Entertainment

Madonna's manager reveals Bernie Brillstein offered him $25K at age 16 with no strings attached

Tim Ferriss Show · The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More · July 7, 2026

Tim Ferriss Show

The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More

"He looks at me and goes, well, hey kid, how much is it gonna cost to put this out? And I knew not to pause 'cause then he'd know I'm a phony. So I said, $25,000. And he said, I'll tell you what, kid, I'll give you the $25,000. If you make it back, pay me back, that's all I ask."

Oseary shared that legendary manager Bernie Brillstein offered him $25,000 at age 16 after a single meeting, asking only to be repaid if the investment succeeded. Oseary declined because he admitted he was a 'phony' who had no idea what to do with the money, though Brillstein believed it was due to integrity. The moment became a pivotal confirmation for Oseary that he was on the right path, and he later sent Brillstein his first gold record.

About this episode

Tim Ferriss interviews Guy Oseary, the legendary music executive, manager, and tech investor, in Oseary's first-ever podcast appearance. Oseary, who has managed Madonna for 36 years, also manages U2 and Red Hot Chili Peppers, and co-founded Sound Ventures with Ashton Kutcher, achieving 86 exits and 26 IPOs including Uber, Airbnb, and Spotify. The conversation reveals Oseary's unconventional path from a teenager using a fake Beverly Hills address to attend high school, to signing Alanis Morissette off one song that sold 30 million albums, to becoming one of Silicon Valley's most successful Hollywood crossover investors. Oseary discloses his $35 million investment in Anthropic at a $5 billion valuation following ChatGPT's launch, made during a focused three-month deployment window for a specialized AI fund. He openly criticizes AI music companies like Suno for building billion-dollar valuations on artists' copyrighted material without compensation, calling for immediate opt-out mechanisms and payment structures. The episode also breaks news that Oseary and Ashton Kutcher are parting ways after 20 years as investment partners, pursuing different visions despite their recent massive AI fund success. Throughout, Oseary explains his extreme decision-making velocity, making 90% of choices within five minutes based on intuition and pattern recognition, a skill honed from decades of rapid artist identification in music's competitive landscape. He attributes much of his forward-momentum mindset to Madonna's influence, describing her relentless drive and refusal to rest on past accomplishments as foundational to his own approach.

Key takeaways

Guy Oseary invested $35 million in Anthropic at a $5 billion valuation after recognizing ChatGPT as a transformational moment, with the company now valued around $60 billion.
Oseary and Ashton Kutcher are splitting after 20 years as investment partners despite massive success, pursuing different visions for the next decade while Oseary continues Sound Ventures with partner Effie.
The music executive publicly demands AI company Suno, valued at $5 billion and climbing, pay artists whose music trained their models, revealing he has met with the CEO multiple times on the issue.
Oseary makes 90% of his decisions within the first five minutes, signing Alanis Morissette off one song that sold 30 million albums and stopping Muse after one song to offer them a deal.
Legendary manager Bernie Brillstein offered 16-year-old Oseary $25,000 with no strings attached after one meeting, a moment Oseary credits as confirmation he was on the right path.
Oseary used a fake Beverly Hills address to attend Beverly Hills High School, crediting the experience of seeing both downtown LA and Beverly Hills as foundational to understanding what was possible in life.
Madonna has mentored Oseary for 36 years since he started Maverick Records with her, with her relentless forward momentum and refusal to celebrate past accomplishments shaping his own approach to work and reinvention.