Please enjoy this transcript of my interview with Guy Oseary (@guyoseary). Guy has managed some of the biggest names in music, including Madonna, the Red Hot Chili Peppers, and U2, and was named Variety‘s Music Mogul of the Year in 2022. He co-founded A-Grade Investments and then Sound Ventures, now with nearly $2 billion under management.
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Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First
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Tim Ferriss: 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?
Guy Oseary: That’s “Purple Rain” lyrics by Prince.
Tim Ferriss: Just incredible.
Guy Oseary: 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.
Tim Ferriss: Wow.
Guy Oseary: Yeah.
Tim Ferriss: How did that happen?
Guy Oseary: The place where I was living with my dad, an apartment building in West Hollywood, was directly across the street from a hotel called Le Parc Hotel. And that’s when I started meeting artists. I started becoming a fan. I loved music, but I became a fan, someone that would actually wait to get their album signed. And Prince actually signed something for me. He wrote “Love God” for me. I told him that years, years, years later. We became friends and became close.
Tim Ferriss: Was it “Love God.” Or Love, God?
Guy Oseary: It was “Love God” and it was signed “Prince.”
Tim Ferriss: Wow.
Guy Oseary: That was a long time ago because later on he became a Jehovah Witness. But yeah, you could see the posters. I had 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, someone up there likes music a lot. And I was on the first floor and there’s a little balcony there.
And then I’d come out a lot. I met INXS. And I met 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.
Tim Ferriss: That’s awesome.
Guy Oseary: And a really cool thing is other kids were around then so I could hang. 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.
Tim Ferriss: I want to talk about addresses and Beverly Hills High School. How did you end up at Beverly Hills High School? And why?
Guy Oseary: Before Beverly Hills High School, I went to a school in downtown L.A. It was on Pico and Arlington, so it’s almost on the way 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.
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 L.A., or they would go to KROQ, which is the alternative radio station in L.A. And I loved them both. And so, I met a lot of really cool kids there who were in these groups of people. They 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.
And one night, I was outside the school dance. There was the L.A. 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 and I guess 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. And he asked me if I was in a gang and I said, “I’m just a kid waiting for my dad. I was at a school dance and this is my school and da, da, da.” And so he got back in the car to chase the guy.
And so there are no such thing as coincidences. But when my dad showed up, I got in the car and I was like, “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 L.A. to Beverly Hills High.
And there was a TV show, 90210, back then.
Tim Ferriss: Sure.
Guy Oseary: 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.
Tim Ferriss: Yeah, that makes sense.
Guy Oseary: Yeah. I don’t know why I didn’t put that together. I just said that to my dad and 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 L.A. and also going to Beverly Hills High right after, I think that’s a big part of who I am today.
Tim Ferriss: Blending the two worlds.
Guy Oseary: Blending the two worlds. One or the other without the other would not have given me the perspective that I needed.
Tim Ferriss: What was the perspective that you got once you were transported to this second chapter at Beverly Hills High?
Guy Oseary: Well, once you walk through those doors, it might as well be a TV show from where I just came from. People have a lot. There’s cars and 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’d better start working.” And I think at like, 14, it really started to kick in where I go, “Ooh, because these people are going 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 looked like, “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, would I do music? And then around 15, I really started to pick that up and at 16, I was already really running with it.
Tim Ferriss: 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 Brillstein, who is that?
Guy Oseary: 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 of these amazing talents. A lot of the talents from SNL, he managed all of them.
Tim Ferriss: Dan Aykroyd, John Belushi, Garry Shandling.
Guy Oseary: All of them.
Tim Ferriss: Yeah.
Guy Oseary: And he was beloved. He looked a little like Santa Claus. He was a really big guy with a white beard.
And so, 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. I had the yearbook person come and take photos of these.
Tim Ferriss: And this was on your own or were you working?
Guy Oseary: On my own.
Tim Ferriss: On your own.
Guy Oseary: 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 that’s what I started.
Tim Ferriss: I’ll have something to show when I get the meeting.
Guy Oseary: Yeah, I’ll have something to show. I think I called it Wise Guy Records. I didn’t know what any of it meant, but I had my little logo. 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 test so I needed to be dropped off. So the week I turned 16, I went to meet with Bernie. And 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?” And 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 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 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 $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.”
And he ended up putting that in his first book, that story. He’s passed away, unfortunately. But he always felt that 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. But until his last days, 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.
Tim Ferriss: Did he pick the people to make the phone calls to?
Guy Oseary: 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 —
Tim Ferriss: Going anywhere.
Guy Oseary: — 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. 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.
Tim Ferriss: Offers you 25k.
Guy Oseary: On that day, that was the 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.
Tim Ferriss: You mentioned two meetings.
Guy Oseary: Yes.
Tim Ferriss: Was the other Freddy?
Guy Oseary: The other was Freddy DeMann.
Tim Ferriss: All right. Who is Freddy DeMann?
Guy Oseary: So, Freddy DeMann, his daughters Neysa and Pilar connected me with their dad, Freddy. And Freddy was iconic as well. I mean, he worked on, I think, “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.
Tim Ferriss: And this meeting was after Bernie.
Guy Oseary: 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.
Tim Ferriss: Yeah. At that point, what was your pitch?
Guy Oseary: Gosh, I think I’m just showing him that I’m in the flow of music. I’m around music. I’m around artists.
Tim Ferriss: The portfolio.
Guy Oseary: Yeah, one of the crews that I was working with was Ice-T. And I got very lucky, got introduced to my friend Chris Boyd. I met when I was working when I was 15 at this 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 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 into the booth and do a few words.” And I’m actually on the album.
