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

0:00 Well hello, boys and girls, ladies and germs. This is Tim Ferris. Welcome to another episode of the Tim Ferris Show. My guest today is Guy O'Seary. 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 four decades. He has different batteries. I've seen it. very different batteries. Under his leadership at Maverick Records, Maverick sold more than one hundred million albums. Guy has managed some of the biggest names in music, including Madonna and Think that's thirty-six years in 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 dollars. Guy was also an early investor in Vita Coco and co-founded A Grade Investments and then Sound Ventures, now with nearly two billion under management. At A Grade, his hits included Airbnb, Uber, and Spotify. Sound Ventures launched even though it has more than two billion now with less than one hundred million and has since had eighty six exits and twenty six IPOs. He's got a lot of stories. I mean he and Ashton invested in Bitcoin when it was at twenty two dollars. There are a lot of stories. How does he do it? How does he make five minute decisions?

1:18 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, O Siri, O-S E A R Y. So without further ado, please enjoy this very wide ranging, very tactical, very colorful Conversation with The one and only guy. Oh Siri.

1:35 Optimal minimal. At this altitude, I can run flat out for a half mile before my hands start shaking. And then also you personal question. No, we're just seeing it. I'm a cybernetic organism, living tissue over metal endoskeleton.

1:55 No So here we are, sitting in this beautiful home. And I wanted you to explain this beautiful Calligraphy behind you.

2:09 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.

2:18 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 twelve.

2:28 Twelve. Yeah. How did that happen? Uh place where I was living with my dad, an apartment building in West Hollywood. was directly across the street from a hotel called a Park Hotel. And that's when I started

2:40 Meeting. artist I started becoming a fan. I love music, but I a fan, s you know, someone that would actually

2:49 wait to get their album signed or you know, 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?

3:01 Period or love comma. God. It was love God. Okay. And it was Sign prints. That was a long time ago.

3:08 'Cause he later on he became a Jehovah's Witness. You could see the posters. I had like Billy Idle and Prints 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

3:23 Someone up there likes music a lot. I was on the first floor. There's a little balcony there and And I come out. A lot to meet I met.

3:30 In XS, and I met some people I became friends with, like Billy Idol became friends with years later, and Michael Hutchins 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 is other kids were around then. They're older than me. But they were kids. And so I could hang with them and

3:46 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?

3:57 And why? Before Beverly Hills High School. I went to a school In downtown LA. It was on Pecorn, Arlington, so it's

4:04 Almost on the way to if you're gonna 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.

4:14 Music was a big piece of that. of my journey there. I took a school bus there and The kids would go between two radio stations on the bus. So the bus driper would play either K D A Y, which was the first hip hop station in in LA. Or they would

4:28 go to K Rock, which is the alternative radio station in LA. And I love them both. And so I met a lot of really cool kids there who were in these groups of people the there were like the punk rockers, the hip hoppers, the Break dancers. Graffiti artists. There's just a great eclectic group of people.

4:46 During that time period where I'm just s I'm a sponge. I'm just picking up all the energies and And really falling in love with with music. One night. I was outside The school dance.

4:58 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.

5:07 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.

5:18 And then I see a car turn the corner. And I guess it was chasing the co the guy down. And a guy jumped out of the passenger seat and pulled a knife out on me and asked me if I was with that guy. He asked me if I was in a gang and I said I'm not I'm just a kid waiting for my dad, I was school dance and this is my school and da.

5:35 And so we got back in the car to chase the guy. And so You know, 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 And someone called out a knife on me and and you were late and

5:49 I want to go to Beverly Hills High School next. And Again, there's no coincidence that just came to me right then and there. That

5:57 I wanna go from downtown LA to Beverly Hills High. And there was a T V show. Nine oh two one oh back then. But uh I wanna check that out. That's a different world from the world I'm in now. I wanna just see it. I didn't know at the time.

6:10 But you have to live in Beverly Hills to go to Beverly Hills High School. Yeah, makes sense. Yeah. I don't know why I didn't put that together. I just said that to my dad and You know, we didn't live in Beverly Hills. And

6:21 He knew that's what I wanted and he Heard me. He came back to me and said uh there's someone who I know who lives in Beverly Hills and They will give you their address. To

6:32 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.

6:47 One or the other, like 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 the second chapter. At Beverly Hills High.

6:59 Once you Walk through those doors. It might as well be a T V show. From where I just came from. People have

7:08 A lot. There's cars and there's Homes with Pools and Just

7:14 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.

7:30 So I better start working. I think at like fourteen it really started to kick in where I go Ooh,'cause there are 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

7:44 I knew that I needed to do something about it. And I So I 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

7:56 was obsessed over And So I thought something in music. And that's when I started to really pay attention to what can I do around music, where I do music and then Around fifteen I really started to pick that up and

8:07 At sixteen I was already like really running with it. So I think This might be a good bridge if I'm missing Something. In between these points, let me know. I'm sure there's a lot that we could talk about, but

8:19 Bernie Brusteen. Mm-hmm. Who is that? So Bernie Brostein is iconic. And Hollywood He's one of the greats.

8:27 You know, he was exceptional. He was one of the original managers and he managed all these amazing talents. A lot of the talents from SNL. He managed all of'em. He started the side of building John Belushi. Gary Shambling.

8:42 All of them. Yeah. And he was beloved. He looked a little like Santa Claus. He's a really big guy with a white beard. When I was

8:49 Fifteen. I started to compile artists that I like that had demos. So I would go out there and try to find artists and try to find new artists and I had like the yearbook person come and take photos of these. On your own. On my own. I didn't know what I was doing. I just thought

9:06 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 to meet.

9:18 I think I called it Wise Guy Records. Just I didn't know what it any of it meant, but I had my little logo. I did every everything I could possibly do. Without knowing anything or anyone. And then The week I turned sixteen, I remember it was the week

9:31 I turned sixteen because I didn't pass my driver test. So I needed to be dropped off. So the week I turned sixteen I went to meet with Bernie. What what happened was is 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

9:48 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 first one I got was Bernie Burlstein.

10:02 And his two boys. Nick and Dave. Both. told their dad, you know, you should meet with Guy. So I go meet with Bernie. He was at the Ninety two hundred building on sunset.

10:13 Um I played him uh 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

10:24 Hey kid, how much is it gonna cost to put this out? And I knew not to pause. 'Cause then he'd know I'm a phony. So I said Twive thousand dollars.

10:37 And he said, I'll tell you what, kid. I'll give you the twenty five thousand dollars. If you Make it back. Pay me back. That's all I ask.

10:45 And at the time I'd never seen twenty five hundred dollars. So I just said Bernie, I'd rather you make three phone calls for me to music people. I don't want your money.

10:57 And he ended up putting that in his first book. that story. He's passed away, unfortunately, in He always felt that I 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 twenty five thousand dollars. And I was

11:09 A phony. But until his You know, last days he always thought in his book he's like the one guy that didn't want to take my money was Guy O'Search. It's not true. I just didn't know what to do with it. So he made those three phone calls for me.

