On this episode of Simply Money presented by Allworth Financial, Bob and Brian take a deep dive into one of the most dangerous phrases in investing—“this time is different”—and why history shows that investor behavior often repeats itself, even when markets, technology, and opportunities evolve. They walk through a century of market cycles, from the optimism of the Roaring 1920s and the devastation of the Great Depression, to the dot-com bubble, the housing crash of 2008, and the more recent frenzy around SPACs, meme stocks, and crypto. Along the way, they share personal stories from their early careers, highlighting how real experience through a full market cycle shapes smarter investors, and why understanding behavioral biases like recency bias and overconfidence is critical—especially for those managing significant wealth.