The Strategy Skills Podcast: Management Consulting | Strategy, Operations & Implementation | Critical Thinking

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