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Guy Raz
Wondery subscribers can listen to how I built this early and ad free right now. Join Wondery in the Wondery app or on Apple Podcasts. I recently stayed at an incredible Airbnb in Palm Springs and I thought to myself, wow, I could live at this place. Have you ever been enjoying your stay at an Airbnb when you suddenly ask yourself, wait a minute, could I do this too? Find out how much your place is worth@airbnb.com airport host listening on Audible helps your imagination soar. Whether you listen to stories, motivation, expert advice, any genre you love, you can be inspired to imagine new worlds, new possibilities, new ways of thinking. Audible has an incredible selection with over 1 million audiobooks, podcasts, and Audible originals all in one easy app. Find the genres you love and discover new ones. Explore bestsellers and new releases, plus thousands of included audiobooks, podcasts and originals that members can listen to all they want with more added all the time. Enjoy Audible anytime while you're doing other things household chores, exercising while you're on the road, or commuting, you name it. Audible makes it easy to be inspired and entertained as part of your everyday routine without needing to set aside extra time. There's more to imagine when you listen. Sign up for a free 30 day Audible trial and your first audiobook is free. Visit audible.com audiobooks if you've started your own business, you know just how many challenges there are, big and small. I mean, look at how I built this building. This show came with a lot of trials, late nights, very, very early mornings. But even though there were challenges getting started, there is something that makes setting up a new business easier. Getting connected with AT&T business it doesn't matter what your business is dealing with, AT&T business helps to make it much, much easier. And that's the point of a provider in the first place. Making building your dream easier. Wake up to the power of att business@business.att.com that's business.att.com.
Simon Cowell
I always respected tough love. Most of the time people aren't very good. You have to be honest. And what I wasn't going to do was change who I was just because I was on tv. I wasn't going to lie to these people and say, oh, I think you're amazing and everything's going to happen because I knew the reality is hard enough if you can sing. I mean, it's impossible if you can't sing.
Unknown
Welcome to How I Built this, a.
Guy Raz
Show about innovators, entrepreneurs, idealists, and the stories behind the movements they built.
Unknown
I'm Guy Raz.
Guy Raz
And on the show today, how Simon Cowell used sharp business skills and blunt opinions to become one of the best known music moguls in the world. Back in 2010, a 16 year old kid walked onto the stage of the talent TV show X Factor. He was charming, polite and slightly nervous. He told the judges about his part time job at a bakery. And then with no music to back him, he launched into a pretty shaky acapella version of Stevie Wonders. Isn't she Lovely? After he finished, one of the judges paused, looked straight at him and said, with a little vocal coaching, this kid could actually be pretty good. That teenager was Harry Styles. And the judge who saw something special in him was Simon Cowell. Simon Cowell is one of the most recognizable personalities in global entertainment. He's the guy who helped bring us shows like American Idol, the X Factor, America's Got Talent. He's helped launch the careers of artists like Kelly Clarkson, Jennifer Hudson, Carrie Underwood and Adam Lambert, to name just a few. But what's maybe more surprising is that Simon never studied music. He doesn't play an instrument, he can't sing. But what he does have is instinct, a deep understanding of what makes a hit and more importantly, what makes a star. Now, long before Idol or One Direction, Simon was working behind the scenes, scouting talent, cutting compilation records and even licensing music tied to shows like power Rangers and WrestleMania. He was able to recognize the connection between pop culture and pop music. And he built not just a company called Psycho Entertainment, but an entire Persona. The brutally honest judge who says what everyone else seems to be thinking and sometimes what no one wants to hear. And if you think he's being rude, well, take a listen to this interview.
Unknown
To get his perspective on why he.
Guy Raz
Says the things he says. Anyway. As a child, Simon grew up in a well to do family in the London suburb of Elstree, where he was exposed to the film and TV studios that were based there. Simon's dad worked in the real estate business and his mom had once been a ballet dancer.
Simon Cowell
Yeah, she was very glam. If I, yeah, if I had to describe her to anyone, it would be Elizabeth Taylor. The hair, the makeup, the dresses. She would always, I remember this, her telling me this, that she would always kind of get herself, I suppose, dolled up when my dad came back from work and I was like, why? She just said, I just like it, you know. She was kind of like very classic in that way.
Unknown
And was she? I mean, I've seen her described as a quote Unquote socialite, which is a bit of a weird word because it conjures up, you know, images of superficiality and things like that. But was she. I mean, did she entertain at the house? Was she sort of known as somebody who, you know, you always wanted to go to? You know, you always want to go to her parties. Like, oh, yeah, Julie's having a party, let's go to her house.
Simon Cowell
Everyone, yeah, used to entertain there was, you know, if it wasn't our house, it would be the neighbor's house. Pretty much every weekend there would be a large party and obviously in the summer when the weather was good, it would be outdoors. And, you know, I always remember my next door neighbor was a guy called Jerry Blackmapp, and he ran, I think it was MGM Studios in the uk. So we all looked, and he was a little guy, but we all kind of looked up to him as, oh, God, he's the producer. You know, he's the guy. Because when we used to look over into the garden during the parties, all we ever saw were film stars. And I always thought that must be the best job in the world, being him.
Unknown
How were you as a. I mean, from. From everything I've read, including in your biography, you really loved your parents. You had a really good relationship with him, but you were not. I mean, you weren't a good student. For example, you talk about this, right?
Guy Raz
Was there.
Unknown
Did that create conflict at all between you and your parents?
Simon Cowell
Well, you know, I think if I, let's say Eric, my son, had turned out like me, I would go, we have a problem. Because I was. I just rebelled against any form of discipline. I just. I couldn't. I couldn't deal with it. If they said, don't do that, I would always do the opposite. There was, you know, one particular school I went to and the teachers were just brutal. I mean, to the point where, I mean, I went home one one day, like I was beaten up because this teacher whacked me so hard. And eventually, you know, I told my mum and my mum came to the school and had this massive fallout with the headmaster and this awful teacher. So I think that didn't help. I think they knew I was kind of bright but not academic.
Guy Raz
Yeah, I guess you never really finished school. I mean, I think you left or dropped out when you were like 16 or maybe 17.
Simon Cowell
Yeah.
Guy Raz
And then a few years later, you.
Unknown
Got one of your first, I guess, quote unquote, real jobs at EMI Music Publishing.
Guy Raz
It was in the mail room. And from what I read, you Pretty much hated it.
Simon Cowell
Right. I, I didn't actually hate the job. I tell you what I experienced, I kind of was bullied a bit. There were people who were my age, by the way, a little bit older, who would work in say, the copyright department of EMI Music Publishing. You know, they, they were what I would call desk jobs. So they were my age and I'm wandering around with my mail card and they used to be sort of sneering, you know, like, oh, here comes, you know, the male guy, you know, and they were just rude. So I just was frustrated, I suppose. I didn't like them, I didn't actually want their job. I just didn't like being sneered at. Having said that, I actually quite liked the job because I thought, eventually I'm going to get out of there and I'll find a job, you know, because I started to understand what a music publishing company actually does. And actually being in the mail room, I used to see some of the checks that turned up like, my God, these people are making a fortune.
Unknown
Yeah.
Simon Cowell
You know, I used to always go into like the executives rooms when I delivered mail and just say, oh, come on, give me a job working for you. And it didn't happen, unfortunately.
Unknown
And I think you left that mailroom job like after a year or maybe two and went to work briefly at your dad's real estate company. But then he went back to emi, but this time with a better, with like a better job.
