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

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 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.

So when I met an artist and I liked them, Alanis Morissette 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.

That's Purple Rain lyrics by Prince.

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.

The place where I was living with my dad, an apartment building in West Hollywood, was directly across the street from a hotel called the 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 and years later. We became friends and became close.

It was 'Love God.'

And it was signed Prince.

That was a long time ago because he later on he became a Jehovah's 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 I come out a lot to meet. I met INXS and some people I became friends with like Billy Idol I became friends with years later and Michael Hutchence I became friends with and Morrissey 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.

Yeah, before Beverly Hills High School, I went to a school in downtown LA. It was on Pico and 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 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 KROQ, which is the alternative radio station in LA. And I loved them both. And so I met a lot of really cool kids there who were in these groups of people. There were like the punk rockers, the hip-hoppers, the break dancers, gang members, graffiti artists. Just a great eclectic group of people during that time period where I'm just 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 group that was performing that night. And I was waiting outside the school. I was very tall. I looked a little older than I was. And it was late. My dad was late to pick me up. And while I was out there, 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 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 at a 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 things as coincidences, but my dad showed up. I got in the car and I was like, you know, I almost died and someone pulled out a knife on me and you were late and I want to go to Beverly Hills High School next. And again, there's no coincidences 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. I don't know why I didn't put that together. I just said that to my dad and you know, we didn't live in Beverly Hills and he knew that's what I wanted and he heard me. 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 who I am today.

Blending the two worlds. One or the other, like without the other, would not have given me the perspective that I needed.

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 with pools and just the optionality and the potential of what they all had was pretty wild. 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, because 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 just didn't live that world. So I knew that I needed to do something about it. And I started to... I looked, 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 was obsessed over. And so I thought something in music. And that's 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 at 16 I was already like really running with it.

So Bernie Brillstein 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 Belushi, Garry Shandling, 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 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.

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 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 remember it was the week I turned 16 because I didn't pass my driver's test, so I needed to be dropped off. So, the week I turned 16, I went to meet with Bernie. What happened was 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 Brillstein. And his two boys, Nick and Dave, both told their dad, you know, 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 put this out?' And I knew not to pause because 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 $25,000. 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 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 want to take my money was Guy Oseary.' It's not true. I just didn't know what to do with it. So he made those three phone calls for me.

Yeah. I had no idea. I said, 'Three music business people.' He did, and I got meetings with a few of them, but they never ended up going anywhere. Going anywhere at all. But what ended up happening was 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 whatever, until someone 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.

The other was Freddy De Man.

So Freddy De Man, his daughters Nissa and Pola connected me with their dad Freddy. And Freddy was iconic as well. I mean he worked on Thriller with Michael Jackson. 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.

Meeting was after Bernie. And he just learned about me. He heard my pitch and I'm trying to do this, I'm trying to do that. And he knew I didn't really have any money.

Gosh, I think I was just showing him that I'm in the flow of music. I'm around music. I'm around artists.

Yeah. But one of the crews that I was working with was Ice-T. I got very lucky, got introduced by my friend Chris Boyd I met when I was working when I was 15 at Fred Segal. And Chris Boyd, another guy was working there and he's like, 'Oh, I know Ice-T 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 Ice-T goes, 'Come in, come into the booth and do a few words.' And I'm actually on the album. Yeah. He had me say a few words on the album. But I started hanging around and I'm like, what could I do? Could I clean up? Could I carry someone's bag? Could I, 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 then I ended up becoming the manager of Ice-T's DJ and his brother, Henji and Eively. Eively is Ice-T'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 a record label.' So he knew there was a guy named Steve Rifkind 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 Eively's brother Henji, and I said, 'Here's the music,' and he said, 'I know a label for you.' So he helped me get my first record deal. So I always write Freddy and go, 'Hey Freddy, I just got my first group signed. I'm a 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 because one day they're going to start a label. They didn't even have a name. They just knew they were going to do it. So I'm scouting. And then one day I find Hole, which is Courtney Love. I find their first song, 'Teenage Whore,' and I go, 'Oh my god, this sounds incredible.' I was just blown away by the sounds and the lyrics and all of it. So I reached out to the lawyer, Rosemary Carroll, and next thing I know, it's in the paper the next day. Madonna is trying to sign Hole.

I mean, I made a phone call. 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 Hole was doing at the Whisky. 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 whore, 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 Geffen Records, but my first artist I ever attempted to sign was Hole.

I think I probably asked five.

Yeah. I mean, I wasn't a 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 one person specifically saying, 'My dad doesn't do that.' Whatever, because it was rap I was trying to play. 'Oh, my dad doesn't do that.' So but I didn't have any shame. I just 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.

No, I went to college. I went for half a semester and I got my first group signed, which was Henji and Eively. And then 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.' Yeah. 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 had no choice. Sometimes having no options and no choice is really the best option.

