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Guy Oseary

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2026-07-07
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2026-07-07
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  1. “We've got some surprises of how we want to build that out too. It's all really good. It's all very supportive. It's just another chapter.”

    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

  2. “It turned out that we just have a new chapter, and I've had many new chapters my whole life. The record label for a certain amount of time, and then I moved on, I went to music management, I went to crypto, and I went to film. I have so many different chapters in my life that this is a beautiful chapter that we're in a celebratory mode. So we're sort of hoping to be on the beach high-fiving each other at some point on the work that we've done and have worked hard to get here and taken a lot of risks and a lot of chances and put in our own money. This decision was made out of joy and to support each other's visions, there are going to be times where we'll cross over and we'll work on things together because we do have some crossover of things that are part of things we both like. But he's very specific on me. He wants to do it. I'm very specific on what I do. Effie and I are going to continue on with sound and what we've built the last 10 years with sound. So continue to build 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

  3. “And I support that vision for him. It isn't my vision. And I will support it financially and I will support it with energy. I want him to win. And I have mine, which is the things that we're talking about today and the things that I want to build. And I have a version of the things I want to do that I haven't shared with everyone in full.”

    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

  4. “We've had an incredible run. And this AI fund is, I don't know what to compare it to other than like winning the Super Bowl. For what we do, right. Between the investments in Open AI and Anthropic. And we also did SPVs the whole way up a lot. So we're really fortunate and blessed. And after 20 years, Ash and I asked the question of now that we've done that and we've hit it out of the park, what are we going to get enjoyment out of doing? And so it's a really strong question. And we all gave it some thought. This is a few months ago. looked at each other's visions of what they want, what he wanted to do that make him happy and what he wanted to build and what I wanted to do. And we have a third partner. Her name's Effie. And what she wanted to do. And it turned out that we had different visions. And when you look at his vision, which he will share at some point, so I'm not going to share any of it, it was pretty awesome vision. It's an incredible vision. And the guy is mind-blowingly smart and talented.”

    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

  5. “The potential and opportunities. And I'm trying to bring in other friends and other people into my world to say plug into this. Let's help you figure this out. I'm not just doing it for myself. You should use what I have. You should meet some of these people. You should come to this event. You should go to this. So I like sharing 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

  6. “How cool that we're survived this period of time? How cool is it that we're even able to do what we love? Waking up and being able to do what you love, there's a Josh Kushner quote that I love that he says about success. He says, Tim, success is being excited to go to work and also being excited to go home. I got that. I'm excited to go to work and I'm excited to go home. That's pretty cool. You know, not a lot of people get to do that. And I don't take that for granted. And I work hard because of that because I go, this is not a given.”

    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

  7. “Just keep it moving. I don't know. At some point, I can visualize being on the beach and high fiving with my friends and having fun. But again, they don't do it either. A lot of my friends, we don't talk about it like that either.”

    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

  8. “I need to step my game up. That's how I feel. I don't feel Accomplished. I feel like I still have so much to prove and so much to do. But at the same time, I do know if I really took a minute, I would go, oh, wow, okay, I should probably take a moment and take that in. But I really don't”

    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

  9. “And so on You know, my friends and I. Don't spend a lot of time talking about what I do. Little bit. I share with them so they're in the know, but we don't spend a lot of time on it. We don't work together on these deals. My wife and I don't talk about work much. I think I just keep it moving too. And again, when you look back 36 years, it's probably Madonna. That is responsible for how I also think of just keep it moving forward, keep it moving forward. And maybe one day, sometimes when I'm I don't think about it that much. Things pop up every now and then. But when I wake up tomorrow, I'm like, I haven't done anything today. I better figure it out.”

    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

  10. “I can bring some of those ideas or some of those new relationships I met while she was off. I found a way to make it work.”

    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

  11. “Touring this year, they're wrapping an album this year. They aren't touring next year. They don't have an album next year. So, you know, there's a lot of time in between where they're coming up with the creative. They're going to make an album. They're going to do all the things that they're going to write songs. So that takes time. So you get these windows of opportunity where you go all in and you get windows of opportunity where you have a moment to breathe, just like they do. They all need it too. Madonna after this cycle will probably need a minute to just sort of catch your breath and figure out what she does next. So these are cyclical things. What I don't do is I'm not out there trying to sign 10 more bands or 10 more artists. So that's where the balance comes in, which is continually be creative through other ways when the cycle starts, my creativity has never stopped so that I still have those things. I'm not starting from scratch. I'm always looking and meeting with people and understanding what's going on in technology. And so when Madonna comes back into psycho”

    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

  12. “When I think of responsibilities, I think of management. That's a really big responsibility and I don't take it lightly. There's no way around it. Something's going on there that's a focus. It is cyclical. So like the peppers are not.”

