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

Honestly, I would say that [clears throat] 90% of the things I do happen in the first 5 minutes. 90%. It drives me crazy when we get in a room and talk about it for 3 months. And I respect process, but I think I know what I want to do very quickly. 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, and we didn't have any artists. Mhm. >> So when I met an artist and I like them, Atlantis Morris said I signed off of one song. Muse, I saw them perform one song. It shows the artist the passion which is very important. This person believes in me that much. 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. So, here we are sitting in this beautiful home and I wanted you to explain this beautiful calligraphy behind you that I was admiring. Some of the most impeccable handwriting I've ever seen. What is it that's sitting behind you? >> That's purple rain lyrics by Prince. >> Just incredible. >> I'm a huge fan of Prince. When I was a kid, I had Prince posters up on my wall and I met him when I was 12. >> 12? Yeah. >> How did that happen? The place where I was living with my dad, an apartment building in West Hollywood, was directly across the street from a hotel called a Park Hotel. And that's when I started meeting artists. I started becoming a fan. I love music, but I became a fan, you know, someone that would actually wait to get their album signed or, you know, and Prince actually signed something for me. He wrote Love God. I told him that years years later. We became friends and became close. Was it love God period or love, God? >> It was love God. >> Okay. >> And it was sign prince. >> Wow. >> That was a long time ago because he later on he he became a Jehovah Witness. >> But you could see the posters. I had like Billy Idol and Prince on my walls and you could see it from the street if you looked up. So you can come out if you're waiting for your car or whatever and you look and you'd see, okay, there's someone up there likes music a lot. I was on the first floor. There's a little balcony there and and I come out a lot to meet I met in excess and some people I became friends with like Billy Idol I became friends with years later and Michael Hutchkins I became friends with and Morrisy I became friends with later but I met them all when I was a kid and a really cool thing is other kids were around then. They were older than me but they were kids and so I could hang with them and really get a little camaraderie with some of the fans out there that were waiting for the bands. >> I want to talk about addresses and Beverly Hills High School. How did you end up at Beverly Hills High School and why? >> Yeah, before Hills High School, I went to a school in downtown LA. It was on Pico in Arlington. So, it's almost on the way to if you're going to go see a Laker game, it's on the way to that. And I went to that school and it was incredible. So many great people, different music was a big piece of that of my journey there. I took a school bus there and the kids would go between two radio stations on the bus. So the bus driver would play either KDAY, which was the first hip-hop station in LA, or they would go to K-Rock, which is the alternative radio station in LA. And I love them both. And so I met a lot of really cool kids there who were in these groups of people. The there were like the punk rockers, the hip hoppers, the break dancers, gang members, graffiti artists. There just a great eclectic group of people during that time period where I'm just I'm a sponge. I'm just picking up all the energies and really falling in love with music. One night I was outside the school dance. There was the LA Dream Team. That's what they were called. This this group that was performing that night. And I was waiting outside the school. I was very tall. I looked a little older than than I was. And it was late. My my dad was late to pick me up. And while I was out there, I saw I saw a guy running past me for his life. And then I see a car turn the corner. I guess he was chasing the guy down. and a guy jumped out of the passenger seat and pulled a knife out on me and and asked me if I was with that guy. >> He asked me if I was in a gang and I said, "I'm not I'm just a kid waiting for my dad. I was school dance and this is my school and so he got back in the car to chase the guy." >> And so, you know, there are no such thing as coincidences, but my dad showed up. I got in the car and I was like, you know, I I almost died and and someone pulled out a knife on me and and you were late and and I want to go to Beverly Hills High School next. And again, there's no coincidences that that just came to me right then and there that I want to go from downtown LA to Beverly Hills High and there was a TV show 90210 back then. So, I thought I want to check that out. >> That's a different world from the world I'm in now. I want to just see it. And I didn't know at the time, but you have to live in Beverly Hills to go to Beverly Hills High School. >> Yeah, it makes sense. >> Yeah. I don't know why I didn't put that together. [laughter] I just said that to my dad and you know, we didn't live in Beverly Hills and he knew I that's what I wanted and he heard me. He he came back to me and said, "There's someone who I know who lives in Beverly Hills and they will give you their address to basically pretend that you live there so you can go to that school that you want to go to." And the combination of going to school in downtown LA and also going to Beverly Hills High right after, I think that's a big part of of who I am today. >> Blending the two worlds. >> Blending the two worlds. one or the other like without the other would would not have given me the perspective that I needed. >> What was the perspective that you got once you were transported to this second chapter at Beverly Hills High? >> Once you walk through those doors, it might as well be a TV show from where I just came from. people have a lot, you know, there's cars and there, you know, there's homes [snorts] with pools and just the optionality and the potential of what they all had was pretty wild. And and that actually inspired me to, oh, I didn't know you can aim this high. I don't have what these people have. I don't have the means. I don't have the money. I don't have the connections. So, I better start working. I think at like 14 it really started to kick in where I go cuz these people are going they go on trips and ski trips and I don't know anything about skiing. I don't know anything about I I just I didn't live that world. >> So I knew that I needed to do something about it. And I started to >> I looked what what could I what am I good at? What could I be good at? And music was my love. It was my passion. It's what I I was obsessed over. And so I thought something in music >> and that's [clears throat] when I started to really pay attention to what could I do around music. I drew music. And then around 15 I really started to pick that up and and at 16 I was already like really running with it. >> So I think this might be a good bridge. If I'm missing something in between these points, let me know. I'm sure there's a lot that we could talk about. But Bernie Brilstein, who is that? >> So Bernie Brilstein is iconic in Hollywood. He's one of the greats. He was exceptional. He was one of the original managers and he managed all these amazing talents. A lot of the talents from SNL, he managed all of them. He started this idea >> John Belalushi, Gary Chandling, >> all of them. >> And he was beloved. He looked a little like Santa Claus. Was a really big guy with a white beard. And when I was 15, I started to compile artists that I liked that were had demos. So, I would go out there and try to find artists and try to find new artists. And I had like the yearbook person come and take photos of these. And >> this was on your own or were you working on your own? >> On my own. I didn't know what I was doing. I just thought, let me put together a portfolio. Let