{"id":13335,"date":"2026-07-09T23:56:54","date_gmt":"2026-07-10T03:56:54","guid":{"rendered":"https:\/\/parmaks.com\/Resources\/the-tim-ferriss-show-transcripts-guy-oseary-the-legendary-hollywood-power-broker-on-5-minute-decisions-36-years-of-managing-madonna-26-ipos-and-spotting-magic-first-874\/"},"modified":"2026-07-09T23:56:54","modified_gmt":"2026-07-10T03:56:54","slug":"the-tim-ferriss-show-transcripts-guy-oseary-the-legendary-hollywood-power-broker-on-5-minute-decisions-36-years-of-managing-madonna-26-ipos-and-spotting-magic-first-874","status":"publish","type":"post","link":"https:\/\/parmaks.com\/Resources\/the-tim-ferriss-show-transcripts-guy-oseary-the-legendary-hollywood-power-broker-on-5-minute-decisions-36-years-of-managing-madonna-26-ipos-and-spotting-magic-first-874\/","title":{"rendered":"The Tim Ferriss Show Transcripts: Guy Oseary \u2014 The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First (#874)"},"content":{"rendered":"<p> <a href=\"https:\/\/hop.clickbank.net\/?affiliate=infohatch&amp;vendor=J1R2C\"><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-10614 aligncenter\" src=\"http:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px.png\" alt=\"Profit Gen\" width=\"400\" height=\"217\" srcset=\"https:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px.png 400w, https:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px-300x163.png 300w\" sizes=\"auto, (max-width: 400px) 100vw, 400px\" \/><\/a><br \/>\n<\/p>\n<div>\n<p class=\"wp-block-paragraph\">Please enjoy this transcript of <a href=\"https:\/\/tim.blog\/2026\/07\/07\/guy-oseary\/\">my interview with Guy Oseary<\/a> (<a target=\"_blank\" href=\"https:\/\/www.instagram.com\/guyoseary\/?hl=en\">@guyoseary<\/a>). Guy has managed some of the biggest names in music, including Madonna, the Red Hot Chili Peppers, and U2, and was named <em>Variety<\/em>\u2018s Music Mogul of the Year in 2022. He co-founded <a target=\"_blank\" href=\"https:\/\/en.wikipedia.org\/wiki\/A-Grade_Investments\">A-Grade Investments<\/a> and then <strong><a target=\"_blank\" href=\"https:\/\/www.soundventures.com\/\">Sound Ventures<\/a><\/strong>, now with nearly $2 billion under management.<\/p>\n<p class=\"wp-block-paragraph\"><a href=\"https:\/\/tim.blog\/2026\/07\/07\/guy-oseary\/\">Guy\u2019s full bio<\/a><\/p>\n<p class=\"wp-block-paragraph\"><a href=\"https:\/\/tim.blog\/2026\/07\/07\/guy-oseary\/#:~:text=All%20episodes-,Show%20Notes,-Connect%20with%20Guy\" target=\"_blank\" rel=\"noreferrer noopener\">Books, people, tools, and resources mentioned in the interview<\/a><\/p>\n<p class=\"wp-block-paragraph\"><a href=\"https:\/\/tim.blog\/2026\/07\/08\/guy-oseary-transcript\/#guy-oseary-legal-conditions\">Legal conditions\/copyright information<\/a><\/p>\n<div class=\"podcast-player\">\n<div class=\"podcast-player-inner-wrap\">\n<p>Guy Oseary \u2014 The Legendary Hollywood Power Broker on 5-Minute Decisions, 36 Years of Managing Madonna, 26 IPOs, and Spotting Magic First<\/p>\n<p><noscript><iframe src=\"https:\/\/www.art19.com\/shows\/58dacbdc-646e-4585-9914-19c3de11d1ba\/episodes\/5ddf31c4-0f63-4bf2-acc5-0bcdb8c643e3\/embed?type=micro\" style=\"width: 100%; height: 30px; border: 0 none;\" scrolling=\"no\"><\/iframe><\/noscript><\/div>\n<\/div>\n<h3 class=\"wp-block-heading\">Additional podcast platforms<\/h3>\n<p class=\"wp-block-paragraph\"><strong>Listen to this episode on\u00a0<a href=\"https:\/\/podcasts.apple.com\/us\/podcast\/874-guy-oseary-the-legendary-hollywood-power-broker\/id863897795?i=1000775866059\" target=\"_blank\" rel=\"noreferrer noopener\">Apple Podcasts<\/a>,\u00a0<a href=\"https:\/\/open.spotify.com\/episode\/2S96zew4ikLt2NEQSfOm6s\" target=\"_blank\" rel=\"noreferrer noopener\">Spotify<\/a>,\u00a0<a href=\"https:\/\/overcast.fm\/+AAKebv9vWKM\" target=\"_blank\" rel=\"noreferrer noopener\">Overcast<\/a>,\u00a0<a href=\"https:\/\/podcastaddict.com\/podcast\/2031148#\" target=\"_blank\" rel=\"noreferrer noopener\">Podcast Addict<\/a>,\u00a0<a href=\"https:\/\/pca.st\/timferriss\" target=\"_blank\" rel=\"noreferrer noopener\">Pocket Casts<\/a>,\u00a0<a href=\"https:\/\/castbox.fm\/channel\/id1059468?country=us\" target=\"_blank\" rel=\"noreferrer noopener\">Castbox<\/a>,\u00a0<a target=\"_blank\" href=\"https:\/\/music.youtube.com\/playlist?list=PLuu6fDad2eJyWPm9dQfuorm2uuYHBZDCB\">YouTube Music<\/a>,\u00a0<a href=\"https:\/\/music.amazon.com\/podcasts\/9814f3cc-1dc5-4003-b816-44a8eb6bf666\/the-tim-ferriss-show\" target=\"_blank\" rel=\"noreferrer noopener\">Amazon Music<\/a>,\u00a0<a href=\"https:\/\/www.audible.com\/podcast\/The-Tim-Ferriss-Show\/B08K58QX5W\" target=\"_blank\" rel=\"noreferrer noopener\">Audible<\/a>, or on your favorite podcast platform.<\/strong><\/p>\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n<p class=\"wp-block-paragraph\">Transcripts may contain a few typos. With many episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!<\/p>\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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\u2019ve ever seen. What is it that\u2019s sitting behind you?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>That\u2019s \u201cPurple Rain\u201d lyrics by Prince.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Just incredible.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I\u2019m 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.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Wow.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>How did that happen?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>The place where I was living with my dad, an apartment building in West Hollywood, was directly across the street from a hotel called Le Parc Hotel. And that\u2019s 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 \u201cLove God\u201d for me. I told him that years, years, years later. We became friends and became close.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Was it \u201cLove God.\u201d Or Love, God?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It was \u201cLove God\u201d and it was signed \u201cPrince.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Wow.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>That was a long time ago because later on he became a Jehovah Witness. But yeah, you could see the posters. I had Billy Idol and Prince on my walls and you could see it from the street if you looked up. So, you can come out, if you\u2019re waiting for your car or whatever, and you look and you\u2019d see, okay, someone up there likes music a lot. And I was on the first floor and there\u2019s a little balcony there.<\/p>\n<p class=\"wp-block-paragraph\">And then I\u2019d come out a lot. I met INXS. And I met some people I became friends with, like Billy Idol, I became friends with years later and Michael Hutchence, I became friends with. And Morrissey, I became friends with later. But I met them all when I was a kid.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>That\u2019s awesome.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>And a really cool thing is other kids were around then so I could hang. They were older than me, but they were kids and so I could hang with them and really get a little camaraderie with some of the fans out there that were waiting for the bands.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I want to talk about addresses and Beverly Hills High School. How did you end up at Beverly Hills High School? And why?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Before Beverly Hills High School, I went to a school in downtown L.A. It was on Pico and Arlington, so it\u2019s almost on the way if you\u2019re going to go see a Laker game. It\u2019s on the way to that. And I went to that school and it was incredible. So many great people.<\/p>\n<p class=\"wp-block-paragraph\">Music was a big piece of my journey there. I took a school bus there and the kids would go between two radio stations on the bus. So, the bus driver would play either KDAY, which was the first hip hop station in L.A., or they would go to KROQ, which is the alternative radio station in L.A. And I loved them both. And so, I met a lot of really cool kids there who were in these groups of people. They were like the punk rockers, the hip hoppers, the break-dancers, gang members, graffiti artists, just a great eclectic group of people during that time period where I\u2019m just a sponge. I\u2019m just picking up all the energies and really falling in love with music.<\/p>\n<p class=\"wp-block-paragraph\">And one night, I was outside the school dance. There was the L.A. Dream Team. That\u2019s 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.<\/p>\n<p class=\"wp-block-paragraph\">And while I was out there, I saw a guy running past me for his life. And then I see a car turn the corner and I guess chasing the guy down and a guy jumped out of the passenger seat and pulled a knife out on me and asked me if I was with that guy. And he asked me if I was in a gang and I said, \u201cI\u2019m just a kid waiting for my dad. I was at a school dance and this is my school and da, da, da.\u201d And so he got back in the car to chase the guy.<\/p>\n<p class=\"wp-block-paragraph\">And so there are no such thing as coincidences. But when my dad showed up, I got in the car and I was like, \u201cI 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.\u201d And again, there\u2019s no coincidences. That just came to me right then and there that I want to go from downtown L.A. to Beverly Hills High.<\/p>\n<p class=\"wp-block-paragraph\">And there was a TV show, <em>90210<\/em>, back then.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Sure.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I thought, \u201cI want to check that out. That\u2019s a different world from the world I\u2019m in now. I want to just see it.\u201d And I didn\u2019t know at the time, but you have to live in Beverly Hills to go to Beverly Hills High School.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah, that makes sense.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. I don\u2019t know why I didn\u2019t put that together. I just said that to my dad and we didn\u2019t live in Beverly Hills. And he knew that\u2019s what I wanted and he heard me. He came back to me and said, \u201cThere\u2019s 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.\u201d And the combination of going to school in downtown L.A. and also going to Beverly Hills High right after, I think that\u2019s a big part of who I am today.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Blending the two worlds.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Blending the two worlds. One or the other without the other would not have given me the perspective that I needed.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>What was the perspective that you got once you were transported to this second chapter at Beverly Hills High?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, once you walk through those doors, it might as well be a TV show from where I just came from. People have a lot. There\u2019s cars and there\u2019s homes with pools and just the optionality and the potential of what they all had was pretty wild.<\/p>\n<p class=\"wp-block-paragraph\">And that actually inspired me to, \u201cOh, I didn\u2019t know you can aim this high. I don\u2019t have what these people have. I don\u2019t have the means. I don\u2019t have the money. I don\u2019t have the connections. So I\u2019d better start working.\u201d And I think at like, 14, it really started to kick in where I go, \u201cOoh, because these people are going on trips and ski trips and I don\u2019t know anything about skiing. I don\u2019t know anything about\u2026\u201d<\/p>\n<p class=\"wp-block-paragraph\">I just didn\u2019t live that world. So I knew that I needed to do something about it and I looked like, \u201cWhat am I good at? What could I be good at?\u201d And music was my love. It was my passion. It\u2019s what I was obsessed over. And so, I thought something in music. And that\u2019s when I started to really pay attention to, what could I do around music, would I do music? And then around 15, I really started to pick that up and at 16, I was already really running with it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So, I think this might be a good bridge. If I\u2019m missing something in between these points, let me know. I\u2019m sure there\u2019s a lot that we could talk about. But Bernie Brillstein, who is that?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>So, Bernie Brillstein is iconic. In Hollywood, he\u2019s 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 <em>SNL<\/em>, he managed all of them.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Dan Aykroyd, John Belushi, Garry Shandling.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>All of them.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>And he was beloved. He looked a little like Santa Claus. He was a really big guy with a white beard.\u00a0<\/p>\n<p class=\"wp-block-paragraph\">And so, when I was 15, I started to compile artists that I liked that had demos. So I would go out there and try to find artists and try to find new artists. I had the yearbook person come and take photos of these.