Brian Crombie Radio Hour - Epi 1621 - The Illusion of Unicorns: Angel Investing and the Psychology of Losing Money

Everyone dreams of backing the next billion-dollar startup—the unicorn that changes everything. But what if that dream is more illusion than reality? On this episode of The Brian Crombie Hour, Brian sits down with angel investor and author Henry Fiorillo for a candid, unfiltered conversation about what really happens in early-stage investing. Drawing from experience with over 80 startup investments, Henry reveals a hard truth: most of them fail—and that’s part of the strategy. This episode dives into the realities, risks, and psychology behind angel investing. From why a handful of winners must carry an entire portfolio, to the cognitive biases that lead even smart investors astray—FOMO, overconfidence, herd thinking, and more. But beyond the numbers and the noise, one insight stands above the rest: you’re not investing in an idea—you’re investing in a person. Brian and Henry explore what really matters when evaluating founders, the limits of due diligence, and why spotting red flags is both critical and incredibly difficult. If you’ve ever been tempted by a “can’t-miss” opportunity, this conversation offers a grounded, honest look at the fine art—and frequent pain—of losing money in pursuit of the next big win. Listen in for a reality check on risk, judgment, and the human side of investing.