Airbnb

includes Airbnb Plus, Airbnb Experiences, Airbnb Guest Favorites, Airbnb Neighborhoods, Airbnb Search

130 statements across 57 episodes · 43 bullish · 13 bearish · 25 people on the record · first statement Jul 31, 2022 by Lenny Rachitsky · said 798 times in 156 episodes since 2022 · across every show →

Mentions by year, the whole family

brought up most by Lenny Rachitsky (530), Brian Chesky (22), Jiaona Zhang (19), Chip Conley (16), Jason Shah (14), Ronny Kohavi (12), Ramesh Johari (12), Vlad Loktev (11)

tap a year for its mentions
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0408020222023202420252026episodes it came up in
0044088020222023202420252026episodesmentions per episode
2026 14 mentions in 7 episodes 2 per episode
2025 120 mentions in 30 episodes 4 per episode
2024 102 mentions in 26 episodes 4 per episode
2023 437 mentions in 67 episodes 7 per episode
2022 125 mentions in 26 episodes 5 per episode

every mention, scene by scene, with the transcript →

Everything said about Airbnb, oldest first

Jul 31, 2022 positive
Assertion Not checkable as stated
Rachitsky: Adding a snooze feature was a major win at Airbnb
“This also reminds me at Airbnb, this was actually one of the biggest wins is adding a snooze feature to your listing.”
Lenny Rachitsky Jul 31, 2022 ▶ 39:44 How to scrappily hire for, measure, and unlock growth | Crystal Widjaja, Gojek and Kumu
Aug 14, 2022 negative
Insight
Mehrotra: Asking candidates company-specific home-court questions is a flawed evaluation method
“A common mistake people make is they do all questions in home court. Hey, you know, if you're joining Airbnb, what would you do about X? And then, you know, what is the candidate going to say? They can't, clearly can't be as thoughtful as you. They haven't tho…”
Shishir Mehrotra Aug 14, 2022 ▶ 1:22:08 The rituals of great teams | Shishir Mehrotra, Coda, YouTube, Microsoft
Aug 14, 2022 positive
Assertion Not checkable as stated
Mehrotra: Brian Chesky prioritizes to-do lists by maximal leverage, not urgency
“Brian also has another one that's in the book. That's about how to rank your to-do list by finding leverage. That's a really fun one as well. And like don't rank your to-do list, but a lot of people do like importance versus urgency or so on. And I guess he so…”
Shishir Mehrotra Aug 14, 2022 ▶ 45:37 The rituals of great teams | Shishir Mehrotra, Coda, YouTube, Microsoft
Sep 15, 2022 positive
Assertion Not checkable as stated
Rachitsky: Airbnb's PM Team Trained Weekly with an Improv Teacher
“Actually at Airbnb, we had an improv teacher come and work with the PM team. It was like for months, we did like improv games every once a week and played all these fun things.”
Lenny Rachitsky Sep 15, 2022 ▶ 6:35 When to invest in new acquisition channels | Adam Grenier (Uber, MasterClass)
Sep 15, 2022 negative
Assertion Not checkable as stated
Rachitsky: Airbnb wasted a month building a useless Apple TV app
“Airbnb, Apple's coming out with Apple TV, I think it was, and they're just like, hey, Airbnb, you should make an app for Apple TV. It'll be huge. And there's a team put on it, I don't know, they spent a month building this app and did not, a bunch of nothing a…”
Lenny Rachitsky Sep 15, 2022 ▶ 36:39 When to invest in new acquisition channels | Adam Grenier (Uber, MasterClass)
Sep 18, 2022 positive
Assertion Not checkable as stated
Rachitsky: Brian Chesky personally reviewed every Airbnb product screen
“Like he used to review every product launch and every screen of every new product. Like we had to show him, here's what we're launching this week and just kind of went through and either blew it up or let it pass.”
Lenny Rachitsky Sep 18, 2022 ▶ 32:57 Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)
Sep 18, 2022 neutral
Insight
Shah: Amazon works backwards from launch; Airbnb works backwards from quality
“I would almost frame it as working backwards from sort of like a moment in time or a launch, like you said with Amazon versus working backwards from a quality standard in some sense of an 11 star experience.”
