#874: Guy Oseary — The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First

Well, hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of The Tim Ferriss Show. My guest today is Guy Oseary. And if you hear birds in the background, that's because I was visiting him for the interview at his home in Los Angeles. He has been spotting talent before anyone else could see it for nearly 4 decades. He has different batteries. I've seen it. Very different batteries. Under his leadership at Maverick Records, Maverick sold more than 100 million albums. Guy has managed some of the biggest names in music, including Madonna, I think that's 36 years and counting, the Red Hot Chili Peppers and U2, and was named Variety's Music Mogul of the Year in 2022. He's got lots of accolades like that. He also executive produced Twilight, you may have heard of, which became one of the most successful franchises in movie history, generating more than $3.5 billion. Guy was also an early investor in Vita Coco and co-founded A-Grade Investments and then Sound Ventures, now with nearly $2 billion under management. At A-Grade, his hits included Airbnb, Uber, and Spotify. Sound Ventures launched Even though it has more than $2 billion now, with less than $100 million and has since had 86 exits and 26 IPOs. He's got a lot of stories. I mean, he and Ashton invested in Bitcoin when it was at $22. There are a lot of stories. How does he do it? How does he make 5-minute decisions? What does he see? What does he feel when he's spotting talent, when he's spotting opportunities? We get into all of it. You can find him online. He's easy enough to find. Guy Oseary, O-S-E-A-R-Y. Yeah. So without further ado, please enjoy this very wide-ranging, very tactical, very colorful conversation with the one and only Guy Osiri. At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

Now it is in a perfect time.

What if I did the opposite?

I'm a cybernetic organism, living tissue over metal endoskeleton.

Leave him there is no.

So here we are sitting in this beautiful home, and I wanted you to explain this beautiful calligraphy behind you that I was admiring, some of the most impeccable handwriting I've ever seen. What is it that's sitting behind you?

That's Purple Rain lyrics by Prince.

Just incredible.

I'm a huge fan of Prince. When I was a kid, I had Prince posters up on my wall. And I met him when I was 12.

12?

Yeah.

How did that happen?

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

Was it Love God, period, or Love, God?

It was Love God.

Okay.

And it was signed Prince. That was a long time ago because later on he became a Jehovah's Witness. 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, there's Someone up there likes music a lot. I was on the first floor. There was a little balcony there. And I'd come out a lot to meet— 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. And a really cool thing is other kids were around then. They were older than me, but they were kids. And so I could hang with them and really get a little camaraderie with some of the fans out there that were waiting for the bands.

I want to talk about addresses and Beverly Hills High School. How did you end up at Beverly Hills High School and why?

Before Beverly Hills High School, I went to a school in downtown LA. It was on Peacorne 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. Music was a big piece of that. of my journey there. I took a school bus there and the kids would go between 2 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 the punk rockers, the hip-hoppers, the breakdancers, gang members, graffiti artists, Just a great eclectic group of people during that time period where I'm a sponge. I'm just picking up all the energies and really falling in love with music. One night I was outside the school dance. There was the LA Dream Team. That's what they were called, this 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 it 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.

Oh, God.

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 the 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 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 LA to Beverly Hills High. And there was a TV show, 90210, back then.

Sure.

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. I didn't know at the time, but you have to live in Beverly Hills to go to Beverly Hills High School.

Yeah, that makes sense.

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 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.

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

What was the perspective that you got once you were transported to this second chapter? Beverly Hills High?

Once you walk through those doors, it might as well be a TV show from where I just came from. People have a lot. 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 better start working. And I think at 14, it really started to kick in where I go, ooh, 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 didn't live that world. So I knew that I needed to do something about it. And I started to— so 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? What do I do in music? And then around 15, I really started to pick that up. And at 16, I was already really running with it.

So I think this might be a good bridge. If I'm missing something in between these points, let me know. I'm sure there's a lot that we could talk about, but Bernie Brillstein, Who is that?

So Bernie Brohlstein 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. He started this idea of building—

Dan Aykroyd, John Belushi, Garry Shandling.

All of them. And he was beloved. He looked a little like Santa Claus. He was a really big guy with a white beard. 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 the yearbook person come and take photos of these—

And this was on your own or were you working?

On my own.

On your own.

On my own. I didn't know what I was doing. I just thought, let me put together a portfolio. Let me have someone take photos of these artists. Let me 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. 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, is 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 2 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 Berlestein and his 2 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 says, he looks at me and 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 3 phone calls for me to music people. I don't want your money. And he ended up putting that in his first book, that story. He's passed away, unfortunately. 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, 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 3 phone calls for me.

Did he pick the people to make the phone calls to?