me have someone take photos of these artists. Let me create get the demos. One day I'll get a meeting with somebody >> and I'll have something to show when I get the meeting. >> Yeah. I'll have something to show. I think I called it Wise Guy Records. Just I didn't know what any of it meant, but I had my little logo. So, I did everything I could possibly do without knowing anything or anyone. And then the week I turned 16, I I remember it was the week I turned 16 because I didn't pass my driver test, [laughter] so I needed to be dropped off. So, the week I turned 16, I went to meet with Bernie. What happened was is I I approached a lot of the kids at school at Beverly Hills High and I said, "Can I meet your dad? Can I meet your dad? Can I meet your dad?" Just anyone that was in entertainment. And out of all the people that I approached, I got two meetings that would end up both being really the most impactful meetings I could ever have. And one of them, the first one I got was Bernie Burlstein. And his two boys, Nick and Dave, both told their dad, you know, you should you should meet with Guy. So I go meet with Bernie. He was at the 9200 building on Sunset. And I played him a song. I don't even remember what group or what it was at this stage, but I played him a song and he just says, he looks at me, he goes, "Well, hey kid, how much is it going to cost to to put this out?" And I knew not to pause cuz then he'd know I'm a phony. So I said, " $25,000." And he said, "I'll tell you what, kid. I'll give you the $25,000. If you make it back, pay me back. That's all I ask." And at the time, I'd never seen $2,500. So, I just said, "Bernie, I'd rather you make three phone calls for me to music people." And I don't want your money. I want you. And and he ended up putting that in his first book, that story. He's passed away, unfortunately. And he always felt I said no because I just couldn't take the money from him. I said no because I didn't know what to do with $25,000 and I was a phony. So until his last days, he always thought in his book, he's like, "The one guy that didn't ask that didn't want to take my money was Guy Oeri." It's not true. I just didn't know what to do with it. So he made those three phone calls for me. >> Did he pick the people to make the phone calls to? >> Yeah. I had no idea. I said, "Three music business people." He did, and I got meetings with with a few of them, but they never ended up >> going anywhere. >> Going anywhere at all. But what ended up happening was is I came back home and I thought to myself, "Wow, I'm 16 years old and this guy offered me as much money as people make a year in one meeting." If people feel they have talent, they don't know really. There's no confirmation on that talent. You know, people think, "Oh, my mom says I'm a good singer or so and so says I'm great at this." But you don't know until someone confirms it. until someone buys your book or goes to your show or or whatever until >> offers you 25K. >> On that day, that was a confirmation I needed that I'm on the right path. And I went, that's it. From this point on, I'm going to turn it up. I'm not looking back. This guy offered me 25K in one meeting. I just turned 16. I'm going to stick to this. I can do this. And many years later when I got my first gold record, I sent it to Bernie because that was so impactful on my life. >> You mentioned two meetings. >> Yes. >> Was the other Freddy? >> The other was Freddy De Man. >> All right. Who is Freddy De Man? >> So Freddy de Man, his daughters Nissa and Polar connected me with their dad Freddy. And Freddy was iconic as well. I mean he worked on Thriller with Michael Jackson. >> Wow. >> He managed Madonna. He managed some of the greatest artists of all time and 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. >> And this meeting was after Bernie. >> Meeting was after Bernie. And he just learned about me. He heard 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. >> Yeah. At that point, what was your pitch? >> Gosh, I think I just showing him that that I I'm in the flow of music. I'm around music. I'm around artists >> the portfolio. >> Yeah. I start but one one of the crews that I was working with was Ice Tea. I got very lucky got introduced my friend Chris Boyd I met when I was working when I was 15 at Fred Seagull and Chris Boyd another guy was working there and he's like oh I know I 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 Tea goes come in come into the booth and do a few words and I'm actually on the album. >> Wow. >> Yeah. He had me say like few words on the album. But um but I started hanging around and I'm like what could I do? Could I could I clean up? Could I carry someone's bag? Could I you know what? 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 and then I ended up becoming the manager of ICT's DJ and his brother who's Henji and Eively. Eve Lee is Ice Te's DJ. So, I managed them. It's 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 Freddy and said, "Fred, I just got my first group signed to record label." So he knew there was a guy named Steve Riiffken who I met who knew the record label. He helped me get that first record deal. >> So when I went to see Steve and I played him he's DJ Evelan Brother Henji and I said here's the music and said I I know a label for you. So he helped me get my first record deal. So I always write Freddy and go hey Freddy 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 was like, okay. So he brought me in as a, you know, scout cuz one day they're going to start a label. They didn't even have a name. They were just they just knew they were going to do it. So I'm scouting >> and and then one day I I find Hole, which is Courtney Love. I find their first song, Teenage [ __ ] and I go, "Oh my god, this sounds incredible." I just just blown away by the sounds and the lyrics and all of it. So I reached out to the lawyer, Rosemary Carol, and next thing I know, it's in the paper the next day. Madonna is trying to sign hole. How did that happen? >> I mean, >> would you ever >> I made a I made a phone call. [laughter] I was very naive back then, but it was like Madonna's trying to sign Hole. So, the next day, there was a show that Hull was doing at the whiskey. I think Kurt was there. Then Madonna was like, "Who's this?" Wanted to talk to me about who is this whole thing that you're think for a second. >> Yeah. So I go in a room and I play the song for Madonna and for Freddy and it's pretty wild. I mean the lyrics are like when I was a teenage [ __ ] my mother said she said baby what for? I was like whoa you got to go back to that like >> that time period. >> They're like okay all right so go go go after it. And so I went after it. I didn't get it. It was between us and Geffen Records and we didn't get it. It went to Geffin Records, but my first artist I ever attempted to sign was Hole. >> So, let me pause you for one second. >> Yeah. >> All right. So, the meetings that you got with Bernie and Freddy. So, you got two introductions. How many how many kids at school do you think you asked in total to end up with those two? >> I think I probably asked five. >> Okay. All right. >> Yeah. I mean, I wasn't 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 around five. I remember I remember one person specific saying my dad doesn't do that. Whatever cuz it was rap. I was trying to play. Oh, my dad doesn't do that. So but I I didn't have any shame. I just I needed I needed to figure this out. I knew that my time was limited before going to college and I better figure this out soon. So I was on a hustle. This is from an LA Times piece way back in the day, 1997. It says something along the lines of I gave myself a year, which is why I kept pushing people for a chance. Maybe that's accurate, maybe it isn't. But did you apply pressure to yourself in that way, like instead of going to college? >> No, I went to college. I went for half a semester and I got my first group signed, which was was just Henjini Vi. And