    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

  13. “Can't be in three places at once. It's hard, but it's sort of tells its own story. You're not going to miss New York. You're not going to miss London. You're not going to miss some of the major moments. And then you look at the calendar and go, oh, we have this time off. Let's go to New Zealand with Madonna or let's go to so-and-so with you two or let's go to so-and-so with the peppers and you find your way around it you just you just make it work”

    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

  14. “Probably just compartmentalize a little bit. But in the last few years, I've stopped doing as much. I still go, but not as much. I've went it down. There was a moment there where I managed the red hot shield peppers, U2 and Madonna, and they're all going on tour. It was a lot to process.”

    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

  15. “Birthday spent here in this house. So I miss three shows out of 240, but we're talking about a different city, a different hotel, a different, in order to like move along, you sort of have to block everything else out. You have to forget, and it's a very selfish, very, for me, otherwise, if you think about, if you're every day, you're thinking about back home or your family or other things, it hurts. So I just go, okay, I'm off and I'll see it. I bet it's what actors do when they go away and make a movie for three months and then they come back.”

    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

  16. “Think it's different as the years go by. There was a point around 10 years ago, 11, 12 years ago, where it was a lot for me. I was also changing and growing and having kids. And I just was just sort of losing myself because you're going to a different city every other day. And the amount of things you're missing back home, you sort of forget you have a family, you forget that you can go do other things or forget to call back Stripe or you forget to things you just forget everything. And then one day your dad calls you and goes, oh, hey, I'm at your house with your kids. And I'm like, oh, I have kids. I have a bad house. So if you look at the first three tours, those three tours that I did, those are 240 shows, 80 average. I missed three of those shows. Three out of the 240. One I was sick. And then I missed two because it was my 40th birthday. And I really didn't feel like being in Seattle that day. I wanted to be home with my friends. So my 40th.”

    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

  17. “Sometimes I go to shows, like I've seen shows where People are so wowed that they're just like this from a show. They didn't even take in all the songs. They're just like, oh my God, what? I mean, if you ever look back at the sex pistols shows, people are just like, what? And they're like, was I actually there? I think I was more blown away by the concept of what Elon was building that I didn't not understand that there was a business model. And I really wish I just would have asked one more question. Hey, how do you monetize this? How does this work? Can we invest? So I have hundreds of those stories, but those are two that stand out today”

    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

  18. “I just made 10 times my money. I'm a genius So I sold then, clearly, not a genius. So that hurts. And I remember Anthony, gentleman on that wall, Elon invited Anthony from the chili peppers to see SpaceX early days, very early days. And I went with Anthony. I tagged along. It's the first time I met Elon. And we went to SpaceX. I was so wowed by the concept that I didn't even pay attention to the business model or what could be the business model. I was just like, wow, this guy's building rockets. That moment in time, Anthony and I had the wherewithal. I go back to that time and go, we just had the wherewithal to go. What business model? I didn't even ask those words. I was 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

  19. “You know, what motivates him is he just keeps it moving forward, and it's awesome. And what motivates me is like, I'm not going to let that happen again.”

    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

  20. “So many, it's endless, endless. One of the things that Ashton was really good about Not looking back like that, he's sort of just keeps it moving forward, and I'm always like, I can't believe we're not in that, and I had it in my, I had it, and we had it. And he's like, come on, let's go, let's go. He always gets.”

    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

  21. “Conversation. Good, good information. What are you looking at? What are you liking? And then they tell me, and then I go, Oh, let me look into it. And some things I just read about, I read every single day. I'm checking things out every single day and I'm making sure I'm not missing an idea or I'm hearing about things. Well, I'm on X a lot. I see a lot of the stuff, a lot of information on X that's flying by. That's sort of my start of information.”

    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

  22. “While I'm working on this platform that I'm going to announce in a few months that you're part of is how we connected you and I. So I'm able to ask investors what companies that they're looking at. And so two of those came from 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

  23. “And find a way to pay the ones that are okay being on there. It's that simple. It's not complicated. I think go in a room, lock yourself in a room for three days and come out and figure out how to pay people and take people off that don't want to be on there. Madonna does not want her music trained on. Don't care what you want to pay her. She is very clear. I do not want my music to be trained on. I want my music to be its own thing. So take her off. It's okay. You'll still do fine. Take her off. You don't have to have her music. So we'll see where this goes, but this is, I've been the last few years. I've really tried to figure this out. And even with Sam at one point, he's really wanted to figure this out too. Like Sam was a lot of people give him a hard time on this stuff, but he really did dedicate time to trying to figure out if there was a music thing to do, how to do it in a way that supported artists.”