Jason Shah Sep 18, 2022 ▶ 28:37 Building a meaningful career | Jason Shah (Airbnb, Amazon, Microsoft, Alchemy)
Sep 29, 2022 positive
Assertion Supported
Airbnb hired a full-time Pixar storyboard artist for Project Snow White
“Airbnb hired a full-time Storyboard artists from Pixar to draw these keyframes.”
Lenny Rachitsky Sep 29, 2022 ▶ 18:30 Customer-led growth | Georgiana Laudi (Forget The Funnel)
Oct 9, 2022
Insight
Hockenmaier: Low-frequency marketplaces struggle with customer retention and reacquisition
“I do think if you go to a place that is low frequency, It comes with all kinds of new challenges because without frequency, customers forget about you. And so what is the hook to get them to come back? Do you have to reacquire traffic? It creates a whole other…”
Dan Hockenmaier Oct 9, 2022 ▶ 54:00 Developing a growth model + marketplace growth strategy | Dan Hockenmaier
Oct 27, 2022
Assertion Supported
Airbnb's complete corporate rebrand took roughly 18 months from start to finish
“It took, I think a year and a half for them from start to finish to get to something they were really excited about, ready to launch.”
Lenny Rachitsky Oct 27, 2022 ▶ 38:24 Category creation and brand building | Barbra Gago (Pando, Miro, Greenhouse, Culture Amp)
Nov 3, 2022
Assertion Not checkable as stated
Rachitsky: Airbnb assigned target engineer profiles to employees during tech meetups
“It reminds me it was time at Airbnb where we had these meetups for engineers. Every month or so, or it's like a tech, oh, it's a tech talk, and then all the engineers get a target engineer that is coming to the end. They get their profile, their picture, and t…”
Lenny Rachitsky Nov 3, 2022 ▶ 26:56 Lessons from one of the world’s top executive recruiters | Lauren Ipsen (Daversa Partners, GC)
Nov 20, 2022 neutral
Insight
McAllister: Correct Product Strategies Fail Without Earning Stakeholder Support
“Well, I would say that if you have a certain approach, now you may be, you believe it's the right one. It may be the right one, but if you don't build the support and the relationships, you know, that they're going to help carry that out and execute on that st…”
Ian McAllister Nov 20, 2022 ▶ 36:24 What it takes to become a top 1% PM | Ian McAllister (Uber, Amazon, Airbnb)
Feb 9, 2023 neutral
Assertion Supported
Rachitsky: Chesky wanted all Airbnb employees to be hosts
“So at Airbnb, we actually had a similar program where Brian wanted everyone to be a host at Airbnb.”
Lenny Rachitsky Feb 9, 2023 ▶ 11:59 Leading with empathy | Keith Yandell (DoorDash, Uber)
Feb 12, 2023 neutral
Disclosure
Rachitsky: Airbnb's segmented host onboarding had minimal success
“Because we actually did something like this at Airbnb and it was a tiny bit successful when for host onboarding, but it wasn't anything big.”
Lenny Rachitsky Feb 12, 2023 ▶ 20:15 Mastering onboarding | Lauryn Isford (Head of Growth at Airtable)
Mar 2, 2023
Insight
Alströmer: Outlier successful startup ideas often do not make logical sense
“Those kind of ideas, like the ones that end up succeeding often don't make sense to people. And there's something, there's some reason that they, that no one has done this before, because they're just not natural next step of the world.”
