#89: From Startup to Grown-Up: Kevin Evers, author of There’s Nothing Like This: The Strategic Genius of Taylor Swift — unpacking Taylor Swift’s rise to the top; when to take big risks; and how to build a rabid fan base

Paul Graham, the founder of Y Combinator, he has talked about the mistakes that startup founders make, especially tech startup founders. And one of the top 10 things that he says that they do is they're obsessed about their product as you should be. But they're not as obsessed about their fans or their users, right?

Yeah, the customers.

And Taylor has always understood she's in a culture market. She has understood, or at least her actions have shown that she understands that superstars aren't self made, they're created by their fans. And she is so incredibly fan obsessed. It reminds me of a quote, quote from Jeff Bezos where he says our customers are delightfully dissatisfied. They may tell us that they love our product, they may tell us that they love everything that we do, but deep down, customers always want more and it's our job to delight them. And that fits Taylor to a T. Everything that she does is about setting high expectations and then exceeding those high expectations for their fans.

Welcome back. This is from Startup to Grown up. My name is Alyssa Cohn and today we have a special guest. We're talking all about Taylor Swift. No, I'm not talking to Taylor Swift, but I'm interviewing Kevin Evers who just wrote a great new book called There's Nothing like the Strategic Genius of Taylor Swift. Nobody can deny that Taylor Swift is an incredible entrepreneur as well as musician. Her most recent tour, the Eras Tour, became the first tour to gross over $2 billion in ticket sales, surpassing all previous records. Her music accounts for about 2% of the entire music business in the United States. How did she go from being a 13 year old girl who wanted to write country music to the global cultural phenomenon she is now? By using a lot of principles that successful startups do. Kevin and I had such a fun conversation talking about all this and we covered the importance of having a solid vision that can withstand a lot of naysayers, the need to go into an untapped market, and the ability to make bold decisions and pivot when necessary. We also talked about her instinct to build an intimate relationship with her fans. And that's one of the foundations of her ability to be so successful for 20 years. Years. We also covered a few of her very famous fights and controversies and how she used them to get even more famous and powerful. This is a super fun discussion which you'll love and you're going to love it if you're a startup founder or a leader and even if you don't really follow Taylor Swift. I didn't. Although I may start now. Let me know what you think. And please enjoy my great conversation with Kevin Evers, author of There's Nothing like the Strategic Genius of Taylor Swift. Kevin, welcome to the show. I'm so excited to have you today. And I just want to say that it is just such an unusual topic that we're talking about today because you're a senior editor at Harvard Business Review, and you've written now this book called There's Nothing like this right here, everybody. There's Nothing like this. The Strategic Genius of Taylor Swift. And I think I first want to understand, like, how did this idea come to you that you wanted to talk about? You know, sort of Taylor Swift and the insights around maybe entrepreneurship and leadership, management.

The sheer volume of. And the sheer. I mean, she is so popular right now, right? The eric car Gross. $2 billion. Over $2 billion. That's almost twice as much as the second place concert series, which was Coldplay's Music of the Spears. And in 2024 alone, Taylor represented close to 2% of the total music market. That's staggering. Staggering numbers. And she's been doing this for two decades.

Right.

So I didn't approach this book any differently than I would if I was writing a book about Steve Jobs or Jeff Bezos. She's a great songwriter, exceptional songwriter, and that's contributed mightily to her success. But you don't get to her position in the music industry without having great entrepreneurial instincts. So that's really what I wanted to explore. How is it that she's been able to do this?

Yes. And I must say, and I told you, this is before we started recording. I'm just like, not really a Taylor Swift fan. I don't really know her music. So when I first heard about your book, I thought, yeah, that totally makes sense. But also, it's not really, like, for me. And then I read your book and I'm like, I love your book. Cause there's so much, so much crossover so to entrepreneurship and leadership and management. And I guess I'd like to start by asking you, like, what was the. You talk a lot about her early vision. You know, she was sort of, I think, 13 years old, and she had this real strong sense of the. Of an internal compass immediately. What. Why was that important? What would you say that was like? And why was that important?

This is the thing that surprised me the most because I did not know much about Taylor's early career. When Taylor was breaking out, I was in grad school for film. I was annoying my classmates with my hot takes about Antonioni Film. So I was not. Not listening to country music at the time. But Taylor had such a clear vision for what she wanted to do. And as you mentioned, very early on, she was 13 or 14 years old. She wanted to write her own music. She wanted to write those songs for an audience of her peers, which was Teen Girls. And she wanted to put out an album as soon as possible. Now, the consensus in country music at the time was she had three checks against her, and she persisted. She had a very clear vision. She thought that her peers would really listen to songs that she wrote. They would listen to songs that were written from a teenage perspective about teenage problems. And she ended up making some really bold decisions based on that clear vision. She left a development deal at RCA Records. Rca, one of the biggest labels on Nashville's Music Row. And she ended up signing up with an executive named Scott Borchetta, who was at Universal at the time. He wasn't selling record contracts out of his Buick. He was well known in the industry. But he decided to start his own label, his own startup. That startup didn't have funding. It didn't have a headquarters, and it didn't have a name at the time. But Taylor went with him because she knew that he believed in her vision. That's a pretty bold decision to make as of then. I believe she was 15 years old when she finally made that decision.

