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Brian Chesky on crisis, culture and loneliness: interview summary

Airbnb CEO: Airbnb Was Worth Billions & I Was Lonely & Deeply Sad

The Diary Of A CEO · Oct 9, 2023 · about 97 min

Uploaded Oct 9, 2023 · 1.3M views (as of Oct 30, 2026)

Good value given

Airbnb started as a way for Chesky and Joe Gebbia to pay rent.
He says chasing success made him neglect friends and who he was climbing with.
In 2020 Airbnb lost most of its business in about eight weeks.
He wrote crisis principles like act decisive and fast.
He says culture starts where your vision and values meet.

How did Brian Chesky lead Airbnb through the 2020 crisis?

Airbnb lost most of its business in about eight weeks. Chesky wrote down principles, like act decisive and fast, because data-driven people struggle when the data keeps changing. He laid off part of the company with a letter that explained why, and says those who stayed came to work even harder.

Worth watching?Good value given. A personal, emotional talk on success, loneliness and leading Airbnb through the 2020 crisis. His lessons on culture and crisis leadership are strong.

ActionableLessons

Actionable

Write three principles to guide you in a crisis, before one hits.
Reach out to one friend you haven't called in months.
Build for a problem you and a friend share.
Explain hard decisions in writing to your team.

Lessons

Success can be lonely.
Principles guide action when data fails.
Small problems can start big companies.
Culture spreads from the founder.

Quick answer

Brian Chesky sat down with The Diary Of A CEO for this interview, published Oct 9, 2023. Here's our summary in our own words: a verdict, the answer to the big question, 5 takeaways, Actionable and Lessons tabs, then the stories, frameworks and how to use them.

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Watch the interview

Watch on YouTube: Airbnb CEO: Airbnb Was Worth Billions & I Was Lonely & Deeply Sad

Channel: The Diary Of A CEO. Published Oct 9, 2023. About 97 minutes.

Who is Brian Chesky?

Brian Chesky co-founded Airbnb in 2008 and is its CEO.

This is an episode of The Diary Of A CEO with Steven Bartlett.

Key stories from the interview

He talks about wanting love and finding success felt empty at times.
He describes the 2020 collapse and the layoff letter.
He shares Daniel Ek's view on culture changing with age.
He talks about staying curious and open in life.

Frameworks and ideas

Act decisive and fast in crisis.
Solve for you and a friend.
Culture as shared consciousness.
Curiosity: put yourself out there.

In their words (paraphrased)

Act decisive and fast.
You just have to solve a problem for like you and your best friend.
People would do in a room without you what they would do if you were there.

How to apply this

Write down how you want to be remembered in a crisis.
Pick one friend to call this week.
Ask your team what they'd do if you weren't in the room.

Read the biography

Want the longer story? Read our The Airbnb Story summary.

A note on this summary

This page reports what was said in the interview, in our own words. Lines under 'In their words' are paraphrased from the transcript, so check the video for exact wording.

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FAQ: questions people ask

How did Airbnb start?

As a way for the founders to pay rent by hosting guests.

How did Brian Chesky handle the 2020 crisis?

He wrote principles like act decisive and fast, and explained the layoffs in a letter.

Is the Brian Chesky Diary of a CEO interview worth watching?

Good value given. Personal and practical.