Simon Cowell
Right.
Unknown
Like helping to, I guess produce cover songs or something like that.
Simon Cowell
Yeah. So my job was sort of a song plugger, which was any copyrights emi, you know, owned from, say, I don't know, country artists from America. I would listen to thousands of songs, you know, over a period of time and then try and get other people to record them. And a lot of these songs were hits in America, weren't hits in the uk. And I would then try and find a well known artist to cover these songs. So I would meet with A and R guys on a regular basis or try to. Which was honestly really, really difficult to do. And once you were in, you had about 30 seconds and if they didn't like what you were doing, they would basically just throw you out.
Unknown
And so you're doing. And did you, did you, I mean, did you sign successfully sign anybody, like, notable?
Simon Cowell
I think I got a lot of songs recorded, so it was enough for my boss to say, I think Simon, you're going to do well, you know, in music. I've been thinking about leaving emi. Would you consider leaving with Me, and I'd only been in that job for about, I don't know, a year. And I was so young and naive, I didn't really know what I was doing. And I was like, well, okay, but I'm quite happy here. You sure this is the right thing to do? And he said, yeah, I've got some financial backing. Cut a long story short, I said yes. I went with him. And then I realized very quickly we just didn't have the money we would need to be an independent music publishing company.
Unknown
This was Ellis Rich, I think, who was your boss. And he formed a label that I guess really went nowhere.
Simon Cowell
Yeah, well, Ellis did well, to be fair to him. I mean, he became, I think, president of one of the publishing associations or something. So he was very well respected. Just for me at that age, I had very itchy feet and I thought, I don't have the patience to try and build something from scratch. And I also didn't really want to be a music publisher. I wanted to be an A and R guy. I'd made that decision.
Unknown
You wanted to be the guy who was going out there, going to shows, going to clubs, looking for up and coming artists to sign? Basically, yeah.
Simon Cowell
I thought the fun job would be to be the person who signs the artists and makes the records. Basically, just for me, it was more exciting than being a music publisher, which is quite slow. So that's why I decided to do that.
Unknown
Did you naturally feel comfortable, like in this role of going to gigs and just going up to artists and bands that didn't know you and. And just kind of introduce yourself and try to strike up a conversation with them?
Simon Cowell
Well, it's a good question. I don't think anyone even today is really trained to be an A and R person. I don't even know how people today, you know, get that job. Because a lot of the A and R people I knew were genuinely tone deaf. Seriously. So it was all about blagging it. I just thought, you know what, I just want to have hit records. That was it. And this was just at the cusp where there was this kind of crossover period between what was happening in a lot of the gay clubs in the uk. They were kind of ahead of the curve. It was like, you want to know what's going to happen in six months time? You went to this club. The music was fantastic, the energy was incredible. So I would sit in the booth and just watch and listen and think, yeah, if I can get a record as good as one of those with an artist signed to Me, I think this is a good way to start. It just made sense and I was fortunate. One night I was out and I. And I met this girl and she told me that she'd be making some demos and I heard her songs and I thought, actually she can really sing. And I felt with her, Sunita, this girl. Actually, if we could find a record that we could break through those clubs, but is commercial enough to then be a record, that might be a good way of starting.
Unknown
What was your sort of criteria in your mind? I mean, I want to kind of dig, dig into the story of Sunita a bit because this is like 1983 and you. She's a teenage singer, right? And, and were you listening for a sound that you, that you just appealed.
Guy Raz
To you, or were you listening for.
Unknown
Something that you thought would have mass appeal, whether you liked it or not?
Simon Cowell
I, I kind of had a benchmark in terms of what I thought the record should sound like. So we made two records. One was called Cruising and one was called so Macho. And I just thought those two words so macho, it's funny. And I thought the lyric is quirky enough to be a crossover record. And I could break the record probably by taking Sunita to every kind of club I could in the UK, you know, we'd manufacture, I don't know, five, 600 white labels, 12 inch vinyls. And I would take the white labels into the club, go out to the dj. Can you play this record? Yes. And then if they liked it, sometimes they would invite her back to actually perform in the club. So we started to build a kind of an audience for her, really, at a grassroots level.
Unknown
It reminds me of so much of the story Troy Carter told about Lady Gaga, you know, going in vans all up and down California in clubs. It's really amazing how, I mean, that's how you have to do it. So there's a song so macho, and I confess, I have heard it and seen the video.
Simon Cowell
We didn't have a big budget.
Unknown
No, clearly you didn't. But I mean, this was a, this was somebody you had kind of quote unquote discovered and had this song written for her. And I guess you borrowed money to, to put, put the song out, to make this record, to press the records and get some kind of video. But, but I, I'm wondering, like in 1984, 85, how do you, how do you then, you know, when you're just, you, you're a young guy with, you know, how do you get, how do you get that on the radio. How do you get that song to be heard?
Simon Cowell
Well, that was the issue. I met this guy, Ian Burton, who I really liked because he ran a management company and an agency, a traditional kind of agency.
Unknown
Was he older than you?
Simon Cowell
Yeah, he was probably about 10 years older than me. And I said to him one day, I said, look, Ian, I really like you and I think you're doing really smart. Have you ever thought about running a record label? He went, I wouldn't know how to start. And I said, well, I could do that for you. So in other words, if you pay me, it's your company, I just need a salary. He said, well, how much you want? I said, I don't know, 65 pounds a week. And I can't remember the number. We ended up. It wasn't as high as that, but it was round about that figure. So I started very quickly, found Sunita and I persuaded him that to, you know, give me enough money to sign her, make a record, make a video and everything else that goes with it. I did the radio promotion myself. I did the television promotion myself. As you could tell by the video, we didn't have much money. It was.
Unknown
It was somebody in the camcorder.
Simon Cowell
It was classically bad. And I had to release this particular record three times. I tried to get into the top 40 each time, whether it was the clubs or whether it was getting the artists on tv, I would do anything I could to get my record in the chart. Even to the point there was a soap opera which was running for years in the uk. I used to phone the producer of this soap opera because they used to have a cafe and in the cafe they had a radio. And I'd say, could you play my record on the radio on the show next week? And he'd be like, what? I'm like, yeah, I just want people to hear this record. So I. I was just. I was a constant hustler, which meant it started to get some radio plays and some traction and then the record just flies up the charts. So I thought, oh, my God, the world's fantastic. This is incredible. You know, it's my first record. Everyone's doing well. I bought a house, I bought a car.
Unknown
And then this was just to interrupt for a moment. I mean, this was all in the strength of that first single, so macho. So you, as the sort of the person behind this song, you didn't write it, but you produced it. And, I mean, you had made quite a bit of cash off of that, off of that song.
Simon Cowell
Well, I was Making. Yeah, I was making more than £65 a week. And it sold, I can't remember, 800,000. A million copies.
Unknown
And I guess you should mention that there was another hit song that she had called Toy Boy, which is like a proto Spice Girls song. Like. Like, It's. It was 10 years before the Spice Girls, but it had elements of what that would be 10 years later. Yeah, it's sort of. There's like a Spice Girls element of, like, wannabe at the beginning with a group of young women kind of rap singing. And then Sunita kind of takes over the song. And it's called Toy Boy. And I. It's a totally ridiculous song, but it became a huge hit. And I. I mean, this is what I'm curious about, right?
Simon Cowell
Because.