11:21 Did he pick the people to make the phone calls to? Yeah, I had no idea. I said three music business people. He did, and I got meetings with a few of them. But they never ended up Going anywhere. Going anywhere at all. What ended up happening was

11:35 As I came back home And I thought to myself Wow, I'm sixteen years old. And this guy offered me. As much money as

11:45 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.

11:57 But you don't know. Mm- Till someone confirms it. Until someone buys your book or goes to your show or Offers you twenty five K.

12:05 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

12:13 I'm going to turn it up. I'm not looking back. This guy offered me twenty five K in one meeting, I just turned sixteen. I'm gonna 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.

12:28 On my life. You mentioned two meetings. Yes. Was the other Freddy? The other was Freddie De Man. All right, who is Freddie De Man? Freddy the man His daughter's Nisa and Pilar.

12:39 Connected me with their dad. Freddy. And Freddy was iconic as well. I mean he worked on Thriller with Michael Jackson. Wow. He managed Madonna.

12:51 He managed some of the greatest artists of all time. And he was just a really Great. Human. Great guy.

12:58 And He heard me out. It took a few meetings to get Freddy to really go for it with me. Not that long. But this meaning was after Bernie. Meaning was after Bernie She just learned about me.

13:09 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 an Any money. Yeah. At that point, what was your pitch? Gosh, I think I 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

13:25 I got very lucky, got introduced with my friend Chris Boyd. I met When I was working Minus fifteen 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

13:38 Would you want to come to the studio and check it out? And I'm like, Oh yeah, I wanna go. So he brought me to the studio and actually my first day in the studio, Iced T goes, come into the booth and do a few words. And I'm actually on the album. Wow. Yeah. Oh, and so he had me say like a few words on the album. But I started hanging around and I'm like, What could I do? Could I

13:57 clean up? Could I carry someone's bag? Could I How do I be helpful or of service. I'm just so happy to be around this energy with music and artists coming in and out. And he had a thing called Rhyme Syndicate. So a lot of the artists came through there.

14:11 And I was able to Be around them and help and And then I ended up becoming the manager of I st And his brother.

14:20 It was hengy. And Evil Lee. Evil Lee is ITZJ. So I managed them. It's my first group I ever managed. And I was seventeen, 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.

14:37 There's a guy named Rifkind. Who I met. Hm. New the record label He helped me get that first record deal. So when I went to see Steve and I was playing him I ST's DJ, Evil En just brother Henji.

14:49 And I said. Here's the music and 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

14:57 My first group signed, I just I'm manager, you know, and he knew I was How is he pulling these things off? On his own without any help or any money. And so I met with him and he said, You know, Madonna and I are gonna start a record label one day.

15:12 So I said from I'd love to To work there. I said I don't need any money, which I did need money. But I wanted to make it really easy.

15:20 For him. I said I don't need money, just give me an Office And a desk. That's all I ask.

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17:05 Tim. I So he brought me in. As a You know, scouts.

17:13 'Cause one day they're gonna start a label. They didn't even have a name. They just knew they were gonna do it, so I'm scouting. And then One day I

17:22 Find a hole. Just Courtney Love, I find their first song. Teenage whore. And I go Oh my God, this sounds incredible. I just just blown away by the sounds and the lyrics and all of it. So

17:35 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 Who How did that happen?

17:45 I mean. I made a 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.

18:00 I think Kurt was there. Madonna. What it's a Talk to me about Who is this whole thing that you're that's yeah, so I go in a room and I play the song for Madonna and for Freddie.

18:13 And it's pretty wild. I mean the lyrics are like When I was a teenage whore my mother said she's a baby, what four? I was like Whoa. And you gotta go back to that like that time period. And it was they were like Okay.

18:30 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 whole. So let me pause you for one second. Yeah.

18:44 Alright, so the meetings That you got. With Bernie and Freddy. So you got Two introductions. How many of you Kids at school do you think you asked in total?

18:54 To end up with those two. I think I probably has five. Okay. All right. I mean I was already I was sort of Wasn't social guy, I'm not on the football team. I was just sort of my own music guy running around and I didn't have much.

19:08 So I did as much asking as I can from who I could figure out to ask. So I probably asked M five, I I remember one person specific saying My dad doesn't do that. Whatever. 'Cause it was rap. I was trying to play Oh, my dad doesn't do that. So

19:22 I didn't have any shame. I I needed to figure this out. I knew that my time was limited before going to college. I better figure this out soon. So I was on a hustle. This is from an LA Times piece way back in the day.

19:34 Nineteen ninety seven. But 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

19:45 Did you apply pressure to yourself in that way? Like instead of going to college? No, I went to college. I went for half a semester and I got my first group signed. Which was just Hen Jean Evelie. And then I I remember going to my English teacher

19:58 I don't know her name. She's 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. Tchau. Yeah. Wild to think about these just chance. That was it.

20:09 And I go, Oh. I could always come back. Okay. So that was it. And by the way, I couldn't even afford the seven hundred dollars Per semester.

20:18 We know and all the things that came with that. So I had no choice. Yeah. Sometimes having no options and no choice is really the best option. Where did the like come from. I mean, just that drive. I mean, was that absorbed from the parents? Were you just out of the box, very different?

20:34 I fell in love with music in a big way. I think I realised How lucky I was to be At Beverly Hills High and C

20:44 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 was wasn't like an easy thing to do.

21:01 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

21:11 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 of any flash point or was it really

21:24 Gradual. The Bernie Burstein moment. Where he offered me twenty five grand. The week I turned sixteen was a big Game changer for me.

21:34 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 f finally got my car

21:44 I remember going to see my old friends from my old school. When I drove it to Beverly Hills High it was Honda Civic. When I drove it to Brothers High, I got not one person commented or said congratulations or nothing, no mention of it at all. Sure. And then I went to my old friends from my old school and then They couldn't believe

22:02 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.

22:15 To go oh These people are barely 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 was to build my name and to build the things I want to do. It wasn't until years later I

22:28 Actually I told that story in that thing you're talking about when I was twenty four. 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

22:40 I think I need a perspective a lot of The opportunities that were in front of me and to Really appreciate them. So

22:50 It's a combination. Of those things. And From The chapters we've discussed so far, I mean, was then the next phase.

22:59 Building your relationship. With Madonna primarily, or where did you kind of hop off? Past the things that we've already discussed. Modern The first real connection was that whole connection where

23:11 It's like play me this thing that you like. And then the second artist I brought was Rage Against the Machine. And I really wanted a sign rage against the machine. And so I took her to the concert in New York. The limelight, I think it was called.

23:24 And I didn't get them either. I didn't get rage. They ended up going with Michael Goldstone at Epic Records. So You know, God, the first two things I competed for I didn't get. Well, not only did you not get them, but they went on to be successes, right? Yeah, it was painful.

23:39 The third one I that I competed for, I did get. It was called Candle Box. And at that time actually I think it outsold both. Both hole and rage at that time. Doing really, really well. But

23:50 Regardless, whole enrage. Even to today I still listen to them. I love them. But I was very lucky to get candle box. The fact that they Bet on me. We didn't have anything. We just had this idea, you know?

