WB063: Jerry, everyone needs US$100mil

The title is a catchy quote from Gambling Man: The Wild Ride of Japan's Masayoshi Son ("Gambling Man"), a book written by Lionel Barber and published by Penguin Books in Oct 2024.

Gambling Man is the biography of Masayoshi Son ("Son"), who is one of the most consequential investors of the 20th and 21st centuries. Yet, prior to this book, little was known about this maverick investor's life story.

The quote was Son's response to Jerry Yang - co-founder of search pioneer Yahoo! - after he (Yang) tried to decline Son's proposed investment. Reason being, Yahoo! had just raised funds, didn't need more and Son's investment was far above the US$3mil valuation ascribed to Yahoo! a few months earlier.

Yang eventually accepted Son's offer after he said he would instead invest in Yahoo!'s competitors to kill Yahoo! if Yang didn't accept the investment.

Making a library book request

I was quite excited when Gambling Man was first published and thought long and hard about buying it.

Not only was I interested in reading about Masayoshi Son, but also because I found Barbers' previous book - The Powerful and The Damned - to be an engaging, informative and easy read. I seldom come across journalists who write content with all three characteristics.

Anyway, because I had limited bookshelf space and only the hardback version (more expensive) was available at the time, I decided to see if my local library had the book.

Unfortunately, this was not the case. So I decided to try my luck and submit a book request application to the library, seeking their help to either find Gambling Man (and another book I had in mind) from another library or to buy the book.

There was little to lose. Worst case, the application is rejected.

Fast forward to last week, and I received a surprising notification that my request for Gambling Man was approved. Perhaps the library saw fit to approve it as Son is a well-known Japanese corporate figure. As to whether he is also respected, well I think that depends who you talk to.

Sadly, my other book request for The Haves and Have-Yachts: Dispatches on the Ultrarich was rejected. I admit this book is probably less educational and more trashy. It is, after all, about how the new battleground for billionaires who want to one-up another is in the size of their yachts.

Go big or go home

Back to Gambling Man.

I am currently mid-way through the book and have learned about Son's early investing exploits and his life growing up as the son of Korean immigrants who immigrated to Japan at the turn of the 20th century.

These Koreans are called zainichi kankokujin (Japanese: 在日韓国人 English: Koreans in Japan).

Early on in his business career, Son had both major investing successes and failures.

I'm now up to the part where Barber gets into the story behind Son's wildly-successful investment in 2000 in Jack Ma's Alibaba, then a tiny start-up. Son famously turned this US$20mil investment into US$75bil (!) by the time Alibaba went for an initial public offering in 2014.

Regardless whether one considers Son an investing genius or a reckless gambler, it's hard to deny the fact that he has made a lasting imprint on the world of investing. His string of successes in Yahoo! and Alibaba, along with failures in WeWork and a host of other startups are the stuff of legends.

I am looking forward to finishing this book, and am on the lookout for newly-published books that I can request the library to find or buy.

--Ends