certain. Sun lost more money than almost anyone in history. Yet somehow his dedication and obsession managed to help him achieve the unthinkable. His career proves that changing the world demands risk.
Risks that often look like madness to the ordinary eye. And yet that mad $20 million bet on Alibaba is worth over $100 billion today. Don't forget to subscribe to the channel for more bite-sized content. Let us know what you want to see next on the channel in the comments section down below.
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