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's possible. And I thought, 'Wow, not everyone is this lucky. Not everyone gets this opportunity.' And by the way, I was scared that they would kick me out because if they found out I didn't live there, they'd kick you out. So I had to watch how I went to school. It 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 need to pay attention to that. And I just realized that if I wanted to change my destiny, I needed to get going.

The Bernie Brillstein 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 because when I drove it to Beverly Hills High, it was a Honda Civic. When I drove it to Beverly Hills High, I got not one person commented or said congratulations or nothing. No mention of it at all. And then I went to my old friends from my old school and then they couldn't believe 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 was put in around this community for a reason, which is to work and which is to build my name and to build the things I want to do.' And it wasn't until years later I told that story in that thing you're talking about when I was 24 and 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 on a lot of the opportunities that were in front of me and to really appreciate them. So it's a combination of those things.

Madonna and I, the first real connection was that Hole connection where I was like, well, play me this thing that you like. And then the second artist I brought was Rage Against the Machine and I really wanted to sign Rage Against the Machine and so I took her to the concert in New York, the Limelight I think it was called, and I didn't get them either. I didn't get Rage. They ended up going with Michael Goldstone at Epic Records. So you know, God, the first two things I competed for I didn't get.

Yeah, it was painful. The third one that I competed for, I did get. It was called Candlebox. And at that time, actually, I think it outsold both 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 bet on me and we didn't have anything. We just had this idea, you know, they ended up selling 4 million albums on that album. But I'll never forget that. I'll never forget that they gave me that shot. That was my first success story.

Going back to that time period. First is the music. I saw them. 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 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 Whisky on Sunset and I walk in and these guys start performing. Now, there was a screen like a video screen on the side of the stage and then there's a stage and I was looking at the video screen. There were maybe like 30 people in the audience. It's a showcase and I'm looking at that screen and I saw thousands of people singing along to that band.

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 always starts with the magic. I don't care if you're a tech company or whatever it is, a film, a product, a book. Magic. You got to have magic. Something has to pull you in. And that night, I saw it. I visualized it. And the songs were there. The songs were so there that when we made the album, their first two singles, we could not beat the demo. They went in to re-record them for the album. So, whatever they made for a few hundred bucks that I had with a lot more money and a lot more time, we couldn't 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 a few years, 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 we really took that time week after week after week developing that one. That's how we got there.

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 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 had 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, Alanis Morissette 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 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, just be clear.' So it shows the artist the passion which is very important. This person believes in me that much.

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.

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 Alanis when she walked in my office with Glenn Ballard. They came in to play me. I didn't know what 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 gut. It was just like I love it. I'm ready to go. You feel it and you have to fall in love, right? And later today, I would say on my tech investing and what I do there, 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 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, you know, let's make sure the car actually shows up when you press the app and it picks you up and well 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.

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 Glenn Ballard. And they played me one song. They played a few songs, but the first song they played was a song called 'Perfect.' I didn't understand how powerful those lyrics were until later when I really listened to it. It's really about earning your parents'... like, do they believe in you? Do they love you? I don't know if you know the 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 Joni Mitchell.' I didn't know Joni Mitchell. So, to me, she was my Joni Mitchell. I never listened to Joni Mitchell before. I listened to it later because of her. I wanted to know what people were talking about. But to me, she was my Joni Mitchell. And I didn't know any of the background. A lot of people prejudged her because she had as a teen done 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.

I knew nothing. They walked in and I thought, 'Oh, wow.' It felt like a hippie group actually. I was like, 'Oh, maybe there's like some sort of hippie vibe kind of what is this going to be like kind of thing.' But it was again another life-changing moment when the story is told. It's that everyone passed. But I got it. 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, because 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 this probably is going to give me more opportunity to do more of these things. So she's such a big part of my life and she's so talented. How lucky that years later she's right now she's still winning awards. She's still out there crushing. She's actually doing incredibly well right now. 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 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.

I mean, there's some clear learnings and there's stuff that with I'm 36 years next to this woman. And there's things that when you look back, you go, 'Okay, you know, I got that like people who think about things that 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 that she's so surrounded herself with a collection of some of the most incredible people in the world and she identified them. By the way, she is the greatest identifier. She found these amazing talents early and was able to, whether they could be painters or Frida Kahlo or they could be designers or musical people, like she's an incredible finder of talent. I think the thing that has really affected me the most is that she doesn't see any kind of... there's no walls around her thoughts. There's no 'oh I can't do that.' Even going back to my first experience at Maverick Records, if you went to any record label, they probably would have put me in a compartment. There's the R&B department, there's a jazz department, the rock department, reggae department, pop department, hip-hop department, and you're, 'Oh, what department are you in?' And they sort of bucket you into these things. And I think that when I look back and I go, how did I not really bucket myself? If I went from this to this to that to that to that. And I think it's really just being around her has allowed me to never think in a limited way. And they all work together. A lot of the stuff I do on technology has allowed me to bring that into my musical world and to understand how these things work together or the relationships and they're so hand in hand. And of course a few decades later now people understand that. But at the time it was 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'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 rock star. I go, that person has music they want to share with the world, they have their album and my job is to identify that artist, that founder before everyone else maybe identifies them. And my job is to help you reach that audience. How do we tell the story? How do we reach the base of your audience? How do we grow your audience? 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.

