Fearless Entrepreneurship: 5 Business Lessons from Taylor Swift’s Career

Whether or not you’re a Taylor Swift fan, there is no denying that she’s one of the most successful artists of our time. From her record-breaking releases to her Eras Tour that has single-handedly boosted economies worldwide and literally caused earthquakes, Swift has forever changed our music landscape.

Aside from being a successful recording artist and performer, Swift is also a savvy businesswoman whose net-worth has surpassed the billionaire threshold.

Here are five lessons for business owners based on her illustrious career:

1. Connect with your audience

“So make the friendship bracelets.”

There are few fan bases as dedicated as Taylor Swift’s fans (aka. Swifties) and it comes as no surprise. Over her career Taylor has turned connecting with Swifties into an art form. From frequently engaging with fans on social media, hosting private listening-parties or sending swag bags to her top fans, to hiding “easter eggs” and secret messages for her audience in her music videos. Her focus and dedication to fan engagement is on-going and continues to build loyalty to her brand.

Key takeaway: Don’t take your customers for granted and treat each customer interaction like it’s your first. Keep showing up and highlight how your product or service is adding value to your customers’ lives.

2. Embrace change

“They never see it comin’, what I do next.”

From humble beginnings as a country music artist to international record-breaking superstar, Taylor Swift has shown that there are huge benefits to trying new things. While staying true to her core as a master songwriter and storyteller, Taylor is constantly reinventing herself with each of her albums, or as her fans call it “eras”. She is a master of keeping people on their toes and finding new ways to surprise her fans. Beyond delighting her existing fanbase with new types of music, her exploration through different genres has provided opportunities for her to grow beyond her existing audience.

Key takeaway: Improvise, pivot, improve. Staying highly adaptable and seeking out new opportunities will give you a competitive edge.

3. Be persistent and resilient

“When you are young, they assume you know nothing.”

The story of Taylor Swift’s career is not one of overnight success. It is one fueled by a strong belief in herself and the ability to persist and “rise from the ashes”. Even at the top of her game, Taylor continues in her pursuit of excellence and finds new ways to reach the next peak in her career. Whether it’s continuing to write new songs to get recognized by a record label at fifteen years-old or preparing for a world tour by performing her entire 3.5-hour setlist while running on a treadmill, Taylor Swift has shown that success comes from dedication and on-going commitment to your craft.

Key takeaway: Success doesn’t come overnight. It requires grit and resilience. Believe in yourself and the product or service you offer and continue to overdeliver.

4. Protect your work

“And when you can’t sleep at night, you hear my stolen lullabies.”

If it seems like there has been a seemingly constant stream of Taylor Swift album releases, there’s a strategic reason for that: Reclaiming ownership of her work. When Taylor Swift signed with Big Machine Records at 15 years-old, by contract the label owned the master recording rights to her first six albums. After mega success and a transition to a new label, Taylor negotiated to buy her own masters back from Big Machine and was ultimately denied. Her masters were first sold to a private equity group and then again to an investment fund for hundreds of millions of dollars. Ultimately, both parties continue to make money off Taylor Swift’s original recordings and can use her music without needing consent from her. To take back ownership and control of her work, Swift completely re-recorded her original albums, releasing them as “Taylor’s Version” editions with new art and additional unreleased tracks that she’s dubbed “From the Vault”. These new versions allow her to make decisions about how recordings are used and ensure she receives royalties for her work.

Key takeaway: Stand up for yourself and don’t let others undermine your worth. Protect your work and intellectual property by registering copyrights and trademarking your company name, product names, logos, etc.

5. Invest in your employees

“Long live all the mountains we moved, I had the time of my life fighting dragons with you.”

While Taylor Swift is a solo artist, she is backed by a team of dedicated employees who keep her business moving. Like all good leaders, she recognizes that success is shared and recently celebrated the team that helped make her latest tour a historic success. In 2023, Swift gave about $55 million in bonuses to staff of her Eras Tour including members of her tour trucking crew, dancers, stylists, and those in catering, video, audio and lighting. It is also rumored that Swift planned the 2-month touring break of her Era’s Tour around the due date of her lead guitarist’s newborn.

Key takeaway: Invest in your most valuable asset—your employees. Recognizing, rewarding, and celebrating your employees demonstrates your care and appreciation for their hard work and dedication.

