Understanding Brian Chesky: Behind Airbnb's Latest Expansion



You can’t understand where Airbnb is going without understanding Brian Chesky. Yes, Skift will be covering all the business angles around the decision to relaunch experiences and add new hotel-style services.

But that’s not the full story. If you know Brian Chesky – and I’ve interviewed and met him many times – you can understand what he’s trying to do.

Founders like him that are driven are always on the search. With Brian, he’s talked a lot about loneliness and how to forge human connection.

When Airbnb was starting, that was the kernel of it, the host and guest connection. And he’s expanded it.

You could do all the business analysis you want, but the experiences relaunch was a manifestation of his need to overcome loneliness. Especially for somebody of his stature — at the level he is – there’s a lot of loneliness involved, as I understand in my own small way as a founder and CEO.

In a world that’s more polarized, he feels it, we feel it, we’re overwhelmed by all these digital channels. The disconnect from human-to-human connection is there.

And this quest for him, in his own way, is trying to connect with the world. And that manifests as experiences. That manifests as all the new things he’s launching. That’s why he doesn’t want to launch a random thing that doesn’t result in human-to-human connection. That’s really at the core of why Airbnb is expanding these other verticals.

It’s a billion-dollar company with a board that Brian is responsible for. It’s still his vision that continues there. “Founder Mode” is very much that he needs to take hold of the company and whatever he’s in search of, and create businesses that build on that.

As a founder who has willed into existence an iconic company, Brian Chesky has this life of searching, which in my own way as a founder of this small company – Skift – I totally empathize with.

If you aren’t able to see the video properly here, check this out directly on my Linkedin post.



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