    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

  24. “Because if Claude or Chat is the distribution, they probably won't carry it because it's got so many lawsuits involved. It's just not worth taking on that responsibility. And again, the guy who runs, I find would be a really good guy. I'm hoping that he does the right thing. But it's really their responsibility. They're sitting at the top of this opportunity. Take off the artists that don't want to be on 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

  25. “Lo and behold, though, it looks like it was trained. Yeah, that's the problem on this corpus. There's a lot of workarounds and they'll look you in the eye and tell you, no, no, you can't. You cannot type in Madonna, but you can sort of describe Madonna. The problem is when in discovery, we're going to find out a lot. And Discovery is going to say all of this music is in there. And they know that. And that's not okay. It's just like literally not okay. I don't understand it. And by the way, what's wrong with paying artists? Why not figure out a way to do it? Sit down with a team, figure out how to pay music artists if you're going to train on their music.”

    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

  26. “Without having to try to piece it together or try to illegally download songs that were not even clean or clear and it could be corrupt to get it clean, to hold on to it, they'll pay for it. And he was right. They have paid for it. Now, are all the payment plans there picture perfect? No. But it is the core of where money is coming in today to music artists is through streaming. And I'm hoping that People figure out how if you're going to Be using people's music, how you pay for it. Fair use is not fair.”

    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

  27. “Build a business using our music without getting those rights. And that's something I've been trying to work on for a long time. I've met with Mikey many times. I've met with lots of people many times. I hope that this gets solved. When Napster first started, I met with Sean and Sean when they started because it was so exciting to see people were all downloading music, but it was illegal. So you were hoping they'd crack the code on, okay, how do you turn this into how artists get paid? I don't know if they were going to or not going to, but before that could even happen, it got shut down. And out of nowhere, Daniel Eck in Stockholm built Spotify and figured out that people would pay for music if you give it to them in this way. They had all the music in the world.”

    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

  28. “The world's music, but yet not one music artist has gotten a dollar. So that's not okay. That has to be fixed. I'm hoping Mikey does the right thing and fixes that comes up with a system that allows artists, if they want to opt in, either let them opt out, do not use my music to build your business. Okay, I'm opting out. But if I opt in, find a way to pay us. And I'm really concerned for that because the other part, which is right now currently, every two weeks more music is made on AI than all of the music that's on Spotify today. That's every two weeks. And all of that is going somewhere. And people are inspired and they're creating songs. Awesome.”

    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

  29. “Say that AI and music content. It's on one level exciting that so many people are experimenting, writing songs for the first time, writing beats, creating sounds for the first time. That's pretty exciting. At the same time, the idea that there's companies out there valued at billions of dollars that are built on the top of other people's music where not one artist has ever gotten paid a dollar is not okay. So I don't want to bundle it all up. That all becomes one thing. It's not all one thing. Mikey, he runs Suno. He's a great guy. I mean, great guy, like I really like him as a person. But every time I read about the company, and it's now at a $5 billion valuation, next thing you know, it's at a $10 billion valuation. And it's all built off of.”

    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

  30. “A generalist. I don't care. That particular AI fund was very specific. And we may have thematic funds from time to time. If an idea comes and you go, you know what? I've got an idea. It's going to be built around this one idea. But usually I'm a generalist. I really like talented people. And in regards to sharing, where can they find out what I'm up to? I'm not really, this is it. You know, as you know, this is my first podcast Depending on how this goes, could be my last. If it goes well, maybe one more. Everything has been fine without doing that. You know, people either find us word of mouth through friends, or I find them. It's okay. It all works out. I'm not out there yelling, hey, find me 1-800, whatever, or it'll work itself out. The right people. We'll find each other”

    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

  31. “People that come through when you work with them. And we're a different kind of investor on the cap table. We're not in the valley. We're here in Hollywood. And we bring a different dynamic, different, you know, obviously narrative is something that I'm very focused on. Marketing is something I've been doing since I was a teen. And so marketing strategy, media, partnerships, narrative, storytelling, hey, if you want someone like that on your cap table, I might be interesting to you. And hopefully I can be helpful. And that's what I need to find that dynamic of a company that I'm in love with. And hopefully the founder believes that having me would be a great advantage to them.”