Yeah, I had no idea. I said, 3 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, is I came back home and I thought to myself, wow, I'm 16 years old and this guy offered me as much money as people make a year in one meeting. So 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—

Offers you $25K.

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.

You mentioned 2 meetings.

Yes.

Was the other Freddie?

The other was Freddie DeMann. All right.

Who is Freddie DeMann?

So Freddie DeMann, his daughters, Nisa and Pilar, connected me with their dad, Freddie. And Freddie was iconic as well. I mean, he worked on Thriller with Michael Jackson. Wow. He managed Madonna. He managed some of the greatest artists of all time, and he was just a really great human, great guy. And he heard me out. It took a few meetings to get Freddie to really go for it with me. Not that long, but—

And this meeting was after Bernie?

Meeting was after Bernie. 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.

Yeah. At that point, what was your pitch?

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

The portfolio.

One of the crews that I was working with was Ice-T, and I got very lucky, got introduced by my friend Chris Boyd. I met when I was working, when I was 15 at this Fred Siegel, 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, oh 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.

Wow.

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 G 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 Freddie and said, Freddie, I just got my first group signed to record label. So he knew. There's a guy named Steve Rifkind who I met who knew the record label He helped me get that first record deal. So when I went to see Steve and I played him— he's DJ Evil-Lyn and his brother, Henji. And I said, here's the music. And he said, I know a label for you. So he helped me get my first record deal. So I always write Freddie and go, hey, Freddie, I just got my first group signed. I just— a manager. 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, 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.

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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.

How did that happen?

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 Whiskey. I think Kurt was there. Then Madonna wanted to talk to me about, who is this Hole thing that you're—

Take it to her for a second.

Yeah. So I go in a room and I play the song for Madonna and for Freddie, And it's pretty wild. I mean, the lyrics are like, when I was a teenage whore, my mother said, she said, baby, what for? I was like, whoa. You got to go back to that time period.

Sure.

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.

So let me pause you for one second.

Yeah.

All right. So the meetings that you got with Bernie and Freddie, so you got 2 introductions. How many kids at school do you think you asked in total to end up with those 2?

I think I probably asked 5. Okay.

All right.

Yeah. I mean, I was already— I sort of 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 5. I remember one person specific saying, my dad doesn't do that.

Whatever.

Because it was rap, I was trying to play, oh, my dad doesn't do that. So I didn't have any shame. I needed to figure this out. I knew that my time was limited before going to college and I better figure this out soon. So I was on a hustle.

This is from an LA 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 where did the— did you apply pressure to yourself in that way instead of going to college?

No, I went to college. I went for half a semester and I got my first group signed, which was just Henjin Ivali. 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.

Wow.

Yeah.

Wild to think about these just chance moments.

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.

Where did the chutzpah come from? I mean, just that drive. I mean, was that absorbed from the parents? Were you just out of the box very different?

I fell in love with music in a big way. I think I realized how lucky I was to be at Beverly Hills High and see the potential of— What was possible. Yeah, of what's possible. And I thought, wow, not everyone is this lucky. 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 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.

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?

The Bernie Berlestein moment where he offered me $25,000 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, I remember going to see my old friends from my old school. When I drove it to Beverly Hills High, 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.

Sure.

And then I went to see my old friends from my old school, and then they couldn't believe I had a brand new Honda Civic. And they got in the car and they were 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 putting 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 actually told that story in that thing you're talking about when I was 24. My dad mentioned it was really hard to even come up with the money for that car back then. It was a really big deal for us. It was expensive back then. And so I think I 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.

And from the chapters we've discussed so far, I mean, was then the next phase building your relationship with Madonna primarily, or where did you kind of hop off past the things that we've already discussed?

Madonna and I, the first real connection was that hole connection where it was like, whoa, whoa, whoa, 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 God, the first 2 things I competed for, I didn't get.

Well, not only did you not get them, but they went on to be successes, right?

Yeah, it was painful. The 3rd 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. We just had this idea. 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 was selling albums.

Yeah, 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. What then goes into helping make a hit album that sells 4 million?

Going back to that time period, first is the music. I was so lucky. I walked into— almost everything that I've been lucky on happens within minutes, not within days or weeks or months to think about it. It's all intuitive and it's very fast. I walked into— I was supposed to be somewhere else that night, but I went to this party and it was so bad that I thought, oh, I have time to go see that showcase of that band from Seattle. So I go to the Lingerie on Sunset 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 may be 30 people in the audience. It's a showcase. And I'm looking at that screen and I saw thousands of people singing along to that band.

In your mind.

