Finding Mastery with Dr. Michael Gervais - The Taylor Swift Playbook — Bold Moves, Loyal Fans, and Lasting Impact | Kevin Evers

Episode Date: May 28, 2025

What if one of the most powerful business minds of our time wasn’t a CEO or a founder—and instead, a singer-songwriter who’s been redefining her brand strategy since age 13?Today, we’...re diving into the business brilliance of Taylor Swift — and to help us do it, I’m joined by Kevin Evers, Senior Editor at Harvard Business Review and author of There's Nothing Like This: The Strategic Genius of Taylor Swift.I got to know Kevin because he was the editor of my most recent book, The First Rule of Mastery. He was fantastic and I fell in love with the way he thought and his deep knowledge and reference points of business. Kevin has spent years studying how great leaders express their ideas, and when he told me he was writing a book about Taylor Swift, I knew we had to have him on to discuss what she’s built. This conversation is not about her songwriting or her latest mega-tour; it’s about how she built a billion-dollar brand using clarity, intense connection, and creative risk-taking. It’s about strategy, reinvention, and staying relentlessly close to what lights you up — even when that comes with severe risk. As you listen, use the conversation as a way to reflect on your own relationship with reinvention. Are you playing it safe when boldness is what’s required? How do you stay connected to the core of who you are – stay connected to your purpose — even when external success might tempt you to stay small?I hope you enjoy this week's awesome conversation with Kevin Evers.__________________Kevin Evers; Instagram https://www.instagram.com/there_is_nothing_like_this/ and Linked In https://www.linkedin.com/in/kevin-evers1/Subscribe to our Youtube Channel for more powerful conversations at the intersection of high performance, leadership, and meaning: https://www.youtube.com/c/FindingMasteryGet exclusive discounts and support our amazing sponsors! Go to: https://findingmastery.com/sponsors/Subscribe to the Finding Mastery newsletter for weekly high performance insights: https://www.findingmastery.com/newsletter Download Dr. Mike's Morning Mindset Routine! https://www.findingmastery.com/morningmindsetFollow us on Instagram, LinkedIn, and X.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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Starting point is 00:00:00 Finding Mastery is brought to you by Remarkable. In a world that's full of distractions, focused thinking is becoming a rare skill and a massive competitive advantage. That's why I've been using the Remarkable Paper Pro, a digital notebook designed to help you think clearly and work deliberately. It's not another device filled with notifications or apps.
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Starting point is 00:00:58 stay present and engaged with my thinking and writing. If you wanna slow down, if you wanna work smarter, I highly encourage you to check them out. Visit remarkable.com to learn more and grab your paper pro today. Taylor Swift is so persistent and she was so headstrong and she ended up breaking into a market
Starting point is 00:01:19 that no one else thought existed. And I don't think we'd be sitting here talking about Taylor Swift today if she hadn't done that. What if one of the most powerful business minds of our time wasn't a CEO or founder, and instead a singer-songwriter who's been redefining her brand strategy since the age of 13? Welcome back, or welcome to the Finding Mastery podcast, where we dive into the minds of the world's greatest thinkers and doers. I am your host, Dr. Michael Gervais, by trade and training, a high-performance psychologist. And today we're diving into the
Starting point is 00:01:49 business brilliance of Taylor Swift and help us do that. I'm joined by Kevin Evers, senior editor at Harvard Business Review and author of There's Nothing Like This, The Strategic Genius of Taylor Swift. Taylor is so successful and she's so popular, yet she makes bold decisions at times when you wouldn't think she would need to make those bold decisions. I got to know Kevin because he was the editor of my most recent book, The First Rule of Mastery. I just fell in love with the way that he thought and I loved his deep knowledge and business reference points. She has never stopped creating. Over 20 years, she's never taken a break.
Starting point is 00:02:27 She's gone through controversies. She's gone through challenges. The industry has shifted around her. Yet she always goes back to her number one priority, and that's making music. This is not about her songwriting or her latest megatour. It's about how she built a billion-dollar brand using clarity, intense connection, and creative risk-taking. She took another big risk when she decided to re-record her older albums. It's a bit of a crazy idea. Re-record your old music and tell your fans,
Starting point is 00:02:53 don't listen to the old stuff, listen to the new stuff. So with that, let's jump right down and have this conversation with you. Congrats on a very successful launch of a book. There's Nothing Like This, the Strategic Genius of Taylor Swift. So let me just start at the top. What made you want to write this book? I mean this title very literally. There's nothing like this. In my mind, Taylor Swift belongs to the pantheon of music legends that include the Beatles, Elvis, Michael Jackson, Madonna. And she is such a great entrepreneur. She's such a great business mind. And I really wanted to dive deep into how she's been able to do this for so long.