Right.

And of course, it ended up working to her advantage because Bruschetta had that startup mentality.

Right?

He had that founder's mentality. He had skin in the game and was really willing to push. Cause there's a lot of challenges.

Right.

They had to win over country music radio. And country music radio did not think that that audience existed for teen girls.

Yeah, there's so much there. And I think that deal with RCA was sort of just gonna be like, it's not gonna be advantageous to Taylor. They kind of offered it. I think she thought she'd be, like, one of many and really not be able to express her own artistic vision. And with Scott, you know, who, as you. I think what you're saying is so true. He was building his own startup, but in fact, he hadn't even started a startup. He said, wait six months for me. And she did, because she felt like he really got her. And I think that's fascinating in terms of, like, to your point, the bold decision that anybody would have to make early on, it's almost like, who do you take money from? Like, which. Which investor do you want to take money from? The ones who are going to give you the highest terms or more traditional terms or even the biggest name as compared to people who really get you and your vision.

I think human nature sometimes is to go for the bigger name.

Right.

I mean, filmmakers do this all the time. Do you go at Warner Brothers or do you go at the indie label?

Right, right.

And people who write books think about this too. Do I go at Penguin Random House or maybe I go at Harvard Business Review. And Taylor faced that same decision. And I'm sure she had people around her that were really guiding her and shaping her decisions. But to make that move, I keep trying to put myself in her shoes as a 14 or 15 year old. And to be so confident in that move and so confident in your own vision and then to go with someone whose label, his startup had no funding at the time, that's a pretty crazy story. And if you look at its, their partnership between Bruschetta and Taylor is one of the best partnerships in music business history.

Totally. That's right. Especially because of what they did. So what you said, this is so true. You spin this out in the book that like there was no real room in country music for this young, you know, teen tween, or I should say teenager kind of moving into young adulthood. That just wasn't really a genre in country music. And they kind of. She really had a vision of creating that genre. Like at some point you quote her as saying, I liked country music. So I thought there were people like me who would like country music as well. And so I realized I really kind of relate that to entrepreneurs as well. Which is by definition, entrepreneurs get a ton of criticism, a ton of pushback. That'll never work. Here are the reasons it won't work, because if it would, if it was so obvious, it would already be being done. So she sort of felt this, found this empty space. The Blue Ocean strategy. Talk about why that was so important. And also why do you think that she was able to withstand and the criticism and I guess I would say the pushback about what she was trying to do.

You're right. This is a classic entrepreneurial story. Swift seized an opportunity that other people were ignoring or other people were blind to, that was really critical because the music industry is a very fickle and brutish industry. It was one of the reasons why I was really attracted to writing a book about Taylor Swift because is probably even more brutal than the startup market. It's really hard to break out in country music.

Right.

And there aren't. So there aren't many slots for people on radio or on streaming service. I mean, there's a ton of people who are putting out music, but there aren't many stars. And because Swift seized that opportunity, she was really able to break out. Now, of course, there was big challenges, and they had to work around those challenges, but once they did, they were going after a customer base that the rest of country music wasn't going after. So she was in a category all of her own.

Right. Which is so important. And that's the whole point about Blue Ocean strategy is the idea of, like, finding a place, a category, a market which is untapped, as opposed to, I think, what's like the red strategy, which is like, where there's. There's red. Red everywhere because it's being tapped. And so her figuring out there was a gap, again, super young, and she must have had the courage of her convictions. Talk about how she overcame those obstacles. This is well before sp, Spotify, before streaming was so big, she had to go almost, like I thought, sort of door to door to radio stations. Talk about how she was able to do that.

So her and Scott Bruschetta and the rest of the team at Big Machine, that's what Scott Bruschetta ended up naming his startup. They use a bunch of strategies, and I call them underdog strategies. So they. They needed country music radio. There is no way Taylor Swift would have been successful without country music radio, because country music radio at the time, that's the number one way people discovered new music. And it was the biggest driver of sales of albums and singles.

Right.

So there's no. Like you mentioned, there was no streaming. There was no workaround. They had to go through country music. So one of the things that they did is Taylor had a pretty decent MySpace following at the time. It wasn't huge.

Remember MySpace, everybody? MySpace before Facebook, right? This is.

Yeah, this is very early on in the social media ecosystem.

Right.

Facebook was still only on college campuses. This is how far back we're going.

Yeah.

So a lot of people in country music weren't using MySpace. There were some indie bands, rap artists were using MySpace. It wasn't. It wasn't used in country music. So they had to convince radio programmers that there was an audience.

Right.

So they went to Swift's MySpace following and said, contact your local radio station and say that you want to hear these songs. And that's what her fans did. So they had a workaround there. They're able to convince radio programmers, hey, you're getting a lot of calls. You're getting a lot of emails about this young girl who's singing country songs. Maybe you should pay attention. But the other thing they did is Taylor's a very charming figure and even at 16, she was very charming. She was very articulate. So there's a lot of boots on the ground strategies as well. They put her on a six month radio tour where she went into local radio stations. She was on morning shows where she really hawked her own product and charmed the DJs, and of course expanded her fan base from there too.