24:02 They ended up selling four million albums on that album. But I'll I'll never forget that. I'll never forget that they Gave me that shot. That was the my first success story was T. But Just to

24:14 Repeat what you just said, like you didn't have Much, right? Like they're placing a bet on you. What then goes into helping make a hit album that sells four million. Going back to that time period. First is the music.

24:29 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's all intuitive and it's very fast. I walked into I was supposed to be somewhere else that night.

24:43 But I went to this party and 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

24:58 screen like a video screen on the side of the stage like And then there's a stage. And I was looking at the video screen There may be like Thirty people in the audience.

25:09 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.

25:18 In my mind, yeah. I went to the payphone. from that performance called Freddie and said, Freddy, I have our band. This is the band. I just saw them. This is the one.

25:28 So it starts with That always starts with the magic. I don't care if you're Tech company. Or your

25:36 Whatever it is, a film, a product, a book. Magic. You gotta have magic. Something has to pull you in. And That night I saw it. I visualized it.

25:44 And the songs were there. The songs were so there that when we made the album Their first two singles We could not beat the demo. They went in to re record them for the album.

25:55 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 be. And so those songs, those first two songs on the album are from the demo. So the music was there. They were talented.

26:08 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 few years for d every week, every week, little by little, little by little. Key word is artist development. And people don't always develop that much.

26:24 But something that we all want. Every artist wants to Have the time to build, have the time to develop and And we really took that time week after week developing that one. That's how We got there.

26:37 This is maybe jumping ahead too far, but what would be an example of that? in your Investing later. Could be tech, could be outside of tech, where You saw something.

26:49 Or you talk to someone. And it was within a matter of minutes or one conversation really. Okay. That is a horse to bet on. Honestly, I would say that

26:59 Ninety percent of the things I do. happen in the first five minutes. Ninety percent. It drives me crazy when we Get in a room and talk about it for three months.

27:09 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.

27:18 It started out I think The Muscle that got built. For fast. sort of response thinking or intuition.

27:27 What's 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. We didn't have any artists. So

27:37 When I met an artist and I like them. Alanis Morris, I signed off of One song. Muse, I saw them perform. One song.

27:47 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 we flew out all the way from London. We'd like to play more music. I go, but I just want you to know

27:59 I do not need to hear another song. But just be clear. So it shows the artist The passion. Which is very important.

28:07 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.

28:23 Or else we would never have to do it. 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. Right.

28:42 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.

28:57 Because you can't bet on everything, especially the small label. So 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 know, you can't fall in love every five seconds. I didn't know I was gonna follow with Alanis when she walked in my office.

29:13 With Glen Ballard. They came in to play me. I don't know what the was going on here. I thought they were banned. He was the producer's co producer, co writer. You just have a feeling.

29:23 There is a lot of pattern recognition later. Like now with experience. Sure. Now I bring other elements into the mix, other things I'm looking for. that are different than back then was just I love it. I'm ready to go.

29:35 I feel it. You have to fall in love. And Later today I I would say on my tech investing and what I do there. It's a combination of

29:42 Got it. Pattern recognition. And then There's a few other things like one of the things I look for is can I help it? I visualize what I can do for the company and that gets me excited too.

29:53 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 gotta make sure

30:05 They do what they say. Hey, let's try this thing out. Then you know, let's make sure the car actually shows up. When you press the app and it picks you up and it Well make sure the things work. Make sure that you can stay at the apartment and it's actually oh, I press the thing and I can get an apartment. These things have to work.

30:21 But For me, it all starts with that initial Pinch. Back in the day, this was 2004 maybe I had someone approach me in a coffee shop and say, Good 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?

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31:55 Tim. Yeah. 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 but just

32:10 Took me to the next level. I mentioned earlier, you know, she appeared in my office with Glenn Ballard and They played me One song. They played a few songs but the first song they played was a song called Perfect. I didn't understand

32:24 How powerful Those lyrics were until later. When I really listen to it. It's really about Earning your parents'

32:33 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.

32:43 Don't forget to win first, please. 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?

32:54 I just had never heard anything like it. Again later I understood Those lyrics were. But at that time I was just In love with

33:03 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 are like, Oh, I thought it was

33:14 Joni Mitchell. People were like, Oh, I didn't know Joni Mitchell. So to me she was my Joni Mitchell. I didn't never listen to Joni Mitchell before. I listen to it later because of her. I wanted to know what people were talking about.

33:25 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 like a pop album in Canada. And so people had all this background. I had no background. I literally was asked

33:38 To meet with her And Glenn and I knew nothing. I knew nothing. They walked in And I thought, Oh wow, it felt like a A hippie group actually. I was like, Oh, maybe there's like some sort of hippie vibe kind of

33:51 What is this gonna be like? Kind of thing. But it was Again, another life changing moment. When the story's told, it's it's that

33:58 Everyone passed. But I just felt it in the first Minute. And then we

34:04 Ended up working together and working on that album and That album ended up selling thirty million albums and s I think Top five debut album of all time. That really just

34:14 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

34:22 Cemented that I'm in a good place right now that I can do these things and I this probably's gonna 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.

34:35 That Years later. She's right now she's still winning awards. She's still out there. Crushing. She's actually

34:42 Doing incredibly well right now. And It makes me so Proud to have played any part of that.

34:52 It would be So sad to have missed that one. So happy to I have been fortunate to have gotten that meeting and to have figured it out.

35:00 A lot of people when they Initially heard it. I remember m 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

35:15 I had not heard anything like this and that this was A Monumental. record. Rest is history.

35:23 Rest is history. I'd love to Spend a little bit of time. On What you've learned from

35:29 Madonna. This is an older variety piece. 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. What did you pick up?

35:46 From Madonna. What are the key sort of learnings? I mean there's some clear learnings and there's stuff that with I'm thirty six years next to this woman. Yeah. And There's things that when you Look back, you go, Oh c got that.

36:00 Like people who think about things that well they 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 uh the Front part is pretty I think obvious, you know, her work ethic is

36:13 Not to be believed. Her commitment to her craft. Not to be believed. Her passion. for Just

36:22 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 surround herself with a

36:36 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 To be painters or Frito Colo.

36:50 Or they can be designers, or they can sh or musical people. She's An incredible finder of talent. So I think the thing that is really affected me.

37:00 The most is That she There's no walls around her. Thoughts. There's no oh I can't do that.

37:09 Right in terms of constraints, right? Yeah, and I think that even going back to my first experience uh Maverick Records. If you went to any record label They would have 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.

37:26 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.

37:37 It's really Just being around her. has allowed me to n never think in the limited way. And they all work together. Lot of the stuff I do on technology. has allowed me to bring that into

37:51 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 so

38:03 It was very much like we're what are you doing? There's just 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

38:13 When you're launching a new company You know, these founders are rock stars. In my mind, every founder I invest in I look at them like They are the rock star.

38:22 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

38:37 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.

38:48 In my mind. We're gonna 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

39:00 Terrain of film. And how you ended up. Executive producing Twilight. 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.

