9 Lessons We Can Learn From The Pop Icon


By Rieva Lesonsky

Do you have a role model? Many business owners can point to someone they view as a role model, someone with attributes they admire, or who just inspires them.

As expected, many small business owners claim legendary entrepreneurs like Steve Jobs, Jeff Bezos, and Sara Blakely as role models. No surprises there. But entrepreneurs often prefer the road less traveled, so if you’re looking for a new or additional role model—let me suggest—Taylor Swift.

Yes, you read that right. Allow me to make the case that singer/songwriter Taylor Swift is not only an excellent entrepreneurial role model but also an accomplished entrepreneur.

Why Taylor Swift is a role model for entrepreneurs

Like most successful entrepreneurs, Swift is driven. At 14, she left the first publishing house that signed her because she says, “I genuinely felt that I was running out of time.” Her goal was to chronicle her early years on an album, and she started writing songs with a professional songwriter once a week after school.

At 16, her first lead single and album was released, which stayed on the U.S. Billboard 200 charts for 275 weeks, peaking at number five. From there, the 34-year-old Swift built an empire reportedly worth $1.1 billion, according to Bloomberg.

She’s released 10 all-original studio albums, four live albums, and four rereleased “Taylor’s Version” albums. Swift’s won 14 Grammys, four of which were “Album of the Year” (a record), and she has more number-one albums than any other female recording artist in history.

The Harvard Gazette reports her current “Eras” world concert tour is likely to be “the highest-grossing concert tour of all time, at $1.4 billion,” and according to The Wall Street Journal, was the first to earn more than $1 billion.

According to Business Insider, the movie version of the tour broke box-office records before it was released and, to date, has grossed nearly $262 million. Instead of going through the movie studios—the typical approach—Swift took the entrepreneurial path and funded the movie herself (which allows her to receive more than 50% of the box office earnings). After meeting with all the movie studios and streamers, she told Time magazine, “Ultimately, I did what I tend to do…which is to bet on myself.” And Disney just paid her $75 million (or more) for the rights to stream Taylor Swift: The Eras Tour (Taylor’s Version) on Disney+ starting in March.

Swift’s phenomenal 2023 culminated with her being named Time magazine’s Person of the Year, partly for “building a world of her own that made a place for so many.”

Sharing a trait with most entrepreneurs, Swift doesn’t like to be controlled. In 2019, the original masters of her albums, videos, and artwork were sold to a private equity company, even though Swift had wanted to buy them. A year later, Swift announced she planned to rerecord her first six albums—and “Taylor’s Version” was born. To date, the four released Taylor’s Versions albums have earned more than $55 million.

Like all great entrepreneurs, Swift has made quite an economic impact nationally:

  • Bloomberg Economics estimates Swift’s 53 U.S. concerts in 2023 added $4.3 billion to the nation’s gross domestic product (GDP).
  • The Federal Reserve noted that her concerts led to an influx of tourism dollars in the cities where they’re held.
  • The U.S. Travel Association estimates that Swift’s fans—the “Swifties”—spent an average of $1,300 each in the 20 cities where her U.S. concerts were held. The Association estimates the “total economic impact likely exceeded $10 billion.”
  • In Los Angeles alone, the California Center for Jobs and the Economy estimates that Swift’s six concerts resulted in a “$320 million bump to Los Angeles County’s GDP,” including earnings of $160 million and an increase of 3,300 jobs.

Entrepreneurial takeaways from Swift’s songs

Swift’s accomplishments are impressive for any entrepreneur. But for fun, let’s look at some of Swift’s song titles and find the entrepreneurial connection.

“Fearless”—It’s critical that business owners don’t let the fear of the unknown paralyze them. It’s important to embrace risks, tackle challenges, and chase your dreams.

“Shake It Off”—In a world where setbacks and criticism are inevitable, this song reminds business owners to shake off negativity and keep moving forward. Mistakes will happen in any entrepreneurial endeavor, but if you can be resilient and move on, applying the lessons you’ve learned, you can overcome any adversity.

“Blank Space”—Most people can’t see what lies ahead when envisioning the future. But entrepreneurs see the endless possibilities, embrace the unknown, and fill in the blanks. As Swift said while writing the Folklore album, “I was inspired to make something differently than I had ever before.”

“The Archer”—“The Archer” reminds us that the entrepreneurial world can be treacherous. Sometimes, we’re the hunter leading the way; sometimes, we’re the hunted, targeted by our competition. As Swift writes, “I’ve been the archer, I’ve been the prey,” but to survive, you need to be “ready for combat.”

“ME!”—If you want to succeed as an entrepreneur, you must be confident. “ME!” addresses common entrepreneurial themes like “never thinking before (you) jump” and being “one of the things (that’s) not like the others.” The song celebrates self-assurance and individuality, boldly proclaiming, “I’m the only one of me.” My favorite entrepreneurial line is the ironical, “There ain’t no I in team, but you know there is a me.” And for the ultimate dose of confidence, Swift reminds us, “You can’t spell awesome without me.”

“Wildest Dreams”—Every entrepreneur starts with a dream—a vision of what could be. All of us need wild dreams. They encourage us to think big, reach for the stars, and never settle for mediocrity. By setting ambitious goals and pursuing their passions, entrepreneurs can turn their wildest dreams into reality.