Right. And that was definitely an important element. I mean, I think, like, we'll talk about this a little bit more, the idea of going direct, like you said, workaround. But actually it was like it was more of going direct to the fans and having them go to the radio station, which is something she kind of replicates over and over. And I definitely want to talk about that. But like, do you have a perspective on what was inside of her? I assume you didn't talk to Taylor Swift during this process, did you?

Doesn't seem like that. I wish I did. She was very busy. She was trotting around the globe for her ERAS tour. So I did not talk to her directly.

I'm sure you tried though. But you have a lot of, you know, a lot of research and also interviews from around her. But I was wondering if you have a personal perspective on what it was about her that allowed her from an early age and then throughout her career, as we'll see, kind of have that inner compass, that inner North Star that was guiding her.

I wish I knew because I would copy it. It's. I was talking to my editor about this and he compares Taylor Swift to Tom Brady. Like if there's sports fans out there, she just has that killer instinct. She. And there's a quote very early on in the book where she says, anytime someone tells me I can't do something, it just makes me want to do it more. And I do feel like that's part of her makeup. She's very stubborn and she wants to excel. And of course, she was also a very talented songwriter at an early age and I think that helped too. She was very confident in her abilities and again, it comes back to that clear vision. But there is something. You can see this all throughout her career, Right. If someone tells her she can't do something, she just pushes more and more.

Yeah, definitely. And you definitely catalog a lot of that in the book. The idea of that inner vision and that inner core, you know, in the startup World. And I think in all companies, there's like this overused term called authenticity. And, like, it's about being authentic and who you are. But you also have to, you know, be strategic in managing your career, managing your company. Certainly if you are Taylor Swift, going from age 15 to, I don't know what, she's in her 30s or 40s now, you know, and sort of being a star for that long, you have to find ways to manage her career. But I guess I would ask you, how did you sort of see the interplay as you studied her and her career between authenticity, which definitely came out especially, you know, to help her break through, and the sort of more strategic calculation that we see?

Authenticity is. It's such a good word. I know it's a controversial way. It's a buzzword these days. Right. And I have a lot of opinions about authenticity. But Taylor has always known, yes, she has built that brand on authenticity, but at the same time, authenticity can hold you back. It can hold you back from growing. And Herminia Bara, who's written very extensively on authenticity, talks about this too. She calls it the authenticity paradox. So a key moment in Taylor's career, she has moved beyond that authentic image of herself. And one of the biggest moments is when she left country music behind completely and moved over to pop music. Now, this was a big move, and it was risky for her because she was a superstar at this point, and she had cornered two markets, she had cornered country music, and she had cornered the pop music market. But by moving over to pop music, she was leaving country music behind. Now, on paper, that sounds like a pretty bad business decision.

Right.

Why would you completely abandon one market? But she felt that even though it went against this image of her as an authentic country music star, that she had to do it because her music was changing at the time, and she was in her mid-20s, her early to mid-20s. She herself was changing. I think she understood that her product is based on her own personal brand, her own experiences, and her ability to convey and communicate those experiences in intimate and emotional ways for her fans. So she ended up making that big move to pop music.

Right.

And it ended up really working out for her. So even though it, what some people may say, went against that authentic image that she'd made of herself, she ended up growing her fan base. Yeah, right. Because that pop album, which was 1989, was one of the most successful albums of the 2010s.

Yeah. I love how you say this understated way. Well, it seems like it's worked out for her. Yeah, I guess I would say that's probably true. But that crossover is very interesting because again, you point out in the book that like entrepreneurs is a way in which, like, you're a startup and you have this one product and you're doing this thing for your fans and that's very good for your customers and that's working. But there comes a time where you have to decide, is this the right market or do I need to expand my market? If I expand my market, am I los leaving some customers behind? If I have double products or more than one product or even if I, you know, sort of pivot altogether, what's, what's going to happen? So I just think it's just a really important like experience of all startups to recognize that they have to grow as well. And you talked about Armenia, Ibera, and you know, she talks about authenticity, but also she talks about identity. And sometimes our identity can hold us back. And you have to, as an entrepreneur, as a founder, as a leader, certainly as a, as a singer, a songwriter, as a creative person, you have to be able to leave your identity behind and grow, but without kind of damaging what you already have. Is there something else you would want to talk about in terms of how she was able to do that crossover?

Big thing for me is when she made the crossover, she made a big splash for that album, no doubt. But around that time, so many other artists were trying to find new creative ways to release their product. This was the time I'm sure many people remember. U2's album all of a sudden was on Oliver iPhones and her itunes. Jay Z did something similar with Samsung and their app. And then Beyonce surprise dropped one of her albums around this time. But Taylor did something different. She was making this big change. She was making this big transformation. So she leaned back on her communication skills and her ability to build stories around her albums instead of doing a surprise drop or finding some new creative way to release that album to get attention. She hosted a live stream that was simulcast on abc. And she didn't have a co host. She was at the front of the stage on a set, looked like she was on a morning TV show. She was the over caffeinated TV host talking directly to her fans. She announced the album, but she talked about her transformation from a country star to a pop star in very clear and personal terms. She framed this move as about personal growth and about empowerment.

Right.

And her fans loved it. Of course, they're online and they loved it too. And some fans were nervous.

Right.

