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The Tim Ferriss Show
The Tim Ferriss Show

Jul 7, 2026 · 1h 33m

Hollywood power broker Guy Oseary shares his playbook for spotting talent and investing

#874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First

Understanding how a legendary manager navigates the intersection of creative talent, venture capital, and emerging artificial intelligence reveals the future of entertainment and investing.

3 key takeaways
  1. 1Decisive action and intuitive talent scouting helped launch iconic music careers, including Alanis Morissette and Candlebox.
  2. 2A transition into venture capital required recovering from dot-com losses to back major tech firms and foundational AI.
  3. 3Protecting creative intellectual property is critical as artificial intelligence models train on copyrighted artist works.

Don't miss

Oseary reflects on his 36-year relationship working with Madonna, highlighting her relentless work ethic and passion for constant reinvention.

The brief

Guy Oseary went from using a fake address to attend Beverly Hills High School to managing icons like Madonna and U2. His nearly four-decade career as a Hollywood power broker was built on rapid decision-making and an intuitive eye for creative talent.

Oseary highlights his early days scouting for Maverick Records, where he signed Candlebox and Alanis Morissette. He attributes his success to acting fast on raw potential, a philosophy that later guided his transition from music into venture capital.

After losing his initial capital in the dot-com crash, Oseary rebuilt his investing career, eventually co-founding a foundational AI fund with Ashton Kutcher to back OpenAI and Anthropic during a highly competitive, narrow window of opportunity.

As artificial intelligence reshapes creative fields, Oseary emphasizes the urgent need to protect artist rights. He warns against AI companies training models on copyrighted music without compensating the creators who built the foundation.

Featuring

Guy OsearyGuy Oseary

Mentioned

Ashton KutcherAshton KutcherArtificial IntelligenceArtificial IntelligenceBeverly Hills High SchoolBeverly Hills High SchoolBBBernie BrillsteinFDFreddie DeMann

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Hollywood power broker Guy Oseary shares his playbook for spotting talent and investing | PodLume