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Taylor Swift and Amazon’s ‘Antifragile’ Secret to Business Success | Entrepreneur

by Brand Post
September 9, 2025
in Business
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Taylor Swift and Amazon’s ‘Antifragile’ Secret to Business Success | Entrepreneur
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If you’ve had internet access since 2005, you’re familiar with Taylor Swift.

Image Credit: Gilbert Flores | Getty Images

The superstar musician is the most-streamed artist in the world. She is the first to win album of the year at the Grammy Awards four times. Her Eras Tour generated more than $2 billion in ticket sales. And she has a net worth of $1.6 billion.

She also has something valuable in common with Amazon, the Jeff Bezos-founded ecommerce giant that boasts a $2.5 trillion market capitalization.

Related: Don’t ‘Shake Off’ These 5 Business, Brand and Legal Lessons From Taylor Swift

Aside from Swift and Amazon’s status as two of the most successful brands in the world, the pair shares a rare trait that’s helped them get there, according to former strategist at Harvard Business School Sinéad O’Sullivan.

In her new book, Good Ideas and Power Moves: Ten Lessons for Success From Taylor Swift, O’Sullivan claims that Taylor Swift and Amazon have both reached the pinnacles of their respective industries by being “antifragile.”

“In an increasingly complex and seemingly random world, some systems perform better in chaos than others.”

The concept of “antifragility” relates to a field of physics called chaos theory. Lebanese American scholar of math and financial markets Nassim Taleb coined the term after noticing a peculiar event unfolding in systems and organizations across a wide range of fields, from biology to urban development, healthcare and more.

“What he saw was that in an increasingly complex and seemingly random world, some systems perform better in chaos than others,” O’Sullivan writes.

Essentially, antifragility flouts the human desire for stability and instinct to fear what’s different or unstable.

“The idea of antifragility goes far beyond saying that uncertainty doesn’t have to be bad,” O’Sullivan explains. “It actually says that uncertainty is good. Antifragility isn’t just about surviving chaos; it’s about flourishing in it. It’s about flipping the script and turning adversity into opportunity, uncertainty into innovation and chaos into creativity.”

Related: Embracing Antifragility — How to Leverage Uncertainty, Volatility and Stress for Unprecedented Growth and Innovation

The immune system and winemaking serve as real-life examples of antifragility at work, O’Sullivan notes. A strong immune system has been exposed to pathogens and can better ward off future threats. Great wine often comes from vines under stress because they grow smaller grapes with more concentrated flavor.

“Amazon’s business actually gets stronger because the volatility wipes out its competitors.”

The pandemic helped reveal which companies were antifragile, too — those that didn’t have to wait for share prices to recover because they’d never really fallen in the first place, according to O’Sullivan. As many major retailers struggled to stock their shelves, Amazon maintained total control over its supply chain and saw its online business soar.

“At Amazon, there is no single point of failure that would prevent toilet paper from being passed from millions of available sellers to millions of eagerly awaiting buyers,” O’Sullivan says. “Amazon’s business actually gets stronger because the volatility wipes out its competitors.”

Likewise, Swift has demonstrated remarkable antifragility while building her business over the years. O’Sullivan cites four career moments when Swift took a “destructive” path that weakened the competition and strengthened her brand:

1. In 2014, Swift withdrew her music from Spotify, the fastest-growing music streaming platform at that time, because she believed its compensation model for artists devalued their work.

Why wasn’t the move “fatal,” as many industry experts assumed it would be? The “friendship first” and “music later” relationship she has with her fans plays an important role, according to O’Sullivan.

“Taylor Swift can be compared to a Rolex watch, not a Swatch,” O’Sullivan writes. “The harder it is for people to access her music, the more they crave her and are willing to follow her. By withdrawing her music, Taylor Swift became what is known as a ‘Veblen’ or a ‘luxury’ good.”

When Swift left Spotify, her music was in the playlists of more than 19 million users; the week she returned in 2017, she hit nearly 48 million streams.

Related: 3 Lessons for Entrepreneurs From Spotify, Which Won Over Taylor Swift and Just Made its Billion-Dollar IPO

2. Swift isn’t afraid to “beef” with other musicians and celebrities — like Kanye West after he told her on stage at the 2009 MTV Music Video Awards that “Beyonce had the best video of all time.”

“The more Kanye West beat down Taylor Swift, the stronger her fan base rallied around her, leading to extravagantly higher levels of emotional connection between Taylor and her fans within the Swiftverse,” O’Sullivan says.

O’Sullivan adds that “at least from the outside, Taylor never starts the fights,” which also tends to fit within three main growth-fueling “vibes”: “powerful men taking advantage of less powerful women,” “women who are bitchy and unkind” and “being on the right side of history.”

Related: 7 Business Feuds With More Beef Than Kanye vs. Taylor

3. During the pandemic, Swift released not one but two surprise albums despite marketing limitations amid lockdowns and industry precedents.

“When everybody else was fumbling to get a handle on their life, how was Taylor Swift able to Amazon herself?” O’Sullivan writes. “Well, most of it comes down to the fact that, like Amazon, she has spent her entire career creating, buying and owning her own ‘value chain,’ or the different parts of the music industry that she needs to engage with to release music.”

The Swiftverse is “one hell of a strategic asset,” O’Sullivan notes — and kept her able to deliver core products into the market.

Related: ‘Historically Unprecedented Demand’: Taylor Swift Fans Caused Ticketmaster’s Site To Crash Over 5000 Times

4. Finally, Swift rerecorded her albums after Big Machine Label Group was sold to Scooter Braun‘s Ithaca Holdings.

Some industry leaders considered the lengthy and expensive move one that “would suck the oxygen out of her career” — but because Swift is antifragile, the opposite proved true, O’Sullivan says.

“As Taylor and Amazon both show us, [during a crisis] is exactly when their stock is going to rise,” O’Sullivan writes. “Investors who pay hundreds of millions of dollars to try to own what they think is Taylor Swift’s ‘core product’ (music) simply don’t understand her empire as well as she understands it.”

Related: Taylor Swift Just Made a Surprise Announcement, Revealing the Marketing Genius Behind Her $1.5 Billion Fortune

Going forward, business and strategy leaders who successfully lead through chaos will all be building antifragile organizations — Swift just happens to be ahead of the game, O’Sullivan says.

What’s more, as beneficial as antifragility is, O’Sullivan acknowledges that adopting it isn’t easy. It requires embracing uncertainty and volatility, building resilience and accepting “weird and bad things.”

O’Sullivan’s Good Ideas and Power Moves offers other takeaways from Swift’s career that entrepreneurs and business leaders might find applicable to their own, including how to be a unicorn, have a strategy and stick to it, build a world instead of products, negotiate with authenticity and more.



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Tags: AmazonAmazonsAntifragileBrandingBrandsBusinessCareerCelebritiesCelebrity EntrepreneursentrepreneurGrowing a BusinessGrowth StrategiesinnovationLeadershipMarketingMoneyMoney & FinanceSecretSocial MediaSuccessSuccess StrategiesSwiftTaylorTaylor Swiftwealth

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