Tim Ferriss: Wow.
Guy Oseary: Yeah. And so, 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? 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, who’s Hen Gee and Evil E. Evil E is Ice-T’s DJ. So, I managed them. It was 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, “Freddy, I just got my first group signed to record label.” So, he knew.
There’s a guy named Steve Rifkind who I met who knew the record label. He helped me get that first record deal. So, when I went to see Steve and I played some of the music, I played him Ice-T’s DJ, Evil E and his brother Hen Gee. And I said, “Here’s the music.”
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, a manager.” And he knew, how was he pulling these things off on his own without any help or any money?
And so I met with him and he said, “Madonna and I are going to start a record label one day.”
And so I said to him, “I’d love to work there.” I said, “I don’t need any money.” 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 asked.
And he was like, “Okay.”
Guy Oseary: So he brought me in as a scout because one day they’re going to start a label. They didn’t even have a name. They just knew they were going to do it.
So I’m scouting and then one day I find Hole, which is Courtney Love. I find their first song, “Teenage Whore” and I go, “Oh, my God, this sounds incredible.” I’m 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’s trying to sign Hole.”
Tim Ferriss: How did that happen?
Guy Oseary: 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 Whiskey. Actually, I think Kurt was there. But then Madonna was like, “Who is this?” Wanted to talk to me about, “Who is this Hole thing?”
Tim Ferriss: “Hey, kid, come here for a second.”
Guy Oseary: Yeah, so I go in a room and I play this 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. And you’ve got to go back to that time period.
Tim Ferriss: Sure.
Guy Oseary: And they were like, “Okay, all right, so go after it.” And so, I went after it. I didn’t get it. It was between us and Geffen Records and we didn’t get it. It went to Geffen Records. But my first artist I ever attempted to sign was Hole.
Tim Ferriss: So, let me pause you for one second.
Guy Oseary: Yeah.
Tim Ferriss: All right. So, the meetings that you got with Bernie and Freddy, you got two introductions. How many kids at school do you think you asked in total to end up with those two?
Guy Oseary: I think I probably asked five.
Tim Ferriss: Okay.
Guy Oseary: I mean, I already 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. And 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.”
But I didn’t have any shame. I needed to figure this out. I knew that my time was limited before going to college and I’d better figure this out soon. So I was on a hustle.
Tim Ferriss: This is from an L.A. Times piece way back in the day, 1997, but 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?
Guy Oseary: Oh, yeah. No, I went to college.
Tim Ferriss: Okay.
Guy Oseary: I went for half a semester and I got my first group signed, which was just Hen Gee and Evil E. 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.”
Tim Ferriss: Wow. It’s wild to think about these just chance moments.
Guy Oseary: 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 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.
Tim Ferriss: Where did the chutzpah come from? I mean, just that drive, was that absorbed from the parents? Were you just out of the box very different?
Guy Oseary: I don’t know. Look, 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 —
Tim Ferriss: What was possible.
Guy Oseary: Yeah, 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 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.
Tim Ferriss: 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 flashpoint or was it really gradual?
Guy Oseary: I think 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. But when I finally got my car, I remember going to see my old friends from my old school. Because it was a Honda Civic. When I drove it to Beverly Hills High, 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, no, these people at Beverly, they’re not really my friends. I’m here for a reason. I was put around this community for a reason, which is to work and which is to build my name or to build the things I want to do.” And it wasn’t until years later, actually, 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 needed 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.
Tim Ferriss: 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 hop off past the things that we’ve already discussed?
Guy Oseary: Well, Madonna and I, the first real connection was that Hole connection where it’s 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 at 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, God, the first two things I competed for, I didn’t get.
Tim Ferriss: Well, not only did you not get them, but they went on to be successes, right?
Guy Oseary: Yeah, it was painful. 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 at that time. They ended up doing really, really well. But regardless, Hole and Rage, even to today, I still listen to them. I love them. But I was very lucky to get Candlebox. The fact that they bet on me, we didn’t have anything.
Tim Ferriss: Yeah.
Guy Oseary: We just had this idea.
They ended up selling four 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 with Candlebox.
Tim Ferriss: So, they give you a shot, but just to repeat what you just said, you didn’t have much, right? They were placing a bet on you.
Guy Oseary: Mm-hmm.
Tim Ferriss: What then goes into helping make a hit album that sells four million?
Guy Oseary: Well, going back to that time period, first is the music. I saw them. I was so lucky. 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. And I was supposed to be somewhere else that night, but I went to this party and it was so bad that I thought, “Oh, I have time to go see that showcase of that band from Seattle.”
So, I go to the Lingerie on Sunset. 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. I was looking at the video screen. There were maybe like, 30 people in the audience. It’s a showcase. I’m looking at that screen and I saw thousands of people singing along to that band.
Tim Ferriss: In your mind?
Guy Oseary: In my mind, yeah. But I went to the payphone from that performance, called Freddy, and said, “Freddy, 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’ve 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 rerecord 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 for every week, every week, little by little, little by little. Keyword is artist development and people don’t artist develop that much. 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.
Tim Ferriss: This may be 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 where you’re like, “Okay, that is a horse to bet on.”
