I Learned More About Business From Taylor Swift

Breaking down Taylor’s success.

Kenny Rivaldi
The Equator
5 min readJan 6, 2023

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Picture of Taylor Swift from Evermore Album

My Spotify rewind indicates that I’m in the top 0.5% of Taylor Swift listeners worldwide, and to be honest, I do feel proud about it until I found out someone on Twitter who happened to be in the top 0.01% — All right, you beat me again internet people.

This year Taylor even broke the record for most tickets ever sold in one single day, people went crazy for her concert, and it even sold ‘All too well’ until the Ticket Master itself faces lawsuits from her fans.

So on my daily listening routine of her Evermore album, I was thinking about how Taylor could pull that out — How she could make people crazy. For me, she’s more than just one of my favorite artists, she’s in fact one of the greatest salespeople, marketers, and strategists.

“What if I could market my products or services the way Taylor markets her songs?” I asked myself. I went into my research mode, analyzing her songs, the marketing strategy from her team, and even her interviews.

It turns out that there were no marvel things that Taylor did. The answer lies within our psychology as human beings. Here are the things that I found out from my research:

#1. Bring the invisible problems.

Imagine yourself selling coconut bowls. Identifying the pain point that your target market might feel is essential to your product's success. You might start by making them realize the current pain that they’re having with regular bowls.

“Don’t you ever hate it when your favorite bowls just break into hundred pieces?” People who have experienced that thing might nod their heads, as you continue “Well, with our coconut bowls, that problem won’t ever happen again”.

The thing about the pain point, most of the audience doesn’t always realize that they’re having it, and Taylor is making sure we realize our pain point.

From her All Too Well song, we all realized that it just sucks when we still remember that person who has sailed the ship. Now take a look at her responses from her All Too Well video.

I truly appreciate how miserable Taylor makes us feel. — @samanthadonjuan9483

“Between me and you …did the love affair maim you too?” It’s so hauntingly beautiful, you can absolutely feel the devastation. It’s perfection. —
@amyfaranso8423

I didn’t always linger about the things that hurt me the most in the past until I listened to this song and realized how painful it was. In a nutshell, Taylor is the one who brought the problem and could fix it by making us feel understood — And only the greatest marketers could pull something like that.

I have a website design agency, and I applied for the same rule when I’m pitching to potential clients. “Don’t you ever hate it, when your competitors have a great functional website, that makes yours feel like shit?”

They probably didn’t even realize that their websites feel like shit until I showed them really great websites from her competitors. So you need to be the problem maker — Someone who makes people realize their invisible problems. Then you also need to be their hero — Someone who could fix that problem for them.

Well played Taylor.

#2. People wanted to be understood

What’s next after you made them realize the pain that they’re having? It’s time to make them feel understood, or as Taylor said in one of her songs:

November flush and your flannel cure

Your brand needs to be the flannel cure, by making them feel understood about the problems that they’re having, you win their loyalty.

A few months ago, my agency was having one of its ambitious projects from a client in Italy. The project was about creating a movie database website, which means having thousands and thousands of data. And uploading the data manually would be a pain in the a**.

My client complained about how long it is to upload one piece of data, and he said that the uploading data process itself could kill the scalability of the project. Now I could just say or argue that this is the only way to do it because in the end, uploading the data isn’t part of my job.

But putting ourselves inside their shoes, and asking ourselves “If I were you, what would I feel?” Selling your products or offering your services requires interactions, and remember that you’re interacting with a human being.

The way Taylor spoke through her songs made me feel validated. “Oh, so I’m not the only one in this world who is feeling this way”. I remember a friend of mine once told me.

“Do extra miles for your clients, so they would also do extra miles for you”

It doesn’t matter if this is part of the previous agreement or not, giving the extra mile makes your client feels validated, and in the end, they’ll be happier to stick with you in the long run.

Taylor might have her own cheat sheets of different scenarios that might happen in people’s love stories. Here are some examples:

The 1 — It’s about reminiscing about bad relationships.

Cardigan — It’s about dejection and finding new love even when you feel left out.

Exile — it’s all about the pain of parting from the people close to you.

This is Me Trying —It’s about swallowing your pride and apologizing to someone that you wronged in the past.

From those scenarios, she turned that into songs, and we don’t know which one that is going to relate to you.

#3. The Learning Curve.

It’s not about making a masterpiece on the first try. It is well known that Taylor made great songs, and the lyrics are just like poetry, but it wasn’t from a coincidence or merely blind luck. It comes from years and years of writing her songs.

It’s the learning curve, you will suck at the beginning and that’s okay. I got cringe the moment I saw the first website that I made for my client, now my design has improved over time, and even just by today, my client sent me this message.

Hello Kenny, how are you? Hope all is good! I got some compliments from journalist colleagues for ET. So just wanted to forward you the compliments.

This is highly debatable, but I would argue that sometimes good it’s better than perfect. For me, it’s always better to just do it and learn to improve it while you’re doing it.

Your first article, song, job, project, or whatever is that will not be good and far from perfect, and that’s okay — Trust the process.

Here comes my favorite lesson from Taylor, and by far I believe this is the most important one, persistence. One of my clients is earning 150k euros every month, but his first year, he only got 3 clients. If he bailed on the first year, he wouldn’t even have imagined earning that much.

Just like Taylor once said,

“There are two ways you can get through pain. You can let it destroy you, or you can use it as fuel to drive you: to dream bigger, work harder.” — Taylor Swift

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