7 quick tips we can learn about entrepreneurship from Taylor Swift

Two lines blast out: “I stay up too late, got nothing in my brain”…

Holy. Crap.

Picture a stadium stuffed with 60,000 people lunging to their feet, screaming their hearts out, going absolutely ballistic. You can feel the music in your chest, lasers are lighting the arena, and the sheer energy is hurting your eardrums. This is what I witnessed last Saturday when I had the privilege of taking my girlfriend to the Taylor Swift concert in Santa Clara.

While I’m not much of a fan of her music, I’m a huge fan of her business sense. With 15 years of focused determination she launched herself into the stratosphere. Here’s what I learned that you can take away from the concert (without having to attend).

1. Want to be a successful entrepreneur? Stop trying to please everyone.

Everyone = no one. I’m so guilty of this too, it’s pathetic.

Even Ignite the Drive started, and is still, a bit too un-targeted.

There are people who don’t like Taylor’s music. There are people who hate her music. Nearly 49% of the population has no interest in her music, it speaks too much to women. Most women over 40 aren’t interested either.

Guess how many “I don’t get a craps” she has? About $39,699,575.60 (in 2013).1

Taylor Swift’s music caters to a specific audience consisting nearly entirely of 14-24 year old women. And that’s made her worth nearly a quarter billion dollars.

Don’t be everything for everyone. Be different.

Be the best for a targeted, but substantial, group. And the critics that aren’t in your target market but sling hate anyways? Screw ’em.

There has never been a statue erected to honor a critic. – Jean Sibelius. 2

While you’re not trying to please everyone, remember that…

2. The best entrepreneurs delight their users

How did Taylor release the 1989 album? She baked her biggest fans cookies and sang for them in a private show. How’s that for delighting her users?

Lately several startups have, in my opinion, taken this advice too literally handing out cookies and water – completely unrelated to their core business.

Notice the difference here. Taylor baked cookies herself – putting in the effort and showing that she cared. More importantly, however, is that she and her team put together an unbelievable experience for the fans who got to come to her home and listen to her newest material long before it was released to the public.

Do your users / fans / customers leap to their feet for you or your product? How much do you invest in delighting them?


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Remember that the best way to delight users is to…

3. Resonate deeply with user’s thoughts and beliefs

“I feel like she’s speaking directly to me.” – Nearly every woman at the concert.

I’ve never had a boy break my heart, I’ve never experienced 99% of the emotions sung at that concert.

But most women have. And that’s what matters.

Further proof? I nearly nodded off once or twice because it wasn’t resonating with me… and that’s a good thing (see “Stop trying to please everyone” above).

As you build, tailor, and grow your products are you resonating with your users? Are you thinking about their problems from their mindset, or are you wondering how you can increase your own sales? Do you both genuinely care about their problems and show that you care?

Ramit’s first rule of marketing: “Nobody gives a damn about you.” – Ramit Sethi of I Will Teach You to be Rich

Speak to them. Address their problems, their wants, their needs, their desires. Your product should resonate so deeply with your target market that they say “wow, I feel like the page speaks directly to me!”

It’s not easy. Neither is growing a $240MM musical empire.

But if you really want a quarter billion dollar empire…

4. Give them an experience. A little spectacle is a good thing

“If you keep up this energy I might have a surprise for you…”

I’ll admit, even I was intrigued. But I was even more impressed with the incredible performance already happening before my eyes.

  • Lasers? Check.
  • A catwalk that became a rotating stage? Check.
  • Confetti cannons? Check.

It was nearly impossible not to be impressed with the sheer work and entertainment happening before me.

It’s one thing for someone to use your product and be happy. It’s another entirely for them to leave it so impressed they have to tell people about it.

For me in 2004 it was Pandora. While it might seem trivial now, 11 years ago “it plays music you like without you doing anything” was unreal. I immediately ran out of my dorm room and told everyone who would listen “It knows my favorite music!”

Of course, once you’ve started delighting your users you can always…

5. Get some free marketing juice, play on memories and/or nostalgia

“Party on Wayne.” “Party on Garth.”

“She turned me into a newt!” “A newt?” “I got better…”

“Milk was a bad choice!”

Did I make you smile? If you’ve seen Wayne’s World, Monty Python and the Search for the Holy Grail, or Anchorman and liked them I bet I did.

There’s something about resurfacing positive, nostalgic experiences that warms us a little from the inside. The smart entrepreneur can utilize this with Easter Eggs, references to movies, utilizing old music, etc.

Taylor briefly mentioned her past work and the crowd went insane.