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And this was on your own or were you working?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>On my own.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>On your own.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>On my own. I didn\u2019t 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\u2019ll get a meeting with somebody. And that\u2019s what I started.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I\u2019ll have something to show when I get the meeting.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, I\u2019ll have something to show. I think I called it Wise Guy Records. I didn\u2019t know what any of it meant, but I had my little logo. I did everything I could possibly do without knowing anything or anyone.<\/p>\n<p class=\"wp-block-paragraph\">And then, the week I turned 16 \u2014 I remember it was the week I turned 16 because I didn\u2019t pass my driver test so I needed to be dropped off. So the week I turned 16, I went to meet with Bernie. And what happened was, I approached a lot of the kids at school at Beverly Hills High and I said, \u201cCan I meet your dad? Can I meet your dad? Can I meet your dad?\u201d And just anyone that was in entertainment.<\/p>\n<p class=\"wp-block-paragraph\">And out of all the people that I approached, I got two meetings that would end up both being really the most impactful meetings I could ever have. And one of them, the first one I got, was Bernie Brillstein and his two boys, Nick and Dave, both told their dad, \u201cYou should meet with Guy.\u201d<\/p>\n<p class=\"wp-block-paragraph\">So I go meet with Bernie. He was at the 9200 building on Sunset and I played him a song. I don\u2019t even remember what group or what it was at this stage, but I played him a song and he just looks at me. He goes, \u201cWell, hey, kid, how much is it going to cost to put this out?\u201d<\/p>\n<p class=\"wp-block-paragraph\">And I knew not to pause because then he\u2019d know I\u2019m a phony. So I said, \u201c$25,000.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And he said, \u201cI\u2019ll tell you what, kid, I\u2019ll give you the $25,000. If you make it back, pay me back. That\u2019s all I ask.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And at the time, I\u2019d never seen $2,500. So, I just said, \u201cBernie, I\u2019d rather you make three phone calls for me to music people and I don\u2019t want your money.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And he ended up putting that in his first book, that story. He\u2019s passed away, unfortunately. But he always felt that I said no because I just couldn\u2019t take the money from him. I said no because I didn\u2019t know what to do with $25,000 and I was a phony. But until his last days, in his book, he\u2019s like, \u201cThe one guy that didn\u2019t want to take my money was Guy Oseary.\u201d It\u2019s not true. I just didn\u2019t know what to do with it. So he made those three phone calls for me.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Did he pick the people to make the phone calls to?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>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 \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Going anywhere.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u2014 going anywhere at all. But what ended up happening was, I came back home and I thought to myself, \u201cWow, I\u2019m 16 years old and this guy offered me as much money as people make a year in one meeting.\u201d<\/p>\n<p class=\"wp-block-paragraph\">If people feel they have talent, they don\u2019t know, really. There\u2019s no confirmation on that talent. People think, \u201cOh, my mom says I\u2019m a good singer or so and so says I\u2019m great at this.\u201d But you don\u2019t know until someone confirms it, until someone buys your book or goes to your show or whatever.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Offers you 25k.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>On that day, that was the confirmation I needed that I\u2019m on the right path and I went, \u201cThat\u2019s it. From this point on, I\u2019m going to turn it up. I\u2019m not looking back. This guy offered me 25k in one meeting. I just turned 16. I\u2019m going to stick to this. I can do this.\u201d And many years later when I got my first gold record, I sent it to Bernie because that was so impactful on my life.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>You mentioned two meetings.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yes.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Was the other Freddy?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>The other was Freddy DeMann.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>All right. Who is Freddy DeMann?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>So, Freddy DeMann, his daughters Neysa and Pilar connected me with their dad, Freddy. And Freddy was iconic as well. I mean, he worked on, I think, \u201cThriller\u201d with Michael Jackson. He managed Madonna. He managed some of the greatest artists of all time. And he was just a really great human, great guy. And he heard me out. It took a few meetings to get Freddy to really go for it with me. Not that long.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And this meeting was after Bernie.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Meeting was after Bernie and he just learned about me. He heard my pitch and, \u201cI\u2019m trying to do this, I\u2019m trying to do that.\u201d And he knew I didn\u2019t really have any money.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah. At that point, what was your pitch?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Gosh, I think I\u2019m just showing him that I\u2019m in the flow of music. I\u2019m around music. I\u2019m around artists.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>The portfolio.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, one of the crews that I was working with was Ice-T. And I got very lucky, got introduced to my friend Chris Boyd. I met when I was working when I was 15 at this Fred Segal and Chris Boyd, another guy, was working there and he\u2019s like, \u201cOh, I know Ice-T and his producer, Johnny Rivers. And would you want to come to the studio and check it out?\u201d<\/p>\n<p class=\"wp-block-paragraph\">And I\u2019m like, \u201cYeah, I want to go.\u201d So, he brought me to the studio and actually my first day in the studio, Ice-T goes, \u201cCome into the booth and do a few words.\u201d And I\u2019m actually on the album.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Wow.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. And so, he had me say a few words on the album, but I started hanging around and I\u2019m like, \u201cWhat could I do? Could I clean up? Could I carry someone\u2019s bag? How do I be helpful or of service?\u201d I\u2019m 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.<\/p>\n<p class=\"wp-block-paragraph\">And then I ended up becoming the manager of Ice-T\u2019s DJ and his brother, who\u2019s Hen Gee and Evil E. Evil E is Ice-T\u2019s DJ. So, I managed them. It was my first group I ever managed. And I was 17. We got them a record deal. So I had that and I always checked in. I checked back with Freddy and said, \u201cFreddy, I just got my first group signed to record label.\u201d So, he knew.<\/p>\n<p class=\"wp-block-paragraph\">There\u2019s a guy named Steve Rifkind who I met who knew the record label. He helped me get that first record deal. So, when I went to see Steve and I played some of the music, I played him Ice-T\u2019s DJ, Evil E and his brother Hen Gee. And I said, \u201cHere\u2019s the music.\u201d<\/p>\n<p class=\"wp-block-paragraph\">He said, \u201cI know a label for you.\u201d<\/p>\n<p class=\"wp-block-paragraph\">So, he helped me get my first record deal.<\/p>\n<p class=\"wp-block-paragraph\">So, I always write Freddy and go, \u201cHey Freddy, I just got my first group signed, a manager.\u201d And he knew, how was he pulling these things off on his own without any help or any money?<\/p>\n<p class=\"wp-block-paragraph\">And so I met with him and he said, \u201cMadonna and I are going to start a record label one day.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And so I said to him, \u201cI\u2019d love to work there.\u201d I said, \u201cI don\u2019t need any money.\u201d I did need money, but I wanted to make it really easy for him. I said, \u201cI don\u2019t need money. Just give me an office and a desk.\u201d That\u2019s all I asked.<\/p>\n<p class=\"wp-block-paragraph\">And he was like, \u201cOkay.\u201d\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary:<\/strong> So he brought me in as a scout because one day they\u2019re going to start a label. They didn\u2019t even have a name. They just knew they were going to do it.<\/p>\n<p class=\"wp-block-paragraph\">So I\u2019m scouting and then one day I find Hole, which is Courtney Love. I find their first song, \u201cTeenage Whore\u201d and I go, \u201cOh, my God, this sounds incredible.\u201d I\u2019m 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\u2019s in the paper the next day. \u201cMadonna\u2019s trying to sign Hole.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>How did that happen?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I made a phone call. I was very naive back then, but it was like, \u201cMadonna\u2019s trying to sign Hole.\u201d So, the next day there was a show that Hole was doing at the Whiskey. Actually, I think Kurt was there. But then Madonna was like, \u201cWho is this?\u201d Wanted to talk to me about, \u201cWho is this Hole thing?\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: \u201c<\/strong>Hey, kid, come here for a second.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, so I go in a room and I play this song for Madonna and for Freddy and it\u2019s pretty wild. I mean, the lyrics are like, \u201cWhen I was a teenage whore, my mother said, she said, \u2018Baby, what for?\u2019\u201d I was like, whoa. And you\u2019ve got to go back to that time period.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Sure.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>And they were like, \u201cOkay, all right, so go after it.\u201d And so, I went after it. I didn\u2019t get it. It was between us and Geffen Records and we didn\u2019t get it. It went to Geffen Records. But my first artist I ever attempted to sign was Hole.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So, let me pause you for one second.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>All right. So, the meetings that you got with Bernie and Freddy, you got two introductions. How many kids at school do you think you asked in total to end up with those two?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I think I probably asked five.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Okay.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I mean, I already wasn\u2019t a social guy. I\u2019m not on the football team. I was just sort of my own music guy running around and I didn\u2019t have much. So, I did as much asking as I can from who I could figure out to ask. So, I probably asked around five. And I remember one person specifically saying, \u201cMy dad doesn\u2019t do that.\u201d Whatever. Because it was rap I was trying to play, \u201cOh, my dad doesn\u2019t do that.\u201d<\/p>\n<p class=\"wp-block-paragraph\">But I didn\u2019t have any shame. I needed to figure this out. I knew that my time was limited before going to college and I\u2019d better figure this out soon. So I was on a hustle.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>This is from an <em>L.A. Times<\/em> piece way back in the day, 1997, but it says something along the lines of, \u201cI gave myself a year, which is why I kept pushing people for a chance.\u201d Maybe that\u2019s accurate, maybe it isn\u2019t. But did you apply pressure to yourself in that way, like instead of going to college?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Oh, yeah. No, I went to college.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Okay.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I went for half a semester and I got my first group signed, which was just Hen Gee and Evil E. And then I remember going to my English teacher. I don\u2019t know her name. She was amazing because I said, \u201cHey, I\u2019m thinking of dropping out and focusing on this thing.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And she just looked at me and said, \u201cYou could always come back.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Wow. It\u2019s wild to think about these just chance moments.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>That was it. And I go, \u201cOh, I could always come back.\u201d Okay. So, that was it. And by the way, I couldn\u2019t 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.