Unknown
Especially because I. You know, in certain kind of parts of our culture, there's a tendency for especially young people to kind of become, like, music snobs. Like, oh, that's not cool. Or, you know, like, at your time, it was like somebody would be listening to the Smiths, not Toy Boy. Right. Like, that kind of person would just have utter contempt for that kind of popular music. And I wonder whether you were. Cause you were onto something. You understood that people were gonna like that song, and it didn't matter what the sort of the Smiths crowd might've thought of it. Right.
Simon Cowell
It's a. You're absolutely spot on. You've hit the nail on the head. This is what I had to deal with. And to your point about, you know, the song itself, I actually thought it's a very commercial song. I could picture in my mind people liking the song. I liked the song. I thought the melody was brilliant. And it just sounded like an obvious hit record. I mean, what I never did, though, I never tried to pretend that I could produce a record or be a musician, because I can't produce records. I can't play instruments. I don't know what note anyone's. Any singing in. Whether it's C, B, D or G, I have no idea. So I only. I base everything I ever do based on do I like it? I never guess. It's like, do I like it? Yes or no.
Guy Raz
All right, so everything's looking good with.
Unknown
These two hit songs you've got with Sunita.
Guy Raz
But then you run into some trouble, right? Because I guess at one point, like, your record label had gotten acquired by a larger company.
Unknown
And then sometime in the late 80s, that company kind of, I guess, went bust.
Simon Cowell
Yeah. So basically, my label was just a tiny part of this much larger company, which I didn't have anything to do with. So when the larger company went broke, we only found out when we turned up for work one day. And, you know, we were told as we tried to get in, the company's bust.
Unknown
So you're broke. You had a mortgage on your house. And what did you do at that point? I mean, did you. I'm assuming that part of you knew that you would be okay because you had already had experience with success or was it a low point? Do you remember feeling like I failed?
Simon Cowell
Well, I was making anything to make money. So there was one sort of craze that happened. They were called megamixes. And what a megamix was is that you would find a session singer and say, I don't know, abba. You do an ABBA megamix. So you would just find singers who sound like ABBA and just record 10 ABBA songs and get a DJ to mix one song into the next into the next, put them on 12 inch and sell them as export records. And we could sell 10,000 at a time if we were lucky, and make a decent profit. So I just jumped on this and I was making tons of these records, and I did make a Wham Megamix. Unfortunately, George Michael didn't like the Wan Megamix. So we were taken to court, and George Michael's lawyer was a guy called Tony Russell. So as we lost this case, I walked up to him And I said, Mr. Russell, you absolutely killed us in there. Would you mind representing me in the future? I just liked him. And so when all this terrible things were happening in my life, the one person I reached out to at that point was this lawyer, Tony Russell. And I said, look, I've got myself into a real mess. I had negative equity on the house. I owed the bank a lot of money. I had nothing, basically. And I said, tony, what do I do? And he said, you're gonna have to find a major label, Simon, now to back you, and that means getting a label deal. I said, what does that mean? He said, well, some of the major labels are offering people like yourself their own label, which you'll own a part of, but they will bankroll everything because without that, there's nowhere else for you to go. Two companies were willing to meet me. One, I was Polydor, which is now part of Universal, and the other company was bmg. And I went in to meet with Polydor. I thought we had a really great meeting. I basically told him, you know, I've had some success. I think there's a massive gap in the market, you know, for pop music. This is what I do best. I had the similar meeting with bmg, which I didn't think went as well. And then two days later I got a phone call from my lawyer and. And he said, they don't want to do it. And I'm like, okay, so where we left, he said, you're left now with bmg. If they say no, you have a big problem. So I had to wait about a week and I'll never forget it, he called me and he went, I've just heard back from bmg. And I went, yeah. He said, they're going to give you one year. And that was probably one of the most exciting phone calls I've ever had in my life.
Unknown
So you become like an independent consultant for. For bmg, like an A and R consultant for a year. You get a year contract. And I'm assuming under the terms of this you had to. You had to sell a minimum number of records for them.
Simon Cowell
Correct is exactly right. That was part of the condition, is that because I didn't have any artists at that point, I had to start really all over again. I had an A and R budget, which wasn't very much, by the way. I was able to hire, I think, an assistant. And I remember we were in their offices the first week in this tiny little office with one telephone, and we just used to stare at it and it never rang. So it's like, okay, fine. I know. I. Well, I did. I didn't have a business plan, nothing. You know, it was literally just sell records. Whatever you can, we can find, just sell records. That's all I kept thinking about.
Unknown
The thing that I'm really interested in is that while you are in that time at bmg, you did something very unusual and risky and kind of crazy, which is you suggested signing like, well, puppets, for example. So I should get some backstory here because I don't think most people will know who Zig and Zag are. Zig and Zag were this. It was this weird TV show, I think it was Irish and weird alien puppets. And they would just sing songs.
Simon Cowell
It'd be the kind of thing today that would just pop up on TikTok or YouTube and be huge. I mean, it was just really funny Irish humor, which kids and adults liked. It was nuts. And I remember there was something about them singing. So, you know, obviously they weren't real puppets. So I found out who the two guys were and I called them and I said, you know, hi, I'm Simon. I work at bmg. Would you ever, you know, consider about putting out a record? Because you are, you know, singing on, on whatever shows they were doing and they went, yeah. And at the same time, the Power Rangers were huge in, in the uk. And was it. No, I can't remember which one came first. Power Rangers or, or the World Wrestlers. But I also, someone told me that the wrestlers had sold out Wembley Stadium, 87,000 seats in two minutes. And I'm like, what? And you know, I'd seen enough of them on TV and saw how much music they used in their shows to go, gosh, they're selling so much merchandise. If I could get the wrestlers on record, this is a no brainer, which I fortunately managed to get them to do. And I did the same thing with the Power Rangers.
Unknown
I mean, so Zig and zag, Power Rangers WrestleMania. So let's, let's kind of take Power Rangers, for example. Like they had music, right? They had their theme song and there was music in the show. So I can imagine how you could take that theme and get some artists together or whoever was making the music for Power Rangers and have them write, you know, eight or 10 songs for a record and put that together and put that out there. WrestleMania that's come. So basically the idea was if I'm, I'm trying to work this out in my head, you thought, okay, let's get these wrestlers, put them in a recording studio and give them, I don't know, things to say or just have them kind of talk or give them some lines to sing and then we'll get professional singers to fill in the gaps and add beats and just make 10 songs. Like what? How did you conceive of what that would be?
Simon Cowell
You know, once I got the deal, I went to see one of the shows and I actually thought the show was brilliant. But I loved more than the wrestling was the entrances because each wrestler had a kind of like a signature theme.
Unknown
Yeah.
Simon Cowell
So I thought actually music's a huge part of what the show is. So, you know, whether you're the undertaker or whether you're the British bulldog or whatever, each person should have a kind of a signature song. You know, by this point I was at bmg. I used to sit in these A and R meetings and it took me back to the times of when I was, you know, delivering the mail. These guys in these A and R meetings used to look at me like I am the lowest form, you know, in the room. They couldn't even make eye contact with me because they were so serious and they were Playing all these cool bands that were trying to sign and not doing great. And I used to, you know, play these crazy songs and they would sometimes just get up and walk out the meeting and tell me to my face what an idiot I was. And I'm like, well, it's the music business. I'm just trying to make money, you know, it doesn't really matter, does it? If someone's enjoying it, let them enjoy it. Who cares?