At this point you’re ready to take it to the next level and…

6. Keep your users hooked, save something for the end

“One more thing” – Steve Jobs

Generally you want to make sure that your users are thrilled throughout whatever you do – be it using your software or watching your keynote. But there’s something intriguing about knowing that a good thing is coming, a really good thing.

Steve Jobs used this repeatably in his keynote announcements. Taylor Swift used it by saving her most popular song for last.

Guess how many people left the stadium early? Just the two drunk girls in front of us who were escorted out. Like any good book, keep some intrigue or risk losing your users.

“But my app is Waze for dogs, how can I keep intrigue?” Is there a non-critical, but fun, feature you can bury in the experience? A joke (woof o-clock – ok that’s terrible but you get the point), or a “hidden feature” that just happens to get leaked? Keep them coming back for more, both with your core benefits and a fun feature or two.

Just remember though, all “overnight successes” take massive, consistent effort so…

7. Don’t, ever, quit. Grit will make you a successful entrepreneur more than anything

When I was 12 I used to sit on the floor of my room with my guitar. I didn’t really have any friends, but my music understood me. Now, just 15 years later, I get to play for all of you [60,000 fans]. – Taylor Swift during the concert

Imagine begging to leave your friends, school, and birth town behind at 14 years old. Taylor Swift knew early that she was going to become a successful artist. It was her destiny.

For over 17 years she’s been working on this plan. Moving to the place with the highest chance of success. Working with the people most likely to help her launch herself into the stratosphere.

More than 26 million album sales later we can say: Good call.

Far too often I see entrepreneurs who get fired up on an idea, try to fit it to a problem, and eventually burn out because they weren’t passionate enough (*cough* myself).

In his book “The Hard Thing About Hard Things“, one of my favorite books on entrepreneurism, Ben Horowitz polled successful, and failed, startup CEOs. The failed ones had every excuse in the book: “We were too early”, “We were too late”, “It was the wrong environment”, on and on it went. Meanwhile, the successful CEOs unilaterally had one answer: “I just didn’t quit”.

So much can be said about grit – the art of never stopping while aiming for a goal – that it’s planned for several other blog posts. Needless to say, just like Taylor, if you want to be an entrepreneur never quit on the road of achieving your goal.

If you liked this post, be sure to stay in touch. Plus you’ll get my eBook for entrepreneurs on productivity and tools to avoid burnout.

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  1. If you care about these things, see Taylor’s estimated net worth
  2. Information about Jean Sibelius and his quote 

About Garrett Dunham

Garrett Dunham is a Silicon Valley born-and-raised entrepreneur, keynote speaker, and startup advisor. His companies have been featured on the New York Times, NBC, TechCrunch, Fast Company, and Venture Beat, among others. He spends his days mentoring startups at Start-up Chile and Singularity University, building products, and blogging about entrepreneurial success and self optimization.

5 thoughts on “7 quick tips we can learn about entrepreneurship from Taylor Swift

  1. Great post, Garrett. Keep it up man.

    I loved how you pulled in Ramit, Ben Horowitz, Taylor Swift, AND Monty Python… genius.

    Great tip on the hidden feature/Easter Egg too. Reward your power users with delightful experiences and talking points w/ their friends.

    1. Thanks Chris! Pulling from every source I know.

      I love Easter Eggs. For example swipe-to-refresh on Yelp and you’ll see a spaceship being built around a hamster. Let go and the rocket takes off.

      Valuable to the core tech? Not really.
      Fun and worth mentioning on a blog (aka free marketing)? Definitely.

  2. I like what you write. In fact as you spoke about Taylor Swift, it mirrored me to an image of similar businessman from the Bollywood. Its not his acting that intrigues me but his business sense. By the way did you know, Taylor Swift, Britney Spears and Ashton Kutcher have more Twitter followers than entire population of Sweden, Switzerland,Norway or Israel. We could learn a few from all of them. You have a good flow to your writing and a great message of “Target the right”. I could use a few tips from you for sure. Thanks

    1. Thanks Jyoti for the kind words and for signing up for out mailing list. It’s always nice to hear when people enjoy my work.

      I had no idea that Taylor Swift, Britney Spears and Ashton Kutcher had that many followers, that’s a ton!

  3. Speaking as a Mom… I have to say I like to point out to my 16yo son how smart Taylor Swift is, but when she first came out, I thought to myself, why was she popular? And, I think your article really hit the spot. I’ve watched her over the years in interviews. She knows how to sell what interest her, which is the thing many other women are dealing with. I found that for me, she’s able to sell her brand without being trashy, but be someone you can point your daughter to as an example to live by. However, I have used her Shake It Off song to help my son to deal with the bullying he’s experienced.

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