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.”
Prediction Not 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.”
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.”
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.”
Insight
Hiring for 'culture add' instead of 'culture fit' improves team diversity
“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 …”
Assertion Supported
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…”
Assertion Not 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.”
Assertion Supported
Brian Chesky consulted ex-CIA head George Tenet during 2011 Airbnb crisis
“I remember back in 2011 when the, you know, the big debacle happened with the apartment getting trashed by a guest and. And so Brian decided he was going to go to find, you know, George Tenet, the former head of the CIA.”
Assertion Not checkable as stated
Product reviews with Brian Chesky kept Airbnb employees up all night
“For the product team, my God, I mean, a product meeting with Brian would keep people up the night before not just because they were actually working all night long to get prepared, but also the, they knew they would work all night long because they probably wo…”
Insight
Avoid relying on slide decks when presenting to combustible startup founders
“PowerPoint or whatever, whatever tool you're using. I mean, like, just be careful about being overly reliant upon it. It just, it's. Especially when you have a combustible founder who may take you off path such that your deck in its current order makes no sens…”
Assertion Not publicly verifiable
Airbnb's early HR leader was 25 years old with zero HR background
“The HR department was reporting to me at one point and she was running HR and she was 25 and had no background in HR at all.”
Insight
Midlife tech workers are judged by their energy over their physical age
“When I talk to someone who's in midlife and wants to be in the tech world or already is, the thing I say is show up with curiosity and a passionate engagement for what you do. And people won't necessarily notice your wrinkles as much as they'll notice your ene…”
Assertion Supported
Airbnb famously reframed its core identity from home-sharing to 'belong anywhere'
“And I think one of the things that we did at Airbnb about a year after I joined and when Jonathan Mildenhall was joining is we really tried to ask ourselves, are we in the home sharing business or are we in some kind of business that is Even bigger and broader…”
Assertion Not checkable as stated
Airbnb hosts were roughly 10 years older than guests, says Conley
“The difference in age between our hosts and our guests was Probably about 10 years maybe, and over time it actually got higher because we started actually reaching out more aggressively to, you know, boomers and Gen Xers to be hosts.”
Insight
Align on goals upfront to anchor meetings with intense founders like Chesky
“You start with that because that actually helps to make sure there's alignment. And frankly, if there's not alignment, You might as well not have the meeting. Let's spend the rest of this meeting talking about alignment. That's what I would do because that's s…”
Assertion Not checkable as stated
Chip Conley had never used a Google Doc before joining Airbnb
“I'd never used a Google doc back then when I joined Airbnb.”
Assertion Supported
Brian Chesky sought out Chip Conley because he loved his book 'Peak'
“I had written a book called peak how great companies get their mojo from Maslow. And it was a book that Brian really liked. And part of the reason he wanted to reach out to me.”
Assertion Not checkable as stated
Chip Conley flatlined nine times in 90 minutes from an allergic reaction
“I went flatline from the allergic reaction to the antibiotic. And so I saw, you know, I, it happened nine times over 90 minutes and I kept dying, kept flatlining.”
Assertion Not checkable as stated
Airbnb's average employee age was 26 when 52-year-old Chip Conley joined
“I was 52, the average age was 26.”
Assertion Not checkable as stated
Chesky initially hired Conley as a 15-hour-a-week mentor to Airbnb's founders
“Brian said, I want you to come in for and work 15 hours a week as a consultant, I want you to be my in-house mentor for both me and Joe and Nate and.”
Disclosure
Chip Conley helped establish the governing board of Burning Man
“I helped found the board of Burning Man.”
Chip Conley