then I I remember going to my English teacher. >> I don't know her name. She was 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. >> It's wild to think about these just chance. >> 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, I I had no choice. Sometimes having no options and no choice is really the best option. Where did the like hutbah come from? Right. I mean, just that drive. I mean, was that absorbed from the parents? Were you just out of the box, very different? >> I fell in love with music in a big way. >> But I think I realized how lucky I was to be at Beverly Hills High and see the potential of what was Yeah. of what's possible. And I thought, "Wow, not everyone is is this lucky. Not everyone gets this opportunity." And and by the way, I was scared that they would kick me out cuz if they found out I didn't live there, they kick you out. >> So I had to watch how I went to school. It was wasn't like an easy thing to do. And so I just thought for every day I'm here, I'm really lucky and I and I need to pay attention to that. And I just realized that if I wanted to change my destiny, I [clears throat] needed to get going. >> And at what moment did you realize, oh, I think this might just work out. I mean, was there a particular person or band you signed? Was there any flash point or was it really gradual? >> The 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. And I remember going to see my old friends from my old school cuz I when I drove it to Beverly Hills High, it was 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. >> Sure. And then I went to my old friends from my old school and then they couldn't believe they couldn't believe that I had a brand new Honda Civic and they got in the car and they were rolling down the windows 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 at Beverly, they're not really my friends. I'm here for a reason. I I was put in in around this community for a reason, which is to work and which is to build my my name and to build the things I want to do. And it wasn't until years later I I told that story in that thing you're talking about when I was 24 and my, you know, 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 a 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. >> And from the chapters we've discussed so far, I mean was then the next phase building your relationship with Madonna primarily or where did you kind of hop off past the things that we've already discussed? Madonna and I the first real connection was that whole connection where I was like well play me this thing that you like and then the second one 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. Well, not only did you not get them, but they went on to be >> Yeah, it was painful successes, right? >> Yeah, it was painful. The third one I that I competed for, I did get. It was called Candlebox. And at that time, actually, I think it outsold both Hole and Rage. They ended up doing really, really well. But regardless, Hole and Rage, even to today, I still listen to those. I love them. But I was very lucky to get Candlebox. The fact that they they bet on me and we didn't have anything. >> Yeah. >> We just had this idea, you know, they ended up selling 4 million albums on that album. But I'll I'll never forget that. I'll never forget that they gave me that shot. That was the my first success story was >> they give you a shot, but just to repeat what you just said, like you didn't have much, right? Like they were placing a bet on you. >> What then goes into helping make a hit album that sells 4 million? >> Going back to that time period. >> Mhm. >> First is the music. I saw them. I 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 was supposed to be somewhere else that night, but I went to I went to this party. 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 and I walk in and and these guys start performing. Now, there was a screen like a [clears throat] like a video screen on the side of the stage like and 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. >> In your mind, >> I just in my mind. Yeah. But I went to the pay phone from that performance, called Freddy and said, "Fred, I have our band. This is the band. I just saw them. This is the one." And so it starts with that. It starts with always starts with the magic. >> I don't care if you're tech company or whatever it is, a film, a product, a book. Magic. You got to have magic. Something 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 into re-record them for the album. So, whatever they made for a few hundred bucks that that I had with a a lot more money and a lot more time, we couldn't beat. 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. They chipped away. They did show after show after show took took few years for every week. Every week little by little little by little keyword is artist development and people don't always develop that much but it's something that we all want. Every artist wants to have the time to build have the time to develop and and we really took that time week after week after week developing that one. That's how we got there. This is maybe jumping ahead too far, but what would be an example of that in your investing later? Could be tech, could be outside of tech where you saw something or you talked to someone and it was within a matter of minutes or one conversation. You're like, okay, that is that is a horse to bet on. Honestly, I would say that 90% of the things I do happen in the first 5 minutes. 90%. It drives me crazy when we get in a room and talk about it for three months. And I respect the process. I know there is a process to these things, but I 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 was so boutique and we're competing with these big companies that have been around forever and have all these other artists and we didn't have any artists. >> So when I met an artist and I liked them, Atlantis Morris said I signed off of one song, Muse. I saw them perform one song and I stopped them after the they flew all the way from London to LA to showcase for me and I 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." I go, but I just want you to know I do not need to hear another song that just be clear. So it shows the artist the passion which is very important. This person believes in me that much. >> High conviction. Yeah, >> 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. So, in any of those examples, and I know this is possibly very hard to verbalize, someone said to me recently, and I thought it was pretty funny. They're like, "Yeah, in Silicon Valley, if you say you're using your intuition, nobody listens. But if you say pattern matching, then they pay attention." But if you were trying to explain what you intuited or noticed in that one song, understanding the music is good, but what else are you picking up [snorts] from those five minutes? because you can't bet on everything, right? Especially as a small label. So, what were you picking up on that allowed you to make a fast decision in that way? >> Uh, well, I have to fall in love and you know, you can't fall in love every 5 seconds. I didn't know I was going to fall in love with Atlantis when she walked in my office with Glenn Ballard. They came in to play me. I didn't know what that was going on here. I thought they were a band. He was the producer co-writer. You just have a feeling and there is a lot of pattern recognition later. Like now with experience, >> now I bring other elements into the mix, other things I'm looking for >> that are different than back then it was just I was just gut. It was just like I I love it. I'm ready to go. You have I feel it and you have to fall in love, >> right? And later today, I I would say on my tech investing and what I do there, it's a it's a combination of gut, a combination of pattern recognition. And then there's a few other things like one of the things I look for is can I help it? I visualize what I can do for the company and that gets me excited