Gustaf Alströmer Mar 2, 2023 ▶ 44:45 Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb)
Mar 2, 2023 positive
Opinion
Alströmer: Airbnb's early business model was so strong it was hard to fail
“The last thing I would say is like, F&B had an incredible business model, an incredible business from early on, and it was hard to fail. And what I mean by that is, it's hard to fail with a company. You can fail with individual things inside the company, but t…”
Gustaf Alströmer Mar 2, 2023 ▶ 9:52 Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb)
Mar 2, 2023 positive
Assertion Supported
Alströmer: Most of Airbnb's first 10 to 15 PMs were former founders
“Like most startups don't have most of the PMs being former founders, but that I believe that was the case for the first like 10 or 12 or 15 PMs that there'd be. A lot of us were former founders. And I think that that made a big difference for how you make deci…”
Gustaf Alströmer Mar 2, 2023 ▶ 8:59 Lessons from working with 600+ YC startups | Gustaf Alströmer (Y Combinator, Airbnb)
Mar 19, 2023
Assertion Supported
Rachitsky: Airbnb hired a Pixar artist to storyboard user journeys
“They basically hired a Pixar storyboard artist to draw out key frames of the journey of a host and a guest. And that became a central element of the strategy of like, let's make each of these moments as amazing as possible. And it was based on the movie, Snow …”
Lenny Rachitsky Mar 19, 2023 ▶ 1:02:42 Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO)
Mar 19, 2023
Assertion Not publicly verifiable
Rachitsky: Airbnb titled product managers 'producers' for roughly 18 months
“There was a period where product managers were actually called producers because one of the founders was like, we just, we don't want to manage product. We want to produce beautiful experiences and like a movie producer. And so that was like a year and a half …”
Lenny Rachitsky Mar 19, 2023 ▶ 1:05:19 Competing with giants: An inside look at how The Browser Company builds product | Josh Miller (CEO)
May 7, 2023
Assertion Not checkable as stated
Airbnb listing photos achieved significantly higher conversion rates without people in them
“That reminds me at Airbnb, the photography team found, and actually the photography team was initially including people in the photos of listings. And that was like the hero images of listing photos. And it turns out when there's no people in the listing photo…”
Lenny Rachitsky May 7, 2023 ▶ 42:04 Mastering paid growth | Jonathan Becker (Thrive Digital)
Jun 1, 2023 positive
Assertion Partly supported
Rachitsky: Airbnb built strategy around six storyboard journey frames
“And they ended up drawing these key frames of the journey, as you described, and they became, they put it right in the center of the office. Here's the journey of a host and a guest. That's like 12 frames of that journey. And that actually became the strategy …”
Lenny Rachitsky Jun 1, 2023 ▶ 1:10:36 Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks
Jun 1, 2023 neutral
Assertion Supported
Rachitsky: Airbnb hired a Pixar artist for a year to storyboard journeys
“And it was actually indeed a Pixar storyboard artist that they hired for like a year. That was his job. Draw these keyframes.”
Lenny Rachitsky Jun 1, 2023 ▶ 1:11:19 Storytelling with Nancy Duarte: How to craft compelling presentations and tell a story that sticks
Jun 11, 2023 neutral
Assertion Supported
Rachitsky: Airbnb renamed its product management function to product marketing
“And I don't know if you know this, but actually at Airbnb, The product management function has been renamed to product marketing. So all the product managers are product marketers because Brian is so big on, you're not just building product, your job is also…”
Lenny Rachitsky Jun 11, 2023 ▶ 1:14:41 Building a long and meaningful career | Nikhyl Singhal (Meta, Google)
Jul 2, 2023
Insight
Zhang: Marketplace platforms struggle to build operational muscles from scratch
“So for example, Airbnb, we weren't that strong in operations. We, again, we're this platform with this marketplace, right? And so if you don't have that muscle and then you're asking the company, the teams to essentially build it from the ground up, that's rea…”
Jiaona Zhang Jul 2, 2023 ▶ 8:04 Building minimum lovable products, stories from WeWork & Airbnb, and thriving as a PM | Jiaona Zhang
Jul 2, 2023 bearish
What-if
Zhang: Airbnb Plus unit economics never would have worked out
“And so I, yeah, I personally don't believe the unit economics ever would have really worked out. I think we should have known that we should have dug into that more at the very beginning and then to get very tailored instead of like one blunt instrument to sol…”
Jiaona Zhang Jul 2, 2023 ▶ 10:33 Building minimum lovable products, stories from WeWork & Airbnb, and thriving as a PM | Jiaona Zhang
Jul 2, 2023 negative
What-if
