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 billi...
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Guy Oseary, Madonna's manager, discussed what he learned from her over 36 years. He highlighted her unmatched work ethic, commitment to her craft, and ability to identify talent early, citing Frida Kahlo as an example. Oseary said Madonna has no walls around her thoughts, which influenced him to avoid self-imposed limits, allowing him to move across music, tech, and film. He explained how he started a film company with Madonna, bringing independent producers under one roof, which led to producing Twilight and Percy Jackson. He described his creative approach to management, including finding William Orbit for Ray of Light and directors Jonas Åkerlund and Chris Cunningham for her videos. Oseary attributed Madonna's longevity to her refusal to celebrate past accomplishments, always moving forward and fighting her way through challenges.
Key takeaways
Oseary has worked with Madonna for 36 years and credits her with teaching him to never think in a limited way.
Madonna is the greatest identifier of talent, finding people like Frida Kahlo early.
Oseary's film company, started with Madonna, produced Twilight and Percy Jackson.
Madonna does not celebrate her accomplishments and always starts fresh, which drives her longevity.
Oseary found William Orbit for Ray of Light and directors Jonas Åkerlund and Chris Cunningham for her videos.
1:48And I think that when I look back and I go, how did I not really bucket myself?
2:26You know, what's your first single? What's your second single?
4:07I'd been signing bands for a long time and running the record label and I thought, well, why don't we do a film company as well?
4:24And the idea was is I'll bring them in and you know house them and and give them support and pay for a lot of the legal things that cost money when you're independent is it's a lot on you, right?
I'd love to spend a little bit of time on what you've learned from Madonna. This is an older Variety piece, but the quote here that's attributed to you is, "She mentored me and by working so hard pushed me to work so hard. I didn't know until she grabbed me by the hand and said, 'Let me show it to you.'" And it goes on and it goes on. But what did you pick up from Madonna? What are the key sort of learnings?
I mean, there's some clear learnings and there's stuff that with I'm 36 years next to this woman. Yeah. And there's things that when you look back, you go, "Okay, you know, I got that like people who think about things that I got that from my brother or my mother or my..." There are things that I didn't realize I was getting the whole time. So, there's both. And the front part is pretty, I think, obvious. You know, her work ethic is not to be believed. Her commitment to her craft not to be believed. Her passion for...
just the greatest gifts of whether it's through the books that she's reading or through the art that she's finding or the people that inspire her or the designers or she's so surrounded herself with a collection of some of the most incredible people in the world and she identified them. By the way, she is the greatest identifier. She found these amazing talents early and was able to whether either could they be painters or Frida Kahlo or they could be designers or musical people like she's an incredible finder of talent. I think the thing that has really affected me the most is that she doesn't see any kind of... there's no walls around her thoughts. There's no, "Oh, I can't do that."
Yeah. Even going back to my first experience at Maverick Records. If you went to any record label, they probably would have they would have put me in a compartment. There's the R&B department, there's a jazz department, the rock department, reggae department, pop department, hip-hop department. And you're oh, what department are you in? And they and they sort of bucket you into these things. And I think that when I look back and I go, how did I not really bucket myself? I went from this to this to that to that to that. And I think it's it's really just being around her has allowed me to never think in a limited way.
And they all work together. A lot of the stuff I do on technology has allowed me to bring that into my musical world and to understand how these things work together or the relationships. And they're so hand in hand. And of course a few decades later now people understand that but at the time it was so it was it was it was very much like what are you doing this tech thing is crazy and you're not doing innovation is innovation and how we can distribute music or how we market and vice versa all the stuff from music is you know when you when you're launching a new company you have you know these founders are rock stars in my mind every founder I invest in I look at them like they are the rockstar I go that person has music they want to share of the world. They have their album and my job is to identify that artist, that founder before everyone else maybe identifies them. And my job is to help you reach that audience. How do we tell the story? How do we reach the base of your audience? How do we grow your audience? You know, what's your first single? What's your second single? I still work in that kind of process, which is very musical in my mind.
We're going to spend a good amount of real estate on on the tech. But before we get to it, I want to take a moment to explore the the terrain of film and how you ended up executive producing Twilight and and all the rest because as as you mentioned in a different environment with a different label, you would have been tightly siloed and you wouldn't have had that ability, right? How did you end up with the foray into film?
I'd been signing bands for a long time and running the record label and I thought, well, why don't we do a film company as well? And Madonna and I were really in a good groove together and thought, let's just let's just start this film company.
I don't really recall that. I just recall thinking about how people do it differently. And so again, I didn't have context. The best thing sometimes is to have zero context. Sometimes fresh is okay. Sometimes having a blank canvas. And with films, I had a blank canvas. I didn't know how it worked, but I knew I wanted to make some films. And I So I had this idea of bringing in a bunch of producers under one roof. And they were all independent producers. And the idea was is I'll bring them in and you know house them and and give them support and pay for a lot of the legal things that cost money when you're independent is it's a lot on you, right? All the back office, all of that stuff. We'll take all that on. We'll help you and then we'll work on these projects together. And we had like a lot of producers that I if I was to to pay for them, I couldn't have afforded it. But we did it that way. and and out of that came a lot of films and a lot of Twilight and and Percy Jackson, a few others that I was very lucky to be part of. The guy who ran it, Mark Morgan, was really good at it. But there were a lot of complications and I was at that same moment that we were that it started to take off. I picked up Madonna as manager with my partner at the time, Angela, and I took on Confessions, which was the pretty massive tour that year, and I think the biggest selling record of that year. So, as a I don't know how old I was back then, but that was a major responsibility for me.
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Ferriss, T. (2026, July 18). Why Madonna Never Celebrates Her Wins — Her Manager Explains [Interview transcript]. Tim Ferriss. CEOInterviews.AI. https://ceointerviews.ai/interview/3004391/
MLA
Tim Ferriss. "Why Madonna Never Celebrates Her Wins — Her Manager Explains." Tim Ferriss, 18 Jul. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3004391/.
BibTeX
@misc{ferriss2026_3004391,
author = {Tim Ferriss},
title = {Why Madonna Never Celebrates Her Wins — Her Manager Explains},
howpublished = {Interview transcript, Tim Ferriss. CEOInterviews.AI},
year = {2026},
month = {jul},
url = {https://ceointerviews.ai/interview/3004391/},
note = {Speaker-attributed transcript with timestamps}
}