Because they loved country Taylor and she was moving to pop. But the other thing she did is she really honored her past as well. She didn't just say, hey, here's the change that I'm going to make. She made sure that her fans knew that the old Taylor wasn't dead. She was still around. And instead of presenting herself as this polished pop Persona, she released her new song, which was Shake it off, and she danced along with her fans. And the one thing about Taylor is she's always had this every girl mentality and Persona. Right. She's goofy, she's funny, she's more Lucille Ball than Beyonce. And this is the Persona that she played up during that livestream. Right?

Yeah.

So it made fans more comfortable.

Yeah, that's beautifully said. I love how you really emphasize her storytelling and, you know, sort of the way she was able to kind of make that bridge and really articulate again, direct to fans. And that's something that I also wanted to talk to you about because through the whole of her career, she has focused on engaging with fans. Even being early on MySpace, like there was a story in the book about how one of her, you know, guys at Big Machine was like holding a flashlight to light her up so that people could take selfies with her and she could sign autographs and like hundreds of people came and how, you know, even with these technologies we have now with Instagram, Instagram Live and whatnot, she was able to really talk directly to her fans, talk about the role of that community that she built and why that was so important. And then what you think entrepreneurs can.

Learn from that, it's so huge. Paul Graham, the founder of Y Combinator, he has talked about the mistakes that startup founders make, especially tech startup founders. And one of the top 10 things that he says that they do is they're obsessed about their product, as you should be. But they're not as obsessed about their fans or their users.

Right?

Yeah, the customers.

And that is. Taylor has always understood. She's in a culture market. She has understood, or at least her actions have shown that she understands that superstars aren't self made. They're created by their fans.

Right.

And she is so incredibly fan obsessed. It reminds me of a quote from Jeff Bezos where he says, I'm going to paraphrase, where he said, our customers are delightfully dissatisfied. They may tell us that they love our product, they may tell us that they love everything that we do, but deep down, customers always want more. And it's our job to delight Them. And that fits Taylor to a T. Everything that she does is about setting high expectations and then exceeding those high expectations for their fans. I mean, she has invited fans to her living room. She has bused fans into her home for listening parties. She doesn't do it anymore, but she did it for about three albums. She did this. And think of the Eras tour. She could have played two hours, two and a half hours. She could have played a greatest hit show and her fans would have loved it. They would have walked away joyous. But she didn't. She played three and a half hours. She played a setlist that exceeded 40 songs. And that had to come at a great emotional cost and physical cost to.

Her physical cost, too.

Her crew, her dancers, her band. And I think this is a big reason why she has found so much longevity in this industry is that she knows it's all about the fans and she gives them sometimes things that maybe they don't even deserve. I mean, that's, that's the. She goes above and beyond. If I could say one word to sum it up, it's. Taylor Swift is extremely extra when it comes to her fans.

Extra when it comes to her fans. When you say they. They may not deserve, what do you mean by that?

Well, she just goes so above and beyond.

Right.

It's like, do you really. Like I mentioned, she could have played 30 songs, right. And her fans would have loved it.

Right.

It's. I think as fans, sometimes we take advantage of our artists and we expect too much of our artists, but Taylor gives us more than we deserve. Sometimes.

Yeah. Over delivers. One other thing. And again, I have not been part of this Taylor Swift mystique. So I was sort of trying to go down the rabbit hole before we talked, and I began to understand through your book and then through my own research, like the hidden message. Like, I mean, it's so funny, all the hidden messages. And also, you know, the cataloging of her past relationships and her bad breakups, and I sort of had known about that. But I think part of what she also sort of over delivers for her fans is the intrigue and excitement of trying to, you know, discern what the messages are and the Easter eggs in the, in the songs that she sings. Is that right?

Oh, yeah.

Oh yeah.

I. Taylor's fan community, I always say it's a combination of what the Beatles did, what the Grateful Dead have done, but also true crime subreddits on Reddit. Like, it's, it's. And it's approaching the latter more and more. The amount of intrigue and speculation that she's able to conjure from her fans is next level. Everything that she does at this point, if she wears something, a necklace like, oh, what does that necklace mean? There's a snake on the necklace. Does that mean this? Does that mean that everything she wears, everything she says on social media becomes a source of speculation for all of her fans? And of course she knows she's doing this. I mean, she's a mastermind at this. She's actually not extremely online anymore. She's not online that much. She not even close to what she was earlier in her career. And she pops up here and there, but every time she does it increases engagement so much on social media.

Right.

And so she's able to, even if she's not putting out new music, that Swifty fandom is. It never sleeps. It's 24 7. And I'd encourage anyone to just go look at some Taylor Swift videos on Instagram or TikTok, and maybe the algorithm will start to do its thing and you'll start to see how that fandom works. It's pretty intense, but it's amazing at.

The same time, at your peril for you to deal with your get. You screwed up your Instagram and TikTok algorithm, so know what you're getting yourself into. But as I personally kind of know, having gone down a little bit myself, I. I just want to point out that once again, what pops up for me is the distinction between authenticity, like, this is really who I am and how I communicate and my vulnerability. And then to your point, the she knows what she's doing, kind of calculated steering of her career by putting out these little, you know, sort of breadcrumbs for fans.