39:16 Ability, right? How did you end up With the foray. Into Film. I'd been

39:23 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.

39:34 Thought let's just start this film company. Why did that? Come to mind. I don't really recall That

39:42 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

39:54 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.

40:07 And they were all Independent producers The idea was is I'll bring them in. And you know, house them and give them support.

40:16 And pay for a lot of the legal things that cost money. When you're independent, it's a lot on you. All the back office, all that stuff. We'll take all that on, we'll help you and then We'll work on these projects together. Do we have like A lot of producers.

40:29 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.

40:38 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.

40:48 And I was at that same moment that it started to take off. I Picked up. Madonna as Manager.

40:56 With my partner at the time, Angela. And I took on confessions. Which was Pretty massive tour that year.

41:03 And I think the biggest laying record of that year. So as a I don't know how old I was back then, but That was a major responsibility. For me. Hard to ride both of those horses at the same time.

41:14 Just that alone, just Madonna at that moment in time for someone I had not been a music manager for And anything near that level. And so to take that on. And to work on And for people who have no

41:29 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?

41:42 When Madonna started working on ray of light. I found the Producer.

41:49 William Orbit. But I was not managing her. I was Her partner at the record label. Maverick Records. Right.

41:56 And not her own, not Warner Brothers, which is where she was on Warner Brothers, but you were just friends and working together But I Fed ideas have found the director, Jonas Auckerland and so I was

42:07 Creatively really working on this project called Ray of Light. So we're already building a creative rapport. Mm-hmm. And on music. Stefan Sidney.

42:17 The director introduced me to a producer named Merways. Gave me a demo. I Loved it and I gave it to my daughter and I ended up becoming music. So I found On those two albums I really

42:27 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

42:36 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 creator point of view. On ideas, ideating. Here's things we could do, here's things we could build. So I think

42:47 That's the management that I am. I'm more creative. When I'm working with someone I I'm Sort of. In it.

42:54 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 of you know, what if we

43:05 There's different kinds of managers. I'm for creative. For example when I Showed her Yonis Arkelin today.

43:12 Video for Prodigy. Which is a band I signed. And it was really provocative. I just showed it to her, This is crazy. And she goes. He's doing my first video or you know, I showed her uh there's a guy named Chris Cunningham.

43:23 He made a song called Come to Daddy by Apex twin. Which is really insane. So thirty thousand Dollar video. I just show her to her just to show her this look at this crazy thing.

43:32 And she's like That guy's doing that video. So she had Chris Cunningham Do frozen. Which is an incredible video.

43:40 And she had Jonas Arkland do Ray of light. So It was just a really great Back and forth.

43:48 Energy together. She was open to my craziness. And then she would take it to the next level. What And this is my

43:56 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

44:09 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.

44:20 And I'm just wondering if you Could add any. color to that. She doesn't

44:28 S Well on her Past. She's not High fiving herself. She's just keeps it moving forward.

44:39 Um I think That is part of the inspiration for Continually.

44:45 try to move forward myself. Is um have a Front row seat. Or shotgun to this incredible

44:53 Journey of the Women who just Continually. Defies all the odds. And

45:01 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.

45:10 She's breaking ground for a lot of other people. We're coming. behind her. Who can say, Oh, Madonna's done it, I can do it. But

45:17 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.

45:27 She just Starts like it's A brand new day. How did you end up I don't know if this is a little bit more than I've been.

45:34 Good starting point, but I'll throw it out there as an example. Your first consumer investment. By Decoco. Well done. Thank you. Uh I don't know if that was Your tenth investment overall or your first, but how did you end up Mm-hmm. Edging into the world. Of

45:51 Investing. C P G and consumer stuff or tech. How did that even come to be? The original Original was I was

46:01 on a plane to Milan for M T V Awards. And I don't remember how old I was. It was in my twenties. And I

46:11 Was reading in a magazine about Sky Dayton. And it said he started Earth Link and He was worth a hundred million dollars. I'm like, wait, what?

46:20 You can't. Wait, what is he doing? And how old is he? And so I go, When I get back home, I want to meet this guy. So I came back and I Took me a while, but I finally tracked them down and we went to have lunch.

46:33 Four seasons with Tell and And he was like, Wow, if you're impressed by me Have you ever heard of Bill Gross? An I D Lab. And I go. No, who's that? He goes, Well he started a incubator. And

46:44 He's launched three billion dollar companies in one year and I go, Sky, I like you, but can you just Can can you get out of the way I wanna this time has been great. Yeah it's time to move on. I need to talk to this Bill Gross guy. So he sets me up with Bill Gross. Bill Gross ran an incubator called Ideal Lab in Pasadena. And I Just

47:01 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?

47:16 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.

47:25 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. But my listeners are gonna kill me if I don't follow up. What's the bad news? Well, I mean the bad news is is that

47:40 I worked there for a year helping. And then one day Someone I really trust. Right. They don't know it to this day.

47:49 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 wanna put

48:02 money into idealab and he goes, Well, you know, I was gonna surprise you and I was gonna 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? And he's like You know, he told me what he thinks when it

48:16 comes out and I was I mean it's worth a lot. And I go, That's not enough. I'm thinking right? I'm thinking to myself, that's not enough. So I go, Bill, I wanna 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 really, really sweet guy.

48:30 And that's the bad news. I He let me do whatever I wanted. What year was this? It was before the crash. It w by the way, it wasn't a year before the crash. Yeah. I think it was like an hour before the crash.

48:41 Okay. So I put Every dollar I have. Plus dollars I didn't have. I picked out three investments at that time. Ideal app.

48:52 Because of Bill Gross. Bill was the first guy in I think in LA To have the Blackberries. So I was the first guy from Hollywood to even know what the

49:03 Hell Blackberries were. So I ended up Buying four hundred of them. And I gave them to all the people in Hollywood so I could connect and when I needed to and talk to them and

49:11 So I made a deal with Jim Bowsley 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 Rotsky brought me Vitamin water. So

49:25 Those are gonna be my first three investments. What happened was Is the ideal app thing, once I put that money in I don't know the Time line'cause I tried. It's almost like I just thought

49:36 It's almost like something you want to wash away from your mind. Right. 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.

49:51 with Jim Belsley in Research and Motion. And I never did my deal with Vitamin water. Which both ended up It's just almost like the

49:58 whole and rage analogy. They both ended up being massive. And then I lost all my money with the first one. So I learned about diversification. I didn't diversify put. The majority of my money in one thing. And I paid the price for it. I really

50:13 For the next Two years I Only thought about that about fifteen 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.

50:28 my whole life. And I ended up I was mad at But Sky Dayton introduced me like I was like Matter all the wrong reasons, you know?

50:34 Everyone was just trying to help me, but now I'm like, Why did I even read that magazine? I should just stay in my music lane. But what happened was years later, after my first Madonna tour. I started to think about it again. And I go. I wasn't so off, really.

50:50 The timing was wrong. on the ideal app part. The other two worked. Had I diversified It would have been fine. Incredibly well. Yeah, you would've been great. And So I went so I got two out of the three.

