All episodes of How I Built This

How I Built This · 2026-11-02 · 73 min · 14,309 words

Airbnb CEO Brian Chesky: “I Was a Great Founder and a Terrible CEO”

Listen to the original audio · Transcribed with NVIDIA Parakeet · Timestamps stay in sync with the live audio

It was a crucible moment. It was the first moment I had to be A good CEO and it was a life or death moment. 'Cause before that it was a nice to have to be CO. Well, we could grow faster, be less chaotic, but at that moment, either I'm a great CEO and the company survives or I'm a bad CO and the company dies. So it became life or death. Welcome to How I Built This.

A show about innovators, entrepreneurs, idealists, and the stories behind the movements. They built. I'm Guy Raz, and on the show today, how Brian Chesky went from an art school student with no business experience to the CEO of Airbnb, a company worth more than$100 billion, and why building Airbnb turned out to be a lot easier. than learning how to lead it. About ten years ago on this show, I interviewed Joe Jebia, one of the three founders of Airbnb.

And Joe told me the incredible story about how he and his friends Brian Chesky and Nathan Blacharzik turned a few air mattresses on the floor of a San Francisco apartment into a business that transformed the travel industry. It is one of my favorite stories we have ever told on this show. And today we're picking up where that story left off. Now, I've interviewed plenty of founders who spent years, sometimes decades, struggling to get their ideas off the ground. Colin Engel, for example, who, by the way, grew up in the same small town as Brian Chesky, spent more than a decade trying to find the product that would make iRobot a success, which, if you don't remember, it was a Roomba. But Airbnb wasn't really one of those stories. Sure, there were some very difficult early days, but once Airbnb found its footing, It took off and it became one of the most successful startups of all time. Product market fit.

That is the first couple of minutes. The rest is $1.49.

We already have this episode, so unlocking it is cheap and permanent: the full transcript (73 minutes, 14,309 words), segment and word-level timestamps, and .txt, .srt, .vtt and word-level JSON downloads, as many times as you like, forever.

No account needed, we create one from your checkout email. With credits it is 1 credit; packs start at 5 episodes for $3.49, and monthly plans are cheaper still.

get it now

Ready in under two minutes.

pay once · credits never expire

monthly · cheapest per episode · cancel any time

One episode is up to 4 hours of audio; a longer one counts as one more for every started 4 hours. Secure checkout by Stripe. Paying once needs no account: we create one from your email. By paying you agree to the terms.