In my mind, yeah. I went to the payphone from that performance, called Freddie, and said, Freddie, I have our band. This is the band. I just saw them. This is the one. So it starts with that. Always starts with the magic. I don't care if you're tech company or your whatever it is, a film, a product, a book, magic. You got to have magic. Something has to pull you in. And that night I saw it, I visualized it, and the songs were there. The songs were so there that when we made the album, their first 2 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 2 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 it to— every week, every week, little by little, little by little. Keyword is artist development. And people don't artist develop that much. But something that we all want. Every artist wants to have the time to build, have the time to develop. And we really took that time week after week after week developing that one. And that's how we got there.

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.

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 the process. I know there is a process to these things, but I think I know what I want to do Very quickly. It started out, I think the muscle that got built for fast sort of response thinking or intuition was really in the music business. We have such a small label, it was so boutique, and we're competing with these big companies that have been around forever and have all these other artists. We didn't have any artists. So when I met an artist and I liked them, Alanis Morissette, I signed off of One song. Muse, I saw them perform one song and I stopped them. They flew all the way from London to LA to showcase for me. After the first song, I stopped them. I said, you do not have to play another song. And they're like, we flew out all the way from London. We'd like to play more music. 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.

High conviction. Yeah.

High conviction. And also, if I left it available, maybe someone will offer them way more money or make them other promises. And I couldn't afford to not make fast decisions or else we would never have gotten to where we got to.

In any of those examples, and I know this is possibly very hard to verbalize, Someone said to me recently, and I thought it was pretty funny, they're like, yeah, in Silicon Valley, if you say you're using your intuition, nobody listens. But if you say pattern matching, then they pay attention. But if you were trying to explain what you intuited or noticed in that one song, understanding the music is good, but what else are you picking up from those 5 minutes? Because you can't bet on everything, especially as a small label.

No.

What were you picking up on that allowed you to make a fast decision in that way?

I have to fall in love, and 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 Glen 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. There is a lot of pattern recognition later. Now with experience, Now I bring other elements into the mix, other things I'm looking for that are different than back then. It was just, I love it, I'm ready to go, I feel it. You have to fall in love. And later today, I would say on my tech investing and what I do there, it's a combination of gut, pattern recognition, and then there's a few other things. One of the things I look for is, can I help it? I visualize what I can do for the company, and that gets me excited too.

Yeah.

So I go, oh, wow. Okay. I have a feeling I can help in a big way, or I have a puzzle starts to come together for me very quickly. So that's important. And then of course, there's the other aspect of, well, you got to make sure they do what they say. Hey, 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 press the thing and I can get an apartment. These things have to work. But for me, it all starts with that initial pitch.

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So how does Alanis Morissette fit into your life? Seems like an important piece of the puzzle.

Yeah, she played a big role in my life. She was the rocket ship that 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 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. 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. Remember, I didn't know that the comparisons where people were like, oh, I thought it was Joni Mitchell. People were like, oh, oh. 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, 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 Glenn, and I knew nothing.

All you had was that meeting.

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 sort of hippie vibe, kind of, what is this going to be like kind of thing? But it was, again, another life-changing moment. When the story is told, it's that everyone passed, but I just felt it in the first minute. And then we ended up working together and working on that album, and that album ended up selling 30 million albums, and I think it's top 5 debut album of all time. That really just took me to the— not only did I sign it, but everyone else didn't want to sign it.

Right.

So it's not like I even competed. So it really cemented that I'm in a good place right now, that I can do these things, and I This probably is going to give me more opportunity to do more of these things. So she's such a big part of my life and she's so 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 Freddie once asking me, what do you think this record could sell? Before it ever came out. And I go, millions of albums. I just had a feeling that I had not heard anything like this and that this was A monumental record.

The rest is history.

The rest is history.

I'd love to spend a little bit of time on what you've learned from Madonna. This is an older Variety piece, but a 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 shit until she grabbed me by the hand and said, let me show it to you. And it goes on and it goes on. But What did you pick up from Madonna? What are the key sort of learnings?

I mean, there's some clear learnings and there's stuff that with— I'm 36 years next to this woman and there's things that when you look back, you go, okay, I got that. Like people who think about things that, well, 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 of whether it's through the books that she's reading or through the art that she's finding or the people that inspire her or the designers or the— 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— they could be painters or Frida Kahlo, or they could be designers or musical people. She's an incredible finder of talent. So I think the thing that has really affected me the most is that there's no walls around her. Thoughts. There's no, oh, I can't do that.

Right.

In terms of constraints, right?

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 a jazz department, the rock department, reggae department, pop department, hip-hop department. And you're, oh, what department are you in? And they sort of bucket you into these things. And I think that when I look back and I go, how did I not really bucket myself? I went from this to this to that to that to that. It's really just being around her has allowed me to never think in 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 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? I still work in that kind of process, which is very musical in my mind.