too. >> So I go, oh wow, okay, I have a feeling I can help in a big way or I have a it starts the 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 that you know let's make sure the car actually shows up when you press the app and it picks you up and it well [clears throat] make sure the things work. Make sure that you can stay at the apartment and it's actually oh I press the thing and I can get an apartment. >> These things have to work. >> But for me it all starts with that initial pitch. >> How does Alanis Moriceet fit into your life? Seems like an important piece of the puzzle. Yeah, she played a big role in my life. She was the rocket ship. It just took me to the next level. She appeared in my office with her with Glenn Ballard. >> Mhm. >> 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 when I really listened to it. Mhm. >> It's really about earning your parents' like, do they believe in you? Do they love you? I don't know if you know lyrics, but sometimes it's 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." I didn't know anything. Remember, I didn't know that comparisons where people were like, "Oh, I thought it was Joanie Mitchell." I didn't know Jonie Mitchell. So, to me, she was my Jonie Mitchell. I didn't never listen to Jonie 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 she was my Jonie Mitchell. And I didn't know any of the background. A lot of people prejudged her because she had as a teen did like a pop album in Canada. And so people had all this background. I had no background. I literally was asked to meet with her and Glenn and I knew nothing. >> All you had was that meeting. >> I knew nothing. They walked in and 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 got it. I got 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, you know, cuz not only did I sign it, but everyone else didn't want to sign it. So it's not like I even competed. So it really cemented that, okay, I'm in a good place right now that I can do these things and I 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 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. And 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 that meeting and to have figured it out. A lot of people when they initially heard it, I remember Freddy 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. The rest is history. Rest is history. 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. 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 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 and was able to whether either could they be painters or Freda Ko 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. >> Right. in terms of constraints, right? >> 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, hiphop 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? if 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 handinand 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 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? 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 fora 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. Why did that come to mind? >> 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 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 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. >> Hard to ride both of those horses at the same time. >> Just that alone, just Madonna at that moment in time for someone I had not been a music manager for, you know, and anything near that level. And so to take that on and to, you know, work on all things the tour and the album and all that. And for people who have no context on music at all, what does a music manager do in that type of situation? >> It's a tricky question because no one manager is the same. Everyone's different, >> I guess. What was your umbrella of responsibilities? >> When Madonna started working on Ray of Light, I found the producer, William Orbit, but I was not managing her. I was her partner at the record label Maverick Records and not her own not Warner Brothers which is where she was she was on War Brothers but I was just we were just friends and working together but I fed ideas I found the director Yonas Aland and so I was creatively really working on this project called Ray of Light. So we're already building a creative rapport and on music Stefan Sidenway the director introduced me to a producer named Her Ways. He 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. >> Mhm. >> 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, but I was coming from the creative point of view on ideas, ideulating. Here's here's things we could do. Here's things we could build. So, I think I think for me as that's the management that I am. I I'm more creative. When I'm working with someone, I I'm I'm sort of in it. And there are other managers [clears throat] I've worked with who they really just they don't do the creative but they do an incredible job managing everything keeping you know putting together the tour but they're not in there going what if we did this of you know what if we there's different kinds of managers I'm creative for example when I showed her Jonas Arland did a video for Prodigy which is a band I signed and it was really provocative and I just showed it to her this guy this is crazy and she goes he's doing my first video or or he's doing that like you I showed her there's a a guy named Chris Cunningham. He made a song called Come to Daddy by AEX Twin, which is really insane. It's a $30,000 video. I just showed it to her just to show her this. 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 Aland do Ray of Light. So, it was just a really great back and forth. We had really great energy together that I she she was open to my craziness and and then she would take it to the next level. What and and this is this is my even when I was very very young and everybody knew Madonna. I was constantly impressed by her longevity and ability to seemingly reinvent herself. And I'm just wondering why you think she has been so consistently good at that over decades. I mean, it was the first example that I remember even as a young pretty young kid be marveling over and I'm just wondering if you could add any any color to that. She doesn't sit well on her past. She's not high-fiving herself. >> [laughter] >> She's not really a Oh my god, I've done all these. She's just keeps it moving forward. Yeah, I think that that's a that is, you know, part of the inspiration for continually trying to move forward myself is I'm 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 it's not just like 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 a lot of [ __ ] to deal with. >> And I think it comes from she just doesn't celebrate her accomplishments. She just starts like it's a brand new a brand new day. >> How did you end up and I don't know if this is a good starting point but I'll throw it out there as an example. Your first consumer investment vitoo well done. >> Thank you. Uh, I don't know if that was your 10th investment overall or your first, but how did you end up edging into the world of investing, whether it was CPG and consumer stuff or tech? How did that even come to be? Wow. Well, the original original original was I was on a plane to Milan for an MTV Awards and I don't remember how old I was. was in my 20s and I was reading in a magazine about Sky Dayton and it said he started Earthlink and he was worth $100 million and he was really I'm like wait what you can wait what is he doing and how old is he? 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 at Four Seasons Hotel and and he was like, "Wow, if you're impressed by me, have you ever heard of Bill Gross?" >> And I go, "No, who's that?" He goes, "Well, he started a incubator." >> Mhm. >> And he's launched three billion dollar companies in one year. And I go, "Sky, I like you, but can you just [laughter] can you get out of the way? I want >> This time has been great." >> Yeah. 