Zhang: Airbnb should have ignored Plus and doubled down on core homes
“So I think that that same lesson would apply to Airbnb would have in my head, like change the way we invested. I think we would have gotten more returns as opposed to spreading ourselves and then like having things that like sort of work, but then didn't quite…”
Jiaona Zhang Jul 2, 2023 ▶ 54:52 Building minimum lovable products, stories from WeWork & Airbnb, and thriving as a PM | Jiaona Zhang
Jul 2, 2023
Disclosure
Zhang: Left Airbnb Home Inspection Team to Focus on Scalable Review System
“And I explicitly, you know, moved off the team and I was like, I'm going to work on the review system. I'm going to continue to evolve this and make it better because that is the actual scalable way to do this as opposed to keep going at it in the very manual …”
Jiaona Zhang Jul 2, 2023 ▶ 15:47 Building minimum lovable products, stories from WeWork & Airbnb, and thriving as a PM | Jiaona Zhang
Jul 27, 2023 positive
Assertion Not checkable as stated
Airbnb's search team drove a 6% revenue gain across 250 experiments
“Another example that I am allowed to speak about from Airbnb Is the fact that we ran some 250 experiments in my tenure there in search relevance. And again, small improvements added up. So this became overall a six percent improvement to revenue.”
Ronny Kohavi Jul 27, 2023 ▶ 12:28 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 negative
Opinion
Airbnb's Online Experiences had poor initial data and became a footnote
“In fact, if you look at one investment, one big investment that was done at the time was online experiences, and the initial data wasn't very promising, and I think today it's a footnote.”
Ronny Kohavi Jul 27, 2023 ▶ 49:49 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 neutral
Disclosure
Airbnb's search relevance team launched nothing without an A/B test
“One is in my team in search relevance, everything was A-B tested. So while Brian can focus on some of the design aspects, the people who are actually doing, you know, the neural networks and the search, Everything was AB tested to help. So nothing was launchin…”
Ronny Kohavi Jul 27, 2023 ▶ 46:23 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 neutral
Assertion Supported
Airbnb's experiment failure rate was 92%, while Google Ads hit 80-90%
“And then at Airbnb this 92% number is You know, the highest failure rate that I've observed. Now I've quoted other sources that, you know, it's not that I worked at groups that were particularly bad booking Google ads, other companies published numbers. There …”
Ronny Kohavi Jul 27, 2023 ▶ 14:03 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 negative
Assertion Not checkable as stated
An early Airbnb feature showing friends' stays had no measurable impact
“At Airbnb early on. There was a big social attempt to make like, here's your friends have stayed at these Airbnb's completely not, had no impact.”
Lenny Rachitsky Jul 27, 2023 ▶ 24:11 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 neutral
What-if
Kohavi: Airbnb's revenue would have grown just as much without COVID pivots
“I think if Airbnb stayed the course, did nothing, the revenue would have gone up in the same way.”
Ronny Kohavi Jul 27, 2023 ▶ 49:41 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 negative
What-if
Kohavi: Airbnb would be in a better state today with more experiments
“I believe that had Airbnb kept people like Greg really, which was pushing for a lot more data driven and had Airbnb run more experiments. It would have been in a better state than today, but it's the counterfactual. We don't know.”
Ronny Kohavi Jul 27, 2023 ▶ 47:00 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023
Disclosure
Airbnb required teams to replicate A/B tests with borderline p-values
“When I worked at Airbnb, one of the things we did is we said, okay, if you're less than .5, but above .1, rerun, replicate. When you replicate, you can combine the two experiments and get a combined p-value using something called Fisher's method or Stauffer's …”
Ronny Kohavi Jul 27, 2023 ▶ 1:04:57 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 neutral
Assertion Supported
A statistically significant Airbnb search result still carried a 26% false-positive risk
“If you're at Airbnb where the success rate of, or Airbnb search where the success rate is only eight percent, if you get a statistically significant result with a p-value less than point oh five, there is a 26% chance that this is a false positive result. Righ…”
Ronny Kohavi Jul 27, 2023 ▶ 1:04:35 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 negative
Opinion
Airbnb's weak experimentation platform forced heavy hiring of data scientists
“I think, you know, one of the things that I will say at Airbnb is the analysis was relatively weak. And so lots of data scientists were hired to be able to compensate for the fact that the platform didn't do enough.”