Starting point is 00:03:46 Okay, Kevin, as someone who's made business strategy or life work to really understand, I mean, you've read more books as a senior editor at Harvard Business Review than most people would ever begin to read on business, if you will. So what made you turn your attention to Taylor Swift as an example of an incredible business framework? I have to say it didn't take much soul searching. Taylor Swift is operating in an industry that's extremely brutal. We tend to cycle through stars and superstars
Starting point is 00:04:21 as if they're fashion trends. And Taylor's been doing this for 20 years and she's more popular now than she's ever been. Stars and superstars as if they're fashion trends. And Taylor's been doing this for 20 years. And she's more popular now than she's ever been. The Heiress Tour grossed over $2 billion. It's the highest grossing tour of all time. So I wanted to look, I wanted to pull back the curtain. And I wanted to figure out how is it she's been able to do this for so long. And you said in your book, you said, I saw no reason to treat Taylor Swift's success any different than that of any business icon. Jobs, Branson, Bezos, Musk. That was one of your quotes. And so can you crosswalk her success to some of theirs just for a quick frame? right we can look back at the Beatles and the Beatles had huge success but they're operating
Starting point is 00:05:05 in a completely different industry that Taylor Swift has been operating in and the startup market is very brutal too right 90 percent of startups tend to fail and you could say the same for musicians so Taylor has been operating in an industry that's been under constant disruption and change over the last 20 years. It started with Napster, and then it went to iTunes, and now streaming, which has had a profound effect on the industry and how fans interact with artists and how artists try to make it in the industry. And Taylor has been able to navigate all those changes, just as Jeff Bezos and Steve Jobs were able to navigate the changes in their industries as well. Okay, so she's a social force. She's taken some great risk. She has been authentic to what matters most to her. So I want to get into all of that. But maybe let's start at the beginning. Her career is, her trajectory, if you will, is a living masterpiece. So can you walk through her ascendancy? We've all seen it. I think we don't understand the rise, like what's happened behind the scenes. So I was thinking we could start when she was 13,
Starting point is 00:06:19 and you've got some great insights about how she was operating as a young 13-year-old. So are you cool to start there? Yeah, let's do it. This is the thing that surprised me the most when I was writing the book, because I didn't know much about her debut era, her first album. And she was 13, 14 years old. She was trying to break through in country music. And she had a very clear vision for what she wanted to do. She wanted to write her own songs, and she wanted to write those songs for an audience of her peers, and that was teenage girls. But the suits and country music didn't think that market existed, the teenage girl market. But Taylor was so persistent, and she was so headstrong, that she persisted through that criticism, and she ended up breaking into a market that no one else thought existed.
Starting point is 00:07:08 And this is a classic entrepreneurial story. She seized an opportunity that other people were ignoring. And I don't think we'd be sitting here talking about Taylor Swift today if she hadn't done that. Okay. 13, just to, you know, point of reference 13, you're, you barely know how the world's working. Like, you know, you of reference, 13, you barely know how the world's working. Like, you know, you're mostly focused on your immediate social circle, trying to figure out where your home school is or home classroom. You know, it's like they're pretty pedestrian concerns for most 13-year-olds. I really don't understand how a 13 year old can shift an industry. So did you learn about how she set her vision or where that process came from? Something around the breakfast table,
Starting point is 00:07:53 something around the dinner table, maybe. Where did that clarity come from for her to have a vision? Oh, I wish I knew that because I would use it in my own life. Part of it comes from her parents. I'm sure her parents were both business savvy professionals. Her mother worked in marketing and her father worked in financial services. So she had that great background. I think a lot of it, and you can look at her, when you look at her career, she's not this top-down strategic thinker. She's not in boardrooms trying to look at the data and trying to figure things out. She really does seem to have an innate sense of what she should be doing.
Starting point is 00:08:32 And you could see that earlier in her career. I couldn't believe it myself because she's 13, 14. Her first album came out when she was 16 years old. And it didn't seem believable because I remember myself when I was 16 years old and I didn't have such a clear vision for what I wanted to do. But since she did have such a clear vision, she made some bold choices that on paper didn't seem to make sense, but in hindsight were the best decisions she could make. She had a development deal with RCA Records, one of the biggest labels on Nashville's Music Row. And she left that development deal. And she ended up signing with a man named Scott Bruchetta, who was an executive at Universal
Starting point is 00:09:11 Label Group at the time. And he told her, I'm never going to tell you to write someone else's songs. And that's why she went with Scott. But Scott was leaving to form his own label. He didn't have funding. He didn't have a headquarters. And the label didn't even have a name yet. But she still went with Scott. She made that bold decision because he believed in her vision. You wrote early in the book, you wrote, she knew exactly who she was. She knew exactly what she wanted to say. She knew exactly where she was going. That clarity is a powerhouse that I've seen for world's best across multiple disciplines, but not at 13. That's something different. And maybe as a 13-year-old, you're like, one day I want to be an astronaut. One day I want to be a professional, whatever.
Starting point is 00:09:59 But this was just a little bit different because writing is so intimate and it's so intellectual and emotional. There's an honesty in the two of them that is usually not available to 13-year-olds. So let's take one more turn of the screw and try to understand how did she know exactly who she was, what she wanted to say, and where she was going. There's a few things. The first thing is she was receiving audience feedback. So she was writing for her peers, all her friends were reacting to her music. She was also listening to country radio at the time. She said, I love country music, but I don't really relate to these songs. And so the fact that her friends were reacting so strongly to her music, I think was a big driver of her vision.
Starting point is 00:10:46 Okay. So wait, she was getting feedback. So she had an idea of something. Maybe it's as simple as she liked how it felt to write, to stretch her ideas, to share ideas. And then she, I didn't know this. So she got, she had a feedback loop with her peers and she probably had a feedback loop with some other really good writers. She was writing with adults, right? And they were probably nodding their head like, yeah, you're good at this kid. Finding Mastery is brought to you by LinkedIn Sales Solutions. In any high-performing environment that I've been part of, from elite teams to executive boardrooms, one thing holds true.