Guy Oseary: Honestly, I would say that 90 percent of the things I do happen in the first five minutes. 90 percent. It drives me crazy when we get in a room and talk about it for three months. And I respect 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 that the muscle that got built for fast sort of response thinking or intuition was really in the music business. We have such a small label, so boutique and we’re competing with these big companies that have been around forever and have all these other artists and we didn’t have any artists. So when I met an artist and I liked them, most of the artists — Alanis Morissette I signed off of one song. Muse, I saw them perform one song and I’d stopped them after — they flew all the way from London to L.A. 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 to be clear. So it shows the artist the passion, which is very important. This person believes in me that much.
Tim Ferriss: High conviction. Yeah.
Guy Oseary: 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.
Tim Ferriss: 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 were 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 from those five minutes? Because you can’t bet on everything, especially as a small label.
Guy Oseary: No.
Tim Ferriss: So what were you picking up on that allowed you to make a fast decision in that way?
Guy Oseary: Well, I have to fall in love and you can’t fall in love every five seconds, but you have to just have — I didn’t know I was going to fall in love with Alanis when she walked in my office with Glen Ballard. They came in to play for me. I didn’t know what was going on here. I thought they were a band. He was the producer, co-writer, but I don’t know until I’m — you just have a feeling and there is a lot of pattern recognition later.
Tim Ferriss: Later, sure.
Guy Oseary: 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. I feel it,” and you have to fall in love. And later today, I would say, on my tech investing and what I do there, it’s a combination of gut, a combination of pattern recognition. And then there’s a few other things. One of the things I look for is, can I help it? I visualize what I can do for the company and that gets me excited too. So I go, “Oh, wow. Okay. Oh, I know exactly what I — I have a feeling I can help in a big way.” The puzzle starts to come together for me very quickly and so that’s important.
And then of course there’s the other aspect of, well, you’ve got to make sure they do what they say. Let’s try this thing out. Let’s make sure the car actually shows up when you press the app and it picks you up. Well, make sure that things work, make sure that you can stay at the apartment and it’s actually, “Oh, I pressed the thing and I can get an apartment.” These things have to work, but for me it all starts with that initial pitch.
Tim Ferriss: So how does Alanis Morissette fit into your life? Seems like an important piece of the puzzle.
Guy Oseary: She played a big role in my life. She was the rocket ship. It just took me to the next level. I mentioned earlier, she appeared in my office with Glen 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’ — do they believe in you? Do they love you? I don’t know if you know lyrics, but:
Sometimes is never quite enough.
When you’re flawless, then you’ll win my love.
Don’t forget to win first place.
Don’t forget to keep that smile on your face.
So I didn’t even understand. To me, it was just, how is she putting these words together and the — 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. I hadn’t heard anything like it and I went, “I’m ready to sign you. I love this. I’m all in.” And I didn’t know anything. I remember I didn’t know that the comparisons where people were like, “Oh, I thought it was Joni Mitchell.” People were like, “Oh, I didn’t know Joni Mitchell.” So to me, she was my Joni Mitchell. I didn’t — never 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, did a pop album in Canada. And so people had all this background. I had no background. I literally was asked to meet with her and Glen and I knew nothing.
Tim Ferriss: All you had was that meeting.
Guy Oseary: 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 some hippie vibe what is this going to be like, kind of thing. But there was, again, another life-changing moment where — so when the story is told, it’s that everyone passed, but I just felt it in the first minute and then we ended up working together and working on that album and that album ended up selling 30 million albums and I think it’s a top five debut album of all time. That really just took me to the — 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, oh, 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, 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. And that’s it.
Tim Ferriss: The rest is history.
Guy Oseary: Rest is history.
Tim Ferriss: 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?
Guy Oseary: 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, I got that…” Like people who think about things that, “I got that from my brother or my mother or my…” There are things that I didn’t realize I was getting the whole time. So there’s both and the front part is pretty, I think obvious. Her work ethic is not to be believed. Her commitment to her craft not to be believed, her passion for just the greatest gifts, whether it’s through the books that she’s reading or through the art that she’s finding or the people that inspire her or the designers, she’s so surrounded herself with a collection of some of the most incredible people in the world and she identified them by the way. She is the greatest identifier. She found these amazing talents early and was able to, whether either they’d be painters or Frida Kahlo or they could be designers or musical people.
She’s an incredible finder of talent.I think that 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.”
Tim Ferriss: Right. In terms of constraints, right?
Guy Oseary: Yeah. And I think that even going back to my first experience at Maverick Records, if you went to any record label, they would’ve put me in a compartment. There’s the R&B department, there’s the jazz department, the rock department, reggae department, pop department, hip-hop department, “Oh, what department are you in?” And they sort of bucket you into these things. I think that when I look back and I go, “How did I not really bucket myself? I went from this to this to that to that to that.” And I think it’s 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. 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, “Well, what are you doing?” This tech thing is crazy and you’re not doing…” No, they’re very — innovation is innovation and how we can distribute music or how we market and vice versa. All this stuff for music is — when you’re launching a new company, these founders are rock stars. In my mind, every founder I invest in, I look at them like they are the rock star. I go, “That person has music they want to share with the world.”
They have their album and my job is to identify that artist, that founder before everyone else maybe identifies them. And my job is to help you reach that audience. How do we tell the story? How do we reach the base of your audience? How do we grow your audience? What’s your first single? What’s your second single? And those are the things I still work in that kind of process, which is very musical in my mind.
Tim Ferriss: And we’re going to spend a good amount of real estate on the tech, but before we get to it, I want to take a moment to explore the terrain of film and how you ended up executive producing Twilight and all of the rest. Because 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?
Guy Oseary: Yeah.
Tim Ferriss: How did you end up with the foray into film?
Guy Oseary: 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.”
Tim Ferriss: Why did that come to mind?