Ronny Kohavi Jul 27, 2023 ▶ 1:11:25 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Jul 27, 2023 positive
Assertion Not publicly verifiable
Airbnb tested its entire rebrand and homepage redesign with a holdout group
“When Airbnb launched the rebrand, even that they ran as an experiment with the entire homepage redesign, the new logo and all that. And I think there was a long-term holdout even, and I think it was positive in the end from what I remember.”
Lenny Rachitsky Jul 27, 2023 ▶ 45:27 The ultimate guide to A/B testing | Ronny Kohavi (Airbnb, Microsoft, Amazon)
Aug 10, 2023 positive
Insight
Miller: Early PLG works with 10 customer interviews over big data
“If you don't have data to tell you exactly what every single person is doing in your product in aggregate, you can still talk to 10 customers and probably get a clear sense of what's happening and why it's happening, which you wouldn't even get from the quant …”
Chris Miller Aug 10, 2023 ▶ 1:07:20 Relentless curiosity, radical accountability, and HubSpot’s winning growth formula | Chris Miller
Sep 3, 2023 neutral
Assertion Not checkable as stated
Airbnb shifted its core focus from host happiness to guest experience
“That's exactly the same transition Airbnb went through. Initially it was focus on hosts, make sure hosts are the happiest people and do everything we need to make them happy. And then eventually realize like the business is the customers buying the product and…”
Lenny Rachitsky Sep 3, 2023 ▶ 23:24 Inside Etsy’s product, growth, and marketplace evolution | Tim Holley (VP of Product)
Sep 3, 2023 positive
Assertion Not checkable as stated
Opening search listings in new tabs boosted Airbnb conversion by 1%
“One of the biggest wins for Airbnb's search experience was this very small idea of just what if you open each listing in the search results in a new tab. Ended up converting like one percent, like increasing conversion by one percent.”
Lenny Rachitsky Sep 3, 2023 ▶ 33:27 Inside Etsy’s product, growth, and marketplace evolution | Tim Holley (VP of Product)
Sep 24, 2023
Assertion Not checkable as stated
Historically, hosts ignored or rejected 50% of early Airbnb booking requests
“Most of Airbnb back in the day was you request to book with a host. You're like, Hey, can I stay in your home? And turned out, 50% of the time the guest was ignored or rejected, and the host was just like, nah, no thank you.”
Lenny Rachitsky Sep 24, 2023 ▶ 24:34 How to drive word of mouth | Nilan Peiris (CPO of Wise)
Sep 24, 2023
Assertion Not checkable as stated
Airbnb measured word-of-mouth growth using an onboarding interstitial survey pop-up
“That's actually at Airbnb exactly how the team did that to understand what percentage of growth was right about. It's just a little interstitial pop-up when you visit, say, airbnb.com. How'd you hear about us?”
Lenny Rachitsky Sep 24, 2023 ▶ 7:27 How to drive word of mouth | Nilan Peiris (CPO of Wise)
Sep 24, 2023 positive
Assertion Not publicly verifiable
Over 80% of current Airbnb bookings are Instant Bookings
“Now, over 80%, as far as I know, of bookings or instant bookings, where you just book and it's done, just like every other place you book online.”
Lenny Rachitsky Sep 24, 2023 ▶ 24:49 How to drive word of mouth | Nilan Peiris (CPO of Wise)
Oct 5, 2023 positive
Assertion Supported
Rachitsky: Chesky dedicated a year and homepage takeover to launch Trips
“Brian basically focused on that full time for a while, for like a year. That's the thing he was focused on. We're going to make this thing work. And I'm going to PM this thing and make it work and make it awesome. And when they launched, the easy thing to do w…”
Lenny Rachitsky Oct 5, 2023 ▶ 1:29:04 Brian Balfour: 10 lessons on career, growth, and life
Oct 15, 2023 positive
Insight
Designers must balance functional community and cross-disciplinary team identities
“You have two t-shirts. You have the design t-shirt and you have the like marketplace t-shirt or whatever, you know, cross-disciplinary team that you work on because both are really important communities to build for slightly different reasons.”