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. Reminded me of the record label where you had all these artists and you had all these project managers >> or the independent producers >> a version of that and you can walk in and out of different rooms and you can say, "Oh, 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 >> and 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 the story, but as like all things, it worked out in the end. >> Well, wait a second. >> My listeners gonna kill me if I don't follow. What's the bad news? >> Well, I mean, the bad news is 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, but they're 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 I called up Bill and and I go, "Bill, I want to put money in into Ideal Lab." And he goes, "Well, you know, I was going to surprise you and I was going to put, you know, X dollars in for you from bottom 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, by the way, it's 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. And he did. He's he's really really sweet guy. And that's the bad news. I he let me do whatever I wanted. >> What year was this? >> It was before the crash. Right. It, by the way, it wasn't a year before the crash. >> I think it was like an hour before the crash. [laughter] >> Okay. So, I put every dollar I have plus dollars I didn't have. >> I picked out three investments at that time. Ideal Lab because of Bill Gross. Bill was the first guy in I think in 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 and so I made a deal with Jim Bowsley to be an adviser because I was 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 Rossky brought me vitamin water. >> Yeah. >> So those were going to be my first three investments. What happened was is the ideal lab thing once I put that money in and I don't know the the timeline cuz I tried it's almost like something you want to wash away from your mind, >> right? >> It collapsed. >> Fever dream you're trying to forget. >> The bubble burst so fast on all of that that I didn't have the heart to invest into. I never signed my deal with Jim Bowsley and Research in Motion. And I never and I never did my deal with Vitamin Water, which both ended up, this is almost like the the hole and rage analogy. They both ended up being massive. >> Yeah. >> And then I and I lost all my money with the first one. So I learned about a lot. I learned about diversification. >> I didn't diversify. I put >> the majority of my money in one thing >> and I paid the price for it. I really for the next two years I only thought about that about 15 times a day. [laughter] It didn't matter if I was sitting here with you right now. Back then I'd be thinking about it. I' I'd have 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. I was mad that Sky Dayton introduced me. Like I was like mad at all the wrong reasons, you know? >> Everyone was just trying to help me. But now I'm like, why did I even read that magazine? I should just stayed in my music lane. Yeah. >> So, 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. >> I was off. The timing was wrong on the ideal lab part. The other two worked. Had I diversified incredibly well. >> Yeah. You would have been great. >> And so, I got two out of the three. And the truth is is, you know, 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 >> a lot of the time >> I think I had done three Madonna tours in a row so I came back at my you know all the money I'd lost I made that back to survive >> and then I had a window where I knew we were three tours in a row we're going to take some time off and I thought to myself I didn't get it so punk. So, I'm going to try this one more time. I'm good at identifying the ideas. I'm good at identifying the talent. I'm going to do it one more time. And that's when I So, I started and the same guy that brought me Vitamin Water, Seth Rossky. >> Did he later work with Reese Witherspoon? >> Exactly. >> Huge. >> 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, of course, I'd heard about coconut water. One, my wife is Brazilian, and you know, my son, my first son, his first words were like, "Awa to cocoa." 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 business. It was nothing. 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 like, wow, every location we went to, we 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. 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 Jazelle 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 water?" I go, "You have to be kidding me. I have >> sitting on my desk. >> 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 todo like I need to figure this thing out and here you are calling me." He goes, "Well, there's a company called Vita Coco and out of New York." And I go, "Uh, count me in." I got on a plane. I went to meet with the founder, Mike Kurban. The company was a 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. And I brought Madonna into that. I brought Demi Moore. I brought Matthew McConnA, Anthony Key. 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." And that was that was the first time back after the the crazy run. >> For people who don't know, how did that turn out? >> It's a public company today. I think it's $4 billion market cap. >> So you were back in the game. >> Yes. It takes time. >> It takes time. Yeah. Didn't happen overnight. >> What were you looking for? How would you replay that meeting with the founder in your mind? You fly out, you meet with the founder. How did you approach that meeting? >> I think I approached it the way I approached everything. It was 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 and I think they were probably overwhelmed by whoa. Okay, let's and we just ran. He's awesome what he's done with the company. We went public I think at like two billion and now it's at five. Like he's done an incredible job. So, we're going to hop to some more recent examples which may or may not include this chair in a moment, but I want to focus on a term or phrase that I've seen applied to you a lot, which is great curator of people. Chris Rock has said this. Matthew, you just mentioned said this. Woody Harlson have have all described you in this way. And you seem very intentional with the people you surround yourself with. Not only that, but you have these very long-term relationships with a lot of people. And I'm wondering how you think about building relationships. I'm not saying you have to come up with the guy's ten commandments of long-term relationships, but how would you think about that? Right? If you're in front of a class of students and you're like, "Look, a lot of people get this wrong." Or at least let me tell you how I approach relationships. like any any particular rules that you use for yourself or just approaches, things you keep in mind because that's certainly not true for everybody, right? You just have this long-term cohesion of these people around you. And I'm just I'm wondering if you can perhaps just speak to that in any way. Well, I think it started early in my teens. There was a a group of us that were running around and all we found each other. >> So you find the other people who are also on the hustle who are also creative. I wasn't a comedian or musician or an actor or a director. I was like an executive. >> Mhm. >> And there's a little responsibility. He's a responsible one. I don't drink. I don't do drugs. So I I found my position was to really be a safe zone for people and they knew I worked with Madonna which pretty 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 you know even when I do events here or anything there's not a lot of photos there's no cameras like I I think safety and support has always been in my DNA from an early age of just making sure that people are protected and again I think I identifying really incredible people to be around same way identify the greatest companies to invest in like I think I identified really amazing incredibly talented friends who inspire me and who've been who you know early days may not you