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The Diary Of A CEO with Steven Bartlett

CEO Diaries: Airbnb’s Founder Brian Chesky on Brutal Rejection, Great Leadership, and The Biggest Mistake Founders Make!

The Diary Of A CEO with Steven Bartlett

FlightStory

Society & Culture, Business, Education

4.613.2K Ratings

🗓️ 28 May 2025

⏱️ 15 minutes

🧾️ Download transcript

Summary

From cold emails to global dominance - the Airbnb story began with rejection. In this unmissable episode of CEO Diaries, Airbnb founder and CEO Brian Chesky reveals the brutal truth about rejection, resilience, building world-changing companies, and the one thing more important than product or profit: culture. Visit - ⁠www.linkedin.com/DOAC⁠ Listen to the full episode here - Spotify -https://g2ul0.app.link/WgBxbVavJTb Apple - ⁠https://g2ul0.app.link/89nODBivJTb Watch the Episodes On YouTube - ⁠https://www.youtube.com/c/%20TheDiaryOfACEO/videos Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

This was one of my favorite business conversations that I've ever had on the Diary of a CEO

0:04.0

podcast and it's frankly set the bar for every CEO or co-founder that I ever interview.

0:09.7

Brian taught me more so than any other guest I've ever had on the show how important hiring,

0:15.0

culture and team building is. The reality of running a small business is that switching off

0:19.5

is never really an option.

0:21.3

Even when you try, the ideas, the excitement and all the responsibility is always there.

0:25.8

And because you're always switched on, it's only fair that your hiring partner should be too.

0:30.4

LinkedIn Jobs, who are the sponsor of this moment's episode, has been that hiring partner for me and for years.

0:35.7

Because it's always working away in the background.

0:38.2

My team can post our jobs for free, share them with our networks and reach top talent all in the

0:43.3

same place. So let's get into today's conversation. At the very beginning, I saw this email,

0:51.4

which I think is really important because maybe it's the most important thing,

0:54.9

because there are going to be people starting companies now that are getting a lot of emails

0:59.4

like that.

1:00.7

This is from August 1st, 2008, by the way, so let me give the context this email.

1:07.0

So Joe Nate and I were trying to raise money.

1:09.3

For everyone trying to raise money, I want you to know that Airbnb was trying to raise $150,000

1:14.5

at a $1.5 million, I think, post-money valuation.

1:19.6

I'll give you that right now.

1:20.8

Exactly.

1:22.3

And here's one of many rejection letters.

1:25.7

Hi, Brian.

...

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