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Where did the chutzpah come from? I mean, just that drive, was that absorbed from the parents? Were you just out of the box very different?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I don\u2019t know. Look, I fell in love with music in a big way. But I think I realized how lucky I was to be at Beverly Hills High and see the potential of \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>What was possible.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, of what\u2019s possible. And I thought, \u201cWow, not everyone is this lucky. Not everyone gets this opportunity.\u201d And by the way, I was scared that they would kick me out because if they found out I didn\u2019t live there, they\u2019d kick you out. So, I had to watch how I went to school. It wasn\u2019t an easy thing to do. And so I just thought, \u201cFor every day I\u2019m here, I\u2019m really lucky and I need to pay attention to that.\u201d And I just realized that, if I wanted to change my destiny, I needed to get going.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And at what moment did you realize, \u201cOh, I think this might just work out\u201d? I mean, was there a particular person or band you signed? Was there any flashpoint or was it really gradual?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I think the Bernie Brillstein moment where he offered me 25 grand the week I turned 16 was a big game changer for me.<\/p>\n<p class=\"wp-block-paragraph\">And then there was a personal moment for me when I got a car when I finally passed my driving test. Took a few times. But when I finally got my car, I remember going to see my old friends from my old school. Because it was a Honda Civic. When I drove it to Beverly Hills High, not one person commented or said congratulations or nothing, no mention of it at all. And then I went to my old friends from my old school and then they couldn\u2019t believe that I had a brand new Honda Civic. And they got in the car and they were rolling down the windows and sticking their arms and heads out and I was like, \u201cOh, wow, okay.\u201d<\/p>\n<p class=\"wp-block-paragraph\">I got a little perspective there to go, \u201cOh, no, these people at Beverly, they\u2019re not really my friends. I\u2019m here for a reason. I was put around this community for a reason, which is to work and which is to build my name or to build the things I want to do.\u201d And it wasn\u2019t until years later, actually, I told that story in that thing you\u2019re talking about when I was 24. And my dad mentioned it was really hard to even come up with the money for that car back then. It was a really big deal for us. It was expensive back then.<\/p>\n<p class=\"wp-block-paragraph\">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\u2019s a combination of those things.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And from the chapters we\u2019ve discussed so far, I mean, was then the next phase building your relationship with Madonna primarily, or where did you hop off past the things that we\u2019ve already discussed?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, Madonna and I, the first real connection was that Hole connection where it\u2019s like, \u201cWell, play me this thing that you like.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And then the second one, second artist I brought was Rage Against the Machine. And I really wanted to sign Rage Against the Machine. And so, I took her to the concert in New York at the Limelight, I think it was called. And I didn\u2019t get them either. I didn\u2019t get Rage. They ended up going with Michael Goldstone at Epic Records.<\/p>\n<p class=\"wp-block-paragraph\">So, God, the first two things I competed for, I didn\u2019t get.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Well, not only did you not get them, but they went on to be successes, right?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, it was painful. It was painful. The third one that I competed for, I did get, it was called Candlebox. And at that time, actually, I think it outsold both Hole and Rage at that time. They ended up doing really, really well. But regardless, Hole and Rage, even to today, I still listen to them. I love them. But I was very lucky to get Candlebox. The fact that they bet on me, we didn\u2019t have anything.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>We just had this idea.<\/p>\n<p class=\"wp-block-paragraph\">They ended up selling four million albums on that album. But I\u2019ll never forget that. I\u2019ll never forget that they gave me that shot. That was my first success story with Candlebox.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So, they give you a shot, but just to repeat what you just said, you didn\u2019t have much, right? They were placing a bet on you.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Mm-hmm.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>What then goes into helping make a hit album that sells four million?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, going back to that time period, first is the music. I saw them. I was so lucky. Almost everything that I\u2019ve been lucky on happens within minutes, not within days or weeks or months to think about it. It\u2019s all intuitive and it\u2019s very fast. And I was supposed to be somewhere else that night, but I went to this party and it was so bad that I thought, \u201cOh, I have time to go see that showcase of that band from Seattle.\u201d<\/p>\n<p class=\"wp-block-paragraph\">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\u2019s a stage. I was looking at the video screen. There were maybe like, 30 people in the audience. It\u2019s a showcase. I\u2019m looking at that screen and I saw thousands of people singing along to that band.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>In your mind?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>In my mind, yeah. But I went to the payphone from that performance, called Freddy, and said, \u201cFreddy, I have our band. This is the band. I just saw them. This is the one.\u201d And so it starts with that.<\/p>\n<p class=\"wp-block-paragraph\">It always starts with the magic. I don\u2019t care if you\u2019re a tech company or whatever it is, a film, a product, a book, magic. You\u2019ve got to have magic. Something has to pull you in. And that night I saw it, I visualized it, and the songs were there. The songs were so there that, when we made the album, their first two singles, we could not beat the demo. They went in to rerecord them for the album. So whatever they made for a few hundred bucks that I had with a lot more money and a lot more time we couldn\u2019t beat. And so those songs, those first two songs on the album are from the demo. So the music was there. They were talented. The band was talented. The singer Kevin is so great. And they really did it the hard way. They chipped away. They did show after show after show. Took a few years for every week, every week, little by little, little by little. Keyword is artist development and people don\u2019t artist develop that much. It\u2019s something that we all want. Every artist wants to have the time to build, have the time to develop. And we really took that time week after week after week developing that one. That\u2019s how we got there.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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\u2019re like, \u201cOkay, that is a horse to bet on.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Honestly, I would say that 90 percent of the things I do happen in the first five minutes. 90 percent. It drives me crazy when we get in a room and talk about it for three months. And I respect process. I know there is a process to these things, but I think I know what I want to do very quickly. It started out, I think that the muscle that got built for <em>fast<\/em> sort of response thinking or intuition was really in the music business. We have such a small label, so boutique and we\u2019re competing with these big companies that have been around forever and have all these other artists and we didn\u2019t have any artists. So when I met an artist and I liked them, most of the artists \u2014 Alanis Morissette I signed off of one song. Muse, I saw them perform one song and I\u2019d stopped them after \u2014 they flew all the way from London to L.A. to showcase for me.<\/p>\n<p class=\"wp-block-paragraph\">And after the first song, I stopped them. I said, \u201cYou do not have to play another song.\u201d And they\u2019re like, \u201cWe flew out all the way from London. We\u2019d like to play more music.\u201d I go, \u201cBut I just want you to know I do not need to hear another song.\u201d Just to be clear. So it shows the artist the passion, which is very important. This person believes in me that much.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>High conviction. Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>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\u2019t afford to not make fast decisions or else we would never have gotten to where we got to.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So in any of those examples, and I know this is possibly very hard to verbalize someone said to me recently and I thought it was pretty funny, they were like, \u201cYeah, in Silicon Valley, if you say you\u2019re using your intuition, nobody listens, but if you say pattern matching, then they pay attention.\u201d But if you were trying to explain what you intuited or noticed in that one song, understanding the music is good, but what else are you picking up from those five minutes? Because you can\u2019t bet on everything, especially as a small label.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>No.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So what were you picking up on that allowed you to make a fast decision in that way?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, I have to fall in love and you can\u2019t fall in love every five seconds, but you have to just have \u2014 I didn\u2019t know I was going to fall in love with Alanis when she walked in my office with Glen Ballard. They came in to play for me. I didn\u2019t know what was going on here. I thought they were a band. He was the producer, co-writer, but I don\u2019t know until I\u2019m \u2014 you just have a feeling and there is a lot of pattern recognition later.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Later, sure.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary:<\/strong> Now, with experience, now I bring other elements into the mix, other things I\u2019m looking for that are different than back then. It was just gut. It was just like, \u201cI love it. I\u2019m ready to go. I feel it,\u201d and you have to fall in love. And later today, I would say, on my tech investing and what I do there, it\u2019s a combination of gut, a combination of pattern recognition. And then there\u2019s a few other things. One of the things I look for is, can I help it? I visualize what I can do for the company and that gets me excited too. So I go, \u201cOh, wow. Okay. Oh, I know exactly what I \u2014 I have a feeling I can help in a big way.\u201d The puzzle starts to come together for me very quickly and so that\u2019s important.<\/p>\n<p class=\"wp-block-paragraph\">And then of course there\u2019s the other aspect of, well, you\u2019ve got to make sure they do what they say. Let\u2019s try this thing out. Let\u2019s 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\u2019s actually, \u201cOh, I pressed the thing and I can get an apartment.\u201d These things have to work, but for me it all starts with that initial pitch.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So how does Alanis Morissette fit into your life? Seems like an important piece of the puzzle.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>She played a big role in my life. She was the rocket ship. It just took me to the next level. I mentioned earlier, she appeared in my office with Glen Ballard and they played me one song. They played a few songs, but the first song they played was a song called Perfect. I didn\u2019t understand how powerful those lyrics were until later, when I really listened to it. It\u2019s really about earning your parents\u2019 \u2014 do they believe in you? Do they love you? I don\u2019t know if you know lyrics, but:<\/p>\n<p class=\"wp-block-paragraph\"><em>Sometimes is never quite enough.<\/em><\/p>\n<p class=\"wp-block-paragraph\"><em>When you\u2019re flawless, then you\u2019ll win my love.<\/em><\/p>\n<p class=\"wp-block-paragraph\"><em>Don\u2019t forget to win first place.<\/em><\/p>\n<p class=\"wp-block-paragraph\"><em>Don\u2019t forget to keep that smile on your face.<\/em><\/p>\n<p class=\"wp-block-paragraph\">So I didn\u2019t even understand. To me, it was just, how is she putting these words together and the \u2014 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\u2019t heard anything like it and I went, \u201cI\u2019m ready to sign you. I love this. I\u2019m all in.\u201d And I didn\u2019t know anything. I remember I didn\u2019t know that the comparisons where people were like, \u201cOh, I thought it was Joni Mitchell.