51:01 The truth is is It's not fair to to Bill'cause 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. But I came back from I think I done

51:19 Three Madonna Tours in a row. You know, all the money I'd lost, I made that back to survive. And then I had a window. Where I knew we were three tours in a row, we're gonna take some time off. And I thought to myself, I didn't get it so wrong.

51:35 So I'm gonna try this one more time. I'm good at identifying The ideas. I'm good at identifying the talent. I'm gonna do it one more time. So I started.

51:44 And The same guy that brought me vitamin water, Sethrotsky. Did he later work with Reese Weatherspoon? Exactly. Huge. Yeah. Yeah. He's done well for himself. And then he called me one day and goes.

51:56 Have you heard of this coconut water? Thing. So Of course I'd heard about coconut water. One, my wife is Brazilian.

52:03 And my first son, his first words were like agua to 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 five or seven million dollar business. It was not tiny. Nothing. But Madonna on tour. On the previous tour.

52:21 She would have the trainer would go in different markets to find Fresh coconut for her. For the coconut water. And I like wow, every location we went to have to find fresh coconuts. And so I started to hear that other people were doing that as well.

52:36 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.

52:48 There's a photo of Giselle drinking from a coconut. And they're talking about coconut water. And I had cut that out. I put that article on my desk. And when Seth called me

52:58 And said, Have you heard about Coconut? I go. You have to be kidding me. I have sitting on my desk. The only thing that I've torn out that's sitting on my desk is an article about coconut water. It's on my desk and it's like my to do, like. I need to figure this thing out.

53:12 And here you are calling me, goes, Well, there's a company called Vitacococo. out of New York and I go, Count me in. I got on a plane, I went to meet with the founder, Mike Kirby. The company was a I think it was a thirty five million dollar valuation at the time.

53:24 And I literally just Here we go. I'm jumping back in and I went in Really big.

53:30 I brought Madonna into that. I brought Dimmy Moore, I brought Matthew McConahe, Anthony Keats. I'm not a bunch of people into this. thing'cause they were all healthy people who drink coconut water. I'm like, let's blow this thing up. That was the first

53:42 Time back. After the Crazy run. For people who don't know, how did that turn out? But it's a public company today. I think it's four billion dollar market cap.

53:51 So you're back in the game. Um yes. It takes time. It takes time. Yeah, just 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.

54:07 How did you Approach that meeting. 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

54:19 We're probably overwhelmed by Whoa, and we just ran. Mm-hmm. And um He's awesome. What he's done with the company. We went public, I think, at a Like two billion and now it's at five. Like he's done an incredible job.

54:31 So we're gonna hop to some more recent examples, which may or may not include this chair. In a moment. 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.

54:45 Matthew, you just mentioned said this, Woody Harelson 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

55:03 Building relationships. I'm not saying you have to come up with like Guy's ten commandments of Long term relationships, but How would you Think about that, right? If you're in front of

55:13 a class of students and you're like, look Lot of people get this wrong, or at least let me tell you how I approach. Any particular rules that you use for yourself or just approaches, things you keep in mind, because that's certainly not true for everybody. And you just have this long term.

55:29 Cohesion. of these people around you and I'm just Wondering If you can perhaps just speak to that. And anyway.

55:36 Well I think it Started Early. In my teens there was a group of us That were running around and

55:45 We found each other. So You find the other people who are also on the hustle. Who are also creative. And

55:53 I wasn't a comedian or musician or an actor. Or director. I was like an executive. And there's a little responsibility. He's a responsible one. I don't drink. I don't do drugs. So

56:08 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's

56:18 She trusts him. Maybe we should trust them, maybe back in the day. But I think over a period of time. My house became the place. That

56:26 People would Come to or People would congregate and feel safe. You know, even when I do events here or anything. There's not a lot of photos there's no cameras. I think safety and support

56:37 Has always been in my DNA from an early age. Just making sure that people are protected. And again I think identifying Really

56:47 incredible people to be around. Same way identify the greatest companies to invest in. Like Think identified really amazing Incredibly talented. Friends who inspire me. Oh

56:57 No, early days you may not have known them thirty years ago, but You identify them, you and they identify you. And so there's a Camaraderie And there's this trust.

57:07 And I do try to bring them all together a lot. I think it's important. That was gonna be actually my next question, which is Along those lines. Which is how often do you

57:18 gather people, whether it's at this house or At events that you put together. Just to f facilitate that. Long term. Cohesion. How often do you

57:28 Organizer host things like that. Yeah, if I'm landing in New York This week they'll probably do a dinner and I'll invite fifteen or twenty friends and we sit down and we talk and we so I I'm always Staying connected and in touch.

57:40 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. We're always checking in on everybody. I grew up Just with my dad. My two sisters were older.

57:52 They weren't around. So My friends are They're everything I had. Before I had a family, my friends were

58:00 Everything to me. I'm lucky I get to work with some of my family. You know, Madonna's I've been beside her for thirty six years. The chili peppers.

58:08 are my best friend in the world. Godfather of my first son is Anthony. The whole band, all of them flee, Chad John, their family. So It's a

58:18 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.

58:28 And again, if someone's in need. This is the number. Call me. Mm-hmm. I wanna hop to the Back to the investing. I mean you've you've had a lot of hits. Airbnb, Uber, Spotify, it goes on and on and on. I mean, I don't know how many

58:41 IPOs and so on that you've had. I mean the gazillion Let's talk about one. So you put in tell me if I'm getting this right, thirty five 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?

58:56 Nine hundred and sixty five billion, something like that? Are those numbers roughly Accurate. Yes. Okay. So that's It's pretty nice multiple so far. You know, we'll see. How things go. How did that Anthropic deal.

59:10 happen. Well it starts a little before The Day that

59:16 Open AI came out. Which was on my dad's birthday. Chat GPT. It was Life changing.

59:23 You remember those moments. And again, I go back to music. I remember when I heard Smells like Teen Sparet by Novana. I pulled over. The car And I went, What?

59:33 Is this. And when ChatGPT came out. That was a what is this moment for me. And if you saw me. Any time after

59:41 GPT came out. I would have harassed you to show you Chat GPT. There's no one every artist, every actor Everyone I walked around and met, I'm like, check this out, check this out, check this out.

59:52 And I was obsessed. And I called uh Ashton. And I said Ashton. This is it. This is open AI. We're doing open AI. This is the greatest thing I've ever seen.

1:00:04 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 gonna go after. But then

1:00:12 We visualize that. You know, when we first started investing, Ashton and I It was when the iPhone and the App Store We're happening. And so for the first time ever.

1:00:25 You can scale companies like Never before. And I think Anyone would have done well at that time. We were like Lucky

1:00:33 People that came in at the right time. And we're looking at the right time. And started our fund at that very moment. Which is crazy. And so

1:00:43 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.

1:00:56 And we felt that This is it. These foundational AI models In ten or fifteen years we'll be How we plug into

1:01:05 All these things. So We really felt like we had a three month window. We told people we have a three month window. No. It came out November th

1:01:14 Thirty of Twenty twenty two. So There's not much you can do. This people are going away. There's Christmas time break, blah blah. As soon as January came.