“Begin Again”—When you own a business, setbacks are inevitable. And when one occurs, after shaking it off, entrepreneurs need to be ready to “Begin Again.” Even if you “break and burn,” remember that every ending leads to a new beginning. If we treat failure as a stepping stone to growth, we can bounce back stronger and forge ahead to entrepreneurial success.

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How entrepreneurs can be like Taylor

Throughout her career, Swift has faced numerous challenges, including criticism, setbacks, and intense public scrutiny. Despite these obstacles, she has consistently demonstrated resilience, perseverance, and the ability to bounce back—all traits common to successful entrepreneurs. There’s a lot you can learn from her.

Adaptability and evolution

Swift has a remarkable ability to evolve and adapt to changes in the music industry. From transitioning between music genres to embracing new technologies and platforms for distribution and promotion, she’s demonstrated how important it is to stay flexible and open to innovation.

Be like Taylor by emulating her willingness to adapt to changing market conditions and embrace new opportunities for growth and expansion.

Creativity and innovation

As a songwriter, musician, and performer, Swift is renowned for her creativity, originality, storytelling prowess, inventive music videos, and immersive concert experiences. She pushes boundaries, experiments with new styles, and continually creates unique experiences for her audience.

Be like Taylor by thinking outside the box, pushing boundaries, and creating unique customer experiences.

Resilience

Throughout her career, Swift has faced public scrutiny, criticism, and personal challenges. Despite these obstacles, she has been resilient, bouncing back from challenges, determined to keep pursuing her goals.

Be like Taylor by learning from your mistakes and powering through setbacks.

Strong work ethic

Swift’s success is a testament to her strong work ethic and commitment to her craft. She has put in relentless effort to achieve her goals.

Be like Taylor by persevering and pursuing excellence.

Authenticity and connection

One of Swift’s most notable strengths is her ability to connect with her fans on a personal level and cultivate a loyal, devoted fan base. Recently, over 96,000 fans packed Australia’s Melbourne Cricket Club for three nights to see her. She prioritizes authenticity, vulnerability, and genuine human connection in her interactions with fans, which has helped her build a strong and enduring brand.

Be like Taylor by being authentic and transparent, staying true to your values, and building genuine connections with your customers.

Business savvy

Beyond her musical genius, Swift has demonstrated sharp business acumen throughout her career. She negotiates her own deals, now owns her masters, and has built a successful merchandise and branding empire.

Be like Taylor by thinking strategically and maintaining control of your own destiny.

Empowerment

Swift’s advocacy for artists’ rights and her vocal stance on issues like intellectual property and gender equality have inspired many. She uses her platform to empower others and effect positive change in the world.

Be like Taylor by advocating for causes you believe in and being a socially conscious business.

Curiosity

Despite her immense success, Swift remains curious and committed to learning and growth. She actively seeks feedback, collaborates with other artists, and strives to improve her craft with each project.

Be like Taylor by committing to continuous learning and self-improvement.

Generosity

Swift has generously donated money throughout her career. She’s given money to fans in need, for disaster relief, and promised to leave a “positive impact” on all the cities she visited on her Eras tour. Billboard says last July, Swift reportedly gave each truck driver on the Eras tour a bonus of $100,000 for a total of $5 million.

And she’s generous with her fans, frequently thanking them for believing in and supporting her. During one of her Melbourne concerts, Swift told the crowd, “Every time I challenge myself and make something new, you said, ‘Go for it.’ I appreciate the belief you have in me.”

Be like Taylor by being generous with your employees and giving back to your community.

Taylor Swift uses her celebrity to support small businesses

Swift is mindful of using her platform to support smaller businesses and female-founded brands. Sports reporter Erin Andrews, who launched a sports clothing and accessory company, told People magazine she admires how Swift “supports small and women-owned businesses, including her own.”

After Swift began dating Travis Kelce of the NFL’s Kansas City Chiefs, she showed up at his football games wearing Chiefs-branded clothes and accessories. NBC News reports that most of the Chiefs gear she wears to the games “comes from local stores and independent fashion designers.” A fashion blog that charts Swift’s look told NBC, “Instead of wearing official NFL merch to every game, (Swift) often reps pieces from small and women-owned businesses.”

Business Insider reports that some small businesses boasted sales increases of 3,000%. After Swift wore a jacket from Kristin Juszczyk, the designer told People, “I’m extremely grateful for her…and the amount of support that she gives women and small businesses.”

Perhaps Swift is so supportive of small businesses because she thinks of her company that way. She told Time, “My dad, my mom, and my brother come up with some of the best ideas in my career. I always joke that we’re a small family business.”

Swift’s journey serves as a testament to the power of perseverance, passion, and unwavering belief in oneself. By emulating her actions, entrepreneurs can gain valuable insights and inspiration as they navigate their own path to entrepreneurial success.

About the Author

Rieva Lesonsky is CEO of GrowBiz Media and SmallBusinessCurrents.com and has been covering small businesses and entrepreneurship for over 30 years. Get more insights about business trends by signing up for her free Currents newsletter.



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