\u201d People were like, \u201cOh, I didn\u2019t know Joni Mitchell.\u201d So to me, she was my Joni Mitchell. I didn\u2019t \u2014 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\u2019t know any of the background. A lot of people prejudged her because she had, as a teen, did a pop album in Canada. And so people had all this background. I had no background. I literally was asked to meet with her and Glen and I knew nothing.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>All you had was that meeting.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I knew nothing. They walked in and I thought, oh, wow. It felt like a hippie group, actually. I was like, oh, maybe there\u2019s some hippie vibe what is this going to be like, kind of thing. But there was, again, another life-changing moment where \u2014 so when the story is told, it\u2019s 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\u2019s a top five debut album of all time. That really just took me to the \u2014 because not only did I sign it, but everyone else didn\u2019t want to sign it. So it\u2019s not like I even competed. So it really cemented that, oh, okay, I\u2019m in a good place right now that I can do these things and this probably is going to give me more opportunity to do more of these things.<\/p>\n<p class=\"wp-block-paragraph\">So she\u2019s such a big part of my life and she\u2019s so talented. How lucky that years later, right now she\u2019s still winning awards. She\u2019s still out there crushing. She\u2019s 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\u2019m so happy to have been fortunate to have gotten that meeting and to have figured it out. A lot of people, when they initially heard it, I remember Freddy once asking me, \u201cWhat do you think this record could sell?\u201d Before it ever came out, and I go, \u201cMillions of albums.\u201d I just had a feeling that I had not heard anything like this and that this was a monumental record. And that\u2019s it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>The rest is history.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Rest is history.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I\u2019d love to spend a little bit of time on what you\u2019ve learned from Madonna. This is an older <em>Variety<\/em> piece, but the quote here that\u2019s attributed to you is, \u201cShe mentored me and by working so hard, pushed me to work so hard. I didn\u2019t know until she grabbed me by the hand and said, \u2018Let me show it to you.\u2019\u201d And it goes on and it goes on. But what did you pick up from Madonna? What are the key sort of learnings?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I mean, there\u2019s some clear learnings and there\u2019s stuff that with, I\u2019m 36 years next to this woman and there\u2019s things that when you look back, you go, \u201cOkay, I got that\u2026\u201d Like people who think about things that, \u201cI got that from my brother or my mother or my\u2026\u201d There are things that I didn\u2019t realize I was getting the whole time. So there\u2019s both and the front part is pretty, I think obvious. Her work ethic is not to be believed. Her commitment to her craft not to be believed, her passion for just the greatest gifts, whether it\u2019s through the books that she\u2019s reading or through the art that she\u2019s finding or the people that inspire her or the designers, she\u2019s so surrounded herself with a collection of some of the most incredible people in the world and she identified them by the way. She is the greatest identifier. She found these amazing talents early and was able to, whether either they\u2019d be painters or Frida Kahlo or they could be designers or musical people.<\/p>\n<p class=\"wp-block-paragraph\">She\u2019s an incredible finder of talent.I think that the thing that has really affected me the most is that she doesn\u2019t see any kind of \u2014 there\u2019s no walls around her thoughts. There\u2019s no, \u201cOh, I can\u2019t do that.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Right. In terms of constraints, right?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. And I think that even going back to my first experience at Maverick Records, if you went to any record label, they would\u2019ve put me in a compartment. There\u2019s the R&amp;B department, there\u2019s the jazz department, the rock department, reggae department, pop department, hip-hop department, \u201cOh, what department are you in?\u201d And they sort of bucket you into these things. I think that when I look back and I go, \u201cHow did I not really bucket myself? I went from this to this to that to that to that.\u201d And I think it\u2019s really just being around her has allowed me to never think in a limited way and they all work together. A lot of the stuff I do on technology has allowed me to bring that into my musical world and to understand how these things work together or the relationships. They\u2019re so hand in hand.<\/p>\n<p class=\"wp-block-paragraph\">And of course, a few decades later now people understand that, but at the time it was very much like, \u201cWell, what are you doing?\u201d This tech thing is crazy and you\u2019re not doing\u2026\u201d No, they\u2019re very \u2014 innovation is innovation and how we can distribute music or how we market and vice versa. All this stuff for music is \u2014 when you\u2019re 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, \u201cThat person has music they want to share with the world.\u201d<\/p>\n<p class=\"wp-block-paragraph\">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\u2019s your first single? What\u2019s your second single? And those are the things I still work in that kind of process, which is very musical in my mind.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And we\u2019re 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 <em>Twilight<\/em> and all of the rest. Because as you mentioned, in a different environment with a different label, you would have been tightly siloed and you wouldn\u2019t have had that ability, right?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>How did you end up with the foray into film?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary:<\/strong> I\u2019d been signing bands for a long time and running the record label and I thought, \u201cWell, why don\u2019t we do a film company as well?\u201d And Madonna and I were really in a good groove together and thought, \u201cLet\u2019s just start this film company.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Why did that come to mind?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I don\u2019t really recall that. I just recall thinking about how people do it differently. And so again, I didn\u2019t have context. The best thing sometimes is to have zero context. Sometimes fresh is okay, sometimes having a blank canvas. And with films, I had a blank canvas. I didn\u2019t know how it worked, but I knew I wanted to make some films. And so I had this idea of bringing in a bunch of producers under one roof and they were all independent producers and the idea was I\u2019ll bring them in and house them and give them support and pay for a lot of the legal. Things that cost money. When you\u2019re independent, it\u2019s a lot on you. I go, \u201cI\u2019ll take that.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>All the back office, all of that \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u201cWe\u2019ll take all that on, we\u2019ll help you and then we\u2019ll work on these projects together.\u201d And we had like a lot of producers that I, if I was to pay for them, I couldn\u2019t have afforded it, but we did it that way and out of that came a lot of films and a lot of different \u2014 <em>Twilight<\/em> and <em>Percy Jackson<\/em>, a few others that I was very lucky to be part of. The guy who ran it, Mark Morgan, was really good at it, but there were a lot of complications and I was at that same moment that it started to take off, I picked up Madonna as manager with my partner at the time, Angela, and I took on Confessions, which was the pretty massive tour that year and I think the biggest selling record of that year. I don\u2019t know how old I was back then, but that was a major responsibility for me.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Hard to ride both of those horses at the same time.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Just that alone, just Madonna at that moment in time for someone \u2014 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-<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And for people who have no context on music at all, what does a music manager do in that type of situation?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It\u2019s a tricky question because no one manager is the same. Everyone\u2019s different.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I guess what was your umbrella of responsibilities?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>My umbrella, when Madonna started working on \u201cRay of Light,\u201d 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 \u2014 she was on Warner Brothers, but we were just friends and working together, but I fed ideas. I found the director, Jonas \u00c5kerlund. And so I was creatively really working on this project called Ray of Light. So we\u2019re already building a creative rapport and on music, St\u00e9phane Sednaoui, the director introduced me to a producer named Mirwais. He gave me a demo. I loved it and I gave it to Madonna and it ended up becoming Music. So I found on those two albums, I really, even though I wasn\u2019t managing her, I was creatively helping here and there bring in some ideas. So we already had a rhythm on the creative side.<\/p>\n<p class=\"wp-block-paragraph\">Now there are some managers that don\u2019t do any creative and there are some that are very creative, but I was coming from the creative point of view on ideas, ideating, here\u2019s things we could do, here\u2019s things we could build. So I think for me, that\u2019s the management that I am. I\u2019m more creative. When I\u2019m working with someone, I\u2019m sort of in it. And there are other managers I\u2019ve worked with who they really just \u2014 they don\u2019t do the creative, but they do an incredible job managing everything, putting together the tour, but they\u2019re not in there going, \u201cWhat if we did this?\u201d There\u2019s different kinds of managers. I\u2019m creative.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>For example, when I showed her, Jonas \u00c5kerlund did a video for Prodigy, which was a band I signed, and it was really provocative. And I just showed it to her, \u201cThis guy, this is crazy.\u201d And she goes, \u201cHe\u2019s doing my first video or he\u2019s doing that.\u201d I showed her, there\u2019s a guy named Chris Cunningham and he made a song called \u201cCome to Daddy\u201d by Aphex Twin, which is really insane. It\u2019s a $30,000 video. I just showed it to her just to show her, \u201cLook at this crazy thing,\u201d and she\u2019s like, \u201cThat guy\u2019s doing that video.\u201d So she had Chris Cunningham do \u201cFrozen,\u201d which is an incredible video and she had Jonas \u00c5kerlund do \u201cRay of Light\u201d. So it was just a really great back and forth. We had really great energy together that she was open to my craziness and then she would take it to the next level.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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\u2019m just wondering why you think she has been so consistently good at that over decades. I mean, it was the first example that I remember even as a pretty young kid marveling over. And I\u2019m just wondering if you could add any color to that.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>She doesn\u2019t sit well on her past. She\u2019s not high-fiving herself. She\u2019s not really a, \u201cOh, my God, I\u2019ve done all these\u2026\u201d She just keeps it moving forward. Yeah, I think that is part of the inspiration for continually trying to move forward myself is I have a front row seat or shotgun to this incredible journey of this woman who just continually defies all the odds and fights the fight. It is not easy. It\u2019s not that she\u2019s maintained or stayed around. It\u2019s actually that she\u2019s had to fight her way through it a lot. She\u2019s breaking ground for a lot of other people who are coming behind her who can say, \u201cWell, Madonna\u2019s done it. I can do it.\u201d But it is no easy feat. There is a lot of bullshit to deal with. And I think it comes from she just doesn\u2019t celebrate her accomplishments. She just starts like it\u2019s a brand new day.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>How did you end up, and I don\u2019t know if this is a good starting point, but I\u2019ll throw it out there as an example, your first consumer investment, Vita Coco.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yes.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Well done.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Thank you.