1:01:23 We went out there and told people This is the vision. We're gonna 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 do it? So we so we so we Ash and spoke to Sam. We were able to get open AI. And

1:01:43 What happened was is I'm very close to Mark Bennyoff. And Salesforce ventures. People don't really understand how

1:01:53 smart they are. Yeah. They don't get really smart. They don't get all the press on they are one of the best investors. In the world. There's two guys there, John Samorja and Paul Drews. Who were When I was doing my research,'cause now I'm on the lookout.

1:02:06 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 gonna do anthropic.

1:02:19 And They were very bullish about it. And I found out from a friend That Works with a

1:02:26 Job Hunter kind of People who f help find jobs for people. Oh like headhunters. Headhunters. That Everyone's going to this company called Anthropic, you know? Like people are really going to this anthropic place and they're not going anywhere else. Oh, okay. I need to pay attention this way.

1:02:42 I asked Paul And John, connect me with this founder. Dario. Say connect me. With

1:02:51 Nirov. And They come here. They're ac here right in this room. And that's where we made the deal. to invest in anthropic.

1:02:59 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.

1:03:11 This is gonna be within three months. We're gonna deploy eighty percent of the money within the next three months. And that's what we did, and that's over Three years ago. How did you know the window was gonna be so narrow, right, I imagine? Did you get any pushback from LPs when you said we're gonna deploy eighty percent of this in three months? Well, we didn't have there was no LPs, meaning that was the pitch.

1:03:30 Yeah, yeah. So it wasn't like we it wasn't like we raised money they either bought in or they didn't like we raised money and then told them the pitch. It was like Here's the pitch. Here's what we're gonna do. There's a window of opportunity here. We think this is the future. And That was it. They had opt in. Yeah, opt in or opt out. We didn't know what we were gonna raise.

1:03:47 It's just whatever came up is what it was gonna be. That was Trying to pull from memory, but looks like Sounds like

1:03:56 At this point is that eighty six exits and twenty six IPOs. That's insane. I mean that is it's been fun. Yeah. You have

1:04:05 Seemingly different batteries, certainly. I mean you 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?

1:04:15 What do you see? Is it switching gears entirely and looking at the prison through a a totally different way. I mean what is What is next for guy? I feel like going back to the core really

1:04:26 Honing in that. And tenne for The greatest talent in the world. The greatest ideas in the world. This is an incredible time.

1:04:35 Where People can Scale up a company. And The quickest

1:04:41 Ways and I'm excited about The potential. What's to come. I've already identified

1:04:48 Three things I want to do. Today. So I can only imagine. You know, what's to come.

1:04:54 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.

1:05:02 help them in every which way that I can. Pick the teams that you want to Back. I'm feeling pretty good about that. The just continuing on this

1:05:11 Best in class talent. Idea. The hard part is For a lot of people з. So we're very lucky we have access.

1:05:20 And we also Do the job. We have More than enough. Proof.

1:05:26 Of People that come through. When you work with them. And we're a different kind of Investor on the cap table.

1:05:33 We're not in the valley. We're here in Hollywood. And we bring a different dynamic, different You know, obviously narrative. is something that I'm very focused on. Marketing is something I've been doing since I was a A teen.

1:05:45 And so, you know, marketing strategy media, partnerships, narrative, storytelling. Hey, if you want someone like that on your cap table, I might be interesting to you. And Hopefully I can be helpful.

1:05:57 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.

1:06:08 Lot of founders listen to this podcast. Is there any uh are there any Particular things that's Have your interest right now, or types of companies, types of founders, anything? That you'd like to So to make

1:06:20 Clear to people who are Listening or otherwise. Also where can people learn More about what you're up to. Like is is there anywhere that you would point them in particular? I'm a generalist.

1:06:31 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 gonna be built around this one idea. Usually I'm a generalist. I really like

1:06:45 Talented people. And in regards to sharing Where can they find out what I'm up to? I'm not really This is it. Yeah. This is it. You know, this as you know, this is my first podcast. Yeah. And depending on how this goes.

1:06:56 Could be my last. If it goes well, maybe one more. Everything has been fine without doing That. You know, uh people either find us Word of mouth, through friends.

1:07:06 Or I find them. It's okay. It all works out. I'm not out there Yelling, Hey, find me one eight hundred. Whatever or

1:07:13 It'll work itself out. The right people We'll 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

1:07:26 AI in music content. It's On one level exciting that So many people are experimenting.

1:07:35 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

1:07:45 There's companies out there Valued at bільans of dollars. That are built on the top of Other people's music. Where not one artist has ever

1:07:56 Gotten paid a dollar. Is not okay. So I don't want to bundle all up. It all becomes one thing.

1:08:03 It's not all one thing. Mikey, he runs Suno, he's a great guy. I mean great guy. I like I really like him as a person. But every time I read about the company and it's now at a five billion dollar valuation, and next thing you know, it's at a ten billion dollar valuation. And

1:08:18 It's all Built off of The world music. But yet not one music artist has gotten a dollar. So

1:08:27 That's not okay. That has to be Fixed. I'm hoping Mikey does the right thing. And

1:08:32 Fixes that, comes up with a system. That allows artist if they want to opt in. Either let them opt out. To not use my music.

1:08:43 To build your business. Okay. I'm opting out. But if I opt in Find a way to pay us.

1:08:50 And I'm really concerned. For that. Because The other part which is Right now, currently

1:08:59 Every two weeks. More music is made on AI. Then all of the music. That's on Spotify today. That's every two weeks.

1:09:09 And all of that is going somewhere. And people are inspired and they're creating songs. Awesome. Don't build a business. Using

1:09:18 Our music. Without getting those rights. And that's something I'm been trying to work on for a long time. I've met with Mikey many times.

1:09:25 I've met with lots of people many times. I I hope that this gets solved, you know, when Napster first started. I met with Sean and Sean. When they started'cause it was so exciting. To see.

1:09:35 People were all You know. Downloading music, but it was illegal. So you were hoping they'd crack the code on okay, how do you turn this into How artists get paid.

1:09:44 I don't know if they were going to or not going to. But before we That can even happen, it got shut down. And out of nowhere. Daniel Eck.

1:09:52 In Stockholm. Build Spotify. And figure it out. That people would pay for music. If you give it to'em.

1:09:59 In this way. They had all the music in the world. Without having to Try to piece it together or try to Illegally download

1:10:09 Songs that were Not even clean or clear and they it could be corrupt. To get it clean. To hold on to it. They'll pay for it.

1:10:18 He was right. They've paid for it. Now Are all the payment plans there picture perfect? No. But

1:10:26 It is the core of where money is coming in today to music artists through streaming. And I'm hoping that People figure out how if you're going to

1:10:37 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. You say, serve me up some music that sounds like Moralica, and you just misspell it. Then lo and behold, it looks like it was trained. There's a lot of workarounds.

1:11:04 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 gonna find out a lot. Sure.

