In the financial world, there are only two types of people who can leave their names in history: those who have made a lot of money and those who have lost a lot of money.
However, what people enjoy the most is the third type: watching those who have made a lot of money lose it even faster.
In 1999, Hangzhou, Alibaba
Masayoshi Son and Jack Ma met for the first time, talked for 6 minutes, and decided to invest 20 million dollars. At that time, Alibaba had zero revenue, zero business model, and didn’t even have a business plan. He later described this moment in an interview: "His eyes were very powerful, shining brightly. I could sense his leadership quality from the way he spoke."
His investment was based on intuition; he didn’t look at financial reports but rather at what he saw.
Among the three types of people mentioned earlier, Masayoshi Son is that third type—only he can lose everything and still earn it back.
Masayoshi Son is one of the most difficult figures to "categorize" in contemporary investment history. He has created the largest single return in the history of venture capital (Alibaba), as well as the largest single failure (WeWork); he once lost 70 billion dollars alone during the internet bubble in 2000 and was recorded by Guinness as "the person who lost the most money in history" for 22 years (until he was surpassed by Elon Musk), and 25 years later, he made a comeback by betting 500 billion dollars on AI.
In the world of value investing, Warren Buffett, Charlie Munger, and Duan Yongping are "positive examples"—they teach you how to control emotions, how to wait, and how to do the right thing within your circle of competence.
But there exists a type of investor whose very existence is a mirror: they embody all the virtues and flaws of humanity, magnifying them to the extreme. Masayoshi Son is such a person.
He has a famous quote that is often repeated: "No one in the financial world has lost more than I have, and no one has made more than I have." To use a metaphor—Masayoshi Son is like Schrödinger's cat: for most of his life, he has been in a superposition of "losing a lot of money" and "making a lot of money"; the only question is, no one knows which state they will see when they open the box now.
His story is captivating, not because he is "always right"—on the contrary, he is often absurdly wrong. What is captivating is: why can someone who openly admits to investing based on intuition, makes decisions in just 6 minutes, and is mocked as a practitioner of the "foolish theory," repeatedly stand up over 40 years and still bet his entire fortune on AI at the age of 68?
If you, like me, have ever over-invested due to FOMO, cut losses because of fear, or ignored prices because "I am optimistic"—then you will also, like me, desperately want to understand Masayoshi Son, essentially to understand the restless shadow within ourselves; I even once thought I should change my name to Yu Zhengyi...
If interested, you can read the full text directly and understand the most FOMO man in the world, "Masayoshi Son: The Madness and Clarity of the King of FOMO."
https://mp.weixin.qq.com/s/vBBawiEcbxt_hvCanVypKw
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