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 when decisions are driven by trust, charisma, or social proof instead of analysis and oversight.
• The warning signs of scams and bad investments, including urgency, pressure tactics, and emotional manipulation.
David also outlines his four-part framework for evaluating opportunities: understand how the business makes money, assess where it is likely to be in five to ten years, evaluate the quality of management, and determine whether the price is reasonable. Even a great business, he argues, can become a money-losing investment if purchased at the wrong valuation.
Beyond investing, the conversation explores how AI is reshaping work and why human capabilities may become more valuable as technology advances. David argues that communication, empathy, relationship-building, and the ability to create "win-win situations" will remain powerful differentiators in a world where intelligence becomes increasingly accessible.
The episode concludes with a deeply personal reflection on a recent medical misdiagnosis that forced him to confront the possibility that time might be limited. The experience led to a simple but profound realization: stop worrying about what other people think, stop waiting for permission, and focus on the work that matters now.
Throughout the discussion, David returns to the same idea: investing, business, and life all improve when decisions are grounded in fundamentals rather than emotion. The challenge is learning to see clearly when everyone else is being pulled by fear, excitement, or the crowd.
Get David's book, Stop Making Stupid Investments, here: https://tinyurl.com/nhaje6jt
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