#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:
Momentous high-quality creatine for cognitive and muscular support: https://livemomentous.com/Tim
AG1 all-in-one nutritional supplement: DrinkAG1.com/Tim
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.
For deals from sponsors of The Tim Ferriss Show, please visit tim.blog/podcast-sponsors
Sign up for Tim’s email newsletter (5-Bullet Friday) at tim.blog/friday.
For transcripts of episodes, go to tim.blog/transcripts.
Discover Tim’s books: tim.blog/books.
Follow Tim:
Twitter: twitter.com/tferriss
Instagram: instagram.com/timferriss
YouTube: youtube.com/timferriss
Facebook: facebook.com/timferriss
LinkedIn: linkedin.com/in/timferriss
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Mila Kunis & Ashton Kutcher
Mila Kunis & Ashton Kutcher rejoin the Armchair Expert to explain how they got into cryptocurrency, how a decentralized currency can exist at the same time as a national currency system, and how El Salvador has recently adopted Bitcoin as their national currency. Mila tells us about her new NFT animation show stoner cats, how people can purchase a token to view it, and how it differs from current production models. Ashton explains that the cost of crypto is linked to the amount of energy used to produce it and what fail-safes you can implement to avoid losing large amount of cryptocurrency to hackers.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Ashton Kutcher Returns
Ashton Kutcher (The Ranch, Jobs, No Strings Attached, That 70s Show) is an American actor, producer, and entrepreneur. Ashton returns to the attic to discuss new decade resolutions, his goal to eliminate child pornography from the Internet and his interest in improving the foster care system. Dax talks about working with Ashton on The Ranch and Ashton talks about his love of a live audience. The two talk about preparing for the apocalypse, intention versus perception and appreciating counterintuitive data.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means
Ashton Kutcher is a Founder & General Partner @ Sound Ventures. Over the last 5 years, Ashton and his partner, Guy Oseary, have built Sound into one of the West Coast's leading new entrants with a portfolio including Lambda School, Calm, Gitlab, Affirm, Bird and many more incredible companies. As for Ashton, he started his investing career as an angel with early home runs including Spotify, Alibaba, Skype, Airbnb and Optimizely. Due to his immense success both in media and technology, Ashton has been named one of TIME magazine's "100 Most Influential People in the World".
In Today's Episode You Will Learn:
1.) How Ashton made his way into the world of startups with his foray into angel investing in Skype, Spotify etc? How did that lead to his founding Sound Ventures most recently?
2.) How does Ashton's background in the world of media impact Sound's investment strategy and the type of deals they get excited by? Question from Daniel Ek @ Spotify: How did your deal sourcing look lin the early days? How has that changed over time and with the institutionalisation of Sound?
3.) Why does Ashton believe people creating the future are perpetually young? What question does Ashton always like to ask founders? What does he look for in their answer? How does Ashton ensure founders feel comfortable with him? What does he do to allow them to open up? What is the hardest thing Ashton feels he has persevered through?
4.) How does Ashton build strong product intuition about products in areas he is not familiar with? In terms of great product, Ashton backed Spotify with Daniel Ek and Shak Khan, what did Ashton see in Spotify way back then? How did Shak and Daniel innovate on distribution and customer acquisition with him and Spotify?
5.) What have been Ashton's learnings in what it takes to truly win the best and most competitive deals? Before as an angel, Ashton's check size was friendly, now with Sound it is competitive with VCs, how does Ashton approach the element of now competing with many VCs he once co-operated with? What does Ashton make of the rise of many celebrity investors today?
Items Mentioned In Today's Show:
Ashton's Fave Book: The Undoing Project: A Friendship that Changed the World, Scale: The Universal Laws of Life and Death in Organisms, Cities and Companies
Ashton's Most Recent Investment: Community
As always you can follow Harry, The Twenty Minute VC and Ashton on Twitter here!
Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Ashton Kutcher
Ashton Kutcher (The Ranch, That 70's Show) is an actor, investor and the prime person Dax credits for his break into Hollywood. In this episode of Armchair Expert, Ashton and Dax discuss their time on Punk'd together, feeling stuck in the cultural zeitgeist as one particular role and the sisyphean climb to satisfaction. Ashton discusses commerce, art, and the importance of social influence in entertainment. They, also, talk about what it's like to be married to powerhouse ladies, the difference between pity and compassion and they delve deep into their mutual struggle against balding.
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Recode Decode: Ashton Kutcher
Actor, producer and investor Ashton Kutcher talks with Recode's Kara Swisher about his life as both a TV star and a tech obsessive. Kutcher, who starred in shows like "Two and a Half Men" and "That '70s Show," has invested over the past five years in companies like Uber, Airbnb and Square. But he passed on Snapchat — twice — because he hated the app's design and feared what would happen when it got hacked. He's currently starring in the Netflix sitcom "The Ranch," and says denying the rise of digital media platforms in Hollywood is like denying climate change.
Learn more about your ad choices. Visit podcastchoices.com/adchoices