by

Tim Ferriss

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

Leave a comment

Topics:

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!

This episode is brought to you by:

  • Momentous high-quality creatine for cognitive and muscular support
  • AG1 all-in-one nutritional supplement
Listen onSpotify
Listen onApple Podcasts
Listen onOvercast
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 Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, YouTube Music, Amazon Music, Audible, 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.

This episode is brought to you by AG1. I’ve taken AG1 for more than a decade. Longtime listeners have heard me call it my nutritional insurance. Here’s the news: they’ve just launched AG1 Pro, designed for people focused on performance and longevity. I’ll be traveling soon, and I’m throwing this in my bag to cover my bases while I travel. Past a certain age, maintaining lean muscle becomes priority number one, and AG1 Pro is formulated to support exactly that. It includes HMB, a clinically studied compound that supports protein synthesis and helps reduce protein breakdown, plus zinc carnosine to support the gut lining. Remember: training is only half the equation. Recovery is where the work compounds, and AG1 Pro is built to support it. It’s NSF Certified for Sport, so what’s on the label is what’s in the pouch. Get your free AG1 Pro Yeti Shaker in the Welcome Kit at Drinkag1.com/Tim.

This episode is brought to you by Momentous Creatine! I’ve used Momentous Creatine for a long time, as it’s been one of the highest-quality creatine options available. Now, Momentous has taken that quality even further with Signature Spec Creatine, their most advanced version yet. Signature Spec is manufactured in a pharmaceutical facility using reverse-osmosis water purification.  It’s verified through a six-stage testing process with four independent agencies—delivering 10x fewer impurities, 2–5x tighter heavy-metal limits, and added PFAS and microplastics screening. 

The ultrafine powder also mixes cleanly, with no grit. Creatine supports strength, power, lean muscle, and recovery, with growing research on enhanced memory and cognitive performance. Head to LiveMomentous.com/Tim and use code TIM for 14% off your first one-time order or a total of 35% off your first subscription order.

Subscribe
Notify of
guest

Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

1 Comment
Rodney
Rodney
4 days ago

Hi Tim, it would be great to hear how you and other successful VC investors like Guy think about an IPO. Do you guys have a framework you use to decide if you will ride the company public or cash out at the IPO? Do you just keep them separate and always take the cash out at IPO and decide on stock market investments using another mindset? I am extremely curious about what it is like getting to an IPO as an investor.
It isn’t something I have heard much about and thought it would be hella interesting.
All the Best ~ Rodney

0
Reply

Keep exploring.