Guy Oseary: 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. I go, “I’ll take that.”
Tim Ferriss: All the back office, all of that —
Guy Oseary: “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 pay for them, I couldn’t have afforded it, but we did it that way and out of that came a lot of films and a lot of different — Twilight and Percy Jackson, 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. I don’t know how old I was back then, but that was a major responsibility for me.
Tim Ferriss: Hard to ride both of those horses at the same time.
Guy Oseary: Just that alone, just Madonna at that moment in time for someone — I had not been a music manager for anything near that level, and so to take that on and to work on all things, the tour and the album and all that-
Tim Ferriss: And for people who have no context on music at all, what does a music manager do in that type of situation?
Guy Oseary: It’s a tricky question because no one manager is the same. Everyone’s different.
Tim Ferriss: I guess what was your umbrella of responsibilities?
Guy Oseary: My umbrella, 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 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, Stéphane Sednaoui, the director introduced me to a producer named Mirwais. He gave me a demo. I loved it and I gave it to Madonna and it 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 — they don’t do the creative, but they do an incredible job managing everything, putting together the tour, but they’re not in there going, “What if we did this?” There’s different kinds of managers. I’m creative.
Guy Oseary: For example, when I showed her, Jonas Åkerlund did a video for Prodigy, which was 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 he’s doing that.” I showed her, there’s a guy named Chris Cunningham and 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, “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.
Tim Ferriss: 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 pretty young kid marveling over. And I’m just wondering if you could add any color to that.
Guy Oseary: 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 is 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, “Well, Madonna’s done it. I can do it.” But it is no easy feat. There is a lot of bullshit 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.
Tim Ferriss: 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, Vita Coco.
Guy Oseary: Yes.
Tim Ferriss: Well done.
Guy Oseary: Thank you.
Tim Ferriss: 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?
Guy Oseary: Wow. Well, the original, original was I was on a plane to Milan for the MTV Awards and I don’t remember how old I was. It was in my 20s and I was reading in a magazine about Sky Dayton and it said he started EarthLink and he was worth a hundred million dollars and he was really — I’m like, “Wait, what? 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 took me a while, but I finally tracked him down and we went to have lunch at Four Seasons Hotel and he was like, “Wow, if you’re impressed by me, have you ever heard of Bill Gross?”
Tim Ferriss: Idealab.
Guy Oseary: And I go, “No, who’s that?” He goes, “Well, he started an incubator and he’s launched three billion companies in one year.” I go, “Sky, I like you, but can you get out of the way I want to…”
Tim Ferriss: This time has been great.
Guy Oseary: 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 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 and everyone, and you’re —
Tim Ferriss: Or the independent producers, right?
Guy Oseary: 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 this story, but it’s like all things it worked out in the end.
Tim Ferriss: Wait a second. My listeners are going to kill me if I don’t follow. What’s the bad news?
Guy Oseary: Well, I mean the bad news is that I worked there for a year helping and then one day someone I really trust that — they don’t know it to this day, 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 Idealab.” And he goes, “Well, I was going to surprise you and I was going to put 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?” He told me what he thinks it’s going to be worth when it comes out and by the way, it was worth a lot and I go, “That’s not enough.”
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.
Tim Ferriss: What year was this?
Guy Oseary: It was before the crash. By the way, it wasn’t a year before the crash. I think it was like an hour before the crash. I put every dollar I have plus dollars I didn’t have. I picked out three investments at that time, Idealab because of Bill Gross, Bill was the first guy in I think in L.A. 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 Balsillie to be an advisor because I was the guy that put it in everyone’s hands. This is smartphones before anyone else was doing it. And then I also, my friend Seth Rodsky brought me Vitamin Water.
Those were going to be my first three investments. What happened was the Idealab 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. It collapsed —
Tim Ferriss: Fever dream you’re trying to forget.
Guy Oseary: 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 Balsillie in Research in Motion and I never did my deal with Vitamin Water, which both ended up — almost like the Hole and the 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 —
Tim Ferriss: Everything in one.
Guy Oseary: — majority of my money in one thing and I paid the price for it 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. And I was mad that Sky Dayton introduced me. I was mad at all the wrong reasons. 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.”
But what happened was years later after my first Madonna tour, I started to think about it again and I go, “I wasn’t so off really.” I was off — the timing was wrong on the Idealab part. The other two worked. Had I diversified, I would have done —
Tim Ferriss: You would have been fine.
Guy Oseary: — incredibly well.
Tim Ferriss: Yeah, you would have been great.
Guy Oseary: And so I got two out of the three and the truth is it’s not fair to Bill because he really built an incredible company and some of the stuff that he had built ended up becoming search for Google and a bunch of amazing things, but it just didn’t work out and that’s life. Sometimes they don’t work out these deals.
Tim Ferriss: A lot of the time.
Guy Oseary: But I came back from, I think I had done three Madonna tours in a row. So I came back, 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 wrong, so I’m going to try this one more time. I’m good at identifying the ideas. I’m good at identifying the talent. I’m going to do one more time. And that’s when I — so I started and the same guy that brought me Vitamin Water, Seth Rodsky —
Tim Ferriss: Did he later work with Reese Witherspoon?
Guy Oseary: Yes, exactly.
Tim Ferriss: Huge.
Guy Oseary: Yeah. Yeah. He’s done well for himself. And then he called me one day and goes, “Hey, have you heard of this coconut water thing?” So of course I’d heard about coconut water. One, my wife is Brazilian and my first son, his first words were like, “Agua de coco.” So we drink coconut water at the house, but the whole coconut water sector in America, if you added all the companies together was maybe a five or seven million dollar business. It was nothing.
