“There's language about culture fit. I like to say culture add because culture fit to me means can actually be quite negative toward somebody who is the aberration. You have to fit in and especially if this is like a demographic thing, a person of color, a gay person, a, you know, a person in a wheelchair. So you have to fit in, but a culture ad suggests that actually having some diversity on the team is helpful because it actually adds to the culture”
quote is from the automated transcript, cleaned for reading:
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More from Chip Conley
What-if
Proactive regulatory strategy might have prevented Airbnb's toxic battles in New York
“If we'd started a little earlier, maybe in New York, it wouldn't have gotten to the point where it has been toxic in New York, the whole, for the last dozen years ever since I was there.”
Chip ConleyAug 3, 2025▶ 24:35Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
PredictionNot checkable as stated
AI is accelerating the tech industry's shift from specialists to generalists
“We're moving out of the era of the specialists and into the era of the generalists, and I think AI is just accelerating this.”
Chip ConleyAug 3, 2025▶ 35:40Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Opinion
Apple alumni resonated better with Airbnb's culture than Amazon alumni did
“In fact, Airbnb saw it, I think when with Amazon people Apple people have resonated pretty well at Airbnb, Amazon people less so.”
Chip ConleyAug 3, 2025▶ 50:04Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Opinion
Ageism remains real in tech, but is slightly less ignored today
“Yeah, it, you know, it's clearly a problem. I'd say it's maybe a little bit less of a problem than it was a dozen years ago, because I think a dozen years ago, it was almost a blind spot.”
Chip ConleyAug 3, 2025▶ 27:28Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
AssertionSupported
Research shows life satisfaction historically bottoms out between ages 45 and 50
“The other data point is something called the U curve of happiness. And it's been around for 20 years and it shows the following. It has changed in the last couple of years because young adults are unhappy like never before. So a 20 or a 22 year old really unha…”
Chip ConleyAug 3, 2025▶ 1:02:43Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
AssertionNot checkable as stated
Airbnb once considered shifting its entire platform to be mobile-only
“I remember one point there was a conversation that was going on about taking Airbnb so it was mobile only.”
Chip ConleyAug 3, 2025▶ 9:40Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
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