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Fearless Entrepreneurship: 5 Business Lessons from Taylor Swift’s Career

Whether or not you’re a Taylor Swift fan, there is no denying that she’s one of the most successful artists of our time. From her record-breaking releases to her Eras Tour that has single-handedly boosted economies worldwide and literally caused earthquakes, Swift has forever changed our music landscape.

Aside from being a successful recording artist and performer, Swift is also a savvy businesswoman whose net-worth has surpassed the billionaire threshold.

Here are five lessons for business owners based on her illustrious career:

1. Connect with your audience

“So make the friendship bracelets.”

There are few fan bases as dedicated as Taylor Swift’s fans (aka. Swifties) and it comes as no surprise. Over her career Taylor has turned connecting with Swifties into an art form. From frequently engaging with fans on social media, hosting private listening-parties or sending swag bags to her top fans, to hiding “easter eggs” and secret messages for her audience in her music videos. Her focus and dedication to fan engagement is on-going and continues to build loyalty to her brand.

Key takeaway: Don’t take your customers for granted and treat each customer interaction like it’s your first. Keep showing up and highlight how your product or service is adding value to your customers’ lives.

2. Embrace change

“They never see it comin’, what I do next.”

From humble beginnings as a country music artist to international record-breaking superstar, Taylor Swift has shown that there are huge benefits to trying new things. While staying true to her core as a master songwriter and storyteller, Taylor is constantly reinventing herself with each of her albums, or as her fans call it “eras”. She is a master of keeping people on their toes and finding new ways to surprise her fans. Beyond delighting her existing fanbase with new types of music, her exploration through different genres has provided opportunities for her to grow beyond her existing audience.

Key takeaway: Improvise, pivot, improve. Staying highly adaptable and seeking out new opportunities will give you a competitive edge.

3. Be persistent and resilient

“When you are young, they assume you know nothing.”

The story of Taylor Swift’s career is not one of overnight success. It is one fueled by a strong belief in herself and the ability to persist and “rise from the ashes”. Even at the top of her game, Taylor continues in her pursuit of excellence and finds new ways to reach the next peak in her career. Whether it’s continuing to write new songs to get recognized by a record label at fifteen years-old or preparing for a world tour by performing her entire 3.5-hour setlist while running on a treadmill, Taylor Swift has shown that success comes from dedication and on-going commitment to your craft.

Key takeaway: Success doesn’t come overnight. It requires grit and resilience. Believe in yourself and the product or service you offer and continue to overdeliver.

4. Protect your work

“And when you can’t sleep at night, you hear my stolen lullabies.”

If it seems like there has been a seemingly constant stream of Taylor Swift album releases, there’s a strategic reason for that: Reclaiming ownership of her work. When Taylor Swift signed with Big Machine Records at 15 years-old, by contract the label owned the master recording rights to her first six albums. After mega success and a transition to a new label, Taylor negotiated to buy her own masters back from Big Machine and was ultimately denied. Her masters were first sold to a private equity group and then again to an investment fund for hundreds of millions of dollars. Ultimately, both parties continue to make money off Taylor Swift’s original recordings and can use her music without needing consent from her. To take back ownership and control of her work, Swift completely re-recorded her original albums, releasing them as “Taylor’s Version” editions with new art and additional unreleased tracks that she’s dubbed “From the Vault”. These new versions allow her to make decisions about how recordings are used and ensure she receives royalties for her work.

Key takeaway: Stand up for yourself and don’t let others undermine your worth. Protect your work and intellectual property by registering copyrights and trademarking your company name, product names, logos, etc.

5. Invest in your employees

“Long live all the mountains we moved, I had the time of my life fighting dragons with you.”

While Taylor Swift is a solo artist, she is backed by a team of dedicated employees who keep her business moving. Like all good leaders, she recognizes that success is shared and recently celebrated the team that helped make her latest tour a historic success. In 2023, Swift gave about $55 million in bonuses to staff of her Eras Tour including members of her tour trucking crew, dancers, stylists, and those in catering, video, audio and lighting. It is also rumored that Swift planned the 2-month touring break of her Era’s Tour around the due date of her lead guitarist’s newborn.

Key takeaway: Invest in your most valuable asset—your employees. Recognizing, rewarding, and celebrating your employees demonstrates your care and appreciation for their hard work and dedication.

Sign up for our newsletter

Sign up for our monthly HIVE newsletter and get tips for finding a job, managing a business and advancing your career right in your inbox.

* indicates required