Tim Ferriss: Tiny.
Guy Oseary: Nothing. But Madonna on tour, on the previous tour, she would have — the trainer would go in different markets to find fresh coconut for her for the coconut water. And I’m like, “Wow, every location went to, 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 was a photo of Giselle drinking from a coconut and they’re talking about coconut water and I had cut that out and 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 —
Tim Ferriss: It’s sitting on my desk.
Guy Oseary: The only thing that I’ve tore 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, “Count me in.” I got on a plane. I went to meet with the founder, Mike Kirban. 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 McConaughey, Anthony Kiedis. 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.
Tim Ferriss: For people who don’t know, how did that turn out?
Guy Oseary: It’s a public company today. I think it’s $4 billion market cap.
Tim Ferriss: So you were back in the game?
Guy Oseary: Yes. It takes time.
Tim Ferriss: It takes time. Yeah, there’s a gestational period.
Guy Oseary: It takes time. Yeah, it didn’t happen overnight.
Tim Ferriss: 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?
Guy Oseary: I think I approached it the way I approached everything. It wasn’t, let’s think about it. It was like, “I’m all in. Let’s go. I want to do this. Here’s what I can do.” And I think they were probably overwhelmed by, “Whoa, okay.” And we just ran. Yeah, 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. He’s done an incredible job.
Tim Ferriss: 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 Harrelson — 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 Guy’s 10 commandments of long-term relationships, but how would you think about that? 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.”
Any particular rules that you use for yourself or just approaches, things you keep in mind? Because that’s certainly not true for everybody. You just have this long-term cohesion of these people around you. And I’m wondering if you can perhaps just speak to that in any way.
Guy Oseary: Well, I think it started early. In my teens, there was a group of us that were running around and we found each other. So you find the other people who are also on the hustle, who are also creative. And I wasn’t a comedian or a musician or an actor or a director. I was like an executive. So there’s a little responsibility. “He’s the responsible one.” I don’t drink. I don’t do drugs. So I found my position was to really be a safe zone for people and to really — and they knew I worked with Madonna, which pretty much gave a lot of credibility to, “Okay, this guy — she trusts him. Maybe we should trust him,” maybe, back in the day.
But I think over a period of time, my house became the place that people would come to or people would congregate and feel safe. Even when I do events here or anything, there’s not a lot of photos, there’s no cameras. I think safety and support has always been in my DNA from an early age, of just making sure that people are protected.
And again, I think identifying really incredible people to be around. Same way I identify the greatest companies to invest in, I think I identified really amazing, incredibly talented friends who inspire me, and who, early days, you may not have known them 30 years ago, but you identify them and they identify you. And so there’s this camaraderie and there’s this trust, and I do try to bring them all together a lot. I think it’s important.
Tim Ferriss: 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 often do you organize or host things like that?
Guy Oseary: A lot. 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. 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 always. I’m always checking in on everybody.
I grew up just with my dad. My two sisters were older. They weren’t around. So my friends are really — they’re everything I had. Before I had a family, my friends were everything to me.
I’m lucky I get to work with some of my family. Madonna’s — I’ve been beside her for 36 years. The Chili Peppers are my best friends in the world. The godfather of my first son is Anthony. The whole band, all of them, Flea, 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, this is the number, call me.
Tim Ferriss: I want to hop back to the investing. I mean, 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 someone 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 five 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?
Guy Oseary: Yes.
Tim Ferriss: Okay. So it’s a pretty nice multiple so far. We’ll see how things go. How did that Anthropic deal happen?
Guy Oseary: Well, it starts a little before. The day that OpenAI came out, which was on my dad’s birthday, ChatGPT, it was life-changing. You remember those moments. And again, I go back to music. I remember when I heard Smells Like Teen Spirit by Nirvana, I pulled over the car and I went, “What is this?” And when ChatGPT came out, that was a “What is this?” moment for me. And if you saw me anytime after ChatGPT came out, I would’ve harassed you to show you ChatGPT. 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. This is OpenAI. We’re doing OpenAI. This is the greatest thing I’ve ever seen. We have to do it, have to do it, have to do it.” And so that was our first, “This is the one we’re going to go after.”
But then we visualized that — when we first started investing, Ashton and I, it was when the iPhone and the App Store were happening. And so for the first time ever, you can scale companies like never before. And I think anyone would have done well at that time. We were 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 still using Uber and Airbnb and Spotify. We’re still using those things from that time period. And we felt that, “This is it. These foundational AI models in 10 or 15 years will be how we plug into all these things.” So we really felt like we had a three-month window. We told people we have a three-month window.
Now, it came out November 30th, 2022. So there’s not much you can do. People are going away. Christmastime 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.”
Tim Ferriss: I got it. LPs.
Guy Oseary: Raise money.
Tim Ferriss: Yeah.
Guy Oseary: Raise money and create this fund, which was a crazy idea at the time.
Tim Ferriss: Now, had you already confirmed that you’d be able to get allocations, or you just had complete confidence?
Guy Oseary: Ashton spoke to Sam and we were able to get OpenAI. And then what happened was is I’m very close to Marc Benioff and Salesforce Ventures, people don’t really understand how smart they are.
Tim Ferriss: Yeah, they’re really smart.
Guy Oseary: They don’t get all the press on — they are one of the best investors in the world. There’s two guys there, John Somorjai and Paul Drews, who were — when I was doing my research, because now I’m on the lookout, “What should I know about an AI?” Once I find out about something, I just lock in and I want to know everything about it. As I was doing my research, I was finding out that they were going to do Anthropic and they were very bullish about it. I found out from a friend that works with a job hunter kind of — people who helped find jobs for people.
