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  4. #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.

This episode is brought to you by:

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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.

*

For show notes and past guests on The
Tim Ferriss Show, please visit
tim.blog/podcast.

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