Katie Dill Oct 15, 2023 ▶ 10:42 Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)
Oct 15, 2023 positive
Assertion Not checkable as stated
Airbnb CEO Brian Chesky acts as the chief editor for all products
“At Airbnb, you know, Brian Chesky is like the editor of all the things that, you know, come together”
Katie Dill Oct 15, 2023 ▶ 31:36 Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)
Oct 15, 2023
Assertion Not checkable as stated
Airbnb's design team achieved the company's highest engagement scores under Katie Dill
“And then, you know, a couple months later, we had the best engagement scores in the company.”
Katie Dill Oct 15, 2023 ▶ 9:17 Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)
Oct 15, 2023 positive
Insight
Katie Dill: Team performance equals potential minus interference
“Performance equals potential Minus interference.”
Katie Dill Oct 15, 2023 ▶ 55:02 Building beautiful products with Stripe’s Head of Design | Katie Dill (Stripe, Airbnb, Lyft)
Nov 5, 2023 neutral
Assertion Supported
Rachitsky: Airbnb removed 'simplify' from its core values for being unrealistic
“At Airbnb, one of the core values at Airbnb for time was simplify is this idea that we should always try to be simplifying. And then it turned out the founders realized we're not actually great at this. And it's unfair for us to say this is a value for not doi…”
Lenny Rachitsky Nov 5, 2023 ▶ 17:11 Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, TripAdvisor)
Nov 9, 2023 positive
Disclosure
Rachitsky: Double-blind reviews at Airbnb primarily boosted review submission rates
“I also led the review system flows for a while at Airbnb. And one of the things I'm most proud of is launching what we call double blind reviews, where you don't see the other person's review until you leave your review. And we, the intention was to create mor…”
Lenny Rachitsky Nov 9, 2023 ▶ 1:07:15 Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor)
Nov 9, 2023
Insight
Johari: Marketplace algorithms should be evaluated on causal outcomes, not historical predictions
“When I think about the distinction about two different, between two different ranking algorithms, I don't want to be only comparing them in terms of how well they recreate the choices people made in the past. The way I'm really going to evaluate those is in my…”
Ramesh Johari Nov 9, 2023 ▶ 36:36 Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor)
Nov 9, 2023
Insight
Johari: Marketplaces sell friction reduction, making both supply and demand their customers
“So those are frictions and what the marketplaces are selling you is taking the friction away. That's what you're paying them for. And it's an important observation because what that means is the marketplace's customers aren't just the people buying the rides o…”
Ramesh Johari Nov 9, 2023 ▶ 7:32 Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor)
Nov 9, 2023 neutral
Assertion Not checkable as stated
Rachitsky: Airbnb's initial Superhost experiment showed no business impact
“We ran an experiment showing the badge to some people and some not actually, which no, no impact at all, which is like super roast itself had no impact at all on the business. As far as we could tell initially, which is also bittersweet because it felt like wi…”
Lenny Rachitsky Nov 9, 2023 ▶ 46:45 Marketplace lessons from Uber, Airbnb, Bumble, and more | Ramesh Johari (Stanford professor)
Nov 12, 2023 positive
Disclosure
Chesky: Airbnb merged product management with product marketing
“What we did is we combined what one might call the inbound product development responsibilities of product manager with the outbound or marketing responsibilities of product marketing.”
Brian Chesky Nov 12, 2023 ▶ 6:59 Brian Chesky’s new playbook
Nov 12, 2023
Disclosure
Chesky: Airbnb eliminated UX writing and combined it with marketing writing
“We got rid of A function called UX writing, and we combined it with marketing writing.”