Tim Ferriss: Oh, like headhunters.
Guy Oseary: Headhunters, that everyone’s going to this company called Anthropic. People are really going to this Anthropic place and they’re not going anywhere else. I’m like, “Whoa, okay. I need to pay attention to this.” So I asked Paul and John, “Connect me with this founder,” Dario.
So they connect me with Dario and Neerav, and they come here. They’re here right in this room and that’s where we made the deal to invest in Anthropic. So we did a bunch of other companies in that foundational AI fund. It was a three-month window.
So it was before a bunch of other things that have come out since, but we set ourselves up for exactly what we did. “This is going to be within three months. We’re going to deploy 80 percent of the money within the next three months.” And that’s what we did and that’s over three years ago.
Tim Ferriss: And how did you know the window was going to be so narrow? Did you get any pushback from LPs when you said, “We’re going to deploy 80 percent of this in three months”?
Guy Oseary: Well, we didn’t have — there was no LPs, meaning that was the pitch. So it wasn’t like we raised money —
Tim Ferriss: I see, I see. They either bought in or they didn’t.
Guy Oseary: Yeah. It wasn’t like we raised money and then told them the pitch. It was like, “Here’s the pitch.”
Tim Ferriss: “Here’s what we’re going to do.”
Guy Oseary: “There’s a window of opportunity here. We think this is the future.” And that was it.
Tim Ferriss: They had opted in.
Guy Oseary: Yeah, opt in or opt out. We didn’t know what we were going to raise. Whatever came up is what it was going to be.
Tim Ferriss: So I was trying to pull from memory, but it looks like Sound at this point is at 86 exits and 26 IPOs. That’s insane. I mean, that is —
Guy Oseary: It’s been fun.
Tim Ferriss: You have seemingly different batteries, certainly. I mean, you’ve got good batteries. What is the next five years, do you think, look like for you? I mean, is it more of this type of investing? What do you see? Is it switching gears entirely and looking at the prism through a totally different way? I mean, what is next for Guy?
Guy Oseary: 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 the quickest ways. 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 — I’m okay doing a version of what I’ve been doing, which is identify great talent and help them, help this talent, help them in every which way that I can, and pick the teams that you want to back. So I’m feeling pretty good about that, just continuing on this best-in-class talent idea.
The hard part is for a lot of people is the access. So we’re very lucky we have access and we also do the job. We have more than enough proof of 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 — obviously, narrative is something that I’m very focused on.
Marketing is something I’ve been doing since I was a teen. And so marketing, strategy, media, partnerships, narrative, storytelling. Hey, if you want someone like that on your cap table, I might be interesting to you and hopefully I can be helpful. And that’s what I — 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.
Tim Ferriss: A lot of founders listen to this podcast. Are there any particular things that have your interest right now or types of companies, types of founders, anything that you’d like to make clear to people who are listening or otherwise? Also, where can people learn more about what you’re up to? Is there anywhere that you would point them in particular?
Guy Oseary: I’m a generalist. I don’t care. That particular AI fund was very specific and we may have thematic funds from time to time. If an idea comes and you go, “You know what? I’ve got an idea,” it’s going to be built around this one idea. But usually I’m a generalist. I just like talented people.
And in regards to sharing, where can they find out what I’m up to? I’m not really — this is it.
Tim Ferriss: Yeah, this is it.
Guy Oseary: As you know, this is my first podcast and, depending how this goes, could be my last. And if it goes well, maybe one more, but I’m not out there — everything has been fine without doing that. People either find us word of mouth through friends or I find them. It’s okay. It all works out. I’m not out there yelling, “Hey, find me 1-800 whatever.” It’ll work itself out. The right people will find each other.
Tim Ferriss: 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?
Guy Oseary: 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. 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 Suno. He’s a great guy. He’s really, really — I mean, great guy. 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.”
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 that I’ve been trying to work on for a long time. I’ve met with Mikey many times. I’ve met with lots of people many times. I hope that this gets solved.
When Napster first started, I met with Shawn and Sean when they started, because it was so exciting to see people were all downloading music, but it was illegal. So you were hoping they’d crack the code on, “Okay, how do you turn this into how artists get paid?” I don’t know if they were going to or not going to, but before that could even happen, it got shut down.
And out of nowhere, Daniel 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 it could be corrupt, to get it clean, to hold onto 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; it’s through streaming. And I’m hoping that people figure out how, if you’re going to be using people’s music, how you pay for it. Fair use is not fair.
Tim Ferriss: 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 Morallica,” and you just misspell it, then lo and behold, it looks like it was trained —
Guy Oseary: Yeah, that’s the problem.
Tim Ferriss: — on this corpus.
Guy Oseary: There’s a lot of workarounds and they’ll look you in the eye and tell you, “No, no, you can’t. You cannot type in Madonna.” But you can sort of describe Madonna. The problem is, is when — in discovery, we’re going to find out a lot, and discovery’s going to say, “All of this music is in there,” and they know that and that’s not okay. It’s just literally not okay. I don’t understand it.
And by the way, what’s wrong with paying artists? Why not figure out a way to do it, sit down with a team, figure out how to pay music artists if you’re going to train on their music?
Tim Ferriss: 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 I’m not singling out Suno. I mean, there are lots of different options here.
Guy Oseary: They’re the main one.
Tim Ferriss: They’re the 800-pound gorilla.
