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The Blog of Author Tim Ferriss

The Tim Ferriss Show Transcripts: How to Legalize Medical Psychedelics in Your Country — Tania de Jong on The Playbook Behind Australia’s World-First Breakthrough (#883) - The Blog of Author Tim Ferriss How to Legalize Medical Psychedelics in Your Country — Tania de Jong on The Playbook Behind Australia's World-First Breakthrough (#883) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Why Kids Can Learn 10x Faster Than We Think — Niels Hoven of Mentava (Tim Coaching Session) (#882) - The Blog of Author Tim Ferriss Why Kids Can Learn 10x Faster Than We Think — Niels Hoven of Mentava (Tim Coaching Session) (#882) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Tales of Overcoming the Odds, and How to Turn Losses Into Wins — Tim McGraw, Terry Crews, Dax Shepard, and More (#881) - The Blog of Author Tim Ferriss Tales of Overcoming The Odds, and How to Turn Losses Into Wins — Tim McGraw, Terry Crews, Dax Shepard, and More (#881) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Relationship Tools That Work — Esther Perel, Brené Brown, Dr. Sue Johnson, Terry Real, and More on Conflict, Repair, and Lasting Love (#880) - The Blog of Author Tim Ferriss Relationship Tools That Work — Esther Perel, Brené Brown, Dr. Sue Johnson, Terry Real, and More on Conflict, Repair, and Lasting Love (#880) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: How to Reinvent Yourself and Make Bold Moves — Decisive Stories from Matthew McConaughey, Steve Young, Samin Nosrat, and More (#879) - The Blog of Author Tim Ferriss How to Reinvent Yourself and Make Bold Moves — Decisive Stories from Matthew McConaughey, Steve Young, Samin Nosrat, and More (#879) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: How to Start When You’re Stuck, Finish What You Begin, and Stop Waiting for Inspiration — Creative Advice from Elizabeth Gilbert, Seth Godin, Joyce Carol Oates, Anne Lamott, and More (#878) - The Blog of Author Tim Ferriss How to Start When You're Stuck, Finish What You Begin, and Stop Waiting for Inspiration — Creative Advice from Elizabeth Gilbert, Seth Godin, Joyce Carol Oates, Anne Lamott, and More (#878) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Q&A with Tim — The Art of Male Friendship, Mini-Retirements, Higher-Resolution Living, Reinvention in The Age of AI, and More (#877) - The Blog of Author Tim Ferriss Q&A with Tim — The Art of Male Friendship, Mini-Retirements, Higher-Resolution Living, Reinvention in The Age of AI, and More (#877) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Dr. Andrew Huberman — Peptides, Performance, and Protocols (#876) - The Blog of Author Tim Ferriss Dr. Andrew Huberman — Peptides, Performance, and Protocols (#876) - The Blog of Author Tim Ferriss Better Than Free: How To Differentiate In The Age Of AI - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (#875) - The Blog of Author Tim Ferriss The Random Show — Tim and Kevin Talk Retreats, Mortality, AI Predictions, Supplements, Rock Climbing at (Almost) 50, and Not Waiting for “Someday” (#875) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First (#874) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: The “Divine Leaf” with 8,000+ Years of Use — Exploring the Many Benefits of Coca with Dr. Andrew Weil and Wade Davis (#871) - The Blog of Author Tim Ferriss The “Divine Leaf” with 8,000+ Years of Use — Exploring the Many Benefits of Coca with Dr. Andrew Weil and Wade Davis (#871) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Sebastian Mallaby, Biographer of Demis Hassabis — Lessons from 100+ AI Insiders on The Race to Superintelligence, The Religion of AI, and Spotting Breakthroughs Early (#870) - The Blog of Author Tim Ferriss Death by 1,000 Compromises: How to Tap Into Founder Mode - The Blog of Author Tim Ferriss Sebastian Mallaby, Biographer of Demis Hassabis — Lessons from 100+ AI Insiders on The Race to Superintelligence, The Religion of AI, and Spotting Breakthroughs Early (#870) - The Blog of Author Tim Ferriss Has AI Already Killed How-To Nonfiction? Sales Trends, My Personal Data, and What It Might Mean for the Future - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Max Levchin, PayPal and Affirm — The Path from The Soviet Union to Building Multi-Billion Dollar Companies (Plus: Real-World Socialism vs. Capitalism) (#869) - The Blog of Author Tim Ferriss Max Levchin, PayPal and Affirm — The Path from The Soviet Union to Building Multi-Billion Dollar Companies (Plus: Real-World Socialism vs. Capitalism) (#869) - The Blog of Author Tim Ferriss The Tim Ferriss Show Transcripts: Tim’s Founder Kitchen — From Brainstorm to the President’s Office in Two Months (Featuring Jake Becraft, Strand Therapeutics) (#868) - The Blog of Author Tim Ferriss Tim’s Founder Kitchen — From Brainstorm to the President’s Office in Two Months (Featuring Jake Becraft, Strand Therapeutics) (#868) - The Blog of Author Tim Ferriss
Guy Oseary — The Legendary Hollywood Power Broker on 5-Mi...
Tim Ferriss · 2026-07-08 · via The Blog of Author Tim Ferriss