We're going to spend a good amount of real estate on 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've been tightly siloed and you wouldn't have had that ability, right?

Yeah.

How did you end up With the foray into film?

I'd been signing bands for a long time and running the record label, and I thought, well, why don't we do a film company as well? And Madonna and I were really in a good groove together and thought, let's just start this film company.

Why did that come to mind?

I don't really recall that. I just recall thinking about how people do it differently. And so again, I didn't have context. The best thing sometimes is to have zero context. So sometimes fresh is okay. Sometimes having a blank canvas. And with films, I had a blank canvas. I didn't know how it worked, but I knew I wanted to make some films. So I had this idea of bringing in a bunch of producers under one roof, and they were all independent producers. The idea was, is I'll bring them in, and house them and give them support and pay for a lot of the legal things that cost money. When you're independent, there's a lot on you.

All the back office, all of that stuff costs.

We'll take all that on, we'll help you, and then we'll work on these projects together. And we had a lot of producers. If I was to pay for them, I couldn't have afforded it, but we did it that way. And out of that came a lot of films and a lot of different— Twilight and Percy Jackson, 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 a 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—

20.

That was a major responsibility for me.

Hard to ride both of those horses at the same time.

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

And for people who have no context on music at all, what does a music manager do?

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

I guess, what was your umbrella of responsibilities?

When Madonna started working on Ray of Light, I found the producer, William Orbit, but I was not managing her. I was her partner at the record label, Maverick Records. And not her own, not Warner Brothers, which is where she was on War Bros., but we were just friends and working together at 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 Sidonoway, the director, introduced me to a producer named Merwaze, gave me a demo. I loved it, and I gave it to Madonna, and it ended up becoming Music. So I found on those 2 albums, even though I wasn't managing her, I was creatively helping here and there bring in some ideas. So we already had a rhythm on the creative side. Now, there are some managers that don't do any creative, and there are some that are very creative. I was coming from the creative point of view on ideas, ideating. Here's things we could do. Here's things we could build. So I think that's the management that I am. I'm more creative when I'm working with someone. I'm sort of in it. And there are other managers I've worked with who, they don't do the creative, but they do an incredible job managing everything, putting together the tour, but they're not in there going, what if we did this? What if we— there's different kinds of managers. I'm for creative. For example, when I showed her— Jonas Åkerlind did a video for Prodigy, which is a band I signed, and it was really provocative. And I just showed it to her like, 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, 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. She was open to my craziness, and then she would take it to the next level.

What— and this is my— even when I was very, very young and everybody knew Madonna, I was constantly impressed by her longevity and ability to seemingly reinvent herself. And I'm just wondering why you think she has been so consistently good at that over decades. I mean, it was the first example that I remember even as a young, pretty young kid marveling over. And I'm just wondering if you could add any color to that.

She doesn't sit well on her past. She's not high-fiving herself. She just keeps it moving forward. And 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, oh, Madonna's done it, I can do it. But it is no easy feat. There is a lot of bullshit to deal with. I think it comes from she just doesn't celebrate her accomplishments. She just starts like it's a brand new day.

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. Well done.

Thank you.

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?

The original Original, original was I was on a plane to Milan for MTV Awards, and I don't remember how old I was. It was my 20s. And I was reading in a magazine about Sky Dayton, and it said he started EarthLink and he was worth $100 million. I'm like, wait, what? 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 Four Seasons Hotel. And he was like, wow, if you're impressed by me, have you ever heard of Bill Gross?

Idea Lab.

And I go, no, who's that? He goes, well, he started an incubator and he's launched $3 billion companies in one year. And I go, Sky, I like you, but can you get out of the way? I want to—

This time has been great. Yeah.

It's time to move on. I need to talk to this Bill Gross guy. So he sets me up with Bill Gross. Bill Gross ran an incubator called Idealab in Pasadena, and I just loved it. I love the idea of a lot of ideas reminding me of the record label where you had all these artists and you had all these project managers.

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 this story, but it's like all things, it worked out in the end.

Well, wait a second. My listeners are going to kill me if I don't follow. What was the bad news?

Well, I mean, the bad news is that I worked there for a year helping, and then one day someone I really trust that They don't know it to this day. They're an incredible human. And I was lucky to sit with them at dinner one night, and they were telling me how Bill Gross is one of the greatest investments they've ever made. So I called up Bill and I go, Bill, I want to put money into Idealab. And he goes, well, I was going to surprise you and I was going to put 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, 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 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.

What year was this?

