Brian Chesky

Brian Chesky likened leading a company to climbing a mountain, where the closer you get to the top, the fewer people are beside you.

the higher you get to the peak, the fewer people there are with you.

Chesky says he has largely abandoned email in favor of texting his team, because replying to a text doesn't feel like work and gets faster responses.

When you get a text message, it doesn’t feel like work to respond.

Chesky says he finds email inferior to almost every other form of communication and rarely drafts original emails.

I just find it inferior to almost every other form of communication

Chesky prefers texting because it is organized around people, creating deeper connection and making responses feel less like work.

You feel a deeper connection to the person. It doesn’t feel like work to respond.

Brian Chesky argues that a leader's psychology tends to become the psychology of the whole organization.

the psychology of the leader often becomes the psychology of the organization.

Chesky says he wishes he were 26 again because today's AI tools are far more powerful for building companies than before.

The Tools Now Are So Much More Powerful

Chesky said regulatory policy on short-term rentals poses a risk to Airbnb but not an existential threat.

CEO Brian Chesky said on the same call that policy is a risk, but not an existential one.

Chesky said guests shouldn't be burdened with checkout chores like running the washer or taking out garbage, though putting trash in a bin is acceptable.

“No one should have to put the towels in the washer and start it,” Airbnb CEO Brian Chesky said in a May interview with The New York Times. He added that putting trash in a bin is fine, but guests should not have to take the garbage out.

Chesky said guests on vacation should be spared chores such as starting the towel wash, and urged hosts to be as hospitable as possible.

“No one should have to put the towels in the washer and start it,” he said. “For hosts, it’s to remember to be as hospitable as possible. These people are on vacation and they’re on vacation from their chores.”

Brian Chesky said Airbnb used Alibaba's Qwen model and described it as fast and cheap.

Airbnb CEO Brian Chesky said in 2025 the company used Alibaba’s Qwen AI model, referring to it as “fast and cheap,” per NPR.

Chesky said Airbnb wants guests to know exactly what they will get before booking, so that check-in is no longer a 'moment of truth'.

“A lot of guests have described booking Airbnb, once they check in, it’s a moment of truth. Is the house exactly what they expected?” he told The Associated Press. “We don’t want this to be a moment of truth. We want you to know exactly what you’re going to get before you book.”