Yep, she does. She does. She definitely does. Both, right? Yeah, you have the intimate, emotional singer songwriter, but then you also have the mastermind strategist behind the scenes that's pulling all the puppet strings for fans and yet really knows how to get her fans fired up and speculating.

Without a doubt, that's probably alchemy. One thing that you talk about in your book that I am always fascinated by and I think is very accurate, is this the concept of the jobs to be done by Clayton Christensen. And so could you just summarize, maybe just briefly, tell everybody what job to be done is and how that fits into your kind of paradigm with Taylor?

It's a pretty simple concept, but of course, not a lot of companies and brands are great at this. So jobs to be done. The theory just says that when we Buy a product. We're not just buying the product. We're hiring that product to do something for us.

Right?

So in terms of our iPhones, right, we're not buying it because it's a phone. We're buying it because maybe it helps us connect with family, et cetera.

Right.

Well, and. But just to jump in on that, we're buying the iPhone to connect with family, but we're also buying the iPhone because we want to be part of the iPhone cult, or we want to be sort of. We wanted to say something about ourselves. There's multiple kind of jobs to be done by the iPhone. But anyway.

For sure.

For sure.

So for Taylor, of course, her fans love her songs, right? But it's something deeper than that, right? It's about the intimacy. It's about the connection. It's about the community that she builds around her songs. And really, her fans have such a close, deep relationship with her that it's more than just sounds that we're listening to through our earbuds. It's learning about Taylor's own experiences, her personal experience, and then relating those experiences back to our own lives.

Right.

And Taylor has such a keen sense of this that she's a. Everything that she does is based around this job to be done, right? It's the experiences she builds around her songs. Her concerts, they're very theatrical. They're very much based on each album, Right. Thematically tied to each album. And then her social media strategy, the same way her songs themselves, I wouldn't call them easter eggs, but one of the. One of the things that really sets Taylor apart as a songwriter is her hyperspecificity, right? And this has increased as her career has gone on. Her songs are very. They're very specific. In many cases, they could only be about her life, Right. She doesn't go broad, she doesn't go general like a lot of pop artists. So, yeah, she creates that intimacy through the ways that she creates those songs, the way that she sings those songs, and then the way that she interacts with people on social media, and then the way that she builds sort of those concerts around her music. So if you look at any decision that she's ever made, and she's made some bad decisions, but mostly she makes good decisions. It's based on that very clear idea of what her fans are hiring her to do.

Totally. And that job to be done. What comes up for me as you talk about that is sort of to be like, if I'm a consumer of her music, I want to feel A certain way. I want to feel close to her, I want to be intimate with her, I want to have a relationship with her for sure. And that's kind of the job to be done. It's not to provide an experience of dance music, for example. I mean, you know, if you think about musicians and their job to be done, it would be different for everybody. But hers is to really create that intimacy. And you talked about your daughter yourself, like listening and watching your daughter experience kind of the spiritual gestalt that is Taylor Swift. And she was quite young, your daughter, when you were talking about this.

She was six years old when I took her to her first ERAs tour show. And yeah, there's a part of it that still remains mysterious to me.

Right.

She had such a profound experience at that concert and she was only six. And there's a part of me, I wanted to get into her brain and realize, like, what really are you feeling? And of course I couldn't. But as an observer, I could just see how joyous she was and it was more than just a fun time at a concert. And I talk about this in the book. That experience was shaped by all of these detailed decisions that Swift had made. Again, the way she sings her songs, the way she packages her albums, the way that she talks on social media where when my daughter went to the show, all those things accumulated and it felt like she had such a close relationship with the person who was popping up from underneath the stage. Yeah, and that's, that's pretty rare. And the fact that a six year old could, could feel that in a deep emotional way was pretty awesome to see.

Yeah. Pretty striking. I'm just curious if you, because most, most startups, maybe all startups, are not Taylor Swift, they're not musicians, they're not trying to the do the job of, you know, inspiring their fans or bringing their fans to a spiritual location or intimacy. So to the extent that like you could think about this, if startups have a lot of jobs to be done, which is probably to, you know, have, make you feel secure, depending on what they do, kind of let you do something that you can't already do. Do you have any advice for startups and for startup founders and how they need to think about this notion of jobs to be done?

When I think of jobs to be done, I think of the emotional lives of customers.

Right.

It's like, what, what is going on inside their head? Like really what is the connect. Why are they really buying your product?

Right.

The closer you can get to that inner life of Your customers, I think the better you'll be at designing the right experiences around those products and also messaging around your products, too. I mean, back to Taylor swift in that 1989 livestream, I mean, that was a reason why she framed this as personal growth and empowerment, because it just went back to her job to be done.

Right.

The job to be done wasn't to come up with some very creative business model or release model to get that album out. It was to communicate that intimacy and that connection with her fans and to really foster that close fan relationship.

Yeah.

So the more you can really understand that, I think, the better. You really need to get into the inner life of your customer, find out what's ticking, what's really driving their purchase decisions, and from there, just make your decisions from that data, which is hard to do. It's extremely hard to do.

Right.

If everyone can do it, then everyone would be Taylor Swift or Nike or another huge brand.

