Episode
669: Stop Making Stupid Investments (with Founder of The Ultimate Investor, David Leiter)
- Published
- Jul 15, 2026
- Duration seconds
- 3433
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Summary
David Leiter learned one of investing's hardest lessons while sitting on a trading desk during the dot-com boom. After watching seemingly everyone around him get rich, he finally gave in to the crowd, bought into the hype, and took a painful loss. The experience shaped a principle that has guided his investing ever since: "avoid big losses." In this conversation, David explains why most investment mistakes are not caused by fraud alone. Many begin with emotion, social proof, fear of missing out, and the assumption that if sophisticated investors or large institutions are participating, an opportunity must be safe. As he puts it, "Wall Street will sell you whatever is popular." Drawing on lessons from his book, Stop Making Stupid Investments, David discusses why successful investors often think differently from the crowd. He shares how contrarian thinking helped him recognize opportunities others ignored, why market euphoria and panic repeatedly create mispriced assets, and how investors can avoid being swept up by speculation. A central theme of the discussion is the distinction between innovation and investment. David believes artificial intelligence will transform the world, but cautions that "the technology is different than the investments." Investors can be right about a trend and still lose money if they pay too much for the underlying asset. Key topics include: • Why "avoid big losses" is the foundation of long-term wealth building. • How investors become vulnerable when they follow popularity, momentum, or fear of missing out. • What Jeff Bezos meant when he said, "the stock is not the company, and the company is not the stock." • Why great businesses can become poor investments when purchased at excessive prices. • How private investment opportunities can fail…