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