1:11:14 And Discovery's gonna say All of This music is in there. And they know that. And

1:11:22 That's not okay. It's just like literally not okay. I don't understand it. And by the way. What's wrong with paying artists? Yeah. Why not figure out a way to do it? Sit down with a team, figure out how to pay. music artists if you're going to train on their music.

1:11:36 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 Sino. I mean there are lots of lots of different options here, but they're the eight hundred pound gala. But I could see a point at which

1:11:57 Possibly. Claude. Chat GPT become the interfaces to everything. It's almost like the app store, but Somewhat like WeChat in China. Like if you want to do anything, you wanna Book.

1:12:08 A restaurant, you wanna make a song. Okay. There are a few interfaces to everything, at which point then those companies, right? OpenAI, Anthropic, can gatekeep in some way. And maybe They end up being

1:12:23 The entities that Incentives. these other companies like the Sunas of the World. to reimburs artists. I guess I'm just wondering if you Have any thoughts on how it gets there.

1:12:33 Yeah. Claude or Chat is the distribution. They probably won't carry it because it's got so many lawsuits involved. It's just not worth

1:12:44 Taking on that responsibility. And again, the guy who runs S 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 the top of this opportunity. Take off the artists that don't want to be on there.

1:12:59 And find a way to pay the ones that are okay being on there. It's that simple. It's not complicated. I think Go in a room. Lock yourself in a room for three days and come out and figure out how to pay people and take people off. That don't want to be on there.

1:13:12 But Donna does not want her music trained on. Don't care what you want to pair. She's very clear. I do not want my music to be trained on. I want My music should be its own thing.

1:13:22 So take her off. It's okay. You'll still do fine. Take her off. You don't have to have Her music. So

1:13:30 We'll we'll see where this goes, but this is I've been the last few years I've really tried to figure this out. And even with Sam at one point, he's really wanted to figure this out too. Like Sam was Sam, a lot a lot of people give more time on the stuff, but He really did. Dedicate.

1:13:46 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 Sunna, someone who comes from behind like a next generation Spotify. Mm-hmm. And figures out how to do it. Yes, or Spotify can do it. Yeah.

1:14:04 You mentioned there were three things that You'd like to do today. I'm not gonna ask you to name those things. But How did

1:14:11 You find those things or how do those things find you. Well I'm working on this platform that we're gonna announce in a few months that You're part of is how we connected, you and I. So I'm able to ask

1:14:22 investors, what companies That they're looking at. And so Two of those came from that. Conversation. Good good information. Yeah. 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.

1:14:34 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.

1:14:42 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

1:14:53 Uh, Blackberry and vitamin water. Do you have and this could go way back In the catalogue. could go back to being ten years old. There's no limitation here. Any favorite failures or parent failures, meaning Failures that taught you a lot or that set you up somehow for later success.

1:15:12 There's so many. It's endless. Endless. Ashton is really was really good about Not looking back like that. He sort of just keeps it moving forward. And I'm always like, I can't believe we're not in that. And I had it in my I had it and we had it and we

1:15:26 And he's like, Come on, let's go. Let's go. He always gives me the like, oh gosh, he's gonna complain about not being in the game. Here we go again. You know what I mean? But you know, what motivates him is he just keeps it moving forward and it's awesome. And what motivates me is like I'm not gonna let that happen again. Looking back, right, it seems like In some ways. Missing hole, missing fill in the blank was almost a

1:15:48 Prerequisite. source of fuel yeah for the things yeah it's scary though it drove you towards the it's scary though. Yeah. Ash and I invested in Bitcoin. On our own.

1:15:59 You know, when it was at twenty two dollars. When it hit two hundred fifty dollars, I thought I just made ten times my money. Yeah, yeah. I'm a genius. So I sold then. Clearly not a genius. So that hurts.

1:16:13 And I remember um Anthony Gentlemen on that wall. Elon invited. Anthony.

1:16:20 From the chili peppers to C SpaceX. Early days. Very early days. And

1:16:26 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

1:16:37 the business model or what could be the business model. I was like wow, this guy's building rockets. That moment in time. Anthony and I had the Wherewithal.

1:16:47 I go back to that time ago. We just have the wherewithal to go. What business model? I didn't even ask those words. I was just You know, sometimes I go to shows, like I've seen shows where People are so wow that they're just like

1:16:59 They're like this from a show. They didn't even take in all the songs were just like, Oh my God, what I mean, if you ever look back at the Sex Pistols shows, people are just like, What? And they're like, Was I actually there? I think I was more blown away by the concept of what Elon was building.

1:17:14 That I did not understand. That there was a business model. And I really wish I just would have asked one more question. Hey, how do you monetize? How does this work? Can we invest? So I have

1:17:27 Hundreds of those stories. But those are Two that stand out today. I wanna talk about the longevity for a second. You mentioned

1:17:35 And fact I may if I'm getting this wrong, but like the three Back to back tours with Madonna. Mm-hmm. I mean that sounds impossible. Yeah. 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,

1:17:54 What were the keys to enduring that and being able to function at a high level for that? I think it's different as the years go by. There was a point. Around Ten years ago, eleven, twelve years ago, where I I was it was

1:18:09 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.

1:18:18 And The amount of things you're missing back home, you sort of Forget you have a family, you forget that You can go do other things, you're forget to call back stripe, or you forget to Right? All the things you just forget everything.

1:18:32 And then one day your dad calls you and goes, Oh hey, I'm at your house with your kids and we go, Oh, I have kids at bad house. So if you look at the first three tours. Those three tours that I did. Those are two hundred and forty shows. eighty average.

1:18:44 I missed. I missed three of those shows. Three out of the two hundred and forty. One I was sick. And then I missed two because it was my fortieth birthday and I really

1:18:53 Didn't feel like being in Seattle that day. I wanted to be home with my friends. So my fortieth birthday spent here in this house. So I missed three shows out of two hundred forty. We're talking about

1:19:03 A different city, a different hotel, a different In order to like move along, you sort of have to block everything else out. You have to forget and it's a very selfish, very For me.

1:19:14 Otherwise if you think about if you're every day you're thinking about you know, back home or your family or other things, y it hurts. So I just go, Okay, I'm off and I'll see ya that's what actors do when they go away and make a movie for three months and then they come back. They probably just Compartmentalize a little bit. Well.

1:19:31 You know, in the last few years I've stopped doing as much. I still go. But not as much. I've I've wanted down a moment there where I Manage the red hot shield peppers U two and Madonna. And it was They're all going on tour.

1:19:43 It was a lot too. Process. How do you even make decisions about where to be in a case like that? It's hard, but it's sort of Tells its own story. You you know, you're not gonna miss New York. You're not gonna miss London. You're not gonna miss some of the major moments

1:20:00 And then you look at the calorie and go, Oh, we have this time off. Let's go to New Zealand with Madonna. Or let's go to so and so with you two, or let's go to so and so with the peppers. And you find your way Around it. You just you just make it work. So if you look at let's just say the last ten years. Yeah.

1:20:15 And Presumably a lot of your focus is on the investing. Mm-hmm. How do you mind? The different responsibilities. Does that make sense?