    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

  32. “Feel like going back to the core, really honing in that Antanifer, the greatest talent in the world, the greatest ideas in the world. This is an incredible time where people can scale up a company in the quickest ways. I'm excited about the potential of what's to come. I've already identified. Things I want to do today. So I can only imagine what's to come. But it's just really just, I'm okay doing a version of what I've been doing, which is identify great talent and help them, help them in every which way that I can pick the teams that you want to back. I'm feeling pretty good about that, just continuing on this best in class talent idea. The hard part is for a lot of people is the access. So we're very lucky we have access and we also do the job. We have more than enough proof of”

    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

  33. “Headhunters, that everyone's going to this company called Anthropic, you know? Like people are really going to this anthropic place and they're not going anywhere else. I'm like, whoa, okay, I need to pay attention. So I asked Paul and John, connect me with this founder, Dario. So they connect me with Dario and Nerov. And they come here. They're here right in this room. And that's where we made the deal to invest in anthropic. So we did a bunch of other companies in that foundational AI fund. It was a three-month window. So it was before a bunch of other things that have come out since. But we set ourselves up for exactly what we did. This is going to be within three months. We're going to deploy 80% of the money in the next three months. And that's what we did. And that's over three years ago.”

    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

  34. “They don't get all the press on, they are one of the best investors in the world. There's two guys there, John Samarjai and Paul Drews, who were, when I was doing my research, because now I'm on the lookout, what should I know about an AI? Once I find out about something, I just lock in. And I want to know everything about it as I was doing my research, I was finding out that they were going to do anthropic and they were very bullish about it. And I found out from a friend that works with a job hunter kind of people who help find jobs for people.”

    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

  35. “So Ashton spoke to Sam. We were able to get OpenAI. And what happened was I'm very close to Mark Benioff. And Salesforce Ventures, people don't really understand how smart they are.”

    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

  36. “Which is crazy. And so we had this incredible success because of that. I saw it again. Back to pattern recognition. If you fast forward, we're still using Uber and Airbnb and Spotify. We're still using those things from that time period. And we felt that this is it. These foundational AI models in 10 or 15 years will be how we plug into all these things. So we really felt like we had a three-month window. We told people we have a three-month window. Now, it came out November 30th, 2022. So there's not much you can do. People are going away, there's Christmas time, break, blah, blah. But as soon as January came, we went out there and told people, this is the vision. We're going to do a foundational AI model fund.”

    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

  37. “That was our first, this is the one we're going to go after. But then we visualize that when we first started investing, Ashton and I, it was when the iPhone and the App Store were happening. And so for the first time ever, you can scale companies like never before. And I think any”

    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

  38. “Well, it starts a little before the day that open AI came out, which was on my dad's birthday, ChatGPT, it was life-changing. You remember those moments? And again, I go back to music. I remember when I heard smells like Teen Spirit by Nirvana, I pulled over the car and I went, what is this? And when ChatGPT came out, that was a what is this moment for me? And if you saw me Anytime after ChatGPT came out, I would have harassed you to show you ChatGPT. There's no one, every artist, every actor, everyone I walked around and met, I've like, check this out, check this out. Check this out. And I was obsessed. And I called Ashton and I said, Ashton, this is it. This is Open AI. We're doing Open AI. This is the greatest thing I've ever seen. We have to do it, have to do it, have to do it. 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

  39. “You know, if I'm landing in New York this week, I'll probably do a dinner and I'll invite the 15 or 20 friends and we sit down and we talk. I'm always staying connected and in touch. It's not like, oh, I haven't talked to you in a year. No, I'm checking in on my friends a lot, finding out how they are. And always, I'm always checking in on everybody. I grew up just with my dad. My two sisters were older. They weren't around. My friends are everything I had. Before I had a family, my friends were everything to me. I'm lucky I get to work with some of my family, you know, Madonna's, I've been beside her for 36 years. The chili peppers are my best friend in the world's godfather of my first son is Anthony. The whole band, all of them flee Chad, John, their family. So it's a dynamic that I've chosen for myself is to really support and be around my friends a lot.”