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I don\u2019t 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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Wow. Well, the original, original was I was on a plane to Milan for the MTV Awards and I don\u2019t remember how old I was. It was in my 20s and I was reading in a magazine about Sky Dayton and it said he started EarthLink and he was worth a hundred million dollars and he was really \u2014 I\u2019m like, \u201cWait, what? Wait, what is he doing and how old is he?\u201d And so I go, \u201cWhen I get back home, I want to meet this guy.\u201d So I came back and took me a while, but I finally tracked him down and we went to have lunch at Four Seasons Hotel and he was like, \u201cWow, if you\u2019re impressed by me, have you ever heard of Bill Gross?\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Idealab.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>And I go, \u201cNo, who\u2019s that?\u201d He goes, \u201cWell, he started an incubator and he\u2019s launched three billion companies in one year.\u201d I go, \u201cSky, I like you, but can you get out of the way I want to\u2026\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>This time has been great.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. \u201cIt\u2019s time to move on. I need to talk to this Bill Gross guy.\u201d So he sets me up with Bill Gross. Bill Gross ran an incubator called Idealab in Pasadena and I just loved it. I love the idea of a lot of ideas, reminded me of the record label where you had all these artists and you had all these project managers and everyone, and you\u2019re \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Or the independent producers, right?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>A version of that. And you can walk in and out of different rooms and you can say, \u201cOh, okay, what are we doing here? What are we doing here?\u201d 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, \u201cOh, okay, an incubator.\u201d I really fell in love with that idea and there\u2019s bad news to this story, but it\u2019s like all things it worked out in the end.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Wait a second. My listeners are going to kill me if I don\u2019t follow. What\u2019s the bad news?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, I mean the bad news is that I worked there for a year helping and then one day someone I really trust that \u2014 they don\u2019t know it to this day, but they\u2019re 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\u2019ve ever made. So I called up Bill and I go, \u201cBill, I want to put money into Idealab.\u201d And he goes, \u201cWell, I was going to surprise you and I was going to put X dollars in for you from bottom of my heart for all the work you\u2019ve done here.\u201d And I go, \u201cOh, what is that worth?\u201d He told me what he thinks it\u2019s going to be worth when it comes out and by the way, it was worth a lot and I go, \u201cThat\u2019s not enough.\u201d<\/p>\n<p class=\"wp-block-paragraph\">I\u2019m thinking to myself, \u201cThat\u2019s not enough.\u201d So I go, \u201cBill, I want to put more in, a lot more in.\u201d And he\u2019s like, \u201cHey, for you, I\u2019ll let you do whatever you want.\u201d And he did. He\u2019s a really, really sweet guy and that\u2019s the bad news. He let me do whatever I wanted.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>What year was this?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It was before the crash. By the way, it wasn\u2019t a year before the crash. I think it was like an hour before the crash. I put every dollar I have plus dollars I didn\u2019t have. I picked out three investments at that time, Idealab because of Bill Gross, Bill was the first guy in I think in L.A. to have the BlackBerries. So I was the first guy from Hollywood to even know what the hell BlackBerries were. So I ended up buying 400 of them and I gave them to all the people in Hollywood so I could connect when I needed to and talk to them. And so I made a deal with Jim Balsillie to be an advisor because I was the guy that put it in everyone\u2019s hands. This is smartphones before anyone else was doing it. And then I also, my friend Seth Rodsky brought me Vitamin Water.<\/p>\n<p class=\"wp-block-paragraph\">Those were going to be my first three investments. What happened was the Idealab thing, once I put that money in and I don\u2019t know the timeline because I tried \u2014 it\u2019s almost like something you want to wash away from your mind. It collapsed \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Fever dream you\u2019re trying to forget.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>The bubble burst so fast on all of that that I didn\u2019t have the heart to invest into \u2014 I never signed my deal with Jim Balsillie in Research in Motion and I never did my deal with Vitamin Water, which both ended up \u2014 almost like the Hole and the Rage analogy. They both ended up being massive and then I lost all my money with the first one. So I learned about a lot. I learned about diversification. I didn\u2019t diversify. I put the \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Everything in one.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u2014 majority of my money in one thing and I paid the price for it really. For the next two years, I only thought about that about 15 times a day. It didn\u2019t matter. If I was sitting here with you right now, back then, I\u2019d be thinking about it. I\u2019d have a conversation with you, but I wasn\u2019t thinking about you. I was thinking about how did I lose all my money on that one investment? Everything I saved my whole life. And I was mad that Sky Dayton introduced me. I was mad at all the wrong reasons. Everyone was just trying to help me, but now I\u2019m like, \u201cWhy did I even read that magazine? I should have just stayed in my music lane.\u201d<\/p>\n<p class=\"wp-block-paragraph\">But what happened was years later after my first Madonna tour, I started to think about it again and I go, \u201cI wasn\u2019t so off really.\u201d I was off \u2014 the timing was wrong on the Idealab part. The other two worked. Had I diversified, I would have done \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>You would have been fine.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u2014 incredibly well.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah, you would have been great.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>And so I got two out of the three and the truth is it\u2019s 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\u2019t work out and that\u2019s life. Sometimes they don\u2019t work out these deals.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>A lot of the time.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>But I came back from, I think I had done three Madonna tours in a row. So I came back, all the money I\u2019d lost, I made that back to survive. And then I had a window where I knew we were three tours in a row, we\u2019re going to take some time off and I thought to myself, I didn\u2019t get it so wrong, so I\u2019m going to try this one more time. I\u2019m good at identifying the ideas. I\u2019m good at identifying the talent. I\u2019m going to do one more time. And that\u2019s when I \u2014 so I started and the same guy that brought me Vitamin Water, Seth Rodsky \u2014<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Did he later work with Reese Witherspoon?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yes, exactly.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Huge.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. Yeah. He\u2019s done well for himself. And then he called me one day and goes, \u201cHey, have you heard of this coconut water thing?\u201d So of course I\u2019d heard about coconut water. One, my wife is Brazilian and my first son, his first words were like, \u201cAgua de coco.\u201d So we drink coconut water at the house, but the whole coconut water sector in America, if you added all the companies together was maybe a five or seven million dollar business. It was nothing.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Tiny.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Nothing. But Madonna on tour, on the previous tour, she would have \u2014 the trainer would go in different markets to find fresh coconut for her for the coconut water. And I\u2019m like, \u201cWow, every location went to, we had to find fresh coconuts.\u201d And so I started to hear that other people were doing that as well. Other people who cared about their health were drinking coconut water. I started to see, again, back to pattern recognition, I started to see this thing and then one day the <em>New York Post<\/em> ran an article about coconut water. There was a photo of Giselle drinking from a coconut and they\u2019re talking about coconut water and I had cut that out and I put that article on my desk and when Seth called me and said, \u201cHave you heard about coconut water?\u201d I go, \u201cYou have to be kidding me.\u201d I have \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>It\u2019s sitting on my desk.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>The only thing that I\u2019ve tore out that\u2019s sitting on my desk is an article about coconut water. It\u2019s on my desk and it\u2019s like my to-do, like, I need to figure this thing out. And here you are calling me. He goes, \u201cWell, there\u2019s a company called Vita Coco out of New York.\u201d And I go, \u201cCount me in.\u201d I got on a plane. I went to meet with the founder, Mike Kirban. The company was, I think it was a $35 million valuation at the time and I literally just, here we go. I\u2019m 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\u2019m like, \u201cLet\u2019s blow this thing up.\u201d And that was the first time back after the crazy run.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>For people who don\u2019t know, how did that turn out?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It\u2019s a public company today. I think it\u2019s $4 billion market cap.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So you were back in the game?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yes. It takes time.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>It takes time. Yeah, there\u2019s a gestational period.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It takes time. Yeah, it didn\u2019t happen overnight.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I think I approached it the way I approached everything. It wasn\u2019t, let\u2019s think about it. It was like, \u201cI\u2019m all in. Let\u2019s go. I want to do this. Here\u2019s what I can do.\u201d And I think they were probably overwhelmed by, \u201cWhoa, okay.\u201d And we just ran. Yeah, he\u2019s awesome. What he\u2019s done with the company, we went public I think at like two billion and now it\u2019s at five. He\u2019s done an incredible job.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So we\u2019re 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\u2019ve seen applied to you a lot, which is <em>great curator of people<\/em>. Chris Rock has said this. Matthew, you just mentioned, said this. Woody Harrelson \u2014 have all described you in this way and you seem very intentional with the people you surround yourself with. Not only that, but you have these very long-term relationships with a lot of people. And I\u2019m wondering how you think about building relationships. I\u2019m not saying you have to come up with Guy\u2019s 10 commandments of long-term relationships, but how would you think about that? If you\u2019re in front of a class of students and you\u2019re like, \u201cLook, a lot of people get this wrong, or at least let me tell you how I approach relationships.\u201d<\/p>\n<p class=\"wp-block-paragraph\">Any particular rules that you use for yourself or just approaches, things you keep in mind? Because that\u2019s certainly not true for everybody. You just have this long-term cohesion of these people around you. And I\u2019m wondering if you can perhaps just speak to that in any way.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>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\u2019t a comedian or a musician or an actor or a director. I was like an executive. So there\u2019s a little responsibility. \u201cHe\u2019s the responsible one.\u201d I don\u2019t drink. I don\u2019t do drugs. So I found my position was to really be a safe zone for people and to really \u2014 and they knew I worked with Madonna, which pretty much gave a lot of credibility to, \u201cOkay, this guy \u2014 she trusts him. Maybe we should trust him,\u201d maybe, back in the day.<\/p>\n<p class=\"wp-block-paragraph\">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\u2019s not a lot of photos, there\u2019s no cameras. I think safety and support has always been in my DNA from an early age, of just making sure that people are protected.