In the financial world, there are only two types of people who will be remembered in history: those who made a lot of money, and those who lost a lot of money.

And what people love to see the most is the third type: watching those who made a lot of money lose it even faster.
In 1999, in Hangzhou, Alibaba
Masayoshi Son and Jack Ma met for the first time, talked for 6 minutes, and decided to invest 20 million US dollars. At that time, Alibaba had zero revenue, zero business model, and not even a business plan. He later described this moment in an interview: "His eyes were very powerful, shining brightly. I could feel his leadership qualities from the way he spoke."
His investment relied on intuition, not financial reports, but his eyes.
As mentioned earlier, there are three types of people, and Masayoshi Son is the third type—except that after losing everything, he can still make it back.
Masayoshi Son is one of the most difficult figures to "archive" in contemporary investment history. He created the largest single return in venture capital history (Alibaba), but also the biggest single failure (WeWork); he once lost $70 billion alone during the 2000 dot-com bubble, recorded in Guinness as "the person who lost the most money in history" for 22 years (until Elon Musk broke the record), and 25 years later, he bet $500 billion on AI to make a comeback.
In the world of value investing, Buffett, Munger, and Duan Yongping are "positive role models"—they teach you how to control emotions, how to wait, and how to do the right thing within your circle of competence.
But there is a kind of investor whose existence itself is a mirror: they embody all the virtues and flaws of human nature, magnified to the extreme. Masayoshi Son is such a person.
He has a frequently quoted phrase: "No one in the financial world has lost more than me, and no one has made more than me." To use a metaphor—Masayoshi Son is like a "Schrödinger's cat": most of his life, he exists in a superposition of "losing a lot of money" and "making a lot of money," and the only question is which one will be revealed when the box is opened.
His story is captivating not because he is "always right"—quite the opposite, he is often wildly wrong. What draws people in is: why can someone who openly admits to investing based on intuition, making decisions in just 6 minutes, and being mocked as a "gambling theory" practitioner, repeatedly stand up over 40 years, and at 68 still bet his entire fortune on AI?
If you and I have ever, in investing, over-committed due to FOMO, sold out in fear, or ignored the price because "I believe in this"—then you and I will also be crazy to want to understand Masayoshi Son, essentially to understand the restless shadow within ourselves. I even once thought I should change my name to Yu Son...
If you're interested, you can read the full ten-thousand-word article to understand the world's most FOMO-driven man: "Masayoshi Son: The Madness and Clarity of the FOMO King."