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Brian Chesky

Co-founder and CEO, Airbnb · 1 appearance on the record.

computed by AI from the episodes · how this works → · full disclaimer →

founderexecutiveinvestor@bchesky ↗LinkedIn ↗airbnb.com ↗Wikipedia ↗Instagram ↗

Brian Chesky co-founded Airbnb in 2008 alongside Joe Gebbia and Nathan Blecharczyk, steering the peer-to-peer home-sharing platform from its inception through its multi-billion-dollar 2020 IPO. A graduate of the Rhode Island School of Design, he is known for applying design-led principles to technology and popularizing hands-on, founder-led operational management.

16statements → 10claims → 6claims resolved → 67%fully supported → 3.88/5average certainty → 1.69/5average debate potential → ≈4.5/5argument clarity, estimated → 30said about them ↓

4 supported 2 partly supported 0 contradicted 4 not checkable as stated how the 10 claims stand · each chip opens the sources

2 predictions · 8 assertions · 2 insights · 4 disclosures · every statement was checked. The predictions and assertions are the 10 claims: statements the public record can support or contradict. 6 are resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Brian argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Chesky: Airbnb bookings rebounded from an 80% drop to 2019 levels
“So it dropped by about 80%, and I mean, you know, nobody knows if this is pent up demand or not, but no, we're around last year's levels.”
Brian Chesky Aug 13, 2020 ▶ 17:14 How I Built Resilience: Brian Chesky of Airbnb

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Brian Chesky on measured tape to publish a rate. This says nothing about how they speak.

Everything Brian Chesky said on How I Built This that made the record, most notable first. Filter by type, assessment or year in the ledger →

Prediction Not checkable as stated
Chesky: Remote work will shift travel to long stays in smaller communities
“I mean, maybe the most fundamental change that I see in our world that's going to happen, if you're so fortunate enough, typically upper middle class person or upper class, not everyone can do this, but for those who can, They're realizing, maybe I'll go a mon…”
Brian Chesky Aug 13, 2020 ▶ 12:19 How I Built Resilience: Brian Chesky of Airbnb
Prediction Not checkable as stated
Chesky: Travelers will shift from crowded cities to outdoor destinations
“People are gonna, instead of traveling to the same 20 cities, going to the same hotel districts that are really crowded, and then standing in line, To get their selfie photo, instead of the same landmarks, to put it on Instagram, say, look, I got that too. The…”
Brian Chesky Aug 13, 2020 ▶ 13:29 How I Built Resilience: Brian Chesky of Airbnb
Disclosure
Chesky: Airbnb gave $250M directly to hosts during the pandemic
“We took a quarter of a billion dollars, two hundred fifty million dollars, and we sent it to our host. Just didn't loan it, just sent it to host.”
Brian Chesky Aug 13, 2020 ▶ 10:40 How I Built Resilience: Brian Chesky of Airbnb
Assertion Not checkable as stated
Chesky: Airbnb is likely one of the world's largest RV rental platforms
“Without having intended to be in that business, we're probably one of the largest, largest RV rental companies in the world. As far as they're not our RVs, it's the communities, but yeah, I'm sure thousands and thousands of RVs.”
Brian Chesky Aug 13, 2020 ▶ 14:51 How I Built Resilience: Brian Chesky of Airbnb
Assertion Supported
Chesky: Airbnb bookings rebounded from an 80% drop to 2019 levels
“So it dropped by about 80%, and I mean, you know, nobody knows if this is pent up demand or not, but no, we're around last year's levels.”
Brian Chesky Aug 13, 2020 ▶ 17:14 How I Built Resilience: Brian Chesky of Airbnb
Disclosure
Chesky: Airbnb will be ready to IPO in 2020 if markets allow
“And we don't know when we'll be public, but I basically said, we'll be ready this year if the market's ready for us. If the market's not ready, we'll be ready when they are.”
Brian Chesky Aug 13, 2020 ▶ 19:51 How I Built Resilience: Brian Chesky of Airbnb
Insight
Chesky: Leaders should reject robotic corporate playbooks when executing layoffs
“There is no playbook, I don't think, to lay people off, and that's the kind of thing that if there was a playbook, you should never use it, because the thing that people want more than anything is, They want humanity. They want compassion, and that means that …”
Brian Chesky Aug 13, 2020 ▶ 2:28 How I Built Resilience: Brian Chesky of Airbnb
Assertion Supported
Chesky: Airbnb lost 80% of its business in eight weeks during COVID-19
“We spent 12 years building Airbnb, and then we lost 80% of business in eight weeks.”
Brian Chesky Aug 13, 2020 ▶ 2:55 How I Built Resilience: Brian Chesky of Airbnb
Assertion Partly supported
Chesky: Airbnb slashed over $1B in planned marketing spend during COVID-19
“We cut over a billion dollars of planned marketing spend.”
Brian Chesky Aug 13, 2020 ▶ 3:18 How I Built Resilience: Brian Chesky of Airbnb
Assertion Partly supported
Chesky: Airbnb raised $2B in emergency financing in 72 hours
“Then we quickly raised two billion dollars... Thankfully we had some great investors step up but we had to do that deal, and that was like over the course of 72 hours to like get that deal done.”
Brian Chesky Aug 13, 2020 ▶ 3:22 How I Built Resilience: Brian Chesky of Airbnb
Assertion Supported
Chesky: Airbnb customers canceled over $1B in bookings at pandemic start
“First thing is we had over, we had customers cancel over one billion dollars of reservations.”
Brian Chesky Aug 13, 2020 ▶ 9:49 How I Built Resilience: Brian Chesky of Airbnb
Insight
Chesky: Hotels require density and cannot serve smaller communities efficiently
“The smaller the community, less likely they have a hotel because a hotel only works with density, right? You need a bunch of rooms, you need efficiency, and so people are basically traveling and going to small communities.”
Brian Chesky Aug 13, 2020 ▶ 17:38 How I Built Resilience: Brian Chesky of Airbnb
Disclosure
Chesky: Airbnb will refocus on core connection rather than travel or real estate
“We didn't start this company to be a travel company. We didn't start this company to be a real estate company. It was about connection, and if it took a crisis for us to get back to that core truth, then that's what we're going to focus on.”
Brian Chesky Aug 13, 2020 ▶ 22:07 How I Built Resilience: Brian Chesky of Airbnb
Disclosure
Chesky: Airbnb planned to file its S-1 in March 2020 before pausing
“We were, we're going to file it late March. We put on the shelf and recently we've been dusting it off, you know, and you have to update it because the business has changed.”
Brian Chesky Aug 13, 2020 ▶ 19:39 How I Built Resilience: Brian Chesky of Airbnb
Assertion Not checkable as stated
Chesky: Airbnb was stretched thin and sprawling across businesses pre-pandemic
“Before a pandemic, Airbnb was stretched thin. We were sprawling. We were going into all these businesses, you know, just kind of feeling pressure of trying to make everyone happy.”
Brian Chesky Aug 13, 2020 ▶ 21:15 How I Built Resilience: Brian Chesky of Airbnb
Assertion Supported
Chesky: Airbnb raised $20K-$30K selling novelty cereal boxes in 2008
“Yeah, like 20 or 30,000. It was yeah, something like that. Joe told the story. We had to raise collectible breakfast cereal. We were air, bed, and breakfast. So we said, well, let's do collectible breakfast cereal for the Democratic-Republican National Convent…”
Brian Chesky Aug 13, 2020 ▶ 8:38 How I Built Resilience: Brian Chesky of Airbnb