<\/p>\n<p class=\"wp-block-paragraph\">And again, I think identifying really incredible people to be around. Same way I identify the greatest companies to invest in, I think I identified really amazing, incredibly talented friends who inspire me, and who, early days, you may not have known them 30 years ago, but you identify them and they identify you. And so there\u2019s this camaraderie and there\u2019s this trust, and I do try to bring them all together a lot. I think it\u2019s important.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>That was going to be actually my next question, which is along those lines, which is, how often do you gather people? Whether it\u2019s 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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>A lot. If I\u2019m landing in New York this week, I\u2019ll probably do a dinner and I\u2019ll invite the 15 or 20 friends and we sit down and we talk. So I\u2019m always staying connected and in touch. It\u2019s not like, \u201cOh, I haven\u2019t talked to you in a year.\u201d No, I\u2019m checking in on my friends a lot. I\u2019m finding out how they are always. I\u2019m always checking in on everybody.<\/p>\n<p class=\"wp-block-paragraph\">I grew up just with my dad. My two sisters were older. They weren\u2019t around. So my friends are really \u2014 they\u2019re everything I had. Before I had a family, my friends were everything to me.<\/p>\n<p class=\"wp-block-paragraph\">I\u2019m lucky I get to work with some of my family. Madonna\u2019s \u2014 I\u2019ve been beside her for 36 years. The Chili Peppers are my best friends in the world. The godfather of my first son is Anthony. The whole band, all of them, Flea, Chad, John, they\u2019re family. So it\u2019s a dynamic that I\u2019ve chosen for myself is to really support and be around my friends a lot. It\u2019s a big part of my life, which is to keep that close. And again, if someone\u2019s in need, this is the number, call me.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I want to hop back to the investing. I mean, you\u2019ve had a lot of hits. Airbnb, Uber, Spotify, it goes on and on and on. I mean, I don\u2019t know how many IPOs and someone that you\u2019ve had, I mean, gazillion.<\/p>\n<p class=\"wp-block-paragraph\">Let\u2019s talk about one.\u00a0<\/p>\n<p class=\"wp-block-paragraph\">So you put in, tell me if I\u2019m getting this right, 35 million at a five billion valuation into Anthropic. This is a company that\u2019s been in the news a lot. I think the last round was what? 965 billion, something like that. Are those numbers roughly accurate?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yes.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Okay. So it\u2019s a pretty nice multiple so far. We\u2019ll see how things go. How did that Anthropic deal happen?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, it starts a little before. The day that OpenAI came out, which was on my dad\u2019s 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, \u201cWhat is this?\u201d And when ChatGPT came out, that was a \u201cWhat is this?\u201d moment for me. And if you saw me anytime after ChatGPT came out, I would\u2019ve harassed you to show you ChatGPT. There\u2019s no one \u2014 every artist, every actor, everyone I walked around and met, I\u2019m like, \u201cCheck this out, check this out, check this out.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And I was obsessed, and I called Ashton and I said, \u201cAshton, this is it. This is OpenAI. We\u2019re doing OpenAI. This is the greatest thing I\u2019ve ever seen. We have to do it, have to do it, have to do it.\u201d And so that was our first, \u201cThis is the one we\u2019re going to go after.\u201d<\/p>\n<p class=\"wp-block-paragraph\">But then we visualized that \u2014 when we first started investing, Ashton and I, it was when the iPhone and the App Store were happening. And so for the first time ever, you can scale companies like never before. And I think anyone would have done well at that time. We were lucky people that came in at the right time and were looking at the right time and started our fund at that very moment, which is crazy. And so we had this incredible success because of that.<\/p>\n<p class=\"wp-block-paragraph\">I saw it again, back to pattern recognition. If you fast-forward, we\u2019re still using Uber and Airbnb and Spotify. We\u2019re still using those things from that time period. And we felt that, \u201cThis is it. These foundational AI models in 10 or 15 years will be how we plug into all these things.\u201d So we really felt like we had a three-month window. We told people we have a three-month window.<\/p>\n<p class=\"wp-block-paragraph\">Now, it came out November 30th, 2022. So there\u2019s not much you can do. People are going away. Christmastime break, blah, blah. But as soon as January came, we went out there and told people, \u201cThis is the vision. We\u2019re going to do a foundational AI model fund.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong><br \/><\/strong><strong><br \/><\/strong><strong>Tim Ferriss: <\/strong>I got it. LPs.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Raise money.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Raise money and create this fund, which was a crazy idea at the time.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Now, had you already confirmed that you\u2019d be able to get allocations, or you just had complete confidence?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Ashton spoke to Sam and we were able to get OpenAI. And then what happened was is I\u2019m very close to Marc Benioff and Salesforce Ventures, people don\u2019t really understand how smart they are.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah, they\u2019re really smart.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>They don\u2019t get all the press on \u2014 they are one of the best investors in the world. There\u2019s two guys there, John Somorjai and Paul Drews, who were \u2014 when I was doing my research, because now I\u2019m on the lookout, \u201cWhat should I know about an AI?\u201d Once I find out about something, I just lock in and I want to know everything about it. As I was doing my research, I was finding out that they were going to do Anthropic and they were very bullish about it. I found out from a friend that works with a job hunter kind of \u2014 people who helped find jobs for people.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Oh, like headhunters.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Headhunters, that everyone\u2019s going to this company called Anthropic. People are really going to this Anthropic place and they\u2019re not going anywhere else. I\u2019m like, \u201cWhoa, okay. I need to pay attention to this.\u201d So I asked Paul and John, \u201cConnect me with this founder,\u201d Dario.<\/p>\n<p class=\"wp-block-paragraph\">So they connect me with Dario and Neerav, and they come here. They\u2019re here right in this room and that\u2019s where we made the deal to invest in Anthropic. So we did a bunch of other companies in that foundational AI fund. It was a three-month window.<\/p>\n<p class=\"wp-block-paragraph\">So it was before a bunch of other things that have come out since, but we set ourselves up for exactly what we did. \u201cThis is going to be within three months. We\u2019re going to deploy 80 percent of the money within the next three months.\u201d And that\u2019s what we did and that\u2019s over three years ago.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>And how did you know the window was going to be so narrow? Did you get any pushback from LPs when you said, \u201cWe\u2019re going to deploy 80 percent of this in three months\u201d?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, we didn\u2019t have \u2014 there was no LPs, meaning that was the pitch. So it wasn\u2019t like we raised money \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I see, I see. They either bought in or they didn\u2019t.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. It wasn\u2019t like we raised money and then told them the pitch. It was like, \u201cHere\u2019s the pitch.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>\u201cHere\u2019s what we\u2019re going to do.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u201cThere\u2019s a window of opportunity here. We think this is the future.\u201d And that was it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>They had opted in.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, opt in or opt out. We didn\u2019t know what we were going to raise. Whatever came up is what it was going to be.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So I was trying to pull from memory, but it looks like Sound at this point is at 86 exits and 26 IPOs. That\u2019s insane. I mean, that is \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It\u2019s been fun.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>You have seemingly different batteries, certainly. I mean, you\u2019ve got good batteries. What is the next five years, do you think, look like for you? I mean, is it more of this type of investing? What do you see? Is it switching gears entirely and looking at the prism through a totally different way? I mean, what is next for Guy?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I feel like going back to the core, really honing in that antenna for the greatest talent in the world, the greatest ideas in the world. This is an incredible time where people can scale up a company in the quickest ways. I\u2019m excited about the potential of what\u2019s to come. I\u2019ve already identified three things I want to do today. So I can only imagine what\u2019s to come, but it\u2019s just \u2014 I\u2019m okay doing a version of what I\u2019ve been doing, which is identify great talent and help them, help this talent, help them in every which way that I can, and pick the teams that you want to back. So I\u2019m feeling pretty good about that, just continuing on this best-in-class talent idea.<\/p>\n<p class=\"wp-block-paragraph\">The hard part is for a lot of people is the access. So we\u2019re 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\u2019re a different kind of investor on the cap table. We\u2019re not in the valley. We\u2019re here in Hollywood and we bring a different dynamic, a different \u2014 obviously, narrative is something that I\u2019m very focused on.<\/p>\n<p class=\"wp-block-paragraph\">Marketing is something I\u2019ve 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\u2019s what I \u2014 I need to find that dynamic of a company that I\u2019m in love with and, hopefully, the founder believes that having me would be a great advantage to them.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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\u2019d like to make clear to people who are listening or otherwise? Also, where can people learn more about what you\u2019re up to? Is there anywhere that you would point them in particular?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I\u2019m a generalist. I don\u2019t 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, \u201cYou know what? I\u2019ve got an idea,\u201d it\u2019s going to be built around this one idea. But usually I\u2019m a generalist. I just like talented people.<\/p>\n<p class=\"wp-block-paragraph\">And in regards to sharing, where can they find out what I\u2019m up to? I\u2019m not really \u2014 this is it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah, this is it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>As you know, this is my first podcast and, depending how this goes, could be my last. And if it goes well, maybe one more, but I\u2019m not out there \u2014 everything has been fine without doing that. People either find us word of mouth through friends or I find them. It\u2019s okay. It all works out. I\u2019m not out there yelling, \u201cHey, find me 1-800 whatever.\u201d It\u2019ll work itself out. The right people will find each other.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Well, Guy, I mean, we\u2019ve covered a lot of ground. Is there anything else that you would like to say before we start landing the plane?<\/p>\n<p><strong>Guy Oseary: <\/strong>I\u2019d say that AI and music content, it\u2019s 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\u2019s pretty exciting. At the same time, the idea that there\u2019s companies out there valued at billions of dollars that are built on the top of other people\u2019s music, where not one artist has ever gotten paid a dollar, is not okay. So I don\u2019t want to bundle it all up where people get \u2014 it all becomes one thing. It\u2019s not all one thing.<\/p>\n<p class=\"wp-block-paragraph\">Mikey, he runs Suno. He\u2019s a great guy. He\u2019s really, really \u2014 I mean, great guy. I really like him as a person, but every time I read about the company and it\u2019s now at a $5 billion valuation, and next thing you know, it\u2019s at a $10 billion valuation, and it\u2019s all built off of the world\u2019s music, but yet not one music artist has gotten a dollar. So that\u2019s not okay. That has to be fixed. I\u2019m 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: \u201cDo not use my music to build your business.