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 start this film company.

I don't really recall that. I just recall thinking about how people do it differently. And so again, I didn't have context. The best thing sometimes is to have zero context. Sometimes fresh is okay. Sometimes having a blank canvas. And with films, I had a blank canvas. I didn't know how it worked, but I knew I wanted to make some films. And 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 I'll bring them in and house them and give them support and pay for a lot of the legal things that cost money. When you're independent 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 if I was to pay for them, I couldn't have afforded it. But we did it that way. And out of that came a lot of films and a lot of Twilight and Percy Jackson and a few others that I was very lucky to be part of. The guy who ran it, Mark Morgan, was really good at it, but there were a lot of complications. And I was at that same moment that 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.

Just that alone, just Madonna at that moment in time for someone I had not been a music manager for, you know, anything near that level. And so to take that on and to work on all things the tour and the album and all that.

It's a tricky question because no one manager is the same. Everyone's different.

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 Warner Brothers, which is where she was. She was on Warner Brothers but we were just friends and working together but I fed ideas. I found the director Jonas Åkerlund 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 Sednaoui the director introduced me to a producer named Marius de Vries. 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. 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, ideating. Here's things we could do. Here's things we could build. So I think for me that's the management that I am. I'm more creative. When I'm working with someone, I'm sort of in it. And there are other managers I've worked with who they really just 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?' or 'What if we...' There's different kinds of managers. I'm creative. For example, when I showed her Jonas Åkerlund 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 I showed her there's a guy named Chris Cunningham. He made a song called 'Come to Daddy' by Aphex 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 Åkerlund do Ray of Light. So, it was just a really great back and forth. We had really great energy together that she was open to my craziness and then she would take it to the next level.

She doesn't sit well on her past. She's not high-fiving herself. She's not really a 'Oh my god, I've done all these.' She just keeps it moving forward. Yeah, I think that that is, you know, part of the inspiration for continually trying to move forward myself is I have a front row seat or shotgun to this incredible journey of this woman who just continually defies all the odds and fights the fight. It is not easy. It's not that she's maintained or stayed around. It's actually that she's had to fight her way through it a lot. She's breaking ground for a lot of other people who are coming behind her who can say, 'Oh, Madonna's done it. I can do it.' But it is no easy feat. There is a lot of shit 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 day.

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. I 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 it took me a while, but I finally tracked him down and we went to have lunch at the Four Seasons Hotel 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 an incubator. And he's launched three billion dollar companies in one year.' And I go, 'Sky, I like you, but can you just get out of the way? I need to talk to this Bill Gross guy.' So, he sets me up with Bill Gross. Bill Gross ran an incubator called Idealab 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, I mean, the bad news is that I worked there for a year helping, and then one day someone I really trust — they don't know it to this day, but they're an incredible human. And I was lucky to sit with them at dinner one night, and they were telling me how Bill Gross is one of the greatest investments they've ever made.

So I called up Bill and I go, "Bill, I want to put money into 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 the 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 a really, really sweet guy. And that's the bad news. He let me do whatever I wanted.

It was before the crash. Right. It, by the way, it wasn't a year before the crash.

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 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 when I needed to and talk to them. And so I made a deal with Jim Bowsley to be an adviser because I was the guy that put it in everyone's hands. This is smartphones before anyone else was doing it. And then also my friend Seth Rossky brought me Vitamin Water.

So those were going to be my first three investments. What happened was the Ideal Lab thing — once I put that money in, and I don't know the timeline because I tried, it's almost like something you want to wash away from your mind, right? It collapsed.

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 did my deal with Vitamin Water, which both ended up — this is almost like the hole and rage analogy — they both ended up being massive.

And then 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. 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. I was mad that Sky Dayton introduced me. Like I was 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 have 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.

And so, I got two out of the three. And the truth 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 and, 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 were 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.

Exactly.

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 go in different markets to find fresh coconut for her for the coconut water. And I was 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 to-do, like I need to figure this thing out, and here you are calling me." He goes, "Well, there's a company called Vita Coco 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, 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 the first time back after the crazy run.

It's a public company today. I think it's a $4 billion market cap.

Yes. It takes time.