Unknown
I mean, the thing about any industry, and it's like, whether it's music or, you know, or my world or whatever, I mean, people get horse blinders on, right? And so all of the people around, like all the people who were in that world, had a certain view of what good music was and what it meant to be respected and appreciated and for a good review from a critic. But essentially you. It sounds like you didn't. That wasn't in on your radar screen. Like, you. You're focused on what is going to sell.
Simon Cowell
Yeah. And look, to be fair, when I made the Power Rangers record and the video, I actually loved it. I mean, I got goosebumps when I saw the video. I just thought it was fantastic. I found it really exciting. I knew the music industry would hate it, but I personally liked it.
Unknown
Yeah.
Simon Cowell
It got to a point, however, where it was so miserable. In one part of BMG I was working for, I just had enough one day because I was sitting in this label meeting, they were making the projections for the final quarter of that year, and everyone had played their songs. And this. My boss turned around to me and said, and what have you got, Simon? I said, well, I've got some pretty good news, you know, I've got the Power Rangers and I've got Zig and Zag and she's what? And I went, yeah. And I said, well, can we hear them? I said, yeah. And I put these records on. There was absolute deadly silence in the room. And there was a huge board, which she was writing on. And she just wrote a massive zero on the board after me playing these two songs. And I just said, that's it. So I went up to the big boss and I said, I'm walking out my contract. I just can't deal with this anymore. You know, I'm making you a lot of money. I'm being humiliated. And he said, look, I'll tell you what, I'll move you to another label, you know, within bmg. Call label. The best label to be on was RCA at that point, and they were really doing well. And they moved me over to rca. So with the same deal. And my boss, you know, direct boss, was head of A and R. And he just said, look, I get it, Simon, you know, I understand what you're doing. Don't let anybody make you lose your confidence. You've got a good track record from where you've come. Just make sure your first records are hit here. And that was it.
Guy Raz
When we come back in just a moment, how Simon taps into television yet again to find his next hit, and then winds up on camera himself. Stay with us. I'm Guy Raz, and you're listening to How I Built this. I just got back from a trip to Germany and I stayed at an awesome apartment right in the heart of Munich, right on the Marienplatz. And it was like one of the coolest places I'd ever stayed at where I could cook and enjoy the city and hear it and feel it and just walk right out into the main square. Right there was a beautiful place. And to be honest, I really didn't want to leave. The next time you're away from your own home, consider hosting your space on Airbnb. Hosting on Airbnb provides you with an extra income stream, plus your earnings could even help offset the cost of your next trip. Your home might be worth more than you think. Find out how much@airbnb.com host this episode of How I Built this was brought to you by Square. In Square's new series the Way Up, I sit down with six local businesses. I chart the entrepreneur's journey, the hurdles and the highs, and how Square played a part in helping the business grow. Think about a thriving local business you admire. Maybe it's a great boutique with the softest towels or a local cafe that has the best scones. Many of these businesses trust Square to help manage their operations and grow. For instance, I absolutely love talking to the father daughter duo behind Vala's pumpkin patch. They started with a tiny plot of land growing pumpkins, and now they make pies and ciders and welcome up to 23,000 people in a single day. And that growth, it was made seamless by Square. Hear the journeys of six rising American businesses. Visit square.comgobilt to learn more. That's sqar e.com go bilt. Learn how square can help your business on the way up. As a founder, you're moving fast toward product market, fit your next round or your first big enterprise. But with AI accelerating how quickly startups build and ship, security expectations are higher earlier than ever. Getting security and compliance right can unlock growth or if you wait too long, stall it with deep integrations and automated workflows built for fast moving teams. Vanta gets you audit ready fast and keeps you secure with continuous monitoring as your models, infrastructure and customers evolve. Fast growing startups like LangChain, Writer and Cursor trusted Vanta to build a scalable foundation from the start. I love that over 10,000 companies from startups to huge enterprises, trust Vanta because it makes me trust them. Go to vanta.combilt to save $1,000 today through the Vanta for Startups program and join over 10,000ambitious companies already scaling with Vanta. That's V a n t a dot com bilt to save $1,000 for a limited time. Hey, welcome back to How I Built this.
Unknown
I'm Guy Raz.
Guy Raz
So it's the early 1990s.
Unknown
Simon is working as an A and.
Guy Raz
R consultant for BMG and scouting around for his next hit record.
Simon Cowell
The way the business worked in those days, we were still manufacturing records. So all the independent shops, all the chains, if they wanted to reorder a record, they would phone the teddy sales department. And I used to go in and talk to all the people in there. What's hot at the moment, you know, what's selling. It just gave me a kind of an idea what was going on. And I was very friendly with a lot of them. And just by luck, one morning I walked in and one of the girls who I think ran the operation, she said, simon, we're getting calls all morning for a song by two actors from a TV show. I said, what is it? She goes, unchained Melody. And I said, okay, leave it to me. So anyway, I track it down, which was the night before. On this show is a drama series called Soldier Soldier. These two actors in a kind of a love triangle story, one of them or both of them are singing this.
Unknown
Song in the show.
Simon Cowell
In the show. Not for long. And it's in the end credits.
Unknown
And it was, I mean, obviously a cover of Unchained Melody, which was written, I think in the 50s and then famously sung by the Righteous Brothers.
Simon Cowell
Yes. And because the story was so powerful, the song just resonated immediately. So the following morning, thousands of people literally are walking into record shops saying, is that record available? And so the shops were phoning all the companies saying, wow, do you have the rights to this record? And they went, no. So I'm like, okay, this is a good opportunity. So anyway, got hold of their agents. Hi, I'm Simon Cowell. Blah, blah, blah. Everyone's trying to buy this record. Would your clients be interested? No. What do you mean, no? They're actors. Let me talk to them personally. No. Anyway, I get a hold of them personally eventually. Would you ever consider doing this? Absolutely not. And I said, well, why? And they just said, we're not interested. So I thought, I can't give up on this. I felt I had an understanding of what the audience wanted and that's always what drove me, which I thought if there was a potential demand for something, give them what they want. So I just was relentless.
Unknown
You hounded these guys.
Simon Cowell
I did hound them, if I'm being honest with you. So finally I was able to meet one of them and I said, look, I know that you're taking this really seriously. I think there will still be a demand for this record. If I can get you in a studio quickly, make the song, I'll get it out. You have to do much on top of that. If you go in the studio, I'll give you £100,000 to split between the two of you. And they went, really? And I went, yeah. So I managed actually to get them on a television show to perform the record. It was actually the National Lottery. The lottery show was big in those days. So we did it. And then the following morning is the day of release, and if you get 3, 4000, 5000 repeat orders on the first morning, you're heading to a top 10, you get 10 to 20,000, you're heading to a top five, you get 50,000 plus repeat orders, you're heading to top two, number one. So I really need to know, because we. We basically had to, on sale of return, give the record stores a ton of records we also manufacture. So the risk now is getting higher and higher and higher. So I'm really in a hole here. I was so nervous that morning. What's the repeat order like this morning? And I looked on the screen and I saw this number and I went, no, what is the real repeat order? This morning that number was 930,000. Wow. It goes ballistic, this record. And I mean ballistic. Everyone, not only did they sell out, once people knew the record was available, everyone's trying to buy the this record. We can't make enough records. So I've got every pressing plant across Europe in 24 hours trying to make enough stock to fulfill the demand. And I think that was my real first, kind of like, you know, oh, my God moment. You know, television is such an important, you know, key here. Emotions are such an important key every, you know, together. If you Manage to make all those things work together, you know, this is incredible.
