Sarah McKinney
7 min readSep 8, 2015

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Entrepreneurs: 7 Lessons From Taylor Swift On Community Building

Photo credit: Ben Sklar for The New York Times

Anyone who knows me well knows that I have a bit of a Taylor Swift obsession. It began much like it did for her other fans, I assume. I related to her lyrics, and found myself singing along to her songs when driving (alone) in my car. Thirteen years her senior and studying business in graduate school at the time, I justified my growing interest in her as a fascination with her entrepreneurial savvy. Flash-forward and I’ve now purchased all of Swift’s music, read and watched countless interviews, and enthusiastically tweeted the article she penned for The Wall Street Journal and her open letter to Apple. I even wrote and released a song in the hopes I’d be able to reach her and she’d want to record it. Like I said, it’s a bit of an obsession.

One of my jobs now is writing articles as a freelance columnist — most often on the topics of entrepreneurship, creativity, and social impact. Recently I was chatting with Kathryn Cicoletti, founder of The MSB Cheat Sheet, about how brilliant I think Taylor Swift is. I’d just returned to Los Angeles after seeing the “1989 World Tour” in Santa Clara, and was explaining some of the things Swift did during her show to create a strong community vibe. “I need to apply what she does to my business! Will you please write an article about this with me in mind?” said Cicoletti. I sparked at the idea. And whenever that happens, I know I have to take action. So here you go entrepreneurs: 7 lessons from Taylor Swift on how to successfully build community:

1. Transparency builds loyalty. Be honest. No excuses.

The intimacy fans feels with Taylor Swift is no accident. Her lyrics have always felt like private journal entries that she decided to let the world read. She grew up in front of us, sharing all of her thoughts and emotions along the way, and has never tried to be anyone other than herself — irritatingly likeable to some, but unarguably likeable all the same. And as a thank you for this commitment to being authentic, her fans have stayed with her and grown exponentially in number over the years.

It’s common knowledge that consumers prefer brands they perceive as being authentic. As an entrepreneur, it’s temping to project an image of success prior to achieving it in the hopes you’ll more quickly attract people to your business. While this strategy may prove fruitful in the short run, people aren’t stupid and will leave you once they realize they’ve been duped. Don’t lose sight of the long view, and let your personality shine through. I’m sure you’re lovely. And even if you’re not, doing this will expedite some important character building life lessons.

2. Know your audience, and honor your responsibility to them.

I was aware that Swift’s core fan base was significantly younger than me, but didn’t anticipate how that would impact the “1989 World Tour” experience. At several points throughout the show the music would stop and Swift would begin chatting with the audience like we were BFFs, sprinkling tidbits of the wisdom she’s gathered over the years. The little girls around us were eating up every word. Even though Swift has grown up, she still takes her responsibility to young fans seriously.

Know who your most loyal customers are — study them and understand what makes them tick. Keep them in mind as you continue to roll out new products and services. Don’t try and serve the people you wish were loyal in the hopes of attracting them. Be true to your mission, your personal passion, and continue to talk to your most loyal customers. Allow things to grow organically from that place. If you don’t know who these people are inside and out, start researching them pronto.

3. Humanize your community. People like to know what they’re joining.

Before the release of her latest album Swift hosted private listening parties at select fan’s houses around the country. She made headlines for randomly sending fans gifts in the mail. During one of her recent shows she devoted a song to a woman in the audience whose son Ronan died of cancer, saying she read the woman’s blog regularly and was deeply touched by her journey. She shares fan-generated content she likes on social media, and shows YouTube videos of people covering her songs and dancing to her music before her concert begins.

Most consumers want to know what kind of community they’re joining before they sign up, and it’s your job to bring your community to life. There are many ways you can do this, but whatever you do must fit with your brand’s personality. Think about how you can bring your audience to the forefront and let people know who they are. The Skimm and SoulCycle are two brands that come to mind, when thinking about startups that have done this very well.

4. Create a strong tribe of (offline) support.

Sure, some have criticized Swift for taking the whole #girlsquad thing to an extreme, but the importance of surrounding yourself with a strong tribe of supportive people can’t be diminished. Besides, her current critics are probably the same people who were vocal about her needing to go have some “girl time” after her relationships with the Kennedy kid and Harry Styles went bust. Having a solid group of girlfriends provides the added benefit of ensuring she doesn’t come across as social media obsessed — confusing her online community with real life friendships.

Being an entrepreneur can be isolating. Long days spent behind your computer screen and checking off a never-ending list of “to do” items can make it easy to replace real life connections with Facebook likes. At least occasionally, when you catch yourself crafting your next clever post in your mind, pick up the phone and call a friend instead. Ask them how they’re doing. We know the business you’re building is important, but offline relationships will keep you sane, and ensure you don’t come across as a needy social media addict to your customers.

5. Have the courage to pivot (before you have to).

Swift didn’t need to leave the Country genre for Pop — her album sales have been pretty insane straight out of the gate and showed no signs of slowing down. Making that leap took some courage. She had to follow her heart and trust that her fans would follow. She was also pretty strategic in her decision to include a few very pop songs (e.g., “We Are Never Ever Getting Back Together”) on her last Country album, Red. And yeah, the popularity of that track probably eased some of her worries about what she planned to do next.

When monthly traffic and sales numbers continue to rise it’s easy to assume clear skies ahead, but it’s important to stay ahead of the market and always be anticipating future needs before consumers can articulate them. Innovation is just like that. And too many big companies die because they stop being nimble enough to innovate ahead of the competition. Don’t get too comfortable. Be diligent about reading industry news, surrounding yourself with “idea” people and read as many books as your brain can handle. Be strategic in your risk taking, and if you get it right, you’re community will grow in ways you can’t currently comprehend.

6. Become an advocate for those with less power.

One of the things I’m most impressed with about Swift is how she advocates for songwriters and artists that aren’t in her same position of power. Removing her music from Spotify and her open letter to Apple make clear that she’s not messing around, and cares about creative people working hard to make it in the music industry. It’s a fantastic example of leadership to set for her young fans, and demonstrates a lack of narcissism. This wins her even more fans, because she’s tapping into the fan bases of every public figure who speaks out in favor of her advocacy work. Brilliant.

I know I know, you don’t have 45.5 million Instagram followers. But you can start doing this kind of thing on a much smaller scale. Say yes to having that coffee with someone who reached out, and wants to learn from your experience. Attend industry events and get involved in issues that don’t just affect you, but others working in your space. Be proactive and positive, and find simple ways to give back. Write blog posts on open platforms like Medium to highlight social issues you care about. Eventually you may be having Swift-like impact within your industry.

7. Don’t take yourself too seriously.

The fact Swift invited Lisa Kudrow on stage during one of her LA shows to sing “Smelly Cat” with her makes clear she doesn’t take herself too seriously. In 2009 she rapped with T-Pain in “Thug Story” — the lyrics poking fun at her squeaky clean image. She played an irritatingly enthusiastic girlfriend in the film Valentine’s Day, said yes to hosting SNL (instead of simply being the musical guest), has admitted to naming her cats after characters in TV shows, and manages to always bounce back from adversity with a smile on her face.

I know it can get overwhelming, but please try and keep your sense of humor. Be silly. Poke fun at yourself. Go out of your comfort zone. Have new experiences that have nothing to do with growing your business. Give yourself permission to take risk. And when you make mistakes? Shake it off.

This piece originally appeared in The Creative Profiles.

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Sarah McKinney

Freelance Columnist. Singer/Songwriter. Research & Strategy Consultant. Encore Innovation Fellow. MBA in Sustainability.