Michael Steinhardt once said “Nothing gives a better feeling to a manager than making money for his or her investors when almost everyone else is losing.” I’d imagine that there are few worse feelings for a money manager than not keeping up when everyone around you is winning.

The tech bubble is the modern day poster child for managers who couldn’t keep up. From 1995-1999, the NASDAQ Composite gained 441%, or 40% compounded annually.

Stanley Druckenmiller is the owner of one of the most remarkable track records of all time. He is one of the few investors to clearly see and navigate the macro landscape. But during the late 90s, like so many others, he was infected with the fear of missing out.

In early 1999, Druckenmiller shorted $200 million worth of tech stocks in George Soros’s Quantum Fund. He went short an inning too early, and was forced to cover a few months later after a $600 million loss. Through May, the fund was down 18%. Meanwhile, the NASDAQ Composite was up 15% and the S&P 500 was up 10%.

Druckenmiller once said, “The first thing I heard when I got in the business….was bulls make money, bears make money, and pigs get slaughtered. I’m here to tell you I was a pig. And I strongly believe the only way to make long-term returns in our business that are superior is by being a pig.” So, practicing what he preaches, he went on a buying spree, and collected $6 billion of tech stocks over the next few months.

One of the high-flying stocks he bought was *VeriSign, which went on a spectacular run. From January 1999 through February, the stock gained 1575%, doubling every 72 days, on average. He first bought the stock at $50, then going for the jugular, doubled up at $240. The very next day, the stock peaked at $251…

…And we know how that movie ended.

When asked about his experience, Druckenmiller said “I bought $6 billion worth of tech stocks, and in six weeks I had lost $3 billion in that one play. You asked me what I learned. I didn’t learn anything. I already knew that I wasn’t supposed to do that. I was just an emotional basketcase and I couldn’t help myself. So maybe I learned not to do it again, but I already knew that.”

I wrote about Druckenmiller’s big mistake in more detail, along with 15 others, myself included, in my book Big Mistakes: The Best Investors and their Worst Investments, which comes out in a few weeks. I hope you like it!

*Because lol, Berkshire Hathaway is now the biggest shareholder in VeriSign, at 10.5% of the company.