    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

  40. “Much gave a lot of credibility to okay, this guy is she trusts him. Maybe we should trust him, maybe back in the day. But I think over a period of time, my house became the place that people would come to or people would congregate and feel safe. Even when I do events here or anything, there's not a lot of photos, there's no cameras. I think safety and support has always been in my DNA from an early age, just making sure that people are protected. And again, I think identifying really incredible people to be around. Same way identify the greatest companies to invest in. I think identified really amazing, incredibly talented friends who inspire me, who early days, you may not have known them 30 years ago, but you identify them. And they identify you. And so there's this camaraderie and there's this trust. And I do try to bring them all together a lot.”

    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

  41. “Well, I think it started early in my teens. There was a group of us that were running around and we found each other. So you find the other people who are also on the hustle, who are also creative. And I wasn't a comedian or musician or an actor or a director. I was like an executive. And there's a little responsibility. He's the responsible one. I don't drink, I don't do drugs. So I found my position was to really be a safe zone for people. And they knew I worked with Madonna, which”

    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

  42. “I think I approached it the way I approached everything. It wasn't let's think about it, it was like, I'm all in, let's go. I want to do this. Here's what I can do. And I think they were probably overwhelmed by, whoa, and we just ran. And he's awesome. What he's done with the company. We went public, I think, at like $2 billion and now it's at five. Like he's done an incredible job.”

    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

  43. “I have the only thing that I've torn out that's sitting on my desk is an article about coconut water. It's on my desk and it's like my to do. Like I need to figure this thing out. And here you are calling me. He goes, well, there's a company called Vitacoco out of New York. And I go, count me in. I got on a plane. I went to meet with the founder, Mike Kirbin. The company was, I think it was a $35 million valuation at the time. And I literally just, here we go. I'm jumping back in and I went in really big. I brought Madonna into that. I brought Demi Moore. I brought Matthew McConaughey, Anthony Kitas. I brought a bunch of people into this thing because they were all healthy people who drank coconut water. I'm like, let's blow this thing up. That was the first time back after the crazy run.”

    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

  44. “So we drink coconut water at the house, but the whole coconut water sector in America, if you added all the companies together was maybe a five or seven million dollar business, it was Nothing. But Madonna on tour on the previous tour, she would have the trainer would go in different markets to find fresh coconut for her, for the coconut water. And I'm like, wow, every location went to, I had to find fresh coconuts. And so I started to hear that other people were doing that as well. Other people who cared about their health were drinking coconut water. And I started to see, again, back to pattern recognition. I started to see this thing. And then one day the New York Post ran an article about coconut water. There's a photo of Giselle drinking from a coconut. And they're talking about coconut water. And I had cut that out. I put that article on my desk. And when Seth called me and said, have you heard about coconut oil? I go.”

    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

  45. “Exactly Yeah, yeah. He's done well for himself. And then he called me one day and goes, Hey, have you heard of this coconut water thing? So Course, I'd heard about coconut water. One, my wife is Brazilian, and my first son, his first words were like agua to cocoa.”

    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

  46. “A lot of the time. But I came back from, I think I'd done three Madonna tours in a row, all the money I'd lost made that back to survive. And then I had a window where I knew we were three tours in a row were going to take some time off. And I thought to myself, I didn't get it so wrong. So, I'm going to try this one more time. I'm good at identifying the ideas. I'm good at identifying the talent Going to do one more time so I started. And the same guy that brought me vitamin water, Sethrotski.”

    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

  47. “And so I went. So I got two out of the three. And the truth is it's not fair to Bill because he really built an incredible company and some of the stuff that he had built ended up becoming search for Google and a bunch of amazing things. But it just didn't work out. And that's life. Sometimes they don't work out these deals.”

    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

  48. “I should just stay in my music lane. But what happened was years later after my first Madonna tour, I started to think about it again. And I go, I wasn't so off, really. The timing was wrong on the ideal lab part. The other two worked. Had I diversified, I would have done fine. Incredibly well.”

    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

  49. “It didn't matter if I was sitting here with you right now back then, I'd be thinking about it. I'd have a conversation with you, but I wasn't thinking about you. I was thinking about how did I lose all my money on that one investment, everything I saved my whole life. And I ended up, I was mad at that Sky Dayton introduced me. I was like mad at all the wrong reasons. Everyone was just trying to help me. But now I'm like.”

    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

  50. “Bubble bursts so fast on all of that that Didn't have the heart to invest into. I never signed my deal with Jim Balsley in Research and Motion. And I never did my deal with vitamin Water, which both ended up almost like the whole and rage analogy. They both ended up being massive. And then I lost all my money with the first one. So I learned about diversification. I didn't diversify, put the majority of my money in one thing, and I paid the price for it. For the next two years, I only thought about that about 15 times a 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