Brian Chesky Nov 12, 2023 ▶ 30:40 Brian Chesky’s new playbook
Nov 12, 2023 positive
Disclosure
Chesky: Airbnb operates on a rolling two-year roadmap updated biannually
“Now what we do is we do, we have a rolling two-year roadmap. We don't even really do an annual plan. I mean, we, as you remember, Lenny, when you were at Airbnb, we would have like three month planning cycles. Now, planning cycle is just a budgeting cycle, and…”
Brian Chesky Nov 12, 2023 ▶ 13:51 Brian Chesky’s new playbook
Nov 12, 2023
Assertion Contradicted
Chesky: Airbnb spent $1B on Google AdWords in 2019
“And by 2019, We're spending a billion dollars on AdWords.”
Brian Chesky Nov 12, 2023 ▶ 18:45 Brian Chesky’s new playbook
Nov 12, 2023 positive
Insight
Chesky: Industrial design training was essential to building Airbnb
“I don't think I could have ever done what I did if I wasn't an industrial designer. I think industrial designer is different than a graphic designer, because an industrial designer, you have to actually understand, you know, you have to work with engineering i…”
Brian Chesky Nov 12, 2023 ▶ 1:09:34 Brian Chesky’s new playbook
Nov 12, 2023
Assertion Supported
Chesky: Airbnb trained a custom computer vision model on 100M photos
“We built this AI powered photo tour where we created our own AI computer visioning language that we trained on a hundred million photos, and it can basically scan all your photos and organize them by room.”
Brian Chesky Nov 12, 2023 ▶ 44:00 Brian Chesky’s new playbook
Nov 12, 2023
Assertion Supported
Chesky: Airbnb analyzed 370M reviews to curate 2M Guest Favorite listings
“We took three hundred and seventy million reviews on Airbnb, plus millions of customer service tickets, plus all the host cancellation data, and we use all the signal to create the top two million homes.”
Brian Chesky Nov 12, 2023 ▶ 40:24 Brian Chesky’s new playbook
Nov 12, 2023
Insight
Chesky: Micromanaging operational details upfront creates long-term executive time
“If you decide to be in the details and get very, very hands on, like I did, it might be a lot more work for about one to two years. And so for one to two years, it was way more work than the old way. But once we turned the corner, suddenly everyone started row…”
Brian Chesky Nov 12, 2023 ▶ 51:13 Brian Chesky’s new playbook
Nov 12, 2023
Disclosure
Chesky: Airbnb replaced outside ad agencies with an in-house creative agency
“So we use production partners, but we don't use Widening Kennedy or Shite or any of those anymore. We actually build our own in-house agency, so to speak, which is a creative group.”
Brian Chesky Nov 12, 2023 ▶ 30:24 Brian Chesky’s new playbook
Nov 12, 2023 positive
Insight
Chesky: Forcing 10x scale unlocks problem solving via first-principles thinking
“One of the best ways to get unstuck from a problem is to imagine a 10 x scale, or 10 x better, or 10 x faster, where you can't do the current process to do it. You have to think differently about the problem. And to think differently about the problem means yo…”
Brian Chesky Nov 12, 2023 ▶ 47:02 Brian Chesky’s new playbook
Nov 12, 2023
Assertion Supported
Chesky: Airbnb lost 80% of its business in eight weeks during COVID-19
“And then the pandemic occurred and we lost 80% of our business in eight weeks.”
Brian Chesky Nov 12, 2023 ▶ 24:20 Brian Chesky’s new playbook
Nov 19, 2023 positive
Assertion Not checkable as stated
Rachitsky: I earn significantly more as a creator than at Airbnb
“I make significantly more doing what I do now. I try not to talk about the income of this stuff, but it's significantly more than I made at Airbnb as a very senior product leader.”
Lenny Rachitsky Nov 19, 2023 ▶ 27:21 Redefining success, money, and belonging | Paul Millerd (The Pathless Path)
Dec 13, 2023 negative
Opinion
Airbnb Plus unit economics never would have worked out, says Jiaona Zhang
“And so I, yeah, I personally don't believe the unit economics ever would have really worked out. I think we should have known that we should have dug into that more at the very beginning”
Jiaona Zhang Dec 13, 2023 ▶ 44:14 Failure
Dec 17, 2023 neutral
Insight
Fried: Pure software products only need venture capital for marketing
“Airbnb is a physical product. Uber is a physical product. Basecamp, Monday, Asana, they're available everywhere instantly anyway. I don't know what you need the money for other than marketing.”