Yeah. Or Coke or Apple or something, for sure. Another thing you talk about, which I certainly did not know about, was also kind of the role of collaborations and how she was very, I guess, specific in who she collaborated with and that the nature of her collaborators changed as she kind of grew musically and grew as a person. Can you talk about that and why that was so important?

Her strategy around collaboration is loyalty with an asterisk. I'll say.

Right.

A lot of pop superstars, they shop for hits, they shop for producers, and Taylor really doesn't do that. I mean, she's really the central creative force in her career, and she has worked with a lot of collaborators, but she tends to work with those collaborators for a long period of time. So the first producer she worked with on her first three albums was a producer named Nathan Chapman. Now, Nathan Chapman had never produced an album before, but Taylor, he produced Taylor's demos, and Taylor liked the sound of her demos. So she insisted that Nathan Chapman produce her albums, and that's what he did. So for her first three albums. So that's why there's a consistency across those first three albums. But Taylor had to grow at a certain point, right? So for her fourth album, she worked with some other producers, but then she went with a producer. She produced three songs with a producer named Max Martin. Now, Max Martin is the most prolific producer and songwriter in music history. He has the most number one hits. I think he's only behind Paul McCartney and John Lennon for the most number one hits. Huge producer. But he produced Britney Spears, he produced NSync, he produced the Backstreet Boys. And of course he's gone on to produce Ariana Grande, the Weeknd, Kelly Clarkson. So uber producer. But this was a big shift for Swift because she had built her Persona around being a DIY songwriter.

Right.

I write my own songs. But now she's going with a guy who is known as an auteur producer.

Right.

He's creating the melodies, he's creating the lyrics, he's doing everything. Essentially. He's a great collaborator. He comes from a Swedish background. They love collaboration in Sweden. Those Swedish producers always work with other producers. But for Taylor, this was a big, big move, right? And it ended up being the right move because she created some number one hits with Max Martin. But then she worked with max Martin for 1989 and then her following album reputation. So she has a history of doing this. She'll work with a producer for a long period of time. They have a great collaboration. But when she needs a positive shock, when she needs that new collaboration to shake things up, that's what she'll do. So after Max Martin, now she works with. She's worked exclusively with Jack Antonoff and Aaron Desner from the national over her last few albums. So she has an ability where she wants that consistency, she wants that collaboration. But when she really needs to shake things up, she will make that big decision and she will seek out other producers to help give that positive shock.

Yeah, you talked about her first two producers in particular, and they were also in line with other of her career moves. They were kind of big risks because you had this first time producer, never produced anything at first. And then with Max Martin, you know, there was a big risk that she'd sound too poppy and too much like Britney Spears or whatever. And so I think that's another aspect of her, you know, making these choices. And you talked about positive shock. Suspend a little more about why, where positive shock comes from, where that term comes from and why that's so important and why that plays a role in Taylor's career.

Well, collaboration is great. Collaborative partnerships are great until they're not right. Sometimes they grow stale and you need to move on. And so that's what she did with Nathan Chapman. She felt that her music was moving in a more pop direction, so she needed someone to really help her realize that vision. So early on in her career, she loved Nathan Chapman because she loved the sound of her music, but eventually she was moving on from that sound, so that's why she went with Max Martin. And you can see this again too. Around 2020, she released an album called Folklore which was another big sonic pivot for her. And she went with a producer named Aaron Desner. Now he's in the band the National. I don't know if you know the national, but they are indie rock, odd time signatures. It's not quite dad rock, but it's the opposite of what you would think is Taylor Swift music.

Right.

And she was at a point in her career where she was kind of plateaued. So that was also, on paper, seemed like an odd decision. Like, why would you go with an indie rock producer? But of course it ended up working out because, again, it's like, that's the way she loved his music. That's the way her music was evolving. So she sought out that positive shock. So in some ways, she's not very calculated, but I think she just realizes, like, okay, my music is moving in a certain direction. Who can help me realize my vision?

Right. Although. And I agree that part of it is instinct and internal creative drive. But. But I think the calculation back to positive shock is maybe an understanding that, like, I need to do something. You talk in the book about at times to surprise, but you actually say not shock. Like, she was known for sort of surprising, as in surprise and delight, but surprising her audience, but not shocking them. But I think there were times that she then took hard pivots. So I think maybe. And again, it's. This is about, like, entrepreneurship as well, that, you know, you want to be predictable and you want to also grow, and you don't want to be in the habit of doing hard pivots all the time, but then sometimes you need to. But it sounds like that she really took that on herself.

And she tends to make hard pivots sometimes when she. You would think that she wouldn't need to.

Right.

When she made that big transition to pop music, she was the biggest superstar on the planet.

Right.

She could have kept baking country music and pop music at the same time. She could have her cake and eat it, too.

Yeah.

That's why it was risky.

Yeah.

But sometimes that's the best time to take the risk is when you have a lot of leverage, you know? Totally.

Yeah.

And also, only the paranoid survive, as you also point out.

Yes, this is very true.

Success leads to complacency, and therefore you stop growing and changing. And therefore, in the words of Andy. Ah, Andy Grove.

Andy Grove.

Yep.

Yeah. How did I forget his last name? Andy Grove. And as you point out in the book a couple of times, only the paranoids survive. So can you talk about how maybe that played into her Decision making?

