Choose Your Investment Guru Wisely

If you want to learn how to play tennis, it makes more sense to take the Masterclass from Serena Williams than to watch a random infomercial or a video from your high school coach. If you want to learn about investing you should also seek out the best.

Warren Buffett is verifiably the best investor of all time, with an audited track record going back several decades. Why, then, do so many would-be investors choose other role models, who all too often turn out to be hucksters and hacks—or just plain misguided?

I’ve asked the question many times. I’ve posed it to my NYU finance students each semester for over 20 years. Still, there’s no satisfying answer. I could hardly believe it when Bloomberg reported that Caroline Ellison of Alameda, FTX, and crypto infamy (and the former girlfriend of Sam Bankman-Fried) had supposedly learned investment strategies from Edwin Lefèvre’s Reminiscences of a Stock Operator, a roman à clef based on the life of Jesse Livermore, the stock trader who made a fortune shorting stocks before the 1906 San Francisco earthquake.

I’ve heard other young stock enthusiasts cite the book before. In 2021, Business Insider published a profile of 20 ambitious teen traders. One even mentioned Reminiscences as a favorite book. It’s one thing to read this book as entertainment. It’s another thing entirely to read it as an instruction manual. That’s because the book was published in 1923—long before Jesse Livermore’s last act.

At the age of 14, young Livermore had his first job posting stock quotes at the Boston branch of Paine Webber. His colorful life makes for great artistic inspiration and Lefèvre was probably unable to resist the allure. Livermore made and lost his fortune many times, not a sign of a good investor but rather the clear profile of a gambler and speculator. Livermore was a flamboyant character. He had a railcar, yacht and an extravagant apartment on the Upper West Side. He belonged to exclusive clubs and kept many mistresses. In the panic of 1907, Livermore made a million dollars in a single day. This was real money back then. But by 1915 he had filed for bankruptcy—and not for the first time. In the end, he lost his entire fortune and filed for bankruptcy a third time. This was in 1934, when his assets were listed at $84,000 and his debts at $2.5 million. That was his final business act. His final personal act was to shoot himself to death in the cloakroom of the Sherry-Netherland hotel in Manhattan on Thanksgiving Day, 1940.

In an era where people get their news from TikTok and Instagram, it’s not surprising that they would take the same dumb approach to learning about investing. But if you ever base your investment technique on a novel, be sure you know the ending of the real story first.