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

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.

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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.

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