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Why more creatives should lead major companies: The story of Airbnb as told by cofounder & CEO Brian Chesky

On the latest episode of Most Innovative Companies podcast, Brian Chesky explains how Airbnb achieved unicorn status three times over by obsessing over ideas, creativity, and customer experience instead of money.

Why more creatives should lead major companies: The story of Airbnb as told by cofounder & CEO Brian Chesky
[Source photo: Fast Company]

“Somebody once said ‘numbers is the language of business.’ No, it’s not. Language is the language of business,” says Brian Chesky, cofounder and CEO of Airbnb. “The key is that, it’s not that creativity should drive everything. It’s that it should be in the room. It should be in the conversation.”

On this week’s Most Innovative Companies Podcast (can’t access a link), Chesky shares how he navigated both the financial crisis and a pandemic to build an iconic brand with staying power. In a world where few creative people helm major companies, Chesky has managed something entirely different.

With $3 billion of free cash flow in the past 12 months (when prior to this, they were a break-even company), Airbnb has achieved unicorn status three times over by obsessing over ideas, creativity, and customer experience instead of money. “Running a company in a design-led way actually is good for business,” Chesky says. “They’re not at odds with each other.”

But how did Airbnb arrive at the place it is today? It wasn’t an easy path, nor was it a straight one. Chesky tells the story of Airbnb in three chapters:

Airbnb’s Chapter One

The first chapter starts with the inception of Airbnb. Shortly after earning his degree in industrial design from Rhode Island School of Design (RISD), Chesky relocated from Los Angeles to San Francisco in 2007 when a former classmate suggested they start a company together. It took persistence, and more than a few credit cards, but they got it off the ground. Moreover, Chesky got Airbnb on international maps, hiring executive teams and adding layers to the business. By all accounts, they were on a rocketship, preparing to take the company public roughly a decade after its founding.

Airbnb’s Chapter Two

Here’s where the second chapter of Airbnb’s story starts. In its push to IPO, Airbnb began to model itself after companies like Amazon.

“We had this pressure of going public on the horizon. So I did probably the opposite of what I should have done. Instead of leaning into what made us different, we started becoming a fairly conventional company,” Chesky says.

The result was a company saddled by 10-plus departments, each with its own subdivisions and each heading somewhere different. “We had leadership issues, process issues, and people were complaining about how it was really hard to get work done,” Chesky says.

There was no central message, no real strategy, he says. That continued for a few years until late 2019 when—thanks in part to a bad dream—Chesky concluded that his company wasn’t heading in the direction he wanted.

But as much as he knew he wanted to do things differently, they’d already written the S1 and were moving forward in January 2020 when the first signs of the COVID-19 pandemic started appearing. “I remember innocently saying in a meeting, ‘Wow, if this thing spread beyond China, it would be really bad.’ Well, within eight weeks, our business dropped by 80%.”

Airbnb’s Chapter Three

That 80% drop would become his defining moment as a CEO and the start of Airbnb’s third chapter.

“Every crisis is an opportunity,” Chesky says. “If you think you’re screwed, everyone else will think they’re screwed. But if you are hopeful and optimistic and [don’t offer] blind optimism that people can’t trust, but [instead offer something] rooted in some reality, then people are gonna have resilience and creativity to keep going. And that became this moment, this rallying cry.”

Taking a cue from Apple’s storied near-bankruptcy moment back in 1997, Chesky returned to his roots as a designer and redesigned Airbnb into the much smaller company it is now. He took its 10 divisions and shuttered almost all of them, bringing the business back to a functional organization with one marketing department and 40% fewer staff due to layoffs and attrition.

“We took a billion dollars of marketing—primarily performance marketing—and we turned it off, and you know what happened? Almost nothing. And we realized our brand is stronger and more differentiated, and we’re gonna lean into our differentiation. We’re gonna do fewer things. We’re gonna be totally functional,” he says. “And we became an entirely creatively led company.”

After realizing that autonomy could actually be disempowering (empowering?), he put the entire company on one single roadmap and stopped running things off of metric. Now, software releases happen twice a year and they emphasize feature marketing, as opposed to brand marketing or performance marketing. Strong ideas benefit from the backing of the entire organization.

Airbnb’s Next Chapter

Now, as Airbnb enters its fourth chapter, they have over six million listings, four million hosts, and one billion guests and counting. Airbnb, in short, has achieved much since 2008—including an IPO in the middle of a global pandemic. In all that time, they’ve been counted out more than once. Early on, many claimed the idea was bound to fail; while years later, headlines professed that COVID-19 would bring about its end. As it turns out, the “worst idea that ever worked” is still working—fueled by creative thinking and an intention to design and deliver something people want, which begs the question: Why aren’t there more creatives at the helm of Fortune 500 companies?

Listen to the episode for the full conversation.

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James Vincent is the guest host of Fast Company’s Most Innovative Companies podcast. He is also a partner and CEO of FNDR, where he has helped founders of some of the world’s biggest companies, including Airbnb and Snap, use the power of narrative to give voice to their vision. Before FNDR and for over a decade, James worked alongside Steve Jobs building Apple’s narrative. More

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