YouSaid · the spoken record

Guy Oseary

lines on the record: 118
first: 2026-07-07
most recent: 2026-07-07
sittings or episodes: 1
sources: podcast

Every line below is reproduced as it was said and linked to the record it came from. Nothing here is summarised or generated. Directory · Search · Corrections

“So I put every dollar I have plus dollars I didn't have. I picked out three investments at that time Ideal app because of Bill Gross. Bill was the first guy in, I think, in LA to have the blackberries. So I was the first guy from Hollywood to even know what the hell blackberries were. So I ended up buying 400 of them and I gave them to all the people in Hollywood so I could connect. And when I needed to and talk to them and so I made a deal with Jim Bassley to be an advisor because I was the guy that put it in everyone's hands. This is smartphones before anyone else was doing it. And then I also, my friend Seth Rotsky brought me vitamin Water. So those are going to be my first three investments. What happened was the ideal lab thing once I put that money in and I don't know the timeline because I tried it's almost like I just like something you want to wash away from your mind.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Well, I mean, the bad news is that I worked there for a year helping. And then one day, someone I really trust that they don't know it to this day. They're an incredible human. And I was lucky to sit with them at dinner one night and they were telling me how Bill Gross is one of the greatest investments they've ever made. So I called up Bill and I go, Bill, I want to put money into Idealab. And he goes, well, you know, I was going to surprise you and I was going to put X dollars in for you from out of my heart for all the work you've done here. And I go, oh, what is that worth? And he's like, you know, he told me what he thinks it's going to be worth when it comes out. And I was worth a lot. And I go, that's not enough. I'm thinking, right? I'm thinking to myself, that's not enough. So I go, Bill, I want to put more in, a lot more in. And he's like, hey, for you, I'll let you do whatever you want.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Version of that you can walk in and out of different rooms and you can say, okay, what are we doing here? What are we doing here? And so he was building all these different companies and I would go in and out of ones that I could be helpful to. I would learn about it. So that was like a oh, okay, an incubator. I really fell in love with that idea. And there's bad news to this story. But like all things, it worked out in the end.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Out of the way, I want him It's time to move on. I need to talk to this Bill Gross guy. So he sets me up with Bill Gross. Bill Gross ran an incubator called Ideal Lab in Pasadena. And I just loved it. I love the idea of a lot of ideas, reminding me of the record label where you had all these artists and you had all these project managers.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“And I go, No, who's that? He goes, Well, he started an incubator and he's launched $3 billion companies in one year. And I go, Sky, like you, but can you just?”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“And so I go, when I get back home, I want to meet this guy. So I came back and I took me a while, but I finally tracked him down and we went to have lunch four seasons hotel. And he was like, wow, if you're impressed by me, have you ever heard of Bill Gross?”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“The original original was I was on a plane to Milan for MTV Awards. And I don't remember how old I was. It was my 20s. And I was reading in a magazine about Sky Dayton. And it said he started Earthlink and he was worth $100 million. I'm like, wait, what? What is he doing? How old is he?”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“She doesn't sit well on her past. She's not high fiviving herself. She just keeps it moving forward. And I think that is part of the inspiration for continually trying to move forward myself is have a front row seat or shotgun to this incredible journey of this woman who just continually defies all the odds and fights the fight. It is not easy. It's not that she's maintained or stayed around. It's actually that she's had to fight her way through it a lot. She's breaking ground for a lot of other people who are coming behind her who can say, oh, Madonna's done it, I can do it. But it is no easy feat. There is a lot of bullshit to deal with. I think it comes from she just doesn't Celebrate her accomplishments. She just starts like it's a brand new day.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“When I showed her Jonas Arkalin did a video for Prodigy, which is a band I signed. And it was really provocative. And I just showed it to her. This is crazy. And she goes, he's doing my first video. Or, you know, I showed her, there's a guy named Chris Cunningham. He made a song called Come to Daddy by Apex Twin, which is really insane. So $30,000 video. I just showed her to her just to show her. Look at this crazy thing. And she's like, that guy's doing that video. So she had Chris Cunningham do frozen, which is an incredible video. And she had Jonas Ockerland do Ray of Light. So it was just a really great back and forth. We had really great energy together. She was open to my craziness. And then she would take it to the next level.