1:20:26 When I think of responsibilities, I Think of Management. That's a really big responsibility. And I don't take it lightly.

1:20:33 There's no way around it. That's something's going on there that's a focus. It is cyclical. So like the peppers are not Touring this year, they don't have an album this year. They aren't twing next year. They don't have an album next year.

1:20:46 So You know, there's a lot of time in between Where there coming up with the creative, they're gonna make an album, they're gonna do All the things that they're gonna write songs. So that takes time. So you get these windows of opportunity.

1:20:59 where you go all in and you get windows option where you have a moment to breathe, just like they do. They all need it too. Madonna after the cycle will probably need a minute to just sort of catch her breath and figure out what she does next. So these are cyclical things. What I don't do is I'm not out there trying to sign ten more bands or ten more artists. So that's where the balance comes in and which is

1:21:18 Continually be creative through other ways. Вене цикл старс My creativity has never stopped. So that I still have the those things. I'm not starting from scratch.

1:21:29 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

1:21:39 Or some of those new relationships I met while she was off. I found a way to Make it work. Uh maybe. I'm sure misquoting, but

1:21:48 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.

1:22:04 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

1:22:18 savoring the time that you have. I mean, I imagine you get a lot of that with Congregating friends and so on, but I'm wondering if you have any thoughts. You know, my friends and I Don't Spent a lot of time talking about

1:22:32 What I do. Mm. A little bit. I share with them so they're in the know. We don't spend a lot of time on it. We don't work together. On these

1:22:39 Deals. My wife and I don't talk about work. Much like I think I just Keep it moving too. And again I

1:22:46 When you look back thirty six years It's probably Madonna. That is responsible for how I Also

1:22:54 think of just keep it moving forward, keep it moving forward and You know, maybe one day Sometimes when I'm telling my kids a story about the past or someone asks me a question and I tell them at 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

1:23:10 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. feel like I still have so much to prove and

1:23:25 So much to do. But at the same time I do know if I really Took a minute. I go, Oh wow, okay. I should probably

1:23:32 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. Uh you know, at some point

1:23:42 I can visualize being on the beach and high fiving with my friends and having fun. But I again I don't they don't do it either. Yeah a lot of my friends were we don't talk about it like that either. I mean I think we're just sort of

1:23:54 How cool that we're surv 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 Cushner. quote that I love that he says.

1:24:06 About success. He says to him success is Being excited to go to work. And also being excited to go home. And

1:24:16 I got that. I'm excited to go to work and I'm excited to go home. That's pretty cool. You know, not a lot of people get to do that and I don't take that for granted. And I work hard because of that,'cause I go, this is not A given. You know, the the the potential and opportunities. And I'm trying to bring in other friends and other people

1:24:32 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.

1:24:41 You should go to this so I like sharing that. So after twenty years You and Ashton are Gonna be doing

1:24:50 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

1:24:58 Run. And This AI fund is I don't know what to Compare it to other than like winning the Super Bowl?

1:25:06 Mm-hmm. For what we do. Right. And you know, between The investments in opening I and Anthropic, and we also did SP Vs the whole way up. A lot. So

1:25:15 We're really fortunate and blessed. And after twenty years, Ashton I Ask the question of Now that we've Done that and we've Hit it out of the park.

1:25:23 What are we gonna get enjoyment out of doing and So That's a really Strong question. And

1:25:31 We all gave it some thought. This is 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 And what I wanted to do and We have a third partner, her name's Effie and

1:25:45 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 gonna share any of it. It was pretty awesome vision. It's an incredible vision and the guy is

1:25:59 Mind blowingly Smart. And talented. And I support that vision for him.

1:26:07 It isn't my vision. And I will support it financially, and I will support it with Energy. I want him to win. And

1:26:14 I have mine. Which is the things that we're talking about today and the things that I wanna build and I have a version of The things I want to do that I haven't shared with everyone.

1:26:24 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.

1:26:32 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've so many different chapters of my life. But this is a beautiful chapter. That We're s in a celebratory mode.

1:26:45 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 I've worked hard to get here. And taking a lot of risks and a lot of chances and putting our own money and

1:26:56 Well, this decision was made out of Joy and To support each other's visions. There

1:27:03 Are gonna be times where we'll Cross over and we'll Work on things together. 'Cause we do have some crossover of things that are part of things we both like. But he's very specific on he wants to do it. I'm very specific on what I do F E

1:27:16 And I are gonna continue on with sound and what we've built the last Ten years was sound. So continue to build that. And then we've got some surprises of how we want to build that out too.

1:27:25 It's all really good. It's all very Supportive. It's just another chapter. Cool. Guy, this has been a wide ranging

1:27:34 Conversation. What a life. What a journey, and it's not over. Obviously, uh lots of battery left. For what's ahead.

1:27:43 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. Exactly. And people can find you on Instagram X.

1:27:58 At Gaioseri, 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 slash podcast. And until next time, everybody.

1:28:12 Thanks for tuning in. Be just a bit kinder than is necessary. To others, but also to yourself. Compassion is not complete if it doesn't include you. Thank you, Jack Cornfield. And as always, thanks for tuning in. Thanks, guy. Thank you. Hey guys, this is Tim again, just one more thing before you take off, and that is Five Bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend? Between one and a half and two million people subscribe to my free newsletter, my super short newsletter called Five 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 kinda like my diary of cool things. It often includes articles I'm reading, books I'm reading.

1:29:00 albums perhaps, gadgets, gizmas, 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 slash Friday. Type that into your browser, Tim dot blog slash. 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, good 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.

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1:30:52 So start your journey with AG1's next gen and experience the difference firsthand. Simply go to drinkag1.com slash Tim That's drinkag1.com slash temp. Now guess what I did just before breakfast? I did what I do every morning, I took some creatine. Today I took five grams. If I'm sleep deprived, I might take 10 or 15. And I have used Mementous Creatine for a long time, as it's been one of the highest quality creatine options available on the market. That's exactly what I used this morning. Now Mementous has taken that quality that they're already known for even further with Signature Spec Creatine, their most advanced version yet. Signature spec is manufactured in a pharmaceutical facility using reverse osmosis water purification. You can hear those birds in the background, man. I'm striving for healthy over here. It's verified through a six stage testing process with

1:31:43 four independent agencies delivering 10 times fewer impurities, two to five times tighter heavy metal limits, and added PFAS, that's the forever chemicals you don't want, and microplastic screening. That's the Mementous standard. The ultra fine powder also mixes cleanly with no grit. Super super easy creatine supports strength. power, lean muscle, and recovery with growing research on enhanced memory and cognitive performance. I take it mostly for the cognitive stuff, but it's great for the gym too. So if you take creatine every day, like I do, make sure it's the best. Do not cut corners. Head to livemomentous.com slash Tim and use code TIM for 14% off. That's an interesting percentage. For 14% off of your first one time order or a total of 35% off your first subscription order. That's Livemomentous.com slash Tim. That's Live Moment O U S Momentus. LivMomentus.com slash Tim for between 14 and 35% off with code. Tim.

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