may not have known them 30 years ago but you identify them you they identify you and so there's camaraderie and there's this trust and I do try to bring them all together a lot. I I think it's important. >> That was going to be actually my next question which is along those lines which is how often do you gather people whether it's at this house or at events that you put together just to facilitate that long-term cohesion. How how often do you organize or host things like that? >> A lot. I think I even 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 and we So, 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. >> I'm finding out how they are and always we're I'm always checking in on everybody. >> Mhm. >> I grew up just with my dad. My two sisters were older. They weren't they weren't around. So, my friends are really like they're my they're everything I had. I didn't 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, my best friend in the world's godfather of my first son is Anthony. The whole band, all of them, Flee, Chad, John, they're family. So, it's a dynamic that I've chosen for myself is to really support and be around my friends a lot. It's a big part of my life, which is to keep that close. And again, if someone's in need, you know, this is the number. Call me. I want to hop back to the investing. I mean, you've you've had a lot of hits. Airbnb, Uber, Spotify, it goes on and on and on. I mean, I don't know how many IPOs and so on that you've had. I mean, gazillion. Let's talk about one. So, you put in, tell me if I'm getting this right, 35 million at a 5 billion valuation into Anthropic. This is a company that's been in the news a lot. I think the last round was what, 965 billion, something like that. Are those numbers roughly accurate? >> Yes. >> Okay. So, that's pretty nice multiple so far. You know, we'll see how things go. How did that anthropic deal happen? Well, it starts a little before the day that OpenAI came out was on my dad's birthday, Chat Chippy PT. It was life-changing. And I 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 Chhat GPT came out, that was a what is this moment for me. And if you saw me any time after Chat GPT came out, I would have harassed you to show you Chat GPT. There's no one, every artist, every actor, everyone I walked around and met. I'm 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. Open AI. We're doing OpenAI. This is the greatest thing I've ever seen. We have to do it. I have to do it. I have to do it. And so that was our first this is the one we're going to go after. But then 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 anyone would have done well at that time. We were like lucky people that came in at the right time and were looking at the right time and started our fund at that very moment, 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 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 3-month window. We told people we have a three-month window. Now, it came out November 30th of 2022. So, there's not much you can do. This people are going away. There's this 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." >> I got it. LPS mean. >> Yeah. Raise money. Raise money and create this fund, which is which was a crazy idea at the time. >> Now, had you already confirmed that you'd be able to get allocations or you just had complete confidence? >> Ashton spoke to Sam, we were able to get OpenAI. What happened was is I'm very close to Mark Beni off and Salesforce ventures. People don't really understand how smart they are. They don't get >> They're really smart. >> They don't get all the press on. They are one of the best investors in the world. There's two guys there, John Simari and Paul Drews, who were when I was doing my research cuz now I'm on the I'm on the lookout. What should I know about an AI? Once I find out about something, I just lock in. So, and and I want to know everything about it. And I I was 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 like a job hunter kind of people who help find jobs for people. >> Oh, like head hunters. >> Head hunters that everyone's going to this company called Enthropic, you know, like people are really going to this anthropic place and they're not going anywhere else. I'm like, whoa, okay, I I need to pay attention. So I I asked Paul and John connect me with with this founder Dario. So they connect me with Dario and Nero. They come here in this room and that's where we made the deal to invest in 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 have come out since. >> But we we set ourselves up for exactly what we did. this is going to be within 3 months. We're going to deploy 80% of the money within the next 3 months. And that's what that's what we did and that's over 3 years ago. >> How did you know the window was going to be so narrow? Right. I imagine did you get any push back from LPs when you said we're going to deploy 80% of this in 3 months? >> Well, we didn't have there was no LPs, meaning we just it was that was the pitch. >> Yeah. Yeah. >> So, it wasn't like we it wasn't like we raised money. >> They either bought in or they >> Yeah. It wasn't like we raised money and then told them the pitch. It was like here's the pitch. >> Here's what we're going to do. There's a window of opportunity here. We think this is the future and that was it. >> They had opted in. >> Yeah. Opt in or opt out. We didn't know what we were going to raise. It just whatever came up is what it was going to be. >> So I was trying to pull from memory, but looks like sound at this point is that 86 exits and 26 IPOs. That's insane. I mean that is >> it's been fun. [laughter] >> You have seemingly different batteries certainly. I mean, you've got good batteries. What is the next 5 years, do you think, look like for you? I mean, is it is it more of this type of investing? What do you see? Is it switching gears entirely and looking at the prison through a totally different way? I mean, what is what is next for Guy? I feel like going back to the core, really honing in that antenna for 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 in the quickest ways. And I'm excited about the potential of what's to come. I've already identified three things I want to do today. So, I can only imagine what's to come. But it's just really just I don't 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 and pick the teams that you want to back. >> So, I I I'm I'm feeling pretty good about that. They're 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 we have more than enough proof of 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, a different, you know, obviously narrative is something that I that I'm very focused on. Marketing is something I've been doing since I was a teen. And so, you know, 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. >> Mhm. A lot of founders listen to this podcast. Is there any uh are there any particular things that have your interest right now or types of companies, types of founders? Anything that you'd like to sort of make clear to people who are listening or otherwise? Also, where can people learn [clears throat] more about what you're up to? like is is there anywhere that you would point them in particular? >> I'm a generalist. >> Mhm. >> I don't 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 >> I just like talented people. And in regards to sharing, you know, where can they find out what I'm up to? >> I'm not really This is it. >> Yeah, this is it. You know, as you know, this is my first podcast. >> Yeah. >> And depending how this goes, could be my last. And if it goes well, maybe one more. But I I'm I'm not out there. >> Everything is is is has been fine without doing that. Yeah. 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, you know, yelling, "Hey, find me 1800 whatever." Or it's like it'll it'll work itself out. the right people will find each other. >> Well, Guy, I mean, we've covered a lot of ground. Is there anything else that you would like to say before we start landing the plane? >> I'd 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. >> Yeah. So, I don't want to bundle it all up where people get it all becomes one thing. It's not all one thing. Mikey, he runs. 