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“And on music, Stefan Sidenaway, the director, introduced me to a producer named Merwaise, gave me a demo. I loved it, and I gave it to Madonna, and I ended up becoming music. So I found on those two albums, I really, even though I wasn't managing her, I was creatively helping here and there bring in some ideas. So we already had a rhythm on the creative side. Now, there are some managers that don't do any creative, and there are some that are very creative. I was coming from the creative point of view on ideas, ideating. Here's things we could do, here's things we could build. So I think that's the management that I am. I'm more creative when I'm working with someone I'm sort of in it. And there are other managers I've worked with who they don't do the creative, but they do an incredible job managing everything, putting together the tour, but they're not in there going, what if we did this? What if we, there's different kinds of managers. I'm for creative, for example.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“When Madonna started working on Ray of Light, I found the producer, William Orbit, but I was not managing her. Her partner at the record label, Maverick Records. Right. And not her own, not Warner Brothers, which is where she was on Warner Brothers, but you were just friends and working together. But I fed ideas. I found the director, Jonas Ockerland. And so I was creatively, really working on this project called Ray of Light. So we're already building a creative rapport.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“That alone, just Madonna at that moment in time for someone I had not been a music manager for anything near that level. And so to take that on and to work on all things, the tour and the album and all that.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“We'll take all that on. We'll help you, and then we'll work on these projects together. We had like a lot of producers. If I was to pay for them, I couldn't have afforded it. But we did it that way. And out of that came a lot of films and a lot of different Twilight and Percy Jackson and a few others that I was very lucky to be part of. The guy who ran at Mark Morgan was really good at it. But there were a lot of complications. And I was at that same moment 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 pretty massive tour that year. And I think the biggest laying 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.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“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. So 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. So I had this idea of bringing in a bunch of producers under one roof. And they were all independent producers. The idea was is I'll bring them in and house them and give them support and pay for a lot of the legal things that cost money. When you're independent, there's a lot on you.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“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 start this film company.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“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 for music is when you're launching a new company, you know, these founders are rock stars. In my mind, every founder I invest in, I look at them like they are the rock star. I go, that person has music they want to share with 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? 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.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, and I think that even going back to my first experience at Maverick Records, if you went to any record label, 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 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. It's really just being around her has allowed me to never think in the 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.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Callo, or they could be designers, or they can, or musical people. She's an incredible finder of talent. So I think the thing that has really affected me the most is that she, there's no walls around her thoughts. There's no, oh, I can't do that.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“There's some clear learnings, and there's stuff that I'm 36 years next to this woman. And there's things that when you look back, you go, okay, you know, I got that. Like people who think about things that they got that from my brother or my mother or 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, obviously. Her work ethic is not to be believed. Her commitment to her craft not to be believed. Her passion for just the greatest gifts, 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 that 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 be painters or freedom.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“So it really cemented that I'm in a good place right now that I can do these things and this probably is going to give me more opportunity to do more of these things. So she's such a big part of my life and she's so talented how lucky that years later she's right now she's still winning awards. She's still out there crushing. She's actually doing incredibly well right now. It makes me so proud to have played any part of that. It would be so sad to have missed that one. I'm so happy to have been fortunate to have gotten that meeting and to have figured it out. A lot of people when they initially heard it. I remember Freddie once asking me, what do you think this record could sell before it ever came out? And I go millions of albums. I just had a feeling that. I had not heard anything like this, and that this was a monumental record.