\u201d Okay? \u201cI\u2019m opting out, but if I opt in, find a way to pay us.\u201d<\/p>\n<p class=\"wp-block-paragraph\">And I\u2019m really concerned for that because the other part, which is right now, currently, every two weeks, more music is made on AI than all of the music that\u2019s on Spotify today. That\u2019s every two weeks, and all of that is going somewhere and people are inspired and they\u2019re creating songs. Awesome, but don\u2019t build a business using our music without getting those rights. And that\u2019s something that I\u2019ve been trying to work on for a long time. I\u2019ve met with Mikey many times. I\u2019ve met with lots of people many times. I hope that this gets solved.<\/p>\n<p class=\"wp-block-paragraph\">When Napster first started, I met with Shawn and Sean when they started, because it was so exciting to see people were all downloading music, but it was illegal. So you were hoping they\u2019d crack the code on, \u201cOkay, how do you turn this into how artists get paid?\u201d I don\u2019t know if they were going to or not going to, but before that could even happen, it got shut down.<\/p>\n<p class=\"wp-block-paragraph\">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\u2019ll pay for it. And he was right. They have paid for it. Now, are all the payment plans there picture perfect? No, but it is the core of where money is coming in today to music artists; it\u2019s through streaming. And I\u2019m hoping that people figure out how, if you\u2019re going to be using people\u2019s music, how you pay for it. Fair use is not fair.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah. I\u2019m curious to see where it goes because if you say, \u201cCreate a song that sounds like Metallica,\u201d it\u2019ll say, \u201cWe cannot serve up any copyrighted music.\u201d If you say, \u201cServe me up some music that sounds like Morallica,\u201d and you just misspell it, then lo and behold, it looks like it was trained \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah, that\u2019s the problem.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>\u2014 on this corpus.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>There\u2019s a lot of workarounds and they\u2019ll look you in the eye and tell you, \u201cNo, no, you can\u2019t. You cannot type in Madonna.\u201d But you can sort of describe Madonna. The problem is, is when \u2014 in discovery, we\u2019re going to find out a lot, and discovery\u2019s going to say, \u201cAll of this music is in there,\u201d and they know that and that\u2019s not okay. It\u2019s just literally not okay. I don\u2019t understand it.<\/p>\n<p class=\"wp-block-paragraph\">And by the way, what\u2019s 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\u2019re going to train on their music?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Where do you think it goes? Because I could see one future, for instance, even if legally they aren\u2019t required, or for whatever reason, that\u2019s not compatible with the vision they\u2019ve pitched to investors, and I\u2019m not singling out Suno. I mean, there are lots of different options here.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>They\u2019re the main one.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>They\u2019re the 800-pound gorilla.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>But I could see a point at which possibly Claude, ChatGPT become the interfaces to everything. It\u2019s almost like the App Store, but somewhat like WeChat in China: if you want to do anything, if you want to book a restaurant, you want to make a song, there are a few interfaces to everything, at which point then those companies, OpenAI, Anthropic, can gatekeep in some way and maybe they end up being the entities that incentivize these other companies, like the Sunos of the world, to reimburse artists. I guess I\u2019m just wondering if you have any thoughts on how it gets there.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It starts with Suno. Because if Claude or Chat is the distribution, they probably won\u2019t carry it because it\u2019s got so many lawsuits involved and it\u2019s just not worth taking on that responsibility.<\/p>\n<p>And again, the guy who runs Suno, I find, would be a really good guy and I\u2019m hoping that he does the right thing, but it\u2019s really their responsibility. They\u2019re sitting at the top of this opportunity.<\/p>\n<p class=\"wp-block-paragraph\">Take off the artists that don\u2019t want to be on there and find a way to pay the ones that are okay being on there. It\u2019s that simple. It\u2019s not complicated. Go in a room, lock yourself in a room for three days and come out and figure out how to pay people and take people off that don\u2019t want to be on there.<\/p>\n<p class=\"wp-block-paragraph\">Madonna does not want her music trained on. Don\u2019t care what you want to pay her. She\u2019s very clear: \u201cI do not want my music to be trained on. I want my music to be its own thing.\u201d So take her off. It\u2019s okay. You\u2019ll still do fine. Take her off. You don\u2019t have to have her music.<\/p>\n<p class=\"wp-block-paragraph\">So we\u2019ll see where this goes, but this is \u2014 the last few years I\u2019ve really tried to figure this out, and even with Sam at one point, he\u2019s really wanted to figure this out too. A lot of people give him a hard time on this stuff, but he really did dedicate time to trying to figure out if there was a music thing to do, how to do it in a way that supported artists.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah. I mean, there may be someone who comes along also if it\u2019s not Suno, someone who comes from behind, like a next generation Spotify, and figures out how to do it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, Spotify could do it.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Yeah, or Spotify could do it. You mentioned there were three things that you\u2019d like to do today. I\u2019m not going to ask you to name those things, but how did you find those things or how did those things find you?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>One of them, well, I\u2019m working on this platform that I\u2019m going to announce in a few months that you\u2019re part of is how we connected, you and I. So I\u2019m able to ask investors what companies that they\u2019re looking at. And so two of those came from that conversation.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>That\u2019s good. Good information for that.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. They\u2019re like, \u201cWhat are you looking at? What are you liking?\u201d And then they tell me and then I go, \u201cOh, let me look into it.\u201d And some things I just read about, I read every single day. I\u2019m checking things out every single day and I\u2019m making sure I\u2019m not missing an idea or I\u2019m hearing about things.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>What do you read?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, I\u2019m on X a lot. I see a lot of the stuff, a lot of information on X that\u2019s flying by. It\u2019s sort of my start of information.<strong><br \/><\/strong><strong><br \/><\/strong><strong>Tim Ferriss: <\/strong>You mentioned missing BlackBerry and Vitamin Water. Do you have, and this could go way back in the catalog, could go back to being 10 years old, there\u2019s 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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, I mean there\u2019s so many. It\u2019s 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\u2019m always like, \u201cI can\u2019t believe we\u2019re not in that. I had it and we had it.\u201d And he\u2019s like, \u201cCome on, let\u2019s move \u2014 let\u2019s go. Let\u2019s go.\u201d He always gives me like, \u201cOh, gosh, he\u2019s going to complain about not being in it again.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Here we go again.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>But what motivates him is he just keeps it moving forward and it\u2019s awesome. And what motivates me is like, I\u2019m not going to let that happen again.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I mean, looking back, it seems like, in some ways, missing Hole, missing fill-in-the-blank, was almost a prerequisite source of fuel for the things.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah. It\u2019s scary, though.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>It drove you towards those things.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It\u2019s scary, though. When you miss it, Ash and I invested in Bitcoin on our own when it was at $22. And then when it hit $250, I thought I just made 10 times my money. I\u2019m a genius. So I sold then and clearly not a genius. So that hurts. And I remember Anthony, gentlemen on that wall, Elon invited Anthony from the Chili Peppers to see SpaceX early days, very early days. And I went with Anthony, I tagged along. It\u2019s the first time I met Elon and we went to SpaceX. I was so wowed by the concept that I didn\u2019t even pay attention to the business model or what could be the business model.<\/p>\n<p class=\"wp-block-paragraph\">I was just like, \u201cWow, this guy\u2019s building rockets.\u201d If we just had had the wherewithal to go, \u201cWhat business model?\u201d I didn\u2019t even ask those words. Sometimes I go to shows. I\u2019ve seen shows where people are so wowed that they\u2019re just like, they\u2019re like this from a show and they didn\u2019t even take in all the songs. They were just like, \u201cOh, my God.\u201d If you ever look back at the Sex Pistols shows, people are just like, \u201cWhat?\u201d And they\u2019re like, \u201cWas I actually there?\u201d 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\u2019ve asked one more question, like, \u201cHey, how do you monetize this?\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>\u201cOh, by the way\u2026\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>\u201cHow does this work? Can we invest?\u201d So I have hundreds of those stories, but those are two that stand out today.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I want to talk about the longevity for a second. You mentioned, and fact check me if I\u2019m getting this wrong, but the three, was it back to back tours with Madonna?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Yeah.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I mean, that sounds impossible just from the demands of the physicality of that. And she\u2019s 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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I think it\u2019s different as the years go by, there was a point around 10 years ago, 11, 12 years ago where it was a lot for me because I was also changing and growing and having kids and I was just losing myself because you\u2019re going to a different city every other day and the amount of things you\u2019re missing back home, you forget you have a family, you forget that you can go do other things or you forget to call back Stripe or you forget to \u2014 all the things, you just forget everything. And then one day your dad calls you and goes, \u201cOh, hey, I\u2019m at your house with your kids.\u201d And I\u2019m going, \u201cOh, I have kids. I\u2019ve got a house.\u201d<\/p>\n<p class=\"wp-block-paragraph\">So if you look at the first three tours that Madonna, those three tours that I did, those are 240 shows, 80 average. I missed three of those shows, three out of the 240. One, I was sick and then I missed two because it was my 40th birthday and I really didn\u2019t feel like being in Seattle that day. I wanted to be home with my friends. So my 40th birthday, I spent here in this house. So I missed three shows out of 240, but we\u2019re talking about a different city, a different hotel, a different \u2014 and in order to move along, you have to block everything else out. You have to forget and it\u2019s a very selfish, very \u2014 for me. Otherwise, if, every day, you\u2019re thinking about back home or your family or other things, it hurts. So I just go, \u201cOkay, I\u2019m off and I\u2019ll see you.\u201d I bet that\u2019s what actors do when they go away and make a movie for three months and then they come back.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Some military do.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>They probably just compartmentalize a little bit. But in the last few years, I\u2019ve stopped doing as much. I still go, but not as much. I\u2019ve worn it down. There\u2019s a moment there where I managed the Red Hot Chili Peppers, U2, and Madonna, and they\u2019re all going on tour, and it was a lot to process.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>How do you even make decisions about where to be in a case like that? You can\u2019t be in three places at once.