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Starting point is 00:13:41 conveniently into a performance-based lifestyle and actually tastes good. Dr. Peter Attia, someone who's been on the show, it's a great episode by the way, is also their chief science officer. So I know they've done their due diligence in that category. My favorite flavor right now is the chocolate chip cookie dough. And a few of our teammates here at Finding Mastery have been loving the fudge brownie and peanut butter. I know, Stuart, you're still listening here. So getting enough protein matters. And that can't be understated, not just for strength, but for energy and focus, recovery, for longevity. And I love that David is making that easier. So if you're trying to hit your daily protein goals with something seamless,
Starting point is 00:14:20 I'd love for you to go check them out. Get a free variety pack, a $25 value and 10% off for life when you head to davidprotein.com slash finding mastery. That's David, D-A-V-I-D, protein, P-R-O-T-E-I-N.com slash finding mastery. Okay. That would be the makings of a performance-based identity, which obviously you know a lot about in our work together. So did you notice if she fell into any of the trappings of a performance-based identity, which is, I am what I do, and I am what I do relative to other people's successes? Which is a radical fuel, but also a very dangerous proposition, especially for a young person. I think another part of this is she understood her strengths and limitations. She has talked about this many times and she has said, I would not be where I am in my
Starting point is 00:15:19 career if it weren't for my songwriting. I'm not a powerhouse vocalist. I'm not a powerhouse performerist. I'm not a powerhouse performer. It's all about the songs for me. And the fact that she was good at songwriting and she was getting so much feedback, I think really drove her to take the approach that she did. Because she wasn't Britney Spears. She wasn't Adele. She wasn't Beyonce. The only way she could really move forward in her career is by writing her own songs. If we were in a room with Taylor Swift right now and we didn't know each other and we asked
Starting point is 00:15:50 her, who are you? Describe yourself. I'm pretty sure she would say singer-songwriter. That's the first thing that would come out of her mouth. And yes, it's a big part of her identity. Is that order right? Would it be songwriter-singer or is it singer-songwriter? I know the cleverness or the colloquial nature of singer, songwriter, but does she see it in that
Starting point is 00:16:09 magnitude herself? I think songwriter would be first, right? It would be songwriter, singer, for sure, without a doubt. Did she have an early mentor that you can point to that helped cultivate and refine that skill, or was it something else? She was working with a lot of professional songwriters at the time as part of her development deal. One of those, his name is Robert Orrell. He released his own music in Nashville, but this is a common story in Nashville. He released a few albums. They do okay. And then you move into the songwriting realm. You start to write songs for other people. And she wrote a lot of early songs with Robert and he mentored her. And this is actually how the book begins. She's in a songwriting room with Robert and another songwriter. They're three to four times her age. They're trying to push her in certain directions and she's not having any of it
Starting point is 00:17:02 because she says, my audience, teen girls, would not respond to those types of lyrics, so we should be pushing this in a different direction. How did she learn to speak truth to power or speak what was on her mind? What did her parents do to support that? Her father seems to be a go-getter. He works in financial services. He works with clients. There's been leaked emails from him that show he's a very strong personality and he tends to get what he wants. And some of she tends to speak her mind. And you could see this as a 13, 14-year-old in these songwriting rooms. And you could see it when she decided to leave that development deal with RCA.
Starting point is 00:17:54 Do you think that we might be over-exaggerating this idea of vision? Would it be something as simple as if we asked her to go back to her 13-year-old self, would she say, I just wanted to write songs. I liked being around music, and I just wanted to do it tomorrow. Or did she have this grand vision? No, I want to create music for the world. I don't think it was a grand vision. But I will say is that in an environment like that, especially when you're a young person, there's so many people who have opinions about what you should be doing. And because she had such a clear vision of what she wanted to do, because she wanted to write her
Starting point is 00:18:30 own songs, and because she wanted to write those songs for an audience of her peers, teenagers, she didn't move in a different direction. There are plenty of people who are telling her that she should move in a different direction. People were telling her, you need to wait until you're 18 to put out an album. You need to perform other people's songs. And she persisted and she was headstrong. And again, I don't think we would be sitting here today talking about Taylor Swift if she hadn't been so headstrong about those two elements of her vision. What was her high school life like? She has talked about how high school was a tough experience for her,
Starting point is 00:19:09 which makes sense. She was a high performer. She was really trying to do things that her other classmates probably never imagined were possible. But she was really, really focused on music from a very early age. Would you call her a risk taker or risk manager?
Starting point is 00:19:25 It depends on what point in her career we're talking about. What I really appreciate about Taylor is she doesn't have one playbook. Every decision that she makes is circumstantial. So very early on in her career, she did make some bold risks. And we talked about a few of them, leaving her development deal, signing with Big Machine Records with Scott Bruchetta, even though that was a new label, a startup label. But for the next one, two, three albums, she was more of a risk manager. She understood that a key to longevity, especially early on in your career, is to build trust with your audience and to be as consistent as possible.
Starting point is 00:20:02 But there's been other points in her career where she's taken huge risks. Like? Her move to pop music in 2014. She was coming off of three straight number one albums. And a big reason why those records were so successful is she had cornered two markets. She had cornered country music and she had cornered pop. And the playbook would say, keep doing the same thing. Have your songs played on country radio and have your songs played on pop radio. But she
Starting point is 00:20:29 decided that she didn't want to do that anymore. She was in her mid-20s at that point. Her musical tastes were changing. And she decided that she didn't want to chase true rabbits anymore. She didn't want to go after the country market anymore. She wanted to go fully into pop. And that's what she did. And that album, 1989, turned out to be one of the most successful pop albums of the 2010s. She expanded her market. She expanded her global appeal. But that would not have been possible if she hadn't taken such a huge risk. The risk you're pointing to is a tactical risk, moving from something to something else when conventional wisdom to say no no stay the course she also has um a high tolerance it seems like to speak the truth about her emotional life you know as people kind of throw around like be careful
Starting point is 00:21:18 if you date you know if you're to date her because your love like it's exposed there in her lyrics. Does that seem like a risk to her? Or is that just the part of the purpose is like, no, I'm going to speak about my truth and my truth is mine uniquely. And if people want to judge it, fine. It's not up to me. Like, can you open up that a little bit? Because so many of us are over-indexed
Starting point is 00:21:44 in worrying about what people think. To put it in business terms, and we can talk about, we can talk about in personal terms too, in business terms, she has such a clear understanding of what her fans need and want from her and great brands are able to do this. Nike does this. Apple does this. I think what fans really want from her are connection, vulnerability, and intimacy. And since Taylor has such a clear idea of this, she infuses this knowledge into everything that she does. And you can hear it in her songs. They're hyper-specific. A lot of them have very clear personal details in them, more so than other country and pop songs.
