The 7-Word Question Airbnb CEO Brian Chesky Says All Founders Should Ask Themselves

When Brian Chesky, CEO and co-founder of Airbnb meets other entrepreneurs, he always asks the same question. It’s one that might sound confrontational to some. Others might see it as a prelude to an investment. But Chesky says it’s the best way to determine what’s to come. 

It’s not an especially hard question, but it’s one that forces founders to quickly get to the core of their business. 

The question is “Why does your company deserve to exist?” and Chesky has heard all sorts of answers. 

“The best kind of generic answer I’ve ever heard is, ‘Because if I don’t do it, no one else will,’” he told the Masters of Scale podcast recently. “I think business leaders should focus on a unique contribution they can make.”

That’s something that’s especially topical as artificial intelligence threatens to become a major guiding force in all manner of worlds, from business to pop culture to art. Chesky acknowledges we’re in revolutionary and exciting times as AI builds. His concern, though, is that there are just a handful of companies building this future – and they are, for the most part, driven by engineers, rather than people who have backgrounds in humanities (who have been responsible for previous eras). That could limit the possibilities, he says.

“My concern with AI is that only a few people are going to be building the future,” said Chesky. “I think the best-case scenario is that everyone’s building the future together. Everyone … should participate. And if you are one of the people building the future, you should enlist as many different types of people to build the future because we want to live in a world that is completely multidisciplinary.”

Brian Chesky himself started as an artist, he said, attending the Rhode Island School of Design, then going into industrial design. That perspective, he says, helped him in ways some investors had trouble envisioning.

Design, he said, means more than figuring out how an app looks. It’s knowing that greatness is often built on simplicity, drilling an experience down to its essence. And that’s something that was at the core of his 2024 talk about founder mode that helped start that movement in the entrepreneur community.

“I tried to redesign our company, hence founder mode, which was this idea that there was a different way to run a company,” he said. ” I think we need more design in the world, and design is just a different way to assemble something, do a job better. In the age of AI where more and more coding can be done by the AI because software is a language, I think increasingly we’re all going to become designers.”

The risk of following trends

With his “Why does your company deserve to exist?” question, Brian Chesky is also looking to push founders to do more than just follow trends. By the time a product or industry becomes a trend, he warns, it’s too late. Often a better strategy is to look at opportunities to be found by bucking those trends.

As an example, he pointed out that the first word in artificial intelligence is “artificial,” making the opposite of that the real world. Focusing on real-world experiences could be a way to avoid getting caught up in the AI tsunami, he said. And the same advice, he said, holds true for the robotics field.

“I don’t think you want a robot to give you a massage anytime soon. And I don’t think you want an AI to do this experience. You want a human connection,” he said. “People want real connections in the real world.”

Airbnb is following this advice, expanding its offerings this year to include experiences and services. The company was founded the same year as the iPhone, but in those 20 years, while some people have used Airbnb to explore the world, a good deal more have become isolated, staring at their phones instead of the world around them.

“I want Airbnb to be the company that gets you off your phone,” he said. “Because I think real connection happens in the real world. And I think a big thing that’s happening is people want to feel like they’re a part of something, they belong. … People think of [Airbnb] as a travel app, and it is, but I think in the future it’s going to be much more than just travel.”