In 2015, someone asked Stanley Druckenmiller: What was the biggest mistake of your career? His answer made the audience laugh, but he wasn’t joking.
In early 1999, he saw through the dot-com bubble and shorted it with $200 million, only to lose $600 million in just a few weeks. A few months later, he switched sides and profited from the bubble’s rise. By March 2000, the Nasdaq had reached a frenzied level, and although he knew it was a bubble, he still invested approximately $6 billion around the peak. Six weeks later, the Quantum Fund had lost about $3 billion, and he left Soros.
This episode doesn’t follow a chronological order, but rather rewinds those months frame by frame: how was the judgment of someone who made the right call gradually rewritten? At the same time, another legendary investor, Julian Robertson, made the completely opposite choice, and what was the outcome? Is riding the bubble inherently wrong?
Finally, let’s take the same question from a different angle and apply it to Nvidia and Evergreen today, and summarize a few “brakes” that you can set yourself: part limits, cooldown periods, scoreboard replacements… Finding the right direction and making money are separated by several human factors.
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