Starting point is 00:22:31 You can hear it in the way she sings her songs. Her voice is always up close in the mix. You can tell she's singing very close to the microphone. It almost sounds like she's whispering secrets into your ear. But you can also see it in her social media strategies, how she's trying to build connection that way with the hidden clues. It's almost like inside jokes with her audience. And then you can see it how she builds experiences around those songs.
Starting point is 00:22:55 At her concert, even though she's playing in front of 70,000 people, she finds a way to make that very intimate. The visuals don't overwhelm the intimacy. There's always a close-up of her face on those big screens. So everything that she does goes back to connection, vulnerability, and intimacy. How did she know that those are the three? Is there a process that you uncovered for her to know what her community, her audience, her customers, if you're in traditional business, how did she come to find out that that's what they wanted? I think a lot of it's trial and error. She starts to write her songs in the beginning of her career, especially her debut
Starting point is 00:23:38 and her second album. Her lyrics aren't too hyper-specific, but they're getting there. And then she's getting feedback from her audience. She knows what her audience likes. She's always interacting with her fans online. She's talking to them in person. So she's getting that feedback, and then that feeds into what she does next. You describe her as a strategic genius. What does her mastery of strategy look like?
Starting point is 00:24:18 Strategy is such a big word, right? And Taylor received the Innovator of the Year Award from iHeartRadio a few years ago. And she gets up on stage and you could tell she was almost sheepish about it. She's like, Innovator of the Year Award, really guys? And she accepts the award and she gets up on stage and you could tell she was almost sheepish about it she's like innovator of the year award really guys and she accepts the award and she says you know i don't wake up every day saying i'm gonna innovate stuff i do what's best for me given the circumstances and it just so happens that those things that are best for me are things that people haven't done before. And I really believe that's what makes her such a great strategic thinker. She doesn't follow the same playbook. Everything is circumstantial. She made decisions early on in her career that she would never make in the latter parts of her career and vice versa. It really seems to come from her personally, her heart, what she wants to do, and then she builds a strategy around that.
Starting point is 00:25:10 It sounds so simple, but I don't think many of us do that. But I do think that's the essence of great decision making and it's the essence of great strategy. Taylor is so successful and she's so popular, Yet she makes bold decisions at times when you wouldn't think she would need to make those bold decisions. She took another big risk when she decided to re-record her older albums. That's something that no one else has ever done before.
Starting point is 00:25:36 Prince threatened to do it in the 90s. He had a very famous fight with Warner Brothers and he said, I'll re-record my old music, but he never did it because it's a bit of a crazy idea. Rerecord your old music and tell your fans, don't listen to the old stuff. All those songs that you have such a strong connection to, listen to the new stuff because the new stuff is most important to me. And because she has built such great relationships with her fans, that's exactly what happened. So my biggest takeaway from Taylor's career is she does what's best for her and she takes bold chances when
Starting point is 00:26:14 she's at the top. Okay. So the reason that she went and re-recorded her music, if I have it correct, is that she ran into a legal snag where somebody owned all of her masters, all of her original IP, if you will. And she said, huh, well, that's not going to work. This hurts. This sucks. Like, what do I do? Well, I'm going to just go create it all over again. Is that correct? Is that- That is correct, right? Her first six albums were owned by her former label, Big Machine. This is very common in the music industry. The labels tend to own the master recordings, not the artists. So when Scott Brachetta, the head of Big Machine, sold Big Machine to a man named Scooter Braun, he sold Swift's masters along with them. So Taylor didn't make anything out of that sale, and she had no control or
Starting point is 00:27:03 ownership over those masters. If there's a sequence of notes that made my song so, and the lyrics that made my song so, and a company X owns that, if I go do those series of notes again and the same exact lyrics, they're now mine? Yes. If I put it onto a new studio? If you put it onto, that's a legal loophole that she found. Yep. Because the only thing that, the master recordings are essentially the actual recordings of those albums. Right? So Taylor still, she's a songwriter. She still owns the IP to those songs.
Starting point is 00:27:37 So she could re-record those albums and re-release them under the same name, although she called them Taylor's versions. And she now owns, she has full ownership over that music. So what does the record label in that case own? The first record label, what do they own? They still own the original master recordings and those older albums. They still make money from those streams if those albums are licensed or if they go you know if they're played on tiktok or other services they still make money off of those albums but taylor has essentially told her fans don't listen to the old stuff and that's a that's what has happened at the peak of those re-records for every one person who bought one of her older albums, 20 bought one of the Taylor versions. And those albums are streamed, the Taylor versions are streamed at lyrics, and went in the studio and created a net new product,
Starting point is 00:28:48 even though it was derivative of the original IP. Yep. The only difference is it's a more mature, older Taylor singing those older songs. That's really the only difference. That's pretty cool. Now, she also took political risk. Early on, I think it was the first time that Trump was in office. I remember there was this clip or scene somewhere that I saw that she, maybe it was her dad or mom, I can't remember, were like, no, you cannot speak out against this man. You don't understand. It's going to be damaging to your future and da, da, da.