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>It\u2019s hard, but it tells its own story. You\u2019re not going to miss New York, you\u2019re not going to miss London, you\u2019re not going to miss some of the major moments. And then you look at the calendar and go, \u201cOh, we have this time off. Let\u2019s go to this place with \u2014 let\u2019s go to New Zealand with Madonna or let\u2019s go to so-and-so with U2 or let\u2019s go to so-and-so with the Peppers.\u201d And you find your way around it. You just make it work.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>So if you look at, let\u2019s 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?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I think when I think of responsibilities, I always think of management. That\u2019s a really big responsibility and I don\u2019t take it lightly. There\u2019s no way around it. Something\u2019s going on there that\u2019s a focus. It is cyclical. So the Peppers are not touring this year, they don\u2019t have an album this year. They aren\u2019t touring next year, they don\u2019t have an album next year. There\u2019s a lot of time in between, where they\u2019re coming up with the creative. They\u2019re going to make an album, they\u2019re going to do all the things, they\u2019re going to write songs, right? So that takes time. So you get these windows of opportunity where you go all in and you get windows of opportunity where you have a moment to breathe, just like they do. They all need it too. Madonna, after this cycle, will probably need a minute to just catch her breath and figure out what she does next.<\/p>\n<p class=\"wp-block-paragraph\">So these are cyclical things. What I don\u2019t do is I\u2019m not out there trying to sign 10 more bands or 10 more artists. And so that\u2019s where the balance comes in and which is the creative, but continually be creative through other ways. And so when the cycle starts, my creativity has never stopped so that I still have those things. I\u2019m not starting from scratch. I\u2019m always looking and meeting with people and understanding what\u2019s going on in technology. And so when Madonna comes back into cycle, I can bring some of those ideas or some of those new relationships I met while she was off. And so I found a way to make it work.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Now maybe I\u2019m sure misquoting, but roughly paraphrasing much earlier in the conversation, I feel like you said part of Madonna\u2019s ability to reinvent was not resting on her laurels, obviously, but not patting herself on the back for what she\u2019s done and marching forward. I\u2019m wondering how you\u2019ve thought about for yourself the drive and velocity of forward-looking achievement versus appreciating what has been done or savoring the time that you have. I mean, I imagine you get a lot of that with congregating friends and so on, but I\u2019m wondering if you have any thoughts on that.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>You know, my friends and I don\u2019t spend a lot of time talking about what I do a little bit. I share with them so they\u2019re in the know, but we don\u2019t spend a lot of time on it. We don\u2019t work together on these deals. My wife and I don\u2019t talk about work much. I think I just keep it moving too. And again, when you look back 36 years, it\u2019s 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\u2019m telling my kids a story about the past or someone asks me a question and I tell them about the past, I go, \u201cOh, my God, I forgot I even did all those things.\u201d Or I see something pop up and I go, \u201cOh, I was there for that.\u201d<\/p>\n<p class=\"wp-block-paragraph\">But I really don\u2019t think about it that \u2014 I don\u2019t think about it that much. Things pop up every now and then, but I wake up and like tomorrow is \u2014 when I wake up tomorrow, I\u2019m like, I haven\u2019t done anything today. I better figure it out. I need to step my game up. That\u2019s how I feel. I don\u2019t feel accomplished. I don\u2019t feel at all. I feel like I still have so much to prove and so much to do, but at the same time, I do know if I really took a minute and I go, oh, wow, okay. I should probably take a moment and take that in, but I really don\u2019t.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Is that okay? Is that a problem? Is it fine?<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>I just keep it moving. I don\u2019t know. At some point, I can visualize being on the beach and high-fiving with my friends and having fun, but again, they don\u2019t do it either. Yeah. A lot of my friends \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>[crosstalk]<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>They don\u2019t talk about it like that either. I mean, I think we just \u2014\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Working dogs.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>How cool that we\u2019re survived this period of time. How cool is it that we\u2019re even able to do what we love? Waking up and being able to do what you love, there\u2019s a Josh Kushner quote that I love that he says about success. And he says, \u201cTim, success is being excited to go to work and also being excited to go home.\u201d And I got that. I\u2019m excited to go to work and I\u2019m excited to go home. That\u2019s pretty cool. Not a lot of people get to do that and I don\u2019t take that for granted. I work hard because of that, because I go, \u201cThis is not a given.\u201d<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>It\u2019s not a given.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>The potential and the opportunities. And I\u2019m trying to bring in other friends and other people into my world to say, \u201cPlug into this. Let\u2019s help you figure this out.\u201d I\u2019m 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.\u00a0<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Well, we\u2019ve had an incredible run and this AI fund is \u2014 I don\u2019t 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\u2019re really fortunate and blessed and after 20 years, Ashton and I asked the question of now that we\u2019ve done that and we\u2019ve hit it out of the park, what do we want to do for the next 10 years? What makes us happy? What are we going to get enjoyment out of doing? And so it\u2019s a really strong question and we all gave it some thought. This is a few months ago. We looked at each other\u2019s visions of what he wanted to do that would make him happy and what he wanted to build and what I wanted to do. And then we have a third partner, her name\u2019s Effie and what she wanted to do and it turned out that we had different visions.<\/p>\n<p class=\"wp-block-paragraph\">And when you look at his vision, which he will share at some point, so I\u2019m not going to share any of it, it\u2019s a pretty awesome vision. It\u2019s an incredible vision and the guy is mind blowingly smart and talented and I support that vision for him. It isn\u2019t my vision. And I will support it financially and I will support it with energy. I want him to win and then I have mine, which is the things that we\u2019re talking about today and the things that I want to build. I have a version of the things I want to do that I haven\u2019t shared with everyone in full, but it turned out that we just have, it\u2019s a new chapter. And I\u2019ve had many new chapters my whole life, with the record label first amount of time and then I moved on. I went to music management, I went to crypto and I went to film.<\/p>\n<p class=\"wp-block-paragraph\">I mean, I have so many different chapters in my life that this is a beautiful chapter that we\u2019re in a celebratory mode. So we\u2019re hoping to be on the beach, high-fiving each other at some point on the work that we\u2019ve done and have worked hard to get here and taken a lot of risks and a lot of chances and put in our own money. And so this decision was made out of joy and to support each other\u2019s visions. There are going to be times where we\u2019ll cross over and we\u2019ll work on things together because we do have some crossover of things that are part of things we both like, but he\u2019s very specific on what he wants to do, I\u2019m very specific on I want to do. Effie and I are going to continue on with Sound and what we\u2019ve built the last 10 years with Sound. So we\u2019ll continue to build that and then we\u2019ve got some surprises of how we want to build that out too. It\u2019s all really good. It\u2019s all very supportive and it\u2019s just another chapter.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss:<\/strong> Cool. Guy, this has been a wide-ranging conversation. What a life. What a journey and it\u2019s not over. Obviously, you\u2019ve got lots of battery left for what\u2019s ahead. Thank you for the time.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Thank you.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>Thanks for inviting me here.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>My first podcast.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>I know. I know. Mine too.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Your first podcast with me, yes.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Tim Ferriss: <\/strong>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\u2019t include you. Thank you, Jack Kornfield. And as always, thanks for tuning in. Thanks, Guy.<\/p>\n<p class=\"wp-block-paragraph\"><strong>Guy Oseary: <\/strong>Thank you.<\/p>\n<hr class=\"wp-block-separator has-alpha-channel-opacity\"\/>\n<h3 id=\"guy-oseary-legal-conditions\" class=\"wp-block-heading\">DUE TO SOME HEADACHES IN THE PAST, PLEASE NOTE LEGAL CONDITIONS:<\/h3>\n<p class=\"wp-block-paragraph\"><em>Tim Ferriss owns the copyright in and to all content in and transcripts of The Tim Ferriss Show podcast, with all rights reserved, as well as his right of publicity.<\/em><\/p>\n<p class=\"wp-block-paragraph\"><em>WHAT YOU\u2019RE WELCOME TO DO:<\/em>\u00a0<em>You are welcome to share the below transcript (up to 500 words but not more) in media articles (e.g.,\u00a0<\/em>The New York Times<em>,\u00a0<\/em>LA Times<em>,\u00a0<\/em>The Guardian<em>), on your personal website, in a non-commercial article or blog post (e.g., Medium), and\/or on a personal social media account for non-commercial purposes, provided that you include attribution to \u201cThe Tim Ferriss Show\u201d and link back to the tim.blog\/podcast URL. For the sake of clarity, media outlets with advertising models are permitted to use excerpts from the transcript per the above.<\/em><\/p>\n<p class=\"wp-block-paragraph\"><em>WHAT IS NOT ALLOWED:<\/em>\u00a0<em>No one is authorized to copy any portion of the podcast content or use Tim Ferriss\u2019 name, image or likeness for any commercial purpose or use, including without limitation inclusion in any books, e-books, book summaries or synopses, or on a commercial website or social media site (e.g., Facebook, Twitter, Instagram, etc.) that offers or promotes your or another\u2019s products or services. For the sake of clarity, media outlets are permitted to use photos of Tim Ferriss from\u00a0<\/em><a href=\"https:\/\/tim.blog\/media\/\" target=\"_blank\" rel=\"noreferrer noopener\"><em>the media room on tim.blog<\/em><\/a><em>\u00a0or (obviously) license photos of Tim Ferriss from Getty Images, etc.<\/em><\/p>\n<\/div>\n<p><script async defer src=\"https:\/\/platform.instagram.com\/en_US\/embeds.js\"><\/script><br \/>\n<br \/><a href=\"https:\/\/hop.clickbank.net\/?affiliate=infohatch&amp;vendor=J1R2C\"><img loading=\"lazy\" decoding=\"async\" class=\"size-full wp-image-10614 aligncenter\" src=\"http:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px.png\" alt=\"Profit Gen\" width=\"400\" height=\"217\" srcset=\"https:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px.png 400w, https:\/\/parmaks.com\/Resources\/wp-content\/uploads\/2025\/05\/profit-gen400px-300x163.png 300w\" sizes=\"auto, (max-width: 400px) 100vw, 400px\" \/><\/a><br \/><\/p>\n","protected":false},"excerpt":{"rendered":"<p>Please enjoy this transcript of my interview with Guy Oseary (@guyoseary). Guy has managed some of the biggest names in music, including Madonna, the Red [&hellip;]<\/p>\n","protected":false},"author":1,"featured_media":13324,"comment_status":"","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[13],"tags":[],"class_list":["post-13335","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-growth"],"_links":{"self":[{"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/posts\/13335","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/comments?post=13335"}],"version-history":[{"count":0,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/posts\/13335\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/media\/13324"}],"wp:attachment":[{"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/media?parent=13335"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/categories?post=13335"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/parmaks.com\/Resources\/wp-json\/wp\/v2\/tags?post=13335"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}