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I knew nothing. They walked in and I thought, oh, wow, it felt like a hippie group, actually. I was like, oh, maybe there's like some sort of hippie vibe kind of, what is this going to be like kind of thing? But it was, again, another life-changing moment when the story is told, it's that everyone passed. But I just felt it in the first minute. And then we ended up working together and working on that album. And that album ended up selling 30 million albums. And I think top five debut album of all time. That really just took me to the not only did I sign it, but everyone else didn't want to sign it. So it's not like I even competed.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I didn't know that the comparisons where people were like, oh, I thought it was Joni Mitchell. People were like, oh, I didn't know Joni Mitchell. So to me, she was my Joni Mitchell. I didn't never listen to Joni Mitchell before. I listened to it later because of her. I wanted to know what people were talking about. But to me, she was my Joni Mitchell. And I didn't know any of the background. A lot of people prejudged her because she had, as a teen, did a pop album in Canada. And so people had all this background. I had no background. I literally was asked to meet with her. Glenn and I knew nothing.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, she played a big role in my life. She was the rocket ship. It just took me to the next level. I mentioned earlier, you know, she appeared in my office with Glenn Ballard. And they played me one song. They played a few songs, but the first song they played was a song called Perfect. I didn't understand how powerful those lyrics were until later, what I really listened to it. It's really about earning your parents. Do they believe in you? Do they love you? I don't know if you know lyrics or sometimes is never quite enough when you're flawless, then you'll win my love. Don't forget to win first place. Don't forget to keep that smile on your face. I didn't even understand. To me, it was just, well, how is she putting these words together? I just had never heard anything like it. Again, later, I understood how powerful those lyrics were. But at that time, I was just in love with what I was hearing and I hadn't heard anything like it. And I went, I'm ready to sign you. I love this. I'm all in. And I didn't know anything.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Now I bring other elements into the mix, other things I'm looking for that are different than back then was just, I love it, I'm ready to go. I feel it. You have to fall in love. And later today, I would say on my tech investing and what I do there, it's a combination of gut, pattern recognition. And then there's a few other things. One of the things I look for is can I help it? I visualize what I can do for the company and I get to be excited too. So I go, oh, wow, okay. I have a feeling I can help in a big way or I have a puzzle starts to come together for me very quickly. So that's important. And then, of course, there's the other aspect of, well, you got to make sure they do what they say. Let's try this thing out. Let's make sure the car actually shows up. When you press the app and it picks you up and it make sure that things work. Make sure that you can stay at the apartment and it's actually, oh, I pressed the thing and I can get an apartment. These things have to work. But for me, it all...”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Have to fall in love. And you can't fall in love every five seconds. I didn't know I was going to fall in love with Alanis when she walked into my office with Glenn Ballard that came in to play me. I didn't know what was going on here. I thought they were a band. He was the producer's co-writer. You just have a feeling there is a lot of pattern recognition later. Like now with experience.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“High conviction and also if I left it available. Maybe someone will offer them way more money or make them other promises. And I couldn't afford to not make fast decisions, or else we would never have gotten to where we got to.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Honestly, I would say that 90% of the things I do happen in the first five minutes. 90%. It drives me crazy when we. Get in a room and talk about her for three months. And I respect the process. I know there is a process to these things. But I think I know what I want to do very quickly. It started out. I think the muscle that got built for fast sort of response thinking or intuition was really in the music business. We have such a small label, so boutique, and we're competing with these big companies that have been around forever and have all these other artists. We didn't have any artists. So when I met an artist that I liked them, Alanis Moore said I signed off of one song, Muse. I saw them perform one song. And I stopped them. They flew all the way from London to LA to showcase for me after the first song I stopped them. I said, you do not have to play another song. And they're like, we flew out all the way from London. We'd like to play more music. But I just want you to know, I do not need to hear another song. Just be clear.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“The way they did show after show after show took a few years for every week, every week, little by little, little by little. Keyword is artist development and people don't artist develop that much, but something that we all want. Every artist wants to have the time to build, have the time to develop. And we really took that time week after week after week developing that one. And that's how we got there.