What Entrepreneurs Can Learn From Taylor Swift

With Taylor Swift’s Eras Tour wrapping up this past weekend in Vancouver, and the ongoing media coverage of her performances, music, and awards, I have been thinking about her tremendous prominence and undeniable impact she is having on an entire generation.  I attended a Taylor Swift concert last summer in Seattle with my two nieces.  It was incredible: audacious sets, lighting, and special effects; flawless execution with multiple dancers, costume changes and stunts; and a joyful, energized audience that radiated kindness and friendship.

Whether you like her music or not, her success is undeniable.  Taylor Swift’s 21-month Eras Tour spanned five continents, 21 countries and 50 cities.  The 149 sold-out shows grossed a record-breaking $2 billion, double the next best tour in history, Elton John’s Farewell Tour.  Swift has won 40 American Music Awards, surpassing the second highest award winner, Michael Jackson, who won 26.  She is the only person to have won the Grammy Album of the Year four times.  Earlier this year, Taylor broke Spotify’s record for the most streams in a single day, less than 12 hours after the release of “Tortured Poets”, which amassed over 300 million streams on the first day of its release. 

Taylor Swift is not only a once-in-a-generation singer, songwriter, and performer, but also a world-class business builder, from whom all entrepreneurs can learn.  Below are some of the lessons I take away as I reflect on what is making Taylor Swift an unprecedented success in the music industry.

Connect with your customers

Swift talks about the importance of her being on tour so she can see and connect with her fans (“customers”).  She plays games with her fans, sends secret messages, and cares deeply about them.  During her concerts, she can be seen giving her hat to an adoring young fan, ordering security guards to be gentler with the audience, speaking in the local language, and laughing alongside fans.  Before the release of 1989 in 2014, Taylor hosted a series of mini concerts in different cities. Small groups of fans got to hear her new album before its release, meet her in person, and sample her homemade cookies. 

As an entrepreneur, how do you connect with your customers?  How do you maintain close customer relationships so you can better meet their needs and anticipate their reactions?  I know an executive who managed a multi-billion business with thousands of employees but spent a day a quarter manning the customer support calls and going with technicians on customer calls.  He used  to say those days had the highest return on time spent than anything else he did at the company.

Love what you do

Taylor Swift claims that she loves to write music and perform in front of her fans.  Seeing her perform live, radiating with energy and joy, it is evident that she is in her element.  She recently said, “I love doing this thing we are fortunate enough to call a job. Writing songs is my life’s work, my hobby, and my never-ending thrill.” 

You can only bring the best of yourself, all your energy, enthusiasm, and passion to an endeavour if you love it.  Launching and scaling a business is tough and most businesses do not make it to their fifth anniversary.  Those that do succeed, and particularly those that go on to build massive businesses and become category-defining companies, require extraordinary leaders who are able to channel their best abilities and leverage all of their creativity, intellect, and drive.  This level of performance is not possible without a deep passion and commitment to the mission.  Or as Ralph Waldo Emerson said, “Nothing great was ever accomplished without enthusiasm”.  

Don’t let the haters get you down

Many people thought that the Eras Tour would be a failure.  As Taylor Swift said, “For the entire six months leading up to the first show of this tour, every headline that I read was: “This is going to be a massive failure” or “This is going to be a flop tour”. … People thought that I was going to be playing to nearly empty stadiums.”  Taylor Swift has faced criticism throughout her career for multiple reasons.  But she powers on and continues to build her fan base and break new records.

While it is important to listen for feedback and consider factors that people suggest will be significant obstacles, when people with limited information or insight assert that you cannot do things, I have found that the best reaction is to not argue, but simply go out and prove them wrong.  Next time someone criticized you with no justification, ask yourself whether you are going to get discouraged or determined. 

Never stop iterating

Taylor Swift has continuously evolved her musical style throughout her career, with her albums ranging from country to indie-folk, pop, rock, and other styles.  She has charted new ground throughout her career, with the Eras Tour being the most recent example.  As Taylor stated, “The best ideas are usually ones without industry precedent.  The biggest crossroad moments of my career came down to sticking to my instincts when my ideas were looked at with skepticism.  When someone says to me, ‘But that has never been done successfully before,’ it fires me up.”

One of the best early indicators of whether a company will be successful is the speed at which founders test, learn, iterate, and then go through the cycle again, with a relentless desire to improve.  No entrepreneur ever builds exactly what she envisioned on the first day of her company.  To be successful, entrepreneurs need to listen to customers, watch the competition, understand market trends, and then iterate to find the best product, pricing, packaging, marketing, sales, and company structure.  The faster and more innovatively that founders are able to do this, the more quickly they will find success.

Work incredibly hard

Taylor is known for her strong work ethic.  For instance, to prepare physically for the Eras Tour, she sang the entire set list while running on a treadmill, every day for the three months leading to the first show.  People in the industry consistently report that she works harder than almost anyone in music, continually honing her skills, mastering the craft, and thinking creatively about how to surprise and delight her fans.

As all entrepreneurs know, there is no substitute for hard work, for putting in the reps, for making the extra effort.  The top performers did not get there by accident.  They thought deeply about where they wanted to go or what they wanted to build, they laid a solid plan, and then executed that plan, even when they did not feel like it.  They showed up when others stayed in bed, they kept improving when others settled, and they made one more call when others called it quits.

Build a world-class team and treat them well

Taylor Swift has a full-time team of 50 people working with her, including management, production, and special projects.  The Eras Tour was produced in-house and employed several hundred additional people, including sound and light technicians, set crew, costume designers, and administration.  Taylor fosters a strong culture within her organization that is aligned with her brand values of authenticity, creativity, and professionalism.  For instance, mid-way through the Eras Tour, Swift distributed $55 million in bonuses to her team, including $100,000 to each of the 50 truck drivers.  With the completion of the tour, it is reported that Swift distributed a total of $197 million in bonuses. She is also known to remember and celebrate her team members’ birthdays and other special occasions.

Entrepreneurs can learn from this and implement company policies that support a cohesive and collaborative culture, and also display authenticity and empathy for team members.  It does not matter how effective a founder or CEO may be, no one has ever built a massively successful enterprise without the support of an outstanding team.

Regardless of whether you are a Taylor Swift fan or not, every entrepreneur can learn valuable lessons from observing how she has built her incredible empire, and continues to connect with her customers, innovate, and build a world-class team.