Guy Oseary: Yeah.
Tim Ferriss: But I could see a point at which possibly Claude, ChatGPT become the interfaces to everything. It’s almost like the App Store, but somewhat like WeChat in China: if you want to do anything, if you want to book a restaurant, you want to make a song, there are a few interfaces to everything, at which point then those companies, OpenAI, Anthropic, can gatekeep in some way and maybe they end up being the entities that incentivize these other companies, like the Sunos of the world, to reimburse artists. I guess I’m just wondering if you have any thoughts on how it gets there.
Guy Oseary: It starts with Suno. Because if Claude or Chat is the distribution, they probably won’t carry it because it’s got so many lawsuits involved and it’s just not worth taking on that responsibility.
And again, the guy who runs Suno, I find, would be a really good guy and I’m hoping that he does the right thing, but it’s really their responsibility. They’re sitting at the top of this opportunity.
Take off the artists that don’t want to be on there and find a way to pay the ones that are okay being on there. It’s that simple. It’s not complicated. Go in a room, lock yourself in a room for three days and come out and figure out how to pay people and take people off that don’t want to be on there.
Madonna does not want her music trained on. Don’t care what you want to pay her. She’s very clear: “I do not want my music to be trained on. I want my music to be its own thing.” So take her off. It’s okay. You’ll still do fine. Take her off. You don’t have to have her music.
So we’ll see where this goes, but this is — the last few years I’ve really tried to figure this out, and even with Sam at one point, he’s really wanted to figure this out too. A lot of people give him a hard time on this stuff, but he really did dedicate time to trying to figure out if there was a music thing to do, how to do it in a way that supported artists.
Tim Ferriss: Yeah. I mean, there may be someone who comes along also if it’s not Suno, someone who comes from behind, like a next generation Spotify, and figures out how to do it.
Guy Oseary: Well, Spotify could do it.
Tim Ferriss: Yeah, or Spotify could do it. 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?
Guy Oseary: 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. So I’m able to ask investors what companies that they’re looking at. And so two of those came from that conversation.
Tim Ferriss: That’s good. Good information for that.
Guy Oseary: 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’m checking things out every single day and I’m making sure I’m not missing an idea or I’m hearing about things.
Tim Ferriss: What do you read?
Guy Oseary: Well, I’m on X a lot. I see a lot of the stuff, a lot of information on X that’s flying by. It’s sort of my start of information.
Tim Ferriss: 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 no limitation here, any favorite failures or apparent failures, meaning failures that taught you a lot or that set you up somehow for later success?
Guy Oseary: Well, I mean there’s so many. It’s endless, endless. One of the things that Ashton 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. I had it and we had it.” And he’s like, “Come on, let’s move — let’s go. Let’s go.” He always gives me like, “Oh, gosh, he’s going to complain about not being in it again.”
Tim Ferriss: Here we go again.
Guy Oseary: But 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.
Tim Ferriss: I mean, looking back, it seems like, in some ways, missing Hole, missing fill-in-the-blank, was almost a prerequisite source of fuel for the things.
Guy Oseary: Yeah. It’s scary, though.
Tim Ferriss: It drove you towards those things.
Guy Oseary: It’s scary, though. When you miss it, Ash and I invested in Bitcoin on our own when it was at $22. And then when it hit $250, I thought I just made 10 times my money. I’m a genius. So I sold then and clearly not a genius. So that hurts. And I remember Anthony, gentlemen on that wall, Elon invited Anthony from the Chili Peppers to see SpaceX early days, very early days. And I went with Anthony, I tagged along. It’s the first time I met Elon and we went to SpaceX. I was so wowed by the concept that I didn’t even pay attention to the business model or what could be the business model.
I was just like, “Wow, this guy’s building rockets.” If we just had had the wherewithal to go, “What business model?” I didn’t even ask those words. Sometimes I go to shows. I’ve seen shows where people are so wowed that they’re just like, they’re like this from a show and they didn’t even take in all the songs. They were just like, “Oh, my God.” 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’ve asked one more question, like, “Hey, how do you monetize this?”
Tim Ferriss: “Oh, by the way…”
Guy Oseary: “How does this work? Can we invest?” So I have hundreds of those stories, but those are two that stand out today.
Tim Ferriss: I want to talk about the longevity for a second. You mentioned, and fact check me if I’m getting this wrong, but the three, was it back to back tours with Madonna?
Guy Oseary: Yeah.
Tim Ferriss: I mean, that sounds impossible just from the demands of the physicality of that. And she’s legendary, of course, for her training and endurance and everything else. But for you, personally, what were the keys to enduring that and being able to function at a high level for that period of time?
Guy Oseary: I think it’s different as the years go by, there was a point around 10 years ago, 11, 12 years ago where it was a lot for me because I was also changing and growing and having kids and I was just losing myself because you’re going to a different city every other day and the amount of things you’re missing back home, you 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 — all the things, you just forget everything. And then one day your dad calls you and goes, “Oh, hey, I’m at your house with your kids.” And I’m going, “Oh, I have kids. I’ve got a house.”
So if you look at the first three tours that Madonna, those three tours that I did, those are 240 shows, 80 average. I missed three of those shows, three out of the 240. One, I was sick and then I missed two because it was my 40th birthday and I really didn’t feel like being in Seattle that day. I wanted to be home with my friends. So my 40th birthday, I 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 in order to move along, you have to block everything else out. You have to forget and it’s a very selfish, very — for me. Otherwise, if, every day, you’re thinking about back home or your family or other things, it hurts. So I just go, “Okay, I’m off and I’ll see you.” I bet that’s what actors do when they go away and make a movie for three months and then they come back.