Guy Raz
All right, let's.
Unknown
So you have this. This sort of mega hit, and you're still in this joint venture with BMG and essentially an A and R, but you've got. You've kind of. It's kind of like your own imprint, like in publishing, essentially, sort of a similar analogy. And one of the acts that kind of slipped through your fingers and you've written about this, which was a regret of yours, was the Spice Girls.
Guy Raz
Not.
Unknown
I don't think it was your. I think you wanted to sign them. Yeah, but you couldn't sign them.
Simon Cowell
I think the girls were told that I'd passed on them. That wasn't the story. We used to have to sit in an A and R meeting once a week and a business affairs meeting once a week. It was a very kind of rigid system, you know, every week you would have to tell everyone what you were working on, you know, whether you had a chance of a hit, who you were signing. And then in the business affairs meeting, you would be told whether you're making money or not. So, you know, it was a really good system they'd created, you know, within bmg to kind of teach us to be entrepreneurs as well as music executives. You know, it was really, really smart, actually. So in a. During one meeting, I remember one of the A and R guys saying, I'm hearing a buzz about a band called Spice. So I just. It was in the back of my mind. And then I went to a meeting with my people who used to plug my records, and they had been hired to work on the Spice Girls at an early stage. And as I pulled up, the girls were in a camper van or something and for some reason knew who I was as an A R person and dragged me into their van and played me Wannabe. And this is before mobile phones. I get in my car, floor it, back to my office, call the manager and said, look, I'll literally double whatever deal you've been offered if you haven't already signed. And he said, too late. They signed. And so whether they had or not, I don't know if that was true or not, but that's how I missed out on them.
Unknown
But soon after that, you sign Westlife, which also becomes a huge act. And I know that you've talked about this, when Westlife, when their record hit number one, you also found out that same day that your father had passed.
Simon Cowell
Yeah. And the terrible thing about it was I was kind of at a point where I never actually could believe that my parents would ever pass away. I just loved them so much. I just couldn't ever imagine it. So when I was playing demos and things like this at home, you know, my dad had a really good ear for music, and he would say, I think that's gonna be a hit, Simon. I would go with that record if you're gonna choose between the two. And he was always right. And he'd heard the first Westlife single, and he said, I think that's gonna be a big hit for you. And I'm like, really? He went, yeah, okay, well, I'm gonna give it a shot. I believe in this band. And I was in. I think I was in. I was in America. I was at a conference and I was waiting to get the news about the first morning's repeat orders, which were great. And it was a, wow, this looks like it's going to go to number one. And then my boss walks into my bedroom and goes, I've got some news for you. And I'm like, oh, my God. And it's just hit me like a train, you know, I just wasn't prepared for it. So, you know, I flew home and went to see my mum and I think I had to take at least one or two months off work. I just couldn't go into work. I was so upset.
Unknown
Yeah, I can imagine.
Guy Raz
And I mean, this happens about the.
Unknown
Time where your career takes yet another.
Guy Raz
Major turn, because, I mean, here you.
Unknown
Are, you've got a bunch of successful records now, right? Westlife. And I mean, you could have been like a super producer, like a Clive Davis, right? Like we could have been Talking about now, 20, 25 years later, all these.
Guy Raz
Artists that you signed, and you signed.
Unknown
This band and that band, but that's.
Guy Raz
Not the direction your career went into. Right, so before we get to where it went, did you, let's say, I.
Unknown
Don'T know, 1999, 2000. Could you have anticipated that for the next 25 years of your life you would become a television star? Like, was that even on your radar?
Simon Cowell
Never. No. I got an approach about this show. It was called Pop Stars, and it was about making the. Making a band, basically on tv. And there was going to be auditions, and if I agreed to be the judge, then I would get the group that was created, which I did think, yes, this sounds like a pretty good idea. Reality TV started to take off and I could sort of see this in my head, which is, yeah, I think people find the whole process interesting and it's a great platform for A new artist. So, you know, whoever the group is, they're going to sell a lot of records. So initially I said yes. And then I thought about it and I went, you know what? No, I'm not going to do it. It's just too much out of my. Out of my time. It's not something I'm. I'm even remotely interested in. So I called back the television company and I said, I'm not going to do it. So they. They gave that role to somebody else, another A and R guy. So. However, I'd heard enough about the show that it was niggling me and I went away on holiday and I think I must have seen something, whether it was. I'd seen one of the episodes, a short bit of it, and I thought, oh, God, this is going to be huge. We've got to find a way of coming up with our own version, which is what me and another guy did.
Unknown
This is Simon Fuller, who is the manager of the Spice Girls. And so you kind of got together with him to create your own concept.
Simon Cowell
Yeah, Me and Simon went into two companies, itv, BBC. Both said yes. However, ITV said, you've got to be on the panel. And I just thought, I can't miss out a second time. So I said, yeah, I'll do it for a year. You know, the artists get signed to me, which is all I really cared about, if I'm being honest with you. And then after a year, someone else could do it. That's honestly what I. What I had in the back of my mind. And then when the show aired, it became an instant hit. And then America instantly made an offer to do their version.
Unknown
So Idol becomes a huge success in the uk and Fox, very soon after, wants to make a version, an American version of it, American Idol. And this really is the first time American audiences are introduced to you. And this is 2002, when terrestrial TV was totally different than what it is now. Like, people would sit down and watch en masse. So, yeah, all of a sudden there's this. There's this Brit on American TV next to Paula Abdul and Randy Jackson. Most people knew who Paula Abdul was. A lot of people might know Randy Jackson. They didn't know who you were. So how were you introduced to American audiences? Like, how were. How is your sort of credibility established? How do they do that?
Simon Cowell
I mean, there was none. I mean, first of all, when they made the offer, I said yes. And then about a day later, I called them back and I went, I'm just not interested. It's not gonna happen. And I really had made my mind up. It was absolutely no.
Unknown
Why were you not interested? I mean, this was massive exposure for.
Guy Raz
Your business at the very least.
Simon Cowell
I just didn't love the whole being on TV that much. I mean, I kind of loved the idea of signing the artist. The being on TV just, you know, wasn't really my thing, if I'm being honest with you, Guy, genuinely. And then a friend of mine who I really respected, I spoke to her and said, I'm in a bit of a dilemma at the moment. You know, they want me to do the show in America and I don't know if it's gonna work there or not. And she said, well, look, Simon, knowing you, either way, you're gonna beat yourself up if it is a hit. And you say, no, you're gonna beat yourself up if it isn't a hit. You could say, if I was on the show, maybe I could have made it better. So I'm like, yeah, you're right, you're right. Okay. So I agreed. And by the way, I didn't ask for any money for myself on both the British show and the American show on the first year. I said, I don't want a contract, I don't wanna be paid. If it works, then we're gonna have another conversation. If it works.
Guy Raz
So you were, you were, you.
Unknown
All you got was you could. You were guaranteed to sign the winner, correct?