Starting point is 00:29:21 And she was adamant. Like, I hear you and I'm not listening to you. I need to speak what's right for me. And the country was divided and she chose to be public about her position. And I know she was very public about the most recent race that Trump was in. Can you open up that story to help understand how she operates? Taylor, for her entire career, did not speak out politically. And I think a big reason for that is she was the biggest superstar on the planet. Why mess with your audience? I'm sure 50% of her audience is conservative. 50% is likely liberal. So there was a business risk for her speaking out, but she was also older at that time. She's in her late 20s. And from that documentary, it sounds like she felt emboldened to speak out. She thought it was really important that she do so, even though, you know, I'm sure as people told her during that film scene that you talk about, that, hey, this could be problematic for you.
Starting point is 00:30:27 You could lose fans, but also it could put your safety in danger because Taylor's had stalkers as many celebrities do. And her dad was the one off camera that was really concerned about this. But again, she persisted and she did end up speaking out. And then during the last election, she also spoke out as well. Was there fallout for her? I mean, you saw at the Super Bowl, she was booed. It's Philadelphia Eagles fans. They tend to boo anyone. They boo Santa Claus. They probably boo baby Jesus. But there were... Finding Mastery is brought to you by Momentus. When it comes to high performance, whether you're leading a team, raising a family, pushing
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Starting point is 00:32:28 subscription order. Finding Mastery is brought to you by Felix Gray. I spend a lot of time thinking about how we can create the conditions for high performance. How do we protect our ability to focus, to recover, to be present? And one of the biggest challenges we face today is our sheer amount of screen time. It messes with our sleep, our clarity, even our mood. And that's why I've been using Felix Grey glasses. What I appreciate most about Felix Grey is that they're just not another wellness product. They're rooted in real science. Developed alongside leading researchers and ophthalmologists, they've demonstrated these types of glasses boost melatonin, help you fall asleep faster, and hit deeper stages of rest. When I'm on the road and bouncing around between time zones, slipping on my Felix Grey's in the evening, it's a simple way to cue my body just to wind down. And when I'm locked into deep work, they also help me stay focused for
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Starting point is 00:33:56 just as an aside, so I obviously was with the CLC Hawks for nine seasons, went to all the away games, or most of them. And that stadium, that fan base, they love it. But it feels like it's the most draconian kind of like Mad Max-esque, you know, from, I don't know, 2060, you know, the dystopian feel. It's what a wild experience.
Starting point is 00:34:29 But at the same time, throughout her career, I always say that Taylor's career follows a modified version of Newton's third law for every positive reaction, there's an equal or greater negative reaction. We're giving Taylor Swifter flowers these days because of the heiress tour. But you can go back very early on in her career and trace this throughout every era of her career. She has faced major criticism and major controversies. And it does seem like a lot of people have a problem with Taylor Swift. Let me hear some of the criticisms and controversy.
Starting point is 00:34:58 The biggest one, 2009, the MTV VMA Awards. Taylor receives the award for best female video. And then all of a sudden, there's Kanye West on stage, takes her mic and says, I'm gonna let you finish. But Beyonce had the best video of all time. What Kanye was saying, yet was he defending Beyonce? Yes. But essentially what he was saying in front of millions of people is you're not good enough. And Taylor was around 18, 19 at the time. And months later at the Grammy Awards, Taylor wins Album of the Year, which is the most prestigious award in the music industry, but has a pretty bad or so-so performance with Stevie Nicks and was skewered online. And during this time, people criticized her voice they criticized her princess dresses they criticized her lack of feminism everything that she did was criticized in some way but she
Starting point is 00:35:54 always has an ability to turn those controversies into moments of empowerment for her and her fans so she receives all this criticism and what does she do for her third album? She essentially said, well, if you're going to criticize me for my talent, I'm going to write this album all by myself. I'm not going to use any co-writers. And then she smartly used that to promote the album. This wasn't a secret. This is a big part of her promotional campaign that I wrote this album all by myself. And that album turned out to be one of her most vulnerable albums that she's created in her career. So she always has this ability to turn those controversies into moments of strength. So let's go back to her psychology for a minute.
Starting point is 00:36:37 And of course, I know you don't know her psychology, but do you have any tips I had about how she managed that radical public pervasive criticism? And I get what you, I get what you said is like, it went through her Tumblr and that's what I want to ask about her Tumblr. And that comes out the other side as a strategy for, uh, for growth, meaning, okay, you don't like my talent.'m gonna show you or i'm gonna i'm gonna write my own or i'm gonna be vulnerable and try to address that criticism and i just gave three different kind of tumblers if you will how did she do it she did two things the first thing is she actually took the criticism to heart because it was true at the time, her voice wasn't very strong, especially in live settings. And she got vocal lessons.