Tim Ferriss: Some military do.
Guy Oseary: They probably just compartmentalize a little bit. But in the last few years, I’ve stopped doing as much. I still go, but not as much. I’ve worn it down. There’s a moment there where I managed the Red Hot Chili Peppers, U2, and Madonna, and they’re all going on tour, and it was a lot to process.
Tim Ferriss: How do you even make decisions about where to be in a case like that? You can’t be in three places at once.
Guy Oseary: It’s hard, but it tells its own story. You’re not going to miss New York, you’re not going to miss London, you’re not going to miss some of the major moments. And then you look at the calendar and go, “Oh, we have this time off. Let’s go to this place with — let’s go to New Zealand with Madonna or let’s go to so-and-so with U2 or let’s go to so-and-so with the Peppers.” And you find your way around it. You just make it work.
Tim Ferriss: So if you look at, let’s just say the last 10 years and presumably a lot of your focus is on the investing. How do you mind the different responsibilities, if that makes sense?
Guy Oseary: I think when I think of responsibilities, I always think of management. That’s a really big responsibility and I don’t take it lightly. There’s no way around it. Something’s going on there that’s a focus. It is cyclical. So 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. There’s a lot of time in between, where they’re coming up with the creative. They’re going to make an album, they’re going to do all the things, 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 of opportunity where you have a moment to breathe, just like they do. They all need it too. Madonna, after this cycle, will probably need a minute to just 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. And so that’s where the balance comes in and which is the creative, but continually be creative through other ways. And so when the cycle starts, my creativity has never stopped so that I still have those things. I’m not starting from scratch. I’m always looking and meeting with people and understanding what’s going on in technology. And so when Madonna comes back into cycle, I can bring some of those ideas or some of those new relationships I met while she was off. And so I found a way to make it work.
Tim Ferriss: Now maybe I’m sure misquoting, but roughly paraphrasing much earlier in the conversation, 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 marching forward. I’m wondering how you’ve thought about for yourself the drive and velocity of forward-looking achievement versus 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 on that.
Guy Oseary: 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. I think I just keep it moving too. And again, when you look back 36 years, it’s probably Madonna that is responsible for how I also think of just keep it moving forward, keep it moving forward. And maybe one day, sometimes when I’m 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 there for that.”
But I really don’t think about it that — I don’t think about it that much. Things pop up every now and then, but I wake up and like tomorrow is — when I wake up tomorrow, I’m like, I haven’t done anything today. I better figure it out. I need to step my game up. That’s how I feel. I don’t feel accomplished. I don’t feel at all. I feel like I still have so much to prove and so much to do, but at the same time, I do know if I really took a minute and I go, oh, wow, okay. I should probably take a moment and take that in, but I really don’t.
Tim Ferriss: Is that okay? Is that a problem? Is it fine?
Guy Oseary: I just keep it moving. I don’t know. At some point, I can visualize being on the beach and high-fiving with my friends and having fun, but again, they don’t do it either. Yeah. A lot of my friends —
Tim Ferriss: [crosstalk]
Guy Oseary: They don’t talk about it like that either. I mean, I think we just —
Tim Ferriss: Working dogs.
Guy Oseary: How cool that we’re survived this period of time. How cool is it that we’re even able to do what we love? Waking up and being able to do what you love, there’s a Josh Kushner quote that I love that he says about success. And he says, “Tim, success is being excited to go to work and also being excited to go home.” And I got that. I’m excited to go to work and I’m excited to go home. That’s pretty cool. Not a lot of people get to do that and I don’t take that for granted. I work hard because of that, because I go, “This is not a given.”
Tim Ferriss: It’s not a given.
Guy Oseary: 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, 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.
Tim Ferriss: 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.
Guy Oseary: Well, we’ve had an incredible run and this AI fund is — I don’t know what to compare it to other than winning the Super Bowl for what we do. And between the investments in OpenAI and Anthropic. And we also did SPVs the whole way up, a lot. So we’re really fortunate and blessed and after 20 years, Ashton 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 are we going to get enjoyment out of doing? And so it’s a really strong question and we all gave it some thought. This is a few months ago. We looked at each other’s visions of what he wanted to do that would make him happy and what he wanted to build and what I wanted to do. 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, it’s a pretty awesome vision. It’s an incredible vision and the guy is mind blowingly smart and talented and I support that vision for him. It isn’t my vision. And I will support it financially and I will support it with energy. I want him to win and then I have mine, which is the things that we’re talking about today and the things that I want to build. I have a version of the things I want to do that I haven’t shared with everyone in full, but it turned out that we just have, it’s a new chapter. And I’ve had many new chapters my whole life, with the record label first amount of 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 we’re in a celebratory mode. So we’re 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 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 what he wants to do, I’m very specific on 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 and it’s just another chapter.
Tim Ferriss: Cool. Guy, this has been a wide-ranging conversation. What a life. What a journey and it’s not over. Obviously, you’ve got lots of battery left for what’s ahead. Thank you for the time.
Guy Oseary: Thank you.
Tim Ferriss: Thanks for inviting me here.
Guy Oseary: My first podcast.
Tim Ferriss: I know. I know. Mine too.
Guy Oseary: Your first podcast with me, yes.
Tim Ferriss: Exactly. And people can find you on Instagram, X @GuyOseary, 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/podcast. 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 Kornfield. And as always, thanks for tuning in. Thanks, Guy.
Guy Oseary: Thank you.
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