Simon Cowell
Yeah, that was. Yeah. And that's what I really wanted. And so when I went to America, I remember we did rented a house. And I got to the house and the real estate agent said, I'm not sure about this new show of yours. And I said, why? He says, well, the network have asked for a one month break in the rental agreement. Oh, great. Anyway, we made the auditions. The auditions were just a mess, if I'm being honest with you. There weren't that many good people. And I just thought, this is a disaster, an absolute disaster. To be honest with you, Guy, genuinely. I finished filming, I didn't even know when the show was going to air in America. I actually didn't know. I'd forgotten about it. I was back busy in the UK and then I get this phone call. I could just hear this guy screaming down the phone, you know, the ratings are in. The ratings are in and it's a hit. I'm like, what? American Idol? Everyone's talking about it and they want to meet you. And I'm like, really? And they went, yeah. I'm like, okay.
Unknown
And that dynamic worked. At least from the viewer's perspective. Worked so well with Paul Abdul and Randy Jackson. Like it just the three of you.
Simon Cowell
It was the perfect chemistry. Yeah.
Unknown
But here's the thing, right? And so that first season, kind of legendary. And I know it very well. Cause I've interviewed Kelly Clarkson twice on different shows that I do. And so I've gone deep into that experience for her, like winning that. Right. And Kelly Clarkson becomes Kelly Clarkson. Right? It's first season and now then she becomes a megastar.
Guy Raz
What?
Unknown
I mean, you didn't want to be on tv, right? It sounds like you were just. It wasn't interesting to you. But the thing about being on TV, because I was on TV for two years back as a reporter 20 years ago, it's a completely different beast. Like there's a charisma you have to find. You've got to jump out of the camera. And some people have it and some people really have to work on it and learn it. You don't come across as a two dimensional person in that you come across as somebody very comfortable on tv. But was it uncomfortable for you?
Simon Cowell
No. Because I'd done so many auditions in my life because we were always creating bands and groups, you know, that was all we ever used to do. I mean, I spent most of my year auditioning people. And I knew what auditions were like, you know, they were like, most of the time, people aren't very good. You have to be honest, they're pretty quick. And what I wasn't gonna do was change who I was just because I was on tv. I wasn't gonna lie to these people and say, oh, I think you're amazing and everything's gonna happen. Because I knew the reality, you know, which is, it's hard enough if you can sing. I mean, it's impossible if you can't sing. So I was just frustrated that first year, thinking, I just wanna find a star. And if we don't find a star, I'm gonna look really stupid. So I'm getting increasingly frustrated.
Unknown
You were just doing what you had already been doing at auditions which were not filmed. You would get people together and you would give them feedback. And the feedback was just very blunt. And then you were doing the same thing. It's not like you created a Persona of like this harsh guy. It's you were just doing what you do.
Simon Cowell
I always respected tough love. And I did make that very clear, by the way, when I agreed to do the show in America, I said, look, just so we're clear, I'm not Going to pretend to like people I don't like. I'm just not.
Unknown
Yeah. And I am not judging you. Maybe a little bit. No, I'm not judging, I promise. But I'm curious about how that kind of played out, because I think your feedback today is slightly kinder a little bit. And maybe that's just because we're in a different era, but in the earlier days, and certainly as it went on, you can see people are deeply hurt. And I get it. Sometimes you would have people come on, or often, and they would say, I'm gonna be the next pop star, I'm gonna be the biggest star in the world. And they'd come on and it would be shocking, like they were so horrible. And you would think, are you delusional? And that's what you want us, like, most of us in our minds are like, are you delusional? But most of us wouldn't say that because we're kind of socialized not to say that. We'd say, oh, thanks so much, that was interesting. I think we're gonna pass.
Simon Cowell
Look, I mean, the point is, going back to what I learned, you know, becoming successful in A and R was when you first start out, you have to have a correct steer. Because if I hadn't had that correct, if I'd had somebody lying to me and saying everything which I was doing wrong was right, I never, ever, I promise you, guy would not have been able to have a successful career. If you're entering into the entertainment full stop, you've got to have thick skin because you're going to get so much rejection. I actually think, for me, I would rather someone say to my face, I think your idea stinks. It's absolutely terrible. And this is why it's terrible. And I'd go, well, I'll disagree, rather than, it's wonderful. And then as I leave the room, they go, that's the worst idea I've ever heard in my life. And you know, that does happen. I've heard it happen. And to give you an example, when I talked about setting up that first, very first business, you know, when I got that job at emi and we, you know, it was a tiny little business and we needed backing, you know, by, by getting money from each territory to give us an advance against earnings. That was the business kind of model. So we had to go to America. So I turn up in my very, very early 20s to LA, and I'm like, oh, my God, this is unbelievable. Look at this place. It's everything and more. And, and I go in to meet all these people. And I thought, my God, I've had 10 meetings in a row and everyone's going to back me. Every single person. This is incredible. I never heard a word from any of those people. And I was really pissed off because I thought, wow, every single one of you lied. Just lied. I would rather someone said, simon, the reason why we are not going to back you is your songwriters aren't very good. The songs you played are terrible. You don't have a business model, blah, blah, blah, blah, blah. And we are not going to risk any money about your wild idea. And I would have gone. I respect that.
Guy Raz
When we come back in just a.
Unknown
Moment, Simon talks about his latest project.
Guy Raz
Which he says is one of the hardest things he's ever done. Stay with us.
Unknown
Hey, guys, I'm Guy Raz, and you're.
Guy Raz
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Unknown
And if you see a candidate you're.
Guy Raz
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Unknown
I'm Guy Raz.
Guy Raz
So by the mid 2000s, Simon Cowell has one of the most recognizable names in TV as the force behind American Idol, America's Got Talent, and the X Factor. And one day, while he's judging one of those shows, a kid who works in a bakery named Harry Styles shows up to sing.
Unknown
He's got a lot of charisma. You can See it already as a.
Guy Raz
16 year old kid.
Unknown
I mean, of course you remember that moment because he became Harry Styles.
Guy Raz
Do you feel like when you see.
Unknown
Somebody like that, you are a hundred percent airtight, sure that they, that they will make it?
Simon Cowell
No, no, I think what you're looking for on a first audition is potential. You know, has this person got potential? That's the only thing I think you can say. I mean, some people, you know, have better voices on their first audition, but may not have charisma. Harry had a good voice. He was nowhere near the peak of, you know, what he could do as a vocalist, but, you know, his charm was just, I mean, crazy charm. I mean, he was 16, he wasn't phased by 7,000 people in front of him. And he's talking to me about pies and cakes and stuff like that. I just really liked him. And that was it.
Guy Raz
I think it was that season where.
Unknown
The other singers would be put together as One Direction. Right. Was that same X Factor, I mean, was like my sort of conspiratorial mind is like that was engineered like to find those guys and have them all audition separately and then for them to come together and make this band, One Direction just seems like totally fantastical.
Simon Cowell
Well, it was, it was interesting. None of them really popped, you know, as they did on their first audition. And I remember seeing, you know, the five of those in particular just going, you know, we don't have room for them as individuals, but this would be crazy, crazy to lose them. And then I just turn around, you know, to the other two sitting at the table, and I went, well, why don't we put them in a band? I mean, it was quite obvious that these five just looked amazing and they had great personalities. And I just thought, you know, having put together a lot of bands, you know, in my life before, I thought, okay, well, maybe we just got lucky here. What have we got to lose?
Unknown
Yeah.
Simon Cowell
So I said, look, we're going to give you a lifeline. You got two weeks to work it out and good luck. And that was just. That was it.