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“My mind, yeah. I went to the payphone from that performance called Freddie and said, Freddie, I have our band. This is the band. I just saw them. This is the one. So it starts with that, always starts with the magic. I don't care if you're a tech company or your whatever it is, a film, a product, a book, magic. You got to have magic. Something has to pull you in. And that night I saw it. I visualized it and the songs were there. The songs were so there that when we made the album, their first two singles, we could not beat the demo. They went in to re-record them for the album. So whatever they made for a few hundred bucks that I had with a lot more money and a lot more time, we couldn't be. And so those songs, those first two songs on the album are from the demo. So the music was there. They were talented. The band was talented. The singer Kevin is so great. And they really did it the hard way.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Going back to that time period, first is the music. I was so lucky I walked into almost everything that I've been lucky on happens within minutes, not within days or weeks or months to think about it. It's all intuitive and it's very fast. I walked into, I was supposed to be somewhere else that night, but I went to this party and it was so bad that I thought, oh, I have time to go see that showcase of that band from Seattle. So I go to the lingerie on sunset. I walk in and these guys start performing. Now there was a screen, like a video screen on the side of the stage. And then there's a stage. And I was looking at the video screen. There were maybe like 30 people in the audience. It's a showcase. And I'm looking at that screen and I saw thousands of people singing along to that band.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, it was painful. Successes, right? Yeah, it was painful. The third one that I competed for, I did get it was called Candlebox. And at that time, actually, I think it outsold both whole and rage at that time. They ended up. Doing really, really well. But regardless, whole enrage, even to today, I still listen to them. I love them. But I was very lucky to get Candlebox. The fact that they bet on me, we didn't have anything. We just had this idea, you know, they ended up selling 4 million albums on that album. But I'll never forget that. I'll never forget that they gave me that shot. That was my first success story.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Madonna, the first real connection was that whole connection It's like, well, tell me this thing that you like. And then the second artist I brought was Rage Against the Machine. And I really wanted to sign Rage Against the Machine. And so I took her to the concert in New York, the limelight, I think it was called. And I didn't get them either. I didn't get rage. They ended up going with Michael Goldstone at Epic Records. So, you know, God, the first two things I competed for I didn't get.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Rolling down the window and sticking their arms and heads out. And I was like, oh, wow, okay. I got a little perspective there to go, oh, these people are Beverly, they're not really my friends. I'm here for a reason. I was put around this community for a reason, which is to work, and which is to build my name and to build the things I want to do. It wasn't until years later. Actually, I told that story in that thing you're talking about when I was 24. My dad mentioned it was really hard to even come up with the money for that car back then. It was a really big deal for us. It was expensive back then. And so I think I need to perspective a lot of the opportunities that were in front of me and to really appreciate them. So it's a combination of those things.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I remember going to see my old friends from my old school. When I drove it to Beverly Hills Highs, Honda Civic, when I drove it to Beverly Hills High, I got not one person commented or said, congratulations or nothing, no mention of it at all. And then I went to my old friends from my old school and then they couldn't believe I had a brand new Honda Civic. And they got in the car and they were.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Bernie Burlstein moment. Where he offered me 25 grand the week I turned 16 was a big game changer for me. And then there was a personal moment for me when I got a car when I finally passed my driving test, took a few times when I finally got my car”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I just thought for every day I'm here, I'm really lucky and I need to pay attention to that. And I just realized that if I wanted to change my destiny, I needed to get going.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Everyone gets this opportunity. And by the way, I was scared that they would kick me out because if they found out I didn't live there, they kick you out. So I had to watch how I went to school. It wasn't like an easy thing to do. And so”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I fell in love with music in a big way. I think I realized how lucky I was to be at Beverly Hills High and see The potential of what was possible, yeah, of what's possible. And I thought, wow, not everyone is this lucky.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“That was it And I go, oh, I could always come back. Okay. So that was it. And by the way, I couldn't even afford the $700 per semester, you know, and all the things that came with that. So it had no choice. Sometimes having no options and no choices is really the best option.