Guy Oseary (@guyoseary) has been spotting talent before anyone else could see it for nearly four decades. Under his leadership at Maverick Records, Maverick sold more than 100 million albums. Guy has managed some of the biggest names in music, including Madonna, the Red Hot Chili Peppers, and U2, and was named Variety‘s Music Mogul of the Year in 2022. He executive produced Twilight, which became one of the most successful franchises in movie history, generating more than $3.5B.  

Guy was also an early investor in Vita Coco and co-founded A-Grade Investments and then Sound Ventures, now with nearly $2 billion under management. At A-Grade, his hits included Airbnb, Uber, and Spotify. Sound Ventures launched with less than $100M and has since had 86 exits and 26 IPOs.

Please enjoy!

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


Additional podcast platforms

Listen to this episode on Apple PodcastsSpotifyOvercastPodcast AddictPocket CastsCastboxYouTube MusicAmazon MusicAudible, or on your favorite podcast platform.


Transcripts

Show Notes

  • Connect with Guy Oseary:

Instagram | Facebook | X

Books & Recommended Reading

Music

Films & TV

People & Bands

Companies & Organizations

Tools & Apps

Timestamps

  • [00:00:00] Start.
  • [00:02:01] How a West Hollywood balcony became a backstage pass.
  • [00:03:51] A knife on Pico Boulevard and the snap decision to switch schools.
  • [00:05:54] Faking a Beverly Hills address to get inside another world.
  • [00:08:10] Wise Guy Records: a 15-year-old builds a portfolio out of nothing.
  • [00:10:09] Guy’s alternative terms when Bernie Brillstein offered $25,000.
  • [00:11:34] The one moment that confirmed Guy was on the right path.
  • [00:12:29] Freddy DeMann enters the picture and Guy proves himself with Ice-T’s crew.
  • [00:15:07] A desk at Maverick Records in exchange for no salary.
  • [00:17:08] Chasing Hole and Rage Against the Machine — and losing both.
  • [00:23:34] Candlebox in five minutes: seeing thousands in a room of 30.
  • [00:24:11] Why “magic” beats everything else.
  • [00:26:37] Signing Alanis off a single song, and stopping Muse mid-audition.
  • [00:31:59] The real Alanis story: “Perfect,” Joni Mitchell, and a 30-million-selling debut.
  • [00:35:24] What Madonna taught Guy about thinking without walls.
  • [00:38:50] From bands to Twilight: the power of a blank canvas.
  • [00:45:30] How Guy got into investing, and the IdeaLab bet that wiped him out before the crash.
  • [00:54:31] Why Guy is known as a great curator of people.
  • [00:58:32] The three-month window that caught OpenAI and Anthropic.
  • [01:06:07] AI music and the battle to ensure human musicians get paid.
  • [01:09:30] How Spotify solved the problems Napster couldn’t overcome.
  • [01:14:50] SpaceX and Bitcoin: the ones that got away.
  • [01:17:32] The rewards, rigors, and responsibilities of back-to-back touring.
  • [01:21:44] Why Guy never stops to celebrate.
  • [01:24:45] Splitting with Ashton Kutcher after 20 years.
  • [01:27:30] Final thoughts on Guy’s first podcast.

Guy Oseary Quotes from the Interview

“Sometimes having no options and no choice is really the best option.”

— Guy Oseary

“It always starts with the magic. I don’t care if you’re a tech company or whatever it is, a film, a product, a book, magic. You’ve got to have magic. Something has to pull you in.”

— Guy Oseary

“In my mind, every founder I invest in, I look at them like they are the rock star. I go, ‘That person has music they want to share with the world.’”

— Guy Oseary

“Fair use is not fair.”

— Guy Oseary

“I don’t feel accomplished. I don’t feel at all. I feel like I still have so much to prove and so much to do.”

— Guy Oseary

Want to hear another episode with someone who has a preternatural gift for spotting world-class talent? Listen to my most recent conversation with legendary music producer Rick Rubin, in which we discussed timeless methods for unlocking creativity, secrets hidden in plain sight, the future with AI, working with strong personalities, breaking out of “the sameness,” reinvention versus going narrow, and much more.