Unknown
And this was a band that you would eventually sign to your label, Psycho, which I want to talk to you a little bit about, because I think you really kind of. It really started in 2005 at Psycho Entertainment as sort of a production company. Tell me a little bit about how you operate that business and also.
Guy Raz
Appear.
Unknown
In the shows and prepare for the shows and edit the shows and then run the business. How do you kind of manage your time?
Simon Cowell
I've, you know, we all evolve and we find, you know, how do we work best? And, you know, even something as basic as working out one year. Well, how many meetings do I actually have per year? And the number was frightening because it was over a thousand. You think about that, a thousand meetings per year. And it's very easy, you know, 365 times three is 1,000, you know, and you. You. I don't think you can function well like that. I think, you know, what I've learned now is less is more. Yeah, don't do two things in the same day. You know, whatever it is, if I'm filming, I won't take a call, won't look at an email. I will only concentrate on filming. And then when I'm doing something else, it has to be just that thing for the day. Whereas years ago I would be doing, you know, seven or eight different things in a day, working till seven in the morning, thinking, I'm doing a great job. And I don't think I was. And it sounds crazy, but in between all of this is, how do you make everything good? You know, how do you make each artist sound good? How do you make the show look good? How do you make each week better than last week? I mean, that's really the only thing that's going on in your head is that. Is that no matter how overwhelming this is, the quality's gotta get better.
Unknown
I wonder about just all of that time. I know you've got a child and that, I'm assuming, changed your life. You know, I've got two kids and it does change your life. It changes how you see the world. But before that time, would you have called? I mean, were you. Such a weird question, and I know Brits particularly hate this question, but were you happy?
Simon Cowell
I think.
Unknown
Would you have called yourself a happy person? I mean, you were so successful outwardly, making a lot of money. You were a celebrity traveling all over the place.
Simon Cowell
I don't think so, particularly. No. No, I don't. I did actually remember saying to myself before Eric was born, is this as good as it gets? Because you get very stupidly get caught up in ratings, battle battles, chart positions. You know, I know this is important, but I started to think that was more important than the quality. And I had to do a massive, massive shift. And luckily, when Eric came along and I started to really, I suppose. Well, first of all, I just looked at everything he loved as a kid, and I realized that actually, he still loves the Jungle book. He loves 101 Dalmatians. He loved every movie I've ever loved, nothing had changed. And it, and it kind of reminded me actually when something's good, it's good. And if it can last a generation, isn't that your main kind of aim? Rather than trying to be so radical one week to get the ratings up that it might damage your long term brand or something. Which I think we all were, were guilty of at some point, you know, where now I'm completely the opposite. I'm thinking, you know, if you get to 20 years with a show, how do you get to the next 20 years? And you don't do it through gimmicks or anything else. You do it by. The talent has to get better, the editing's gotta get better, everything has to get better. You know, that's the kind of the drive I still have.
Guy Raz
What, what is, where does the drive come from?
Unknown
Is it you against yourself? Is it you against, I don't know, someone else or an idea of what people had of you?
Guy Raz
Because you're driven by something that keeps you going.
Unknown
Like you could stop working now and I would. Of course that would be interesting because working is interesting. But, but, but you are still. I wonder if you're still chasing something.
Simon Cowell
I'm always chasing something. I'm doing something at the moment where I am really putting myself in the public eye to prove that I can do something I was well known for doing a few years ago, but I haven't done it recently. And I did it to prove a point, I think to myself, that I either can or can't do it.
Unknown
This is your launch to find a new band? A new, A new boy band.
Simon Cowell
Yeah, yeah. And I did it, you know, not with any, you know, buffer in any form whatsoever was this is when we are going to launch it. And this is going to see if, if we get enough people to audition and, and if we don't get enough people, we're going to have to do what I used to do years ago and just promote, promote, promote. And to the point on the first day, genuinely Guy, I had no idea whether there was going to be two people or 400 people waiting for me. I just didn't know. And it was absolutely terrifying. And then when I finished the auditions, because I'd only auditioned them once, I honestly didn't know whether they were any good or not. I just didn't know. And so there were times when I was making this thinking, why have I put myself through this? And I suppose it's because, you know, when I'm sitting on a show and People want my opinion. I don't want them to base that opinion on something I did 10 years ago or 20 years ago, because I'm not really interested in that. I'm only really interested in what I'm.
Unknown
Doing today and tomorrow and to launch this idea of launching a search for a new band. And by the way, I think you.
Guy Raz
Found the band, right?
Unknown
The band's created.
Guy Raz
Is it public yet?
Simon Cowell
No.
Unknown
No. Okay, so when will it be made public?
Simon Cowell
I think round about maybe the end of the year, I'm thinking.
Unknown
Got it.
Guy Raz
Okay.
Unknown
So from everything I read, it was a struggle. It probably is a struggle, right, to find, big time, the right mix of guys, right, who can do this.
Simon Cowell
It's one of the hardest things I've ever done. And with the pressure that this is all being documented and if this goes wrong, this is gonna be really, really embarrassing. But I think, you know, and I was thinking about this before, you know, we' this conversation today, because I was thinking, you know, we're going to touch on this. And I. I do think, as much as I don't like thinking about the past, I do love that hustle I used to have to do on a daily basis because it was that or you don't survive. I mean, you know, I wasn't left any money. I. I didn't really make any money until I was in my 30s. I had to really kind of just hustle everything, and I really loved it. And so when I. I like to sometimes put myself back in that position where the odds are against me and can we make it work without any guarantee? It's kind of this weird thrill I still get. I don't know why, but I do.
Unknown
Simon, when you think about the journey you've taken right, from the. From, you know, dropping out and mailroom, and here you are now, right? Sort of. I mean, certainly one of the most well known, if not the best known kind of music executive in the world, maybe. How much of that do you attribute to how hard you worked and how much do you think had to do with just luck and circumstance?
Simon Cowell
Everything. You have to have luck. I think you have to work hard. I mean, there's no question about that. I mean, you know what I called the hustle? That was the hard work. I mean, you know, when I was promoting that first record, I would be, you know, driving hours to clubs all over the country every single night, you know, just to get my record in front of an audience. It was the only way. So the idea of not doing that meant failure. So I just no one else was going to do it for me because I had no resources. So it was just that it was single swim.
Unknown
Yeah.
Simon Cowell
You know, this whole path I've been on, it's worked because I've also had amazing people working with me. You know, I've just been very, very fortunate. And I do believe I've been a good mentor and many people have been an amazing mentor to me as well. I really believe in that whole mentorship thing, you know, which is, you know, someone comes in without much experience and, you know, you hope that after working with you for, say, 10 years, they're going to go on and do wonderful things on their own. I get a real kick out of that.
Guy Raz
That's music mogul Simon Cowell, by the way. When it comes to musical recommendations, One of Simon's favorite influencers is his own son, who is now 11.
Simon Cowell
I mean, he came to me about three years ago, really excited, came running into my door, bedroom dad, you gotta hear this band. They're really good. And he plays me a One Direction song. I know this band. No, you don't. I said, well, yeah, I do. How do you know them? I said, well, I used to work with them and. No, you didn't. And you must have found out afterwards. He went, seriously, you work with them? Yeah. But it was. I was very flattered because he. The song still sounds good today, you know, and that's what I think we've been talking a lot about today, is that I like to feel that, you know, the things I'm most proud of are the things that have lasted the longest.