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. Okay? So I put every dollar I have, plus dollars I didn't have. I picked out 3 investments at that time. Idealab, because of Bill Gross. Bill was the first guy in, I think, in LA to have the BlackBerrys. So I was the first guy from Hollywood to even know what the hell BlackBerrys 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 Vitaminwater. So those were going to be my first 3 investments. What happened was, is the Idealab thing, once I put that money in, and I don't know the timeline because I tried, it's almost like I just thought, almost like something you want to wash away from your mind. Right.

It collapsed. It's a fever dream you're trying to forget.

The bubble burst so fast on all of that that I didn't have the heart to invest into— I never signed my deal with Jim Balsillie and Research in Motion, and I never did my deal with Vitaminwater, which both ended up— it's 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 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 2 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 then I ended up, 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've 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. The timing was wrong on the Idealab part. The other 2 worked.

Yeah.

Had I diversified, I would've done incredibly well.

Yeah, you would've been great.

And so I got 2 out of the 3. 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.

A lot of the time.

But I came back from, I think I had done 3 Madonna tours in a row. All the money I'd lost, I made that back to survive. And then I had a window where I knew we were 3 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 it one more time. So I started. The same guy that brought me Vitaminwater, Seth Rothske.

Did he later work with Reese Witherspoon?

Yes, exactly.

Huge.

Yeah. He's done well for himself. And then he called me one day and goes, hey, have you heard of this coconut water thing? So of course I'd heard about coconut water. One, my wife is Brazilian and my first son, his first words were like, água 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, it was maybe a $5 or $7 million business. It was nothing.

Tiny.

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 was like, wow, every location we went to, we have to find fresh coconuts. And so I started to hear that other people were doing that as well. Other people who cared about their health were drinking coconut water. And I started to see Again, back to pattern recognition, I started to see this thing. And then one day the New York Post ran an article about coconut water. There was a photo of Gisele 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 my to-do. 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 a— I think it was a $35 million valuation at the time. And I literally just, here we go. I'm jumping back in. And I went in really big and I brought Madonna into that. I brought Demi Moore. I brought Matthew 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. That was the first time back after the crazy run.

For people who don't know, how did that turn out?

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

So you were back in the game.

Yes. It takes time.

It takes time.

It takes time. Didn't happen overnight.

What were you looking for? How would you replay that meeting with the founder in your mind? You fly out, you meet with the founder, How did you approach that meeting?

I think I approached it the way I approach everything. It wasn't, let's think about it. It was like, I'm all in. Let's go. I want to do this. Here's what I can do. And I think they were probably overwhelmed by, whoa, and we just ran. And he's awesome. What he's done with the company, we went public, I think, at $2 billion and now it's at $5 billion. He's done an incredible job.

So we're going to hop to some more recent examples, which may or may not include this chair, In a moment. But I want to focus on a term or phrase that I've seen applied to you a lot, which is great curator of people. Chris Rock has said this. Matthew, you just mentioned, has 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. 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 just wondering if you can perhaps just speak to that in any way.

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. And so there's a little responsibility. He's a responsible one. I don't drink, I don't do drugs. So I found my position was to really be a safe zone for people. And they knew I worked with Madonna, which pretty much gave a lot of credibility to, okay, this guy is— she trusts him. Maybe we should trust him. Maybe back in the day. But I think over a period of time, My house became the place that people would come to or people would congregate and feel safe. Even when I do events here or anything, there's not a lot of photos, there's no cameras. I think safety and support has always been in my DNA from an early age, just making sure that people are protected. And again, I think identifying really incredible people to be around, same way I identify the greatest companies to invest in. I think I identified really amazing, incredibly talented friends who inspire me, who early days, you may not have known them 30 years ago, but you identify them and they identify you. And so there's this camaraderie and there's this trust, and I do try to bring them all together a lot. I think it's important.

That was going to be actually my next question, which is along those lines, which is how often do you gather people, whether it's at this house or at events that you put together, just to facilitate that long-term cohesion? How often do you organize or host things like that?

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. Finding out how they are. And always, I'm always checking in on everybody. I grew up just with my dad. My 2 sisters were older, they weren't around. So my friends are— 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 friend in the world's 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.

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 so on that you've had, I mean, a gazillion. Let's talk about one. So you put in, tell me if I'm getting this right, $35 million at a $5 billion valuation into Anthropic. This is a company that's been in the news a lot. I think the last round was what, $965 billion, something like that? Are those numbers roughly accurate?

Yes.

Okay. So that's a pretty nice multiple so far. We'll see how things go.

