What Every Entrepreneur Can Learn From Taylor Swift

Written by

Michael Collins

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4 min

Prompted by Time magazine and other media outlets proclaiming 2023 as “the Year of Taylor Swift,” I considered her success through the lens of entrepreneurship. I’ve listed five traits from Swift’s journey that embody true entrepreneurial ideals. Here’s what I see.

Taylor Swift: Person of the Year? Entrepreneur of the Year!

1. Intense Work Ethic

Swift’s commitment to her dual crafts — 3.5-hour live performances and crafting chart-toppers in the studio — speaks volumes about her exceptional work ethic. As a prolific force in music production, Swift’s early triumphs never led to complacency. In fact, she seems to work harder now than earlier in her career.

Even during the COVID-19 pandemic, when many artists took a hiatus, Swift surprised her fans with the release of Folklore, followed by Evermore just five months later. Her Eras Tour, featuring 151 three-plus hour shows across five continents, resembled a Broadway production in its grandeur.

Unwavering drive distinguishes the exceptional from the merely good in every field. And for entrepreneurs, 70-hour weeks are table stakes. Work-life balance is for those less interested in putting a dent in the universe.

2. Mastering Community

Swift has forged an exceptionally powerful and huge community of Swifties. By consistently revealing her authentic self, she has cultivated a positive and inclusive community among her fans, who see themselves as integral to her journey. Swift effortlessly combines personal gestures, such as surprising fans at weddings, with a global social media presence. She incorporates easter eggs, lucky numbers, and sneak peeks for her community to discover and weave stories around. She’s constantly looking to expand her community with an open embrace of individuals from diverse backgrounds.

This ability to make connections is an essential entrepreneurial skill — even more so for women startup founders than men. There’s an affinity bias in the venture world, with white, male VCs naturally biased to invest in those from their own tribe. The ability of a woman entrepreneurs to create their own community is essential. We can all follow Taylor who almost daily gives a Masterclass in community development and management.

3. Strategic Partnering

Swift’s career, boasting over 30 musical collaborations with artists ranging from Beyoncé to Keith Urban and the Jonas Brothers, is a testament to her strategic approach. Actively seeking out talented musicians and producers, she continually expands her appeal and those of her collaborators. It is classic 2+2= 5. Of note, while climbing the ladder of success, she not only aims higher in scouting collaborators but also reaches out to those a few steps down. In every case, however, it expands her market.

And don’t send hate mail, but consider the win-win nature of her relationship with Chiefs Pro Bowler Travis Kelce. We’ve seen how this partnership brought a new audience to NFL games and a sharp rise in Kelce jersey sales. At the same time, countless hardcore football fans now have the 2023 re-release of Swift’s single “Cruel Summer” on their commute playlist.

Partnering and collaborating are also critical skills for entrepreneurs. In my experience, I’ve seen more examples of female entrepreneurs effectively doing this than men. Less ego and need to dominate? Perhaps. But as Swift has shown, for every entrepreneur, it is a fantastic way to build your market.

4. Grit

Swift’s career exemplifies grit. Take Swift’s resilience to the infamous 2009 incident with Kanye West during the MTV Video Music Awards. She didn’t retaliate or crumble but seemed fueled by it to focus on the work.

It was also displayed during her well-publicized legal battles over her master recordings. Instead of succumbing to defeat, she boldly re-recorded her earlier albums, reclaiming her narrative and intellectual property. And turned a seemingly insurmountable challenge into a huge creative and financial triumph. She views obstacles as opportunities and negatives as inspiration to write a hit song.

For female entrepreneurs, particularly, Swift’s grit is inspiring. In male-dominated industries, women often face unique challenges and biases — as Swift herself remarks. Entrepreneurs should take note of her unwavering spirit in the face of adversity.

5. People

Swift’s smarts and business skills are complemented by EQ. She takes care of her people, keeping her family and friends close. Again, this is authentic and genuine. She is known for remembering small details about her team and fans, making them feel seen and valued. She also pays people. Notably, she generously gifted $100k to each of the 50 truck drivers on her Eras Tour.

And she does more than write checks. She expresses gratitude personally, like sending a box of merchandise and a handwritten note to a frontline nurse during COVID-19. Taylor knows that greatness is achieved through the agency of others.

Conclusion

Taylor Swift’s journey isn’t just a story of musical success; it’s a masterclass in entrepreneurship. Her robust work ethic, relentless community building, intelligent partnerships, grit, and people skills are a blueprint for current and aspiring business builders. We can all learn from her, and I expect Swift’s example will impart more lessons as her journey continues.

This is my list. What would you add?