Starting point is 00:37:29 She improved her voice. And her voice has improved astronomically since that period of time. But she's also said that that moment really devastated her. She hasn't talked too much about it, and she didn't talk too much about it at the time. But if I'm putting myself in her shoes, that had to be really tough. Even though you're receiving all these accolades, you're receiving all these awards, to have millions of people criticize you online, to have Kanye West, who at the time was the biggest innovator in rap, one of the biggest superstars, gets on stage and says you're not good enough. She said that that criticism really
Starting point is 00:38:05 leveled her, right? But again, I'm sure she really struggled. But for me, it's how did she come out of it? And what's most impressive about her, she tends to just double and triple down on what she's really good at. She doesn't change because she's getting criticized. She still sticks to those core values. She still sticks to the intimacy, the connection, the vulnerability, and she never shies away from those things. What does she do exceptionally well for the connection piece? I get that when she is intimate and vulnerable, that there is the aperture opens up for connection,
Starting point is 00:38:46 but is there anything that she explicitly does to be great at connecting with her customers, clients, her, her audience? I call her fan obsessed. Jeff Bezos would call it customer obsessed. And Jeff Bezos has a great quote. one of his shareholder letters. He says, I'm paraphrasing. He says, our customers are delightfully dissatisfied. They may tell us that they love our product, but deep down, customers always want more. It's our job to continually delight them. And that fits Taylor to a T. Everything that she does, she has her fans in mind.
Starting point is 00:39:23 She spends as much time she does obsessing over her craft. And that comes from humility. Because superstars aren't self-made. They're created by the fans. And Taylor really seems to have a deep sense of this. And we saw this with the Heiress tour. She could have played two hours, a greatest hit show. She'd never done something like that before. And I'm certain her fans would have walked away and they would have been joyous. They would have loved it. But instead, she plays three and a half hours. She plays over 40 songs each night. And she's playing three nights in a row in most cities. That had to come at great emotional, physical cost to her. But she did it anyway, because she's always three nights in a row in most cities. That had to come at great emotional and physical cost to her.
Starting point is 00:40:05 But she did it anyway. Because she's always trying to find new ways to delight her fans. And that's a big reason why they stick around for so long. Yeah. When I saw what she was actually doing, I spent my whole career with elite athletes, elite performers. That was exceptional. That is exceptional.
Starting point is 00:40:25 Games are played between around two hours. With elite athletes, elite performers, that was exceptional. That is exceptional. Games are played like between around two hours, 90 minutes to three hours is kind of the upper limits. But there's like in the NFL, there is a full halftime, a full break, and you're not playing every rep. You know, like there's defense will go on, offense will come on. Like, so it's extraordinary what she has done. And I know football is different than singing and, and, but there's a physicality and emotion, emotionality to what she's doing that requires a rich reservoir.
Starting point is 00:40:55 So I do want to get to deliberate practice in a bit, but I want to stay with this connection piece because I'm thinking about like Henry Ford says, you know, if I were to ask people what they wanted, they would ask for, you know, another, a faster horse and buggy. Yeah. Right. Rick Rubin in modern times is, is waving the flag saying, no, you got to go inward and, and you must listen to your art and then bring that forward rather than tune to what you think people want from you, because that's like this siphon, this exhausted siphon of creative energy. So she is not doing what those three titans have suggested as a best practice. She's actually spending more time tuning to what her community wants, her customers want, her audience, and giving them that, but doing it in an honest way to her experience.
Starting point is 00:41:49 Do I have the framing right? I think so, yeah. Paul Graham, who's the co-founder of Y Combinator, he's worked with every unicorn you can think of and has helped scale great startups. And he has talked about one of the biggest mistakes that he sees startup founders make, especially tech co-founders, is they're obsessed about their product,
Starting point is 00:42:12 as they should be, but they're not very obsessed about their users. And in some ways that makes sense because a lot of tech founders are engineers, they're coders, they're not salespeople, they're not worried about their users. But that's what sets Taylor apart, I think, is how obsessed she is with her fans. You can see it in her social media strategies. You can see it in her concert strategies.
Starting point is 00:42:39 And she's done this from the beginning. Her manager at the time, when she was 16 years old, told her, if you want to be a superstar, you need to meet 100,000 people, hundreds of thousands of people. And that's what Taylor did. After all of her shows, she was doing meet and greets. She's doing autograph sessions for hours, right? She's always had this sense that the fans are the ones that made her into a superstar. And everything that she can do to forge those deconnections with her fans, that's really what scales someone's success in the music industry. You can have an extraordinary amount of talent,
Starting point is 00:43:19 but that doesn't mean you're going to be a superstar, right? The only way you can be a superstar is if you have millions upon millions of fans. She's really agile, right? Even when she's being criticized or she is in a tough spot, meaning that her masters are owned and she doesn't like that. There's a psychological agility,
Starting point is 00:43:41 a mental agility about how she navigates her next choices. Do you have any insight on what are the conditions that were true for her environmental conditions and psychological conditions to be more agile? And the reason I'm asking that question is because I think agility is one of the hallmarks for successful companies moving forward, especially in our modern world. So I'm just wondering if you can open up your insights on environmental insights and or psychological for greater agility. I don't know what you'll think about this term, but it's a business term. It's called productive paranoia, and it's been actively researched. And the term
Starting point is 00:44:21 means, and it comes from Andy Grove, who's the founder of Intel, who famously said only the paranoid survive. What productive paranoia means to me is so many of us grow complacent, especially if we're really successful. And Taylor has never grown complacent, at least as far as I can tell. She has always had this paranoia that her popularity may dwindle. And I don't think that's any logical fear. Because you can lose fans as quickly as you gain them. Elvis was worried about this too. He has a famous quote where he says, I'm worried that the light's going to go out just as quickly as it went on. And at multiple points in her career, Taylor has voiced this concern. But she's always turned that paranoia into production. She's always used it to drive her to change. And she tends to do
Starting point is 00:45:16 this at times when you wouldn't think she would need to, right? She's very proactive in her paranoia, so to speak, right? She's at the top of her game. She's coming off of so many number one albums, yet she has this sense that, well, I need to keep moving. I need to keep growing. I need to keep learning. I need to keep surprising my audience because if I don't, well, my songs will sound the same and my audience will get bored.