How did that 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 like lucky people that came in at the right time and were looking at the right time and started our fund at that very moment, which is crazy. And so we had this incredible success because of that. I saw it again, back to pattern recognition. If you fast forward, We're still using Uber and Airbnb and Spotify. We're still using those things from that time period. And we felt that this is it. These foundational AI models in 10 or 15 years will be how we plug into all these things. So we really felt like we had a 3-month window. We told people we have a 3-month window. Now, it came out November 30th, 2022. So There's not much you can do. People are going away. There's Christmas time break, blah, blah. But as soon as January came, we went out there and told people, this is the vision. We're going to do a foundational AI model fund.

I got it.

LPs.

Raise money. Raise money and create this fund, which was a crazy idea at the time.

Now, had you already confirmed that you'd be able to get allocations or did you just have to completely come up with this?

So Ashton spoke to Sam. We were able to get OpenAI and What happened was, is I'm very close to Marc Benioff and Salesforce Ventures. People don't really understand how smart they are. Yeah, they're really smart. They don't get all the press on— they are one of the best investors in the world. There's 2 guys there, John Samorajai and Paul Drewes, who were, when I was doing my research, because now I'm on the lookout, what should I know about an AI? Once I find out about something, I just lock in and I want to know everything about it. As I was doing my research, I was finding out that they were going to do Anthropic and they were very bullish about it. And I found out from a friend that works with a job hunter, kind of people who help find jobs for people.

Oh, like headhunters.

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. So I asked Paul and John, connect me with this founder, Dario. So they connect me with Dario and Nirav, and they come here. They're actually 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 3-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 3 months. We're going to deploy 80% of the money within the next 3 months. And that's what we did. And that's over 3 years ago.

How did you know the window was going to be so narrow? I imagine, did you get any pushback from LPs when you said, we're going to deploy 80% of this in 3 months?

Well, we didn't have— there was no LPs, meaning that was the pitch. So it wasn't like we raised money.

I see.

They either bought in or they didn't.

Yeah. It wasn't like we raised money and then told them the pitch. It was like, Here's the pitch.

Here's what we're going to do.

There's a window of opportunity here. We think this is the future. And that was it.

They had opted in.

Yeah. Opt in or opt out. We didn't know what we were going to raise. It's just whatever came up is what it was going to be.

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—

It's been fun.

You have seemingly different batteries, certainly. I mean, you've got good batteries. What does the next 5 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?

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. And I'm excited about the potential of what's to come. I've already identified 3 things I want to do today. So I can only imagine what's to come. But it's just really just, I'm okay doing a version of what I've been doing, which is identify great talent and help them, help them in every which way that I can. Pick the teams that you want to back. I'm feeling pretty good about that, just continuing on this best-in-class talent idea. The hard part is, for a lot of people, is the access. So we're very lucky we have access. And we also do the job. We have more than enough proof of people that come through when you work with them. And we're a different kind of investor on the cap table. We're not in the Valley, we're here in Hollywood, and we bring a different dynamic, different— obviously narrative is something that I'm very focused on. Marketing is something I've been doing since I was a teen. And so marketing strategy, media, partnerships, narrative, storytelling. Hey, if you want someone like that on your cap table, I might be interesting to you, and hopefully I can be helpful. And that's what I need to find, that dynamic of a company that I'm in love with, and hopefully the founder believes that having me would be a great advantage to them.

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 sort of 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?

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 really like talented people. And in regards to sharing, where can they find out what I'm up to? Not really. This is it. Yeah, this is it. As you know, this is my first podcast. And depending on how this goes, could be my last. And if it goes well, maybe one more. 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, or— it'll work itself out. The right people will find each other.

Well, Guy, I mean, we've covered a lot of ground. Is there anything else that you would like to say before we start landing the plane?

I'd say that AI and music content, it's on one level exciting that so many people are experimenting, writing songs for the first time, writing beats, creating sounds for the first time. That's pretty exciting. At the same time, the idea that there's companies out there valued at billions of dollars that are built on the top of other people's music where not one artist has ever gotten paid a dollar, Is not okay. So I don't want to bundle it all up. It all becomes one thing. It's not all one thing. Mikey, he runs Suno. He's a great guy. 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.

Yeah.

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 2 weeks more music is made on AI than all of the music that's on Spotify today. That's every 2 weeks. And all of that is going somewhere and people are inspired and they're creating songs. Awesome. Don't build a business using our music. Without getting those rights. And that's something I've been trying to work on for a long time. I've met with Mikey many times. I've met with lots of people many times. I hope that this gets solved. When Napster first started, I met with Sean and Sean when they started because it was so exciting to see people were all downloading music, but it was illegal. So you were hoping they'd crack the code on, okay, how do you turn this into how artists get paid? I don't know if they were going to or not going to, But before that could even happen, it got shut down. And out of nowhere, Daniel 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 is through streaming. And I'm hoping that people figure out how, if you're going to be using people's music, how you pay for it. Fair use is not fair.