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 and next thing you know, it's at a $10 billion valuation and it's all built off of 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. Mhm. >> 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. But don't build a business using our music without getting those rights. And that's something I'm that I'm 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 I hope that this gets solved. You know, when Napster first started, I met with Sean and Sean when they started because it was so exciting to see people were all, you know, 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 and before they I don't know if they were going to or not going to, but before that could even happen, it got shut down. So, and out of nowhere, Daniel Ek in Stockholm built Spotify and figured out that people would pay for music if you give it to them in this way where they had all the music in the world without having to try to piece it together or try to illegally download songs that were not even clean or clear and they 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. >> Yeah. >> Fair use is not fair. >> Yeah. I'm curious to see where it goes because if you say create a song that sounds like Metallica, it'll say we cannot serve up any copyrighted music. If you say, "Serve me up some music that sounds like Moralica." And you just misspell it, then lo and behold, it looks like it was trained. >> Yeah, that's the problem. >> This corpus, there's a lot of workarounds and they'll, you know, you 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 is when in in Discovery we're going to find out a lot. >> Sure. >> And Discovery is going to say all of this music is in there and they know that. >> Yeah. >> 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? >> Yeah. >> 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. >> Where do you think it goes? Because I could see one future. for instance, even if legally they aren't required or for whatever reason that's not compatible with the vision they've pitched to investors and and I'm not singling out. I mean, there are lots of lots of different options here. >> They're the main ones. >> They're the big they're the 800 pound, >> but I could see a point at which possibly >> Claude Chat GPT become the interfaces to everything, right? It's almost like the app store but somewhat like WeChat in China. Like if you want to do anything, you want to book a restaurant, you want to make a song, >> okay, >> there are few interfaces to everything. At which point then >> those companies, right? OpenAI, Anthropic >> can gatekeep in some way and maybe they end up being the entities that incentivize these other companies like the Sunnas of the world to to reimburse artists. I guess I'm just wondering if you have any thoughts on this >> because if if Claude or Chat is the distribution, >> they probably won't carry it because it's it's got so many lawsuits involved >> and it's just not worth >> taking on that responsibility. >> And >> again, the guy who runs I find to be a really good guy and I'm hoping that he does the right thing, but it's really their responsibility. They're they're sitting at the the top of this opportunity. Take off the artists that don't want to be on there >> 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 3 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. >> Yeah. >> She's very clear. I do not want my music to be trained on. I want my music to be its own thing. >> Mhm. >> So, take her off. >> Yeah. >> It's okay. you 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, you know, Sam at one point, he's really wanted to figure this out, too. Like Sam was a lot of people give my 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. >> Yeah. Yeah, I mean there may be someone who comes along also if it's not Sununo. Someone who comes from behind like a next generation Spotify >> and figures out how to do it. >> Spotify can do it. >> Yes, more Spotify can do it. >> Yeah. >> You mentioned there were three things that you'd like to do today. I'm not going to ask you to name those things, >> but how did you find those things or how did those things find you? >> Right. one of them. Well, 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. And I'm able to ask investors what companies >> that they're looking at and and so >> two of those came from that >> conversation. Good good information. >> Yeah. They're like, "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 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 on X that's flying by. So, it's sort of my my start of information. >> You mentioned missing Blackberry and Vitamin Water. Do you have And this could go way back in the catalog. Could go back to being 10 years old. There's there's no limitation here. Any favorite failures or parent failures, meaning failures that taught you a lot or that set you up somehow for later success? >> There's it's endless endless. You know, uh, one of the things that Ashton is really was really good about not looking back like that. He 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 and my I had it and we had it and we and he's like, come on, just move. Let's go. Let's go. He's like, he always gives me like, oh gosh, he's going to complain about not being in a but 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. >> Yeah. I mean looking back right it seems like >> in [snorts] some ways like missing hole missing fill in the blank was almost a prerequisite source of fuel. >> Yeah. >> For the things. >> Yeah. It's scary though. It drove you towards the >> It's scary though when you miss it. I, you know, when Ash and I invested in Bitcoin on our own, you know, when it was at $22 [laughter] >> and then it when it hit $250, I thought I just made 10 times my money. >> Yeah. Yeah. >> I'm a genius. So, I sold then and clearly not a genius. So, that hurts. And I remember um Anthony, gentleman on that wall. >> Mhm. >> Elon invited Anthony from the Chili Peppers to see SpaceX. Early days. >> Yeah. >> Very early days. >> And I went with Anthony. I tagged along. It's the first time I met Elon. When 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 to go what business model I didn't even ask those words. I was just, you know, sometimes I go to shows like I've seen shows where people are so wowed that they're just like they're like this from a show and they they didn't even take in all the songs or 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 did not understand that there was a business model and I really wish I just would have asked one more question like >> 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. >> I want to talk about the longevity for a second. you mentioned, and fact check me if I'm getting this wrong, but like the three was it back-toback tours with Madonna. >> I mean, that sounds impossible just from a the demands of the the physicality of that and she's kind of legendary, of course, for her >> training and [snorts] endurance and everything else, but for you personally, what were the keys to end enduring that and being able to function at a high level for that? >> I think it's different as the years go by. There was a point around 10 years ago, 11, 12 years ago where I was, it was a lot for me. I was also changing and growing and having kids and I was just sort of losing myself cuz you're really in a you're going to a different city every other day. >> And the amount of things you're missing back home, you sort of you sort of, you know, forget you have a family. You forget that you can go do other things. or you forget to call back Stripe or you forget to right all the things you just 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 oh I have kids I have a house so