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.

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Key takeaways

AI companies are currently valued in the billions, yet Guy Oseary contends not a single artist has been paid for their music used to train these models. He calls this an unacceptable IP grab. Read more →
Before the dot-com crash, Guy Oseary invested “every dollar I have plus dollars I didn't have” into Ideal Lab, founded by Bill Gross, losing his entire net worth. Read more →
Hollywood power broker Guy Oseary built his empire by committing to '90% of things in the first 5 minutes,' rejecting prolonged deliberation as a weakness. Read more →
Guy Oseary's near-death experience in downtown LA led him to demand a transfer to Beverly Hills High, forging a unique perspective by blending two distinct worlds. Read more →
For 36 years, Madonna acted as a demanding mentor to Guy Oseary, pushing him to adopt a work ethic "not to be believed" and a relentless commitment to craft. Read more →
To spot emerging trends, look beyond traditional market research. Guy Oseary noticed Madonna's team sourcing fresh coconuts globally and a New York Post article featuring Gisele drinking coconut water, signaling a market shift. Read more →

6 articles from this episode

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.

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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.

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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.

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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.

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