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 Merallica, and you just misspell it, then lo and behold, it looks like it was trained on this corpus.

Yeah, that's the problem. 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.

Sure.

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.

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.

They're the main one.

They're the 800-pound gorilla. But I could see a point at which possibly Claude, ChatGPT become the interfaces to everything. almost like the App Store, but somewhat like WeChat in China. If you want to do anything, 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. It starts with Suno.

Because if Claude or ChatGPT is the distribution, they probably won't carry it because it's got so many lawsuits involved. It's just not worth taking on that responsibility. And again, the guy who runs Suno, I find him to be a really good guy. I'm hoping that he does the right thing, but it's really their responsibility. They're sitting at top of this opportunity. Take off the artists that don't want to be on there and find a way to pay the ones that are okay being on there. It's that simple. It's not complicated. I think go in a room, lock yourself in a room for 3 days and come out and figure out how to pay people and take people off that don't want to be on there. Madonna does not want her music trained on. Don't care what you want to pay her. 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— I've been— the last few years, I've really tried to figure this out. And even with Sam, at one point, he really wanted to figure this out too. Sam was— Sam, a lot of people give him a hard time on this stuff, but he really did dedicate time to try and figure out if there was a music thing to do, how to do it in a way that supported artists. 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.

Well, Spotify could do it.

Yes.

Or Spotify could do it.

Yeah.

You mentioned there were 3 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?

Well, I'm working on this platform that I'm going to announce in a few months that you're part of. It's how we connected, you and I. So I'm able to ask investors what companies that they're looking at. And so 2 of those came from that conversation.

Good information flow. Yeah.

I'm 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. What do you read? Well, I'm on X a lot. I see a lot of the stuff, a lot of information on X that's flying by. That's sort of my start of information.

You mentioned missing BlackBerry and Vitaminwater. 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?

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. And I had it and we had it. And he's like, come on, let's go. Let's go. He always gives me the, oh, gosh, he's going to complain about not being in it again. Here we go again. But what motivates him is he just keeps it moving forward and it's awesome. And what motivates me is I'm not going to let that happen again.

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 that drove you towards the things you did.

Yeah. It's scary though. It's scary though. When you miss it, Ash and I invested in Bitcoin on our own when it was at $22. When it hit $250, I thought, I just made 10 times my money. I'm a genius. So I sold then. Clearly not a genius. So that hurts. And I remember Anthony, gentleman on that wall, Elon invited Anthony from the Chili Peppers to see SpaceX early days, very early days. And I went with Anthony. I tagged along. It's the first time I met Elon. And we went to SpaceX. I was so wowed by the concept that I didn't even pay attention to the business model or what could be the business model. I was just like, wow, this guy's building rockets. That moment in time, Anthony and I had the wherewithal. I go back to that time and go, we just had the wherewithal to go, what business model? I didn't even ask those words. I was just— 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. They didn't even take in all the songs. They were just like, oh my God. I mean, if you ever look back at the Sex Pistols shows, people are just like, what? And they're like, was I actually there? I think I was more blown away by the concept of what Elon was building that I did not understand that there was a business model. And I really wish I just would've asked one more question. Hey, how do you monetize this? How does this work? Can we invest? So I have hundreds of those stories, but those are 2 that stand out today.

I want to talk about the longevity for a second. You mentioned, and fact-check me if I'm getting this wrong, but the 3 back-to-back tours with Madonna. I mean, that sounds impossible just from the demands of the physicality of that. And she's kind of 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?

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. I was also changing and growing and having kids, and I was just sort of losing myself because you're going to a different city every other day and amount of things you're missing back home. You sort of forget you have a family. You forget that you can go do other things. 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 like, oh, I have kids? I have a house? So if you look at the first 3 tours, those 3 tours that I did, those are 240 shows, 80 average. I missed I missed 3 of those shows, 3 out of the 240. One, I was sick, and then I missed 2 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 spent here in this house. So I missed 3 shows out of 240, but we're talking about a different city, a different hotel, a different— in order to move along, you sort of have to block everything else out. You have to forget. And it's a very selfish, very— for me. Otherwise, if you think about— if 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 3 months and then they come back.

That's what military do as well.

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 wound it down. There was a moment there where I managed the Red Hot Chili Peppers, U2, and Madonna. And they're all going on tour. It was a lot to process.

How do you even make decisions about where to be in a case like that? Because you can't be in 3 places at once.

It's hard, but it sort of tells its own story. You're not going to miss New York. You're not going to miss London. You're not going to miss some of the major moments. And then you look at the calendar and go, oh, we have this time off. Let's go to New Zealand with Madonna. Or let's go to so-and-so with U2, or let's go to so-and-so with the Peppers. And you find your way around it. You just make it work.