Starting point is 00:45:42 And in the music industry, if your audience is bored and your songs start to sound the same, you're in trouble. Yeah, I know the phrase. I don't like it. I know that that's why you framed it that way. I understand it. I don't like it because working from a core state of paranoia, let's call it what it is, extreme anxiety, it's not the way of the good life. I understand that frenzied, maniacal, prickly energy that can get us to move into spaces and to take action in an
Starting point is 00:46:15 uncommon way that most people won't do because there's that unsettled nature. I just don't know if it's the requirement. And I'm surprised that you went that direction, that her psychological agility is, there's a parallel to at least really embrace the struggle of my community and I want to be there for them. And maybe as I'm saying it, you would say, yeah, I think that there's probably more of that or no, there's not enough of that. It really is a paranoia. But if you were to juxtapose those two kind of core positions, is it more about the paranoia? Is it more about a love affair with what could be? It's likely a mix of both, but I like where you're going with that because if you're Taylor Swift, and we can go back to the Heiress tour again, I don't think you're playing three and a half hours and going above and beyond for your fans if it's not coming from a
Starting point is 00:47:21 perspective of joy and happiness and delight. I don't see that as driven by some sort of productive paranoia. And she genuinely seems to love to do this stuff. I don't think you can fake this type of fan engagement. She genuinely seems to love her fans. She genuinely seems to love to fans and to she genuinely seems to love to build relationships with them i mean at one point she invited her fans into her home for listening parties that's pretty extreme i'm not famous but i don't even answer the doorbell when it rings i don't think
Starting point is 00:47:59 i'm gonna invite all these people into my home, my fans. But this is what she does. And I do think it's driven from love and delight. Finding Mastery is brought to you by Cozy Earth. Over the years, I've learned that recovery doesn't just happen when we sleep. It starts with how we transition and wind down. And that's why I've built intentional routines into the way that I close my day. And Cozy Earth has become a new part of that. Their bedding, it's incredibly soft, like next level soft.
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Starting point is 00:50:26 off your first order. That's calderalab, C-A-L-D-E-R-L-A-B.com slash finding mastery. You have such a rich understanding of a true business titan. One of her insights that you pulled forward is I want to surround myself with passionate people. And at Finding Mastery, we have this first principle that nobody does it alone. We need each other. Even individual contributors like herself, people, she's, you know, she's the one singing into the microphone, but there's a full team that surrounds her just like a singles in tennis or golf or surfing, you know, there's a full team that surrounds her, just like a singles and tennis or golf or surfing, you know, there's a full team. Did you pull back any insights on how she deliberately shaped her people or her environment,
Starting point is 00:51:14 you know, towards the sustained excellence that she certainly has accomplished? There's not much known about her team. They're very secretive, but she does run her business like a family business. Her parents are both actively involved. Her brother's actively involved. But one thing I did unearth is how she works with her creative collaborators. She's not the type of artist who shops for hits or who shops for producers. She tends to work with the same collaborators for long periods of time. I would say she's loyal with an asterisk. Very early on in her career, she worked with one producer, his name's Nathan Chapman, and he had never produced an album before, but she loved the way
Starting point is 00:51:57 that her demo sounded. So she really pushed for Nathan Chapman. Her record label didn't want her to just go with Nathan Chapman, and they hooked her up with other producers. But then she persisted and said, I don't like the way this is sounding. Again, she's 15, 16 years old. And she went with Nathan Chapman and worked with Nathan for the first three albums into the fourth album of her career. And she does this continually. She picks a collaborator that will really help her shape the sound that she wants and then she sticks with that collaborators over multiple albums and i think this is a big reason why
Starting point is 00:52:31 she's been so consistent over a career so many other artists especially artists who don't write their own songs really need to work with a ton of different collaborators right and if you're not in full control of what you're doing that can can be problematic. It can be hard to remain consistent from album to album to album. But since Swift is so loyal and tends to stick with the same collaborators, that's a big reason for her longevity. For somebody listening right now, for a leader that's listening right now, that is, you know, never going to be a global superstar, but they are leading. They're a founder, they're executive,
Starting point is 00:53:08 they're creative maybe, and they've got a creative team that they're leading. Could be a parent, somebody who's really trying to make a difference. What can we learn from Taylor Swift to be a little bit better at what we're trying to do in our lives? Taylor has been doing this for 20 years. And one of the most astounding thing
Starting point is 00:53:26 about her longevity is she has never stopped creating. She's never stopped making music. Without fail, every two years, there's a new album. Over 20 years, she's never taken a break. She's gone through controversies. She's gone through challenges. The industry has shifted around her. Yet she always goes back to her number one priority and that's making music and she's making more music now than she ever has in the last four years she's released four new studio albums and four new re-recordings right so for her it all goes back to the love of what she's doing. We can call her a great business strategist, which she is, but at her heart, she's a songwriter. And that's what really drives everything that she does. She goes back to her songs again and again, and she never stops.
Starting point is 00:54:20 Two final questions here. One is, she's emotionally honest. Do you have any insights on what her process is to ready herself to speak the truth and or to take the dive down into the darker recesses of herself to understand who she actually is and how she wants to communicate that. A lot of the personal details come out in the music. She's not online revealing much about her personal life. It all goes back to the music. It all gets infused into her art. So when she's being very honest and emotional, it all gets filtered into the songs. And I think that's important. If she was online spilling out all these personal details, I don't think she would have the relationship she does with her fans.
