Brian Chesky

10 statements across 9 episodes · 8 bullish · 0 bearish · 6 people on the record · first statement Jan 11, 2017 by Sam Altman · said 54 times in 23 episodes since 2014 · across every show →

Mentions by year

brought up most by Sam Altman (17), Garry Tan (10), Gustaf Alströmer (8), Michael Seibel (4), Craig Cannon (3), Dylan Field (2), Tom Blomfield (1), Rujul Zaparde (1)

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0352014201520162017201820192020202120222023202420252026episodes it came up in
002.52.5552014201520162017201820192020202120222023202420252026episodesmentions per episode
2026 7 mentions in 3 episodes 2 per episode
2025 9 mentions in 5 episodes 2 per episode
2024 1 mention in 1 episode
2023 4 mentions in 2 episodes 2 per episode
2022 9 mentions in 2 episodes 5 per episode
2018 6 mentions in 4 episodes 2 per episode
2017 15 mentions in 4 episodes 4 per episode
2016 2 mentions in 1 episode
2014 1 mention in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Brian Chesky, oldest first

Jan 11, 2017 positive
Assertion Not checkable as stated
Altman: Evan Spiegel and Brian Chesky are both lightly technical founders
“So first of all, I'd say they're both lightly technical, both of those guys. They both know a little bit. Brian is a great designer and was able to design the first version.”
Sam Altman Jan 11, 2017 ▶ 9:16 Office Hours with Sam Altman · Y Combinator
Mar 17, 2017 neutral
Assertion Supported
Altman: Chesky asked if candidates would work with one year to live
“He used to ask people before he hired them at Airbnb if they would take the job if they got a medical diagnosis that they had one year left to live.”
Sam Altman Mar 17, 2017 ▶ 9:05 Team and Execution with Sam Altman (How to Start a Startup 2014: Lecture 2) · Y Combinator
May 31, 2017 positive
Assertion Not checkable as stated
Altman: Brian Chesky spent 20 nights a month dining with non-reporting employees
“I can't, I'm not a hundred percent sure who told me this. I think it was Brian Chesky. he used to spend, or still does spend, like, 20 of his 30 nights a month taking key Airbnb employees that don't report him out to dinner. And is just like, let's talk, I…”
Sam Altman May 31, 2017 ▶ 31:29 From Startup to Scaleup | Sam Altman and Reid Hoffman · Y Combinator
Mar 6, 2018 positive
Insight
Altman: Seed investors must evaluate founder growth rate, not current polish
“If you look at a founder who comes to meet you for a seed round and compare that founder to Brian Chesky, you'll be disappointed a hundred percent of the time. That is the wrong comparison. You will never write a check. However just like startups, you look at …”
Sam Altman Mar 6, 2018 ▶ 19:39 Sam Altman - Startup Investor School Day 1 · Y Combinator
Mar 8, 2018 positive
Opinion
Brian Chesky and Ben Silbermann scaled rapidly by internalizing new domains
“Ben, the CEO of Pinterest is a great example of this, where every time you talk to him, ah, six months, ah, ah, later he'll have, ah, internalized everything and have learned way more than you ever knew about a topic. And so that's an example of somebody who's…”
Elad Gil Mar 8, 2018 ▶ 15:44 Elad Gil and Pejman Nozad - Startup Investor School Day 3 · Y Combinator
Dec 1, 2022 positive
Assertion Not checkable as stated
Airbnb co-founders still receive host calls on their personal cell phones
“Still today, Brian and Joe gets calls from hosts on their personal cell phone numbers. I remember them telling me that on the first day I worked at Airbnb, Why do they do that? Well, it's the number that they put on the website and share with all of their host…”
Gustaf Alströmer Dec 1, 2022 ▶ 2:39 How To Talk To Users | Startup School · Y Combinator
Dec 1, 2022 neutral
Assertion Supported
Brian Chesky spent a weekend with Airbnb's very first guest
“Brian is the co-founder and CEO of Airbnb. On the left side of the photo is Amol. Amol was the very first guest on Airbnb. They actually spent a weekend together in San Francisco when Airbnb kind of launched.”
Gustaf Alströmer Dec 1, 2022 ▶ 1:04 How To Talk To Users | Startup School · Y Combinator
Jan 11, 2023 positive
Disclosure
Seibel: Brian Chesky Angel Invested in Socialcam via a Brief Email
“I remember when I was starting social cam, I emailed Brian Chesky saying, do you want to angel invest? He was like, sure. That's it. Like that was like, that was the entire time that he spent probably less than”
Michael Seibel Jan 11, 2023 ▶ 25:25 The Secrets To Setting Smarter Goals · Y Combinator
Jan 8, 2025 positive
Opinion
Zaparde: Airbnb needed conflict to stop promotion-driven projects
“There was like, there was a need for change, right? And like a need for like creating conflict within the company to actually ask the hard questions and say, Hey, do we need these folks or are, or, you know, are we actually doing this project because somebody …”
Rujul Zaparde Jan 8, 2025 ▶ 13:33 Building A $2 Billion SaaS Company: Lessons From A Two Time Founder · Y Combinator
Jun 25, 2026 positive
Opinion
Pincus: 'Founder mode' applies to every founder, not just elite exceptions
“Founder mode is for Every founder. I like to say to founders, you went and became a founder to bet on yourself, and now you don't, you shouldn't abdicate that to somebody else, to your board or your investors.”
Mark Pincus Jun 25, 2026 ▶ 22:47 Zynga Founder: Consumer Is Not Investible Right Now - Thats Why You Should Build It · Y Combinator
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