No. Every musician has some sort of paranoia, and it's actually rational for musicians. Elvis said at the peak of his fame, he told a journalist, I'm afraid the light's gonna go out as soon as it went on, as quickly as it went on. And Taylor was. She has voiced this many times. She was afraid of the same thing, that her popularity would decrease. And, of course, how couldn't it? You know, it's like she's been a superstar for so long. It's a culture. Market fans are fickle. They move on to other artists. But she's always had a sense that this may not last forever.

Yeah, right.

And I think she's afraid of complacency. She has said another time with her fourth album, when she tried to move a little more toward pop, where she said, I'm just the thing that scares me the most is my song sounding the same. And she's always been able to balance this distinction between. Or she's been able to strike a balance between changing enough so it keeps her fans interested, but not changing so much that they get alienated.

Right.

And of course, she has made big pivots, but she's always made sure that, okay, I'm gonna constantly delight and surprise you, but I'm not gonna shock you. And I do think that's where that productive paranoia comes in.

Right.

Or as Jeff Bezos would say, it's always day one. And I feel like that's the mentality that she has. She knows that in order to grow her popularity and to grow as an artist, that she needs to change. She can't stay in the same place for too long.

It's always day one. I love that. So part of also her career trajectory in terms of just the ups and downs of her music experience is also. She had some controversies, a few different controversies. And you talked about also the. Let's see, what did you say? You said the reputation. The reputation reality gap. And so can you talk about a few of those controversies and how they led to crises and what she did to manage the crisis?

So the first one happened. Kanye west pops up all over Swift's career. The first time this was 2019 or no, 2009. Taylor wins video of the Year at the Video Music Awards. And she gets up on stage, and all of a sudden, there's Kanye west on stage with her. It looked like a skit. If you were watching from home, it didn't seem like this was real. Well, Kanye takes her mic and he says, I'm gonna let you finish, but Beyonce had the best video of all time. What Kanye was saying is, you don't belong here. You're not as talented as Beyonce. And he was doing this in front of millions of people.

Right?

And Swift has since said that that was a major, devastating moment for her to be talked down like that in front of so many people. And that caused a social media firestorm, and some people sided with Swift and some people sided with Kanye. But a lot of the conversation was around her talent.

Right?

She's not talented enough. She doesn't have a good enough voice. And she was around 18 at this time. And she. About three months later, she had a bad performance at the Grammys. But no, she won album of the year, most prestigious award at the Grammys. So she wins this great award, but has a bad performance with Stevie Nicks.

Right?

So that only added to the controversy. Does she deserve all this? Why are we giving her so many awards? She can't sing. She has a princess fixation. Her lyrics are tweet. So what does she do after this? She takes some of the criticism and she works on her voice, right? So she improves. But for her third album, she doesn't change that much. She doubles down on what she does best, and that's creating intimate and vulnerable albums around what it's like to be a teenager, in this case, as being a teenager and transitioning into your early 20s.

Right.

So the one hand, she's able to really take criticism, but also fight back and say, hey, like, I'm gonna. You're gonna criticize me? And the other thing she did is she decided to write that album all by herself. She didn't use any co writers.

Right.

And a defiant move against her haters. She's like, hey, if you're gonna question my talent, I'm just gonna do it all myself. And then she used that as part of the promotional campaign. She didn't let fans figure that out by themselves. That was a big part of the promotional campaign.

Right.

I wrote this album all by myself. Take it or leave it. So she has a way of turning those controversies into moments of empowerment for her and her fans.

Right.

I'm sure she wouldn't like to go through those controversies, but the way that she talks about them and the way that she comes out from them, I think her and her fans grow closer.

Yeah. And the same is true. It seems like when, you know, she had the break with Big Machine and then Scooter Braun bought the catalog and Tell us about that and how that turned into a moment of again, for Her. It kind of helped her emerge stronger. And I think. Excuse me. And I think ultimately helped her really take control of her own business in a very fundamental way, for sure.

And it grew her fan base at the same time, too. That should not have worked. Let me just. That strategy should not have worked. Re recording her old music. Her first six albums were sold from Big Machine to Scooter Braun, who was a music manager at the time.

And the issue with Scooter was that he had. He was representing Kanye and that, you know, there was some sort of, like, there was that blood between the two of Taylor.

And for sure there was something personal going on there too. And, you know, Swift knew that her masters would be sold. I just don't think she liked who they were sold to. And of course she had a right to be upset about it. It's her life's work and she felt like she should own her masters. Well, Taylor used her leverage. Her only leverage she had was her fans, really, because contractually she had no right to those old recordings. And when those were sold, she came out and she went direct to Tumblr, direct to her fans. She didn't use the mainstream media. And her response was, let's call it vitriolic, like it was. She. She went after it, right? She did not hold back her emotions and her dissatisfaction and her anger that her former masters, that her master recordings were sold. So what does she do? She decides, you know what? If I can't own these, I'm going to re record all of them and I'm going to release them. And there's a reason why no one else has done this before. Prince has threatened to do it. Back in the 90s he had a famous battle with Warner Brothers, but he never followed through. And the reason why it shouldn't work is think about your favorite albums that you grew up listening to. We have such a close connection to those. When you re record them, you almost miss some of that magic or you think that you would. But since, again, Swift is so good at communicating and she has such a close relationship with those fans that she was able to convince those fans, essentially, this is extremely important to me. This is about me owning my music, so this should be important to you. And she was essentially telling them, don't listen to my old music. Don't listen to it. Listen to the new stuff instead.

