The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More

Guy Oseary 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 [00:00] Start. [01:14] Meeting Prince at 12. [02:45] A knife on Pico Boulevard and the snap decision to switch schools. [05:22] Faking a Beverly Hills address to get inside another world. [07:58] Wise Guy Records: a 15-year-old builds a portfolio out of nothing. [08:39] Bernie Brillstein offers $25,000 — Guy asks for three phone calls instead. [10:51] The one moment that confirmed Guy was on the right path. [11:50] Freddy DeMann, Madonna, and a desk in exchange for no salary. [14:49] Chasing Hole and Rage Against the Machine — and losing both. [21:23] Candlebox in five minutes: seeing thousands in a room of 30. [23:10] Why "magic" beats everything else. [25:24] Stopping Muse mid-audition to prove conviction. [28:15] Signing Alanis off a single song. [31:47] What Madonna taught Guy about thinking without walls. [34:46] Why Guy treats every founder like a rock star. [35:23] From bands to Twilight: the power of a blank canvas. [42:22] The IdeaLab bet that wiped Guy out an hour before the crash. [48:49] The coconut-water article already sitting on Guy's desk. [56:28] The three-month window that caught OpenAI and Anthropic. [59:07] How the Anthropic deal happened in this room. [01:05:14] The fight to make AI pay artists. [01:14:24] SpaceX and Bitcoin: the ones that got away. [01:16:03] Three back-to-back tours and being away from family. [01:20:22] Why Guy never stops to celebrate. [01:23:42] Splitting with Ashton after 20 years. [01:26:34] Parting thoughts. Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded one billion downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

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