Guy Oseary has spent 36 years managing Madonna while building a $2 billion investment portfolio that includes 26 IPOs. From spotting Alanis Morissette in one song to backing Airbnb, Uber, and Anthropic, he reveals how he makes five-minute decisions based on intuition, pattern recognition, and an unwavering ability to identify magic before anyone else sees it. Oseary signs artists and invests in companies within five minutes of meeting them, driven by intuition and the ability to visualize potential rather than lengthy due diligence.