Guy Oseary: AI Is Stealing Billions, 'Fair Use Is Not Fair'
Legendary power broker Guy Oseary unloads on AI companies building multi-billion dollar valuations on artists' music without a dime of compensation. Here's why.
The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More
With Tim Ferriss, Guy Oseary · Sunday, July 12, 2026
Guy Oseary, a legendary Hollywood power broker and venture capitalist, delves into his career, from his formative years and early breaks in the music industry to his strategic tech investments. He shares his philosophy on fast decision-making, the profound influence of Madonna, overcoming significant investing setbacks, and his urgent advocacy for fair artist compensation in the era of AI.
Guy Oseary's Million-Dollar Blunder: Why 'All-In' Is a Trap
Hollywood power broker Guy Oseary lost everything in the dot-com crash betting on one lab. Learn his hard lessons on diversification and avoiding investment paralysis.
Guy Oseary: Win by Deciding '90% in 5 Minutes'
Forget analysis paralysis. Music mogul Guy Oseary reveals how his '90% in 5 minutes' rule and gut intuition became a competitive edge, signing stars like Alanis Morissette after one song.
Guy Oseary's $25K Bluff: How He Broke Into Hollywood
Guy Oseary left his downtown LA school for Beverly Hills High after a near-death experience. He used this blend to meet industry titans, making a bold $25,000 bluff and offering to work for free.
Madonna Taught Guy Oseary: No Walls in Your Head
Guy Oseary credits Madonna for his relentless work ethic and unique ability to spot talent, urging founders to adopt a 'no boundaries' mindset.
Guy Oseary's Vita Coco Play: How Madonna Sparked a $4B Exit
Learn how Guy Oseary spotted a market trend with Madonna, invested big in Vita Coco, and used star power to build a $4B company.