Starting point is 00:55:19 And I don't think she'd be as popular as she is. I think the big reason why she's able to connect with her fans so well, yes, it's their social media strategies, but it all goes back to the music. The way that she's revealing these personal details, but doing it in such an artistic way, is what really is that first point of connection between her and her fans. What is the makeup of her team? I know you said they haven't talked about it much, but is her team, is her intimate team 12 to 20? Is it, does she have a social media team? Does she have a strategist team? Does she
Starting point is 00:55:51 have a music? Like, do you, do you have a sense of how it's constructed or is that really something that is beyond view? A lot of it's beyond view, but as far as I can tell, it's a pretty small team. It's another thing that really shows why she's been able to find so much longevity in the music industry is that she's in full control of what she's doing. She's making most of the decisions. And then, of course, her team are supplementing her decisions and are guiding her in many ways. But make no mistake, Taylor's in charge of most of her career. Yeah. You wrote in the book, like, ownership is power.
Starting point is 00:56:32 So she has taken ownership of her honest approach to sharing what her experience in life is. She's taken ownership, it sounds like, of her intellectual property. She's taken ownership of her relationship with her community. So ownership is power is an interesting frame that I think that she's fully embodied. So thank you for that. Okay, last question. What has been the most important lesson or insight that you've learned and how has the research and the writing of this book changed you? When I set out to write this book, I wanted to unearth a cultural phenomenon. I want to figure
Starting point is 00:57:09 out how is it that Taylor Swift has been able to reach a Beatles-esque level of success and popularity. But as I was writing, I realized that I was writing a book about a high performer. I was writing a book about a human who is trying to navigate a career and challenges. And I was along with her for every step of her ride. And I felt inspired and empowered by that. Right. Because writing a book is, as you know, is really hard. There's plenty of people who have a lot of opinions. Some of those opinions are good.
Starting point is 00:57:49 Some of those opinions are bad. And you have to deal with your own demons to push through and realize your own vision. And that's something that Taylor's done her entire career. And I really, really think that there's a lot we can learn from her. We can all be inspired by her and we can all feel empowered by what she's been able to do over these last 20 years. Kevin Evers, as I mentioned in the intro, it was great to write a book with you. You're a very thoughtful, supportive, challenging editor. And so I'm so happy that you found something that captured your attention, pulled you into
Starting point is 00:58:32 a raptus, as Beethoven described it, to be able to share with the world's best practices and insights of somebody who is a titan in business and in art. So thank you for doing this deep dive and helping us understand how to live our lives just a little bit better as well. So I appreciate you, Kevin. I'm rooting for you and congratulations on a well-written book on a legend. Oh, thanks so much, Mike. This is really fun. I really appreciate it. And where do you want to drive people to? Where would you want us to go to be able to purchase your book now? The book is available wherever books are sold.
Starting point is 00:59:08 You can go to Amazon. You go to your local bookshop. It's always good to shop local. And you can find me on LinkedIn at Kevin Evers and Instagram at there's nothing like this with an underscore between each word. Okay, brother. Appreciate you, Kevin. Thank you so much.
Starting point is 00:59:23 Thank you. There's a lot of takeaways in that conversation. 100% like a gift that keeps on giving. Right. And if I'm not mistaken, we've got another gem in here, which is our friend of the court, Scott Barry Kaufman. Well remembered. Tis indeed. Scott's new book is out. So he stopped by to talk all things empowerment. It's so wonderful to sit down with a friend and a colleague. There's a shorthand there that, I don't know, it just feels electric. I hope that our community will feel that. And, you know, he was wrestling with this central question.
Starting point is 00:59:57 How do we move from helplessness to empowerment? And along the way, not losing the sensitivity required to be great in this community that we're part of. And Scott is a researcher. And so he really rolled up his sleeves and he wrote a book on it. It's his new book. It's called Rise Above. Overcome a victim mindset, empower yourself and realize your full potential. In our conversation, we explored the distinction between being victimized and adopting a victim mindset and why that mindset might be the single biggest barrier to reaching your potential. This one's vulnerable. It's practical.
Starting point is 01:00:32 It's powerful. And I can't wait for you to hear it. All right. Thank you so much for diving into another episode of Finding Mastery with us. Our team loves creating this podcast and sharing these conversations with you. We really appreciate you being part of this community. And if you're enjoying the show, the easiest no-cost way to support is to hit the subscribe or follow button wherever you're listening. Also, if you haven't already, please consider dropping us a review on Apple or Spotify. We are incredibly grateful for the support and
Starting point is 01:01:04 feedback. If you're looking for even more insights, we have a newsletter we send out every Wednesday. Punch over to findingmastery.com slash newsletter to sign up. The show wouldn't be possible without our sponsors and we take our recommendations seriously. And the team is very thoughtful about making sure we love and endorse every product you hear on the show. If you want to check out any of our sponsor offers you heard about in this episode, you can find those deals at findingmastery.com slash sponsors. And remember, no one does it alone. The door here at Finding Mastery is always open to those looking to explore the edges and the reaches of their potential so that they can help others do the same. So join our community, share your favorite episode with a friend,
Starting point is 01:01:48 and let us know how we can continue to show up for you. Lastly, as a quick reminder, information in this podcast and from any material on the Finding Mastery website and social channels is for information purposes only. If you're looking for meaningful support, which we all need, one of the best things you can do is to talk to a licensed professional. So seek assistance from your healthcare providers. Again, a sincere thank you for listening. Until next episode, be well, think well, keep exploring.

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