Guy Raz
Hey, thanks so much for listening to the show this week. Please make sure to click the Follow button on your podcast app so you never miss a new episode of the show. And please sign up for my newsletter@guyraz.com or on substack. This episode was produced by Josh Lash with music composed by Ramtin Erabloui. It was edited by Neva Grant with research from Iman Ma'. Ani. Our audio engineers were Patrick Murray and Jimmy Keeley. Our production staff also includes Kathryn Cipher, Karla estevez, Casey Herman, J.C. howard, Sam Paulson, Alex Chung, Keri Thompson, Andrea Bruce, and Elaine Coates. I'm Guy Raz and you've been listening to How I Built this. If you like How I Built this, you can listen early and ad free right now by joining Wondery plus in the Wondery app or on Apple Podcasts. Prime members can listen ad free on Amazon Music. Before you go, tell us about yourself by filling out a short survey@wondery.com survey.
Podcast: How I Built This with Guy Raz
Host: Guy Raz
Guest: Simon Cowell
Release Date: August 4, 2025
Episode Duration: Approximately 70 minutes
In this compelling episode of How I Built This, Guy Raz delves into the extraordinary journey of Simon Cowell, one of the most influential figures in the global entertainment industry. From his humble beginnings to becoming a television icon, Cowell shares intimate moments of doubt, failure, and the relentless drive that propelled him to the pinnacle of success.
Simon Cowell's story begins in the London suburb of Elstree, where he was raised in a well-to-do family. His father worked in real estate, and his mother, once a ballet dancer, exuded glamour reminiscent of Elizabeth Taylor. Cowell reminisces about his mother's classic style and the vibrant social life of their household, where weekends were often filled with large outdoor parties attended by film stars and industry producers like Jerry Blackmapp of MGM Studios.
Simon Cowell (05:43): "If I had to describe her to anyone, it would be Elizabeth Taylor. She would always get herself dolled up when my dad came back from work."
Despite a loving upbringing, Cowell struggled academically. He rebelled against discipline, leading to conflicts with teachers and eventual dropout from school around the age of 16 or 17. This rebellious streak set the stage for his unconventional path to success.
Cowell's entry into the music industry began in the mailroom of EMI Music Publishing. Although he faced bullying and disdain from older colleagues, he leveraged this experience to understand the workings of a music publishing company. His relentless ambition led him to seek roles beyond the mailroom, eventually becoming a song plugger—evaluating and promoting songs for potential hits.
Simon Cowell (08:53): "I thought, eventually I'm going to get out of there and I'll find a job."
After a year, Cowell decided to partner with his boss, Ellis Rich, to form an independent music publishing venture. However, lacking sufficient financial backing, the enterprise struggled, leading Cowell to pivot back to his passion for being an A&R (Artists and Repertoire) executive.
Determined to be at the forefront of discovering and promoting new talent, Cowell founded Psycho Entertainment. His first major success came with the promotion of Sunita, a teenage singer whose singles "Cruising" and "So Macho" became substantial hits. Through grassroots promotion—distributing white-label records to clubs and leveraging local media—Cowell showcased his knack for identifying commercially viable music.
Simon Cowell (20:08): "I was making more than £65 a week. And it sold, I can't remember, 800,000. A million copies."
Despite limited resources, Cowell's hands-on approach and unyielding hustle paid off, establishing him as a formidable force in the music industry.
The late 1980s brought significant challenges when Cowell's label became part of a larger company that eventually went bankrupt. Faced with insolvency and personal financial strain, Cowell adapted by capitalizing on emerging trends like megamixes. However, legal issues ensued when his Wham Megamix led to a lawsuit from George Michael's lawyer, Tony Russell.
Refusing to succumb to despair, Cowell sought counsel from Russell, who advised him to secure backing from a major label. This advice led Cowell to secure a one-year contract with BMG, under which he continued to innovate and push boundaries in music promotion.
Simon Cowell (12:56): "I thought the fun job would be to be the person who signs the artists and makes the records."
Cowell's transition into television marked a pivotal shift in his career. Witnessing the success of television-based talent hunts, he co-created his own version, leading to the birth of iconic shows like American Idol, The X Factor, and America's Got Talent. Initially reluctant to embrace the spotlight, Cowell recognized the potential of these platforms to discover and launch new artists.
In the early 2000s, Cowell resisted an American television offer but was eventually persuaded to participate, leading to his breakthrough in the U.S. market. His direct and honest feedback became a hallmark of his on-screen persona, resonating with audiences and cementing his reputation as a tough-love mentor.
Simon Cowell (55:49): "I always respected tough love. I did make that very clear, by the way, when I agreed to do the show in America."
One of Cowell's notable discoveries was Harry Styles during an X Factor audition. Recognizing Harry's potential beyond his initial performance, Cowell's intuitive judgment highlighted his ability to see the charisma and star quality in emerging artists.
Simon Cowell (61:37): "Harry had a good voice. He was nowhere near the peak of what he could do as a vocalist, but his charm was just, I mean, crazy charm."
Additionally, Cowell's role in forming One Direction showcased his strategic vision in creating successful musical groups by identifying complementary personalities and talents.
Despite his professional triumphs, Cowell faced personal challenges, including the loss of his father coinciding with the success of Westlife's debut single. This period of grief led him to reassess his priorities, ultimately shifting his focus towards long-term quality and sustainability over immediate ratings and chart positions.
Simon Cowell (66:16): "I don't think [I was] particularly happy... Eric started to, I suppose, remind me that when something's good, it's good."
The birth of his son, Eric, further influenced Cowell's perspective, instilling a sense of balance between professional ambition and personal fulfillment.
Simon Cowell's journey is a testament to resilience, hard work, and the ability to adapt to changing industries. From a rebellious youth in a loving family to a pioneering music mogul and television star, Cowell's story underscores the importance of mentorship, both as a mentee and a mentor, in achieving sustained success.
In recent endeavors, Cowell continues to seek new opportunities to innovate within the entertainment sphere, exemplifying his enduring passion for discovering and nurturing talent.
Simon Cowell (73:23): "I'm always chasing something. I'm doing something at the moment where I am really putting myself in the public eye to prove that I can do something I was well known for doing a few years ago."
Simon Cowell's narrative, as explored in this episode, offers invaluable insights into the makings of a successful entrepreneur and media personality. His unwavering commitment to quality, paired with a keen sense for market trends and talent, has solidified his standing as a luminary in the entertainment industry. Cowell's story serves as an inspiring blueprint for innovators, creatives, and aspiring business leaders navigating their own paths to success.
Notable Quotes with Timestamps:
Simon Cowell (05:43): "If I had to describe her to anyone, it would be Elizabeth Taylor."
Simon Cowell (08:53): "I thought, eventually I'm going to get out of there and I'll find a job."
Simon Cowell (20:08): "I was making more than £65 a week. And it sold... a million copies."
Simon Cowell (12:56): "I thought the fun job would be to be the person who signs the artists and makes the records."
Simon Cowell (55:49): "I always respected tough love."
Simon Cowell (61:37): "Harry had a good voice... but his charm was just, crazy charm."
Simon Cowell (66:16): "I don't think [I was] particularly happy... Eric started to remind me that when something's good, it's good."
Simon Cowell (73:23): "I'm always chasing something... prove that I can do something I was well known for doing a few years ago."
This summary encapsulates the key moments and insights from Simon Cowell's conversation on How I Built This, providing a comprehensive overview for those who haven't listened to the episode.