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?

When I think of responsibilities, I think of management. That's a really big responsibility. And I don't take it lightly. There's no way around it. Something's going on there that's a focus. It is cyclical. So the Peppers are not touring this year. They don't have an album this year. They aren't touring next year. They don't have an album next year. So 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. So that takes time. So you get these windows of opportunity where you go all in and you get windows of opportunity where you have a moment to breathe, just like they do. They all need it too. Madonna, after this cycle, will probably need a minute to just sort of catch her breath and figure out what she does next. So these are cyclical things. What I don't do is I'm not out there trying to sign 10 more bands or 10 more artists. So that's where the balance comes in, which is continually be creative through other ways. When the cycle starts, my creativity has never stopped. So that I still have those things. I'm not starting from scratch. I'm always looking and meeting with people and understanding what's going on in technology. And so when Madonna comes back into cycle, I can bring some of those ideas or some of those new relationships I met while she was off. I found a way to make it work.

I may be, 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 sort of marching forward. And I'm wondering how you've thought about for yourself the drive and velocity of forward-looking achievement versus sort of appreciating what has been done or savoring the time that you have. I mean, I imagine you get a lot of that with congregating friends and so on. But I'm wondering if you have any thoughts on that.

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. And I don't think about it that much. Things pop up every now and then. But when I wake up tomorrow, I'm like, I haven't done anything today. I better figure it out. I need to step my game up. That's how I feel. I don't feel accomplished. I feel like I still have so much to prove and so much to do. But at the same time, I do know if I really took a minute, I would go, oh, wow, okay, I should probably take a moment and take that in. But I really don't.

Is that okay?

Is that a problem? Is it fine?

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. A lot of my friends are really— we don't talk about it like that either. I think we just sort of—

Work in darkness.

How cool that we survived this period of time. How cool is it that we're even able to do what we love? Waking up and being able to do what you love. There's a Josh Kushner quote that I love that he says about success. He says, Tim, success is being excited to go to work and also being excited to go home. 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. And I work hard because of that, because I go, this is not a given. It's not a given. 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.

So after 20 years, you and Ashton are going to be doing different things, it sounds like. And I was wondering if you could just share a bit of the background and what that looks like.

We've had an incredible run, and this AI fund is— I don't know what to compare it to other than 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 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 was a few months ago. We looked at each other's visions of what they want, what he wanted to do that would make him happy and what he wanted to build and what I wanted to do. And we have a third partner, her name's Effie, and what she wanted to do. And it turned out that we had different visions. And when you look at his vision, which he will share at some point, so I'm not going to share any of it, it'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 I have mine, which is the things that we're talking about today and the things that I want to build. And I have a version of the things I want to do that I haven't shared with everyone in full. It turned out that we just have— it's a new chapter. And I've had many new chapters my whole life. The record label for a certain amount of time, and then I moved on. I went to music management, I went to crypto, and I went to film. I 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 sort of hoping to be on the beach high-fiving each other at some point on the work that we've done and have worked hard to get here. And taken a lot of risks and a lot of chances and put in our own money. And 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 what I want to do. Effy and I are going to continue on with sound and what we've built the last 10 years with sound. So we'll continue to build that, and then we've got some surprises of how we want to build that out too. It's all really good. It's all very supportive. It's just another chapter. 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.

Thank you.

Thanks for inviting me here.

My first podcast.

I know, I know. Mine too.

Your first podcast with me. Yes.

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.

Thank you.

Hey guys, this is Tim again. Just one more thing before you take off, and that is 5-Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun, Before the weekend, between 1.5 and 2 million people subscribe to my free newsletter, my super short newsletter called 5-Bullet Friday. Easy to sign up, easy to cancel. It is basically a half page that I send out every Friday to share the coolest things I've found or discovered or have started exploring over that week. It's kind of like my diary of cool things. It often includes articles I'm reading, books I'm reading, albums, perhaps gadgets, gizmos, all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast guests. And these strange esoteric things end up in my field, and then I test them, and then I share them with you. So if that sounds fun— again, it's very short, a little tiny bite of goodness before you head off for the weekend, something to think about— if you'd like to try it out, just go to tim.blog/friday, type that into your browser, tim.blog/friday. Drop in your email and you'll get the very next one. Thanks for listening. Back in the day, this was 2004 maybe, I had someone approach me in a coffee shop and say, g'day, mate, and introduce himself. Who was that? It turned out to be the founder of AG1, believe it or not, way back in the day. And people often ask me what has survived after 20 Plus years of testing every supplement under the sun, just about, what actually has stayed in the rotation, in the toolbox. This episode's sponsor, AG1, is at the top of that very, very short list.

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