Right.

Which are near facsimiles of the old stuff, but they're not quite the same. And her fans have followed suit. Now, those old albums, they're still streamed a lot. But she has still undercut the investment that others made by buying her masters because she has essentially replaced some of those with her older music. And her fans are listening to those new recordings more than the old ones.

Yeah. A remarkable business strategy story and a remarkable testament again, to sort of her real. Her connection with her fans, which she's been investing in since she was 13 years old. That's such a story of like the long game.

Yeah. And it's worked out too, because streaming has changed the way we listen to music in many ways. And artists aren't only in competition with other artists, they're in competition with their older music too, because as streamers, I think it's close to 80% of the music we listen to is older music. It's not. Not. It's not new music that has just come out within the last year or so. But by re releasing that old music, Swift is playing into those. Into that data.

Right.

She is allowing us to relive those old albums.

Right.

She's turned those old albums into new content and she's bringing along new fans at the same time, because fans who, who didn't know much about Taylor Swift or maybe jumped in about halfway through her journey were able to relive those or to listen to those old albums in new ways.

Right?

Yeah, yeah, totally. Yeah. It's really fascinating how it all kind of has played out and plays out. You know, at the end of the book, you have this almost like I sort of thought as a meditation on antifragility and your thoughts about antifragility in light of Taylor Swift, could you talk a little bit about that?

Anti fragility. It's such a great concept. It's one step above resiliency. When we think of resiliency, we think, okay, I withstood the pressure, I withstood the challenges, and I got through it. Antifragility is not only did I get through it, but now I'm stronger as a result.

Right.

And this term was popularized by a thought leader scholar named Nassim Taliban. He's the one who came up with the concept of the Black Swan. And he uses a metaphor of the wind and fire. Now, sometimes wind will extinguish a flame, but other times wind will make a flame grow stronger. So he says, you want to be the flame and wish for the wind.

Right?

You want that wind. If you're the flame, you want that wind to make your flame turn into a radiant inferno, essentially. And this is something that Swift's done her entire career. We talked about some of her controversies. And it seems like every. I always say that Swift's career follows a modified version of Newton's third law, where every positive reaction is met with an equal or greater negative reaction. But she just has a way of moving through these challenges or plateaus in her career and coming out stronger as a result. So I think that's why. That's why I use the term anti fragility.

Right.

Where she's not just withstanding the pressure and the challenges, she is growing her popularity. Even after these controversies, she always comes out stronger than what she was when she began.

Yeah. It's really remarkable. Did it make you think anything yourself, like advice to yourself or advice to others how to become more antifragile?

That's a great question. I wish I knew. I really do. I don't know how she does it. I mean, it's. She's more popular now than she's ever been. Right. She's 20 years in her career. And this is pretty unique, right? Because most artists 20 years into their career, if they're lucky enough to be 20 years into their career, they transition in the legacy acts.

Right?

Yeah, great point.

But she is both a legacy act and a truly relevant modern pop star at the same time as superstar. I don't even think superstar is the right word. I don't really know what to call her. It's not megastar.

It's something else, cultural phenomenon.

Phenomenon. And this is 20 years into her career. I mean, she's been doing this more than twice than the Beatles were a band.

Right.

So this is unprecedented in many ways.

Yeah, Well, I think it's worthy of studying. Is there anything else that really surprised you as you were researching and diving deep into, I'm sure, music and psychology and all these management tactics and, you know, Taylor in particular. What other, if anything, were like the biggest surprises for you?

Her mentality? I think just her to go back to the Tom Brady example, or we could think of any other sports icon. She doesn't seem. If she was a company, she wouldn't be satisfied with 3% growth each year. Let's just say that she is really looking to excel in all aspects of her career. She's a student of songwriting.

Right.

She's always trying to improve her craft, and you can sort of trace that evolution over the last 20 years. But she's also trying to sharpen that business savviness too.

Right.

And she's unrelenting in that. She's never stopped making music.

Right.

She's never taken a Long break and yeah, I think that's the thing that's was most surprising to me is that she's very obsessed with her craft, but equally obsessed with her business savviness.

Yeah. Well, I always ask the same last question, Kevin, and we'll see if it resonates for you. What advice do you have for founders as they embark on their journey to grow into leaders? And I guess I would say through your research, your Taylor Swift ology now experience, what advice do you have for founders as they grow into leaders?

That's a great question. I would say I think it goes back to risk.

Right.

I think sometimes when we're doing really well, we. I don't know if we get complacent, but it's hard to make those big decisions because things are going well. We're afraid of the downside. And if we look at Swift's career, I think she's a case in point that it's really important to take calculated risks, even if you're extremely successful and extremely popular.

I love it. Kevin, what a joy to talk to you. This has been so fun and it's so enlightening and I want to just show everyone the book. There's nothing like this. The strategic genius of Taylor Swift. Everyone should go buy it, whether or not they're a Taylor Swift fan. Thank you so much for talking to me today, Kevin.

Thank you. This was great.

Thank you.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website, alyssacon.