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“No, I went to college. I went for half a semester. I got my first group signed. Was just Hen Genie Vali. And then I remember going to my English teacher. I don't know her name. She's amazing because I said, hey, I'm thinking of dropping out and focusing on this thing. And she just looked at me and said, you could always come back. Wow. Yeah.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“I mean, I was already, I sort of wasn't so social guy. I'm not on the football team. I was just sort of my own music guy running around and I didn't have much. So I did as much asking as I can from who I could figure out to ask. So I probably asked her I'm five. I remember one person specific saying my dad doesn't do that. Whatever because it was rap. I was trying to play, oh, my dad doesn't do that. So I didn't have any shame. I needed to figure this out. I knew that my time was limited before going to college and I better figure this out soon.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Yeah, so I go in a room and I play the song for Madonna and for Freddie. And it's pretty wild. I mean, the lyrics are like when I was a teenage whore My mother said she said, Baby, what for? I was like, whoa. And you gotta go back to that time period. And they were like, okay, all right. So go after it. And so I went after it. I didn't get it. It was between us and Gefen Records. And we didn't get it. It went to Geffen Records. But my first artist I ever attempted to sign was whole.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“But it was like Madonna's trying to sign whole. So. The next day, there was a show that Hole was doing. At the whiskey, I think Kurt was there. Then Madonna wanted to talk to me about who is this whole thing that you're that”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“So he brought me in as a scout because one day they're going to start a label. They didn't even have a name. They just knew they were going to do it. So I'm scouting. And then one day I find a hole, which is Courtney Love. I find their first song, Teenage Whore. And I go, oh my God, this sounds incredible. I just blown away by the sounds and the lyrics and all of it. I reached out to the lawyer, Rosemary Carroll. And next thing I know, it's in the paper the next day. Madonna's trying to sign.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“So, when I went to see Steve and I was playing his DJ, Evelyn, his brother Henji. And I said, here's the music. And he said, I know a label for you. So he helped me get my first record deal. So I always write Freddie and go, hey, Freddie, I just got my first group signed. I just, I'm manager, you know, and he knew I was, how is he pulling these things off on his own without any help or any money? And so I met with him and he said, you know, Madonna and I are going to start a record label one day. So I said to him, I'd love to work there. I said, I don't need any money, which I did need money, but I wanted to make it really easy for him. I said, I don't need money. Just give me an office and a desk. That's all I ask. And he's like, okay.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Of iced teeth's DJ and his brother, who's Henji and Eville. Evilee is ICJ. So I manage them. My first group I ever managed. And I was 17, we got them a record deal. So I had that and I always checked in. I checked back with Freddie and said, Freddie, I just got my first group signed to record label. So he knew there's a guy named Steve Rifkind, who I met who knew the record label. He helped me get that first record deal.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“And so he had me say like a few words on the album. But I started hanging around and I'm like, what could I do? Could I clean up? Could I carry someone's bag? Could I, how do I be helpful or of service? I'm just so happy to be around this energy, the music and artists coming in and out. And he had a thing called Rhyme Syndicate. So a lot of the artists came through there and I was able to be around them and help. And then I ended up becoming the manager.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“One of the crews that I was working with was iced tea. And I got very lucky, got introduced. My friend Chris Boyd, I met when I was working when I was 15 at this Fret Siegel. And Chris Boyd, another guy was working there. And he's like, oh, I know iced tea and his producer, Johnny Rivers. And I go, would you want to come to the studio and check it out? And I'm like, yeah, I want to go. So he brought me to the studio, and actually, my first day in the studio, Iced goes, come into the booth and do a few words. And I'm actually on the album.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“Meaning was after Bernie. She just learned about me. He heard my pitch and I'm trying to do this. I'm trying to do that. And he knew I didn't really have any money.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT
“So, Freddie, the man, his daughters, Nissa and Pilar, connected me with their dad, Freddie. And Freddie was iconic as well. I mean, he worked on Thriller with Michael Jackson. He managed Madonna of the greatest artists of all time He was just a really great human, great guy. And he heard me out. It took a few meetings to get Freddy to really go for it with me. Not that long, but.”
2026-07-07 · The Tim Ferriss Show · #874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First · IDENTIFIED FROM THE TRANSCRIPT