if you look at the first three tours those three tours that I did those are 240 shows 80 average I [snorts] 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 I wanted to be home with my friends. So, my 40th birthday spent here in this house. So, I missed three shows out of 240. But we're talking about a different city, a different hotel, a different and you 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 is otherwise if you think about back home or your family or other things, it hurts. So, I just go, "Okay, I'm off and I'll see you. I bet I bet it's what actors do when they go away and make a movie for 3 months and then they come back. >> They probably just compartmentalize a little bit, but you know, in the last few years, I've I've stopped doing as much. I still go, but not as much. I've I've went it down. There's a moment there where I managed the Red Hot Shield Peppers, you two and Madonna. They're all going on tour. It was a lot to >> process. How do you even make decisions about where to be in a case like that? You can't be in three places at once. It's hard, but it sort of tells its own story. You, you know, 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. >> So, if you look at let's just say the last 10 years. >> Yeah. And presumably a lot of your focus is on the investing. How do you mind the different responsibilities if that makes sense? >> I think when I when I think of responsibilities I always think of management. That's a really big responsibility and I don't take it lightly. >> Mhm. >> This is just there's no way around it. That's that's something's going on there that's a focus. It is cyclical. >> Mhm. >> So like the Peppers are not touring this year. They don't have an album this year. They aren't touring next year. They don't have an album next year. So, you know, there's there's a lot of time in between and they're going to where they're coming up with the creative. They're going to make an album. They're going to do all the things. They're going to write songs, right? So, that takes time. So, you get these windows of opportunity where you go all in and you get windows opportunity where you have a moment to breathe just like they do. They all need it too. Madonna after the cycle will probably need a minute to just sort of catch her 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 and which is continually be creative through other ways. >> And so when the cycle starts, my creativity has never stopped. >> Mhm. >> So that I still have those things. I'm I'm not starting from scratch. I'm I'm always looking and meeting with people and understanding what's going on in technology. And so when when Madonna comes back into cycle, I can bring some of those ideas or some of those new relationships I met while she was off. >> And so I just I found a way to to to make it work. Maybe I'm sure misquoting, but roughly paraphrasing much earlier in the conversation. And I feel like you said part of Madonna's ability to reinvent was not resting on her laurels obviously, but not patting herself on the back for what she's done and sort of marching forward. >> And I'm wondering how you've thought about for yourself the drive and velocity of forward-looking achievement versus sort of appreciating what has been done or savoring the time that you have. I mean, I imagine you get a lot of that with congregating friends and so on, but I'm wondering if you have any thoughts. >> You know, my friends and I don't spend a lot of time talking about what I do. >> A 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. Like, I think I just keep it moving, too. And again, I 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 and you know, maybe one day sometimes when I'm telling my kids a story about the past or someone asks me a question and I tell them about the past, I go, "Oh my god, I forgot I even did all those things." Or I see something pop up and I go, "Oh, I was I I you know, I was there for that." And but I really don't think about it that much. Things pop up every now and then. When I wake up tomorrow, I'm like, I haven't done anything today. I better figure it out. [snorts] I need to step my game up. That's how I feel. I don't feel accomplished at all. I feel like I still have so much to prove and so much to do. Well, at the same time, I do know if I if I really took a minute, I would go, "Oh, wow. Okay. Oh, that's Oh, I didn't I should probably >> take a moment and take that in." But I really don't. >> Is that okay? Is that a problem? Is it fine? >> I just keep it moving. I I don't know. You know, at some point, you know, there I I can visualize being on the beach and and, you know, high-fiving with my friends and having fun. >> But I I again, I don't they don't do it either. A lot of my friends were we don't talk about it like that either. I mean, >> I think we just sort of >> how cool that we're survive this period of time. How cool is it that we're even able to do what we love? Mhm. >> Waking up and being able to do what you love. There's a Josh Kushner quote that 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. >> Yeah. >> And I got that. I'm excited to go to work and I'm excited to go home. That's pretty cool. >> Yeah. >> And 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 cuz I go this is not a given. you know, the potential and the 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. Like, 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. So after 20 years, you and Ashton are going to be doing different things, it sounds like, and I was wondering if you could just share a bit of the background and what that looks like. >> 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? >> And you know, between the investments in Open Eye, 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 do we want to do for the next 10 years? What makes us happy? What what are we going to get enjoyment out of doing? And it's a really strong question and we all gave it some thought. This is a few months ago. We we we looked at each other's visions of what he wanted to do that make him happy and what he wanted to build and what I wanted to do and and then 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 pretty awesome vision >> it's an incredible vision and the guy is mind-blowingly smart and talented And I support that vision for him. >> Mhm. >> It isn't my vision. >> And I will support it financially and I will support it with energy. I want him to win. And then 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. But it's a new chapter and I've had many new chapters my whole life. I went with the record label for a certain time and then I moved on. I went to music management. I went to crypto and I went to film. I mean, I have so many different chapters in my life that this is a beautiful chapter that is we're in a celebratory mode. >> Mhm. >> 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. And so this decision was made out of joy and 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 he wants to do it. I'm very specific I want to do. Effie and I are going to continue on with sound and what we've built the last 10 years with sound. So we'll continue to build that. And then 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. >> Guy, this has been a wide-ranging conversation. What a life. What a journey. And it's not over. Obviously, you got lots of battery left for what's ahead. Thank you for the time. >> Thank you. >> Thanks for inviting me here. >> My first podcast. >> I know. I know. Mine, too. [laughter] Your first podcast with me. Yes, >> exactly. And people can find you on Instagram XGO Siri, no apostrophe. Guy O S E A R Y. And we will link to everything in the show notes as per usual at tim.blog/mpodcast. And until next time everybody, thanks for tuning in. Be just a bit kinder than is necessary to others, but also to yourself. Compassion is not complete if it doesn't include you. Thank you, Jack Cornfield. And as always, thanks for tuning in. Thanks, Guy. >> Thank you.