The other half of the tape: Brian Chesky's own voice is left out of every number here. Other people bring the name up 24 times in 4 episodes on How I Built This. 6 statements on the record name them. every mention, with the transcript →

Who brings them up most Guy Raz 13Joe Gebbia 10Adam Grant 1

Statements about Brian Chesky, by other people (6)

Assertion Not checkable as stated
Airbnb founders made $20,000 selling $40 novelty Obama O's cereal
“Well, it almost didn't matter, because at 40 dollars a box times 500 boxes, we made 20,000 dollars in breakfast cereal.”
Joe Gebbia Oct 17, 2016 ▶ 23:41 Airbnb: Joe Gebbia
Assertion Not checkable as stated
Airbnb’s SXSW launch yielded just six listings and two bookings
“We actually had six people put up listings in Austin, and we had two people book those listings. One of them was Brian.”
Joe Gebbia Oct 17, 2016 ▶ 11:30 Airbnb: Joe Gebbia
Assertion Not checkable as stated
First prospective guests submitted resumes and LinkedIn profiles for airbeds
“People actually started sending us their resumes, their LinkedIn profiles, to vie for one of these limited three airbeds.”
Joe Gebbia Oct 17, 2016 ▶ 7:07 Airbnb: Joe Gebbia
Assertion Not checkable as stated
Landlord raised their rent by 25% immediately after they quit
“Who politely states that our rent is now 25% higher than it was the month before.”
Joe Gebbia Oct 17, 2016 ▶ 3:14 Airbnb: Joe Gebbia
Assertion Supported
Airbnb originally charged guests $80 per night to sleep on an airbed
“For 80 dollars a night. You could stay in San Francisco with Brian and I.”
Joe Gebbia Oct 17, 2016 ▶ 7:15 Airbnb: Joe Gebbia
Disclosure
Chesky and Gebbia simultaneously quit their jobs to brainstorm startups
“Both of us simultaneously quit our jobs. He left his, I was at Chronicle Books full-time at that point, and I left to dream up something with him.”
Joe Gebbia Oct 17, 2016 ▶ 2:18 Airbnb: Joe Gebbia

Every mention by year

tap a year for its mentions
001012012016201720182019202020212022202320242025episodesmentions
0112016201720182019202020212022202320242025episodes it came up in
00100.52012016201720182019202020212022202320242025episodesmentions per episode
2025 2 mentions in 1 episode
2021 1 mention in 1 episode
2018 3 mentions in 1 episode
2016 18 mentions in 1 episode

Appearances (1)

EpisodeDateSpeaking time
How I Built Resilience: Brian Chesky of Airbnb Aug 13, 2020 16m
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