Jason Fried Dec 17, 2023 ▶ 32:49 Jason Fried challenges your thinking on fundraising, goals, growth, and more
Dec 27, 2023 positive
Insight
Tavel: High supply heterogeneity allowed Airbnb to escape competition
“There's such heterogeneity in the supply for Airbnb that that's what has let Airbnb really close and escape competition.”
Sarah Tavel Dec 27, 2023 ▶ 1:17:55 The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest)
Jan 4, 2024 negative
Insight
Antin: Companies must stop siloing separate research and insights disciplines
“They were like, listen, we have all these different people throwing insights over the transom. And it's great. We want to hear from the data scientists, from the product specialists, from the customer service people and the voice of the customer, whatever, all…”
Judd Antin Jan 4, 2024 ▶ 49:44 The UX Research reckoning is here | Judd Antin (Airbnb, Meta)
Jan 4, 2024 positive
Assertion Not checkable as stated
Antin: Airbnb made millions by changing seven characters on a CTA button
“We changed the text on the button with help from our amazing content design or UX writing team. We basically changed seven characters and made Airbnb millions of dollars.”
Judd Antin Jan 4, 2024 ▶ 35:58 The UX Research reckoning is here | Judd Antin (Airbnb, Meta)
Jan 7, 2024 neutral
Assertion Supported
Rachitsky: Airbnb cut 'simplify' from values for not reflecting reality
“So at Airbnb, we had six values initially. One of them was simplify. And a year or two later, everyone just realized we're not actually good at this. We want to simplify, but we're not great at the skill and value should describe who you are, not who you want …”
Lenny Rachitsky Jan 7, 2024 ▶ 1:01:48 The engineering mindset | Will Larson (Carta, Stripe, Uber, Calm, Digg)
Mar 10, 2024 neutral
Assertion Not checkable as stated
Rachitsky: Most features in Airbnb seasonal releases are already live
“Airbnb is actually in that same model. Most of the stuff they announced every couple of times a year is already out or in an experiment to most people.”
Lenny Rachitsky Mar 10, 2024 ▶ 1:11:26 Product management theater | Marty Cagan (Silicon Valley Product Group)
Mar 10, 2024 bullish
Opinion
Cagan: Rivian Is the 'Airbnb of Car Companies' Due to Design-Led Leadership
“I recently got a Rivian, which is amazing that they did an absolutely beautiful job. You know, they're kind of the Airbnb of car companies because the founder is a designer and it is just imagine if a designer designed the next generation car, it's a phenomena…”
Marty Cagan Mar 10, 2024 ▶ 1:20:07 Product management theater | Marty Cagan (Silicon Valley Product Group)
Mar 17, 2024
What-if
Rachitsky: Airbnb would not have survived without shifting to instant booking
“I've written about it here and there, but honestly, very quietly is one of the biggest transformations Airbnb went through shifting from, I'm going to go request a book to basically every booking now on Airbnb is instant. And that was a very difficult and pain…”
Lenny Rachitsky Mar 17, 2024 ▶ 31:57 The happiness and pain of product management | Noam Lovinsky (Grammarly, FB, Thumbtack, YT)
Apr 11, 2024 neutral
Insight
Jackson: Extreme PMF on a core product does not make expansion PMF free
“Just because you got to level four on your main product doesn't mean product market fit is free on all these new products. Right. And you've been inside Airbnb and I've been inside, you know, Dropbox and Twitter, like getting new products to be successful is h…”
Todd Jackson Apr 11, 2024 ▶ 1:04:49 A framework for finding product-market fit | Todd Jackson (First Round Capital)
Apr 18, 2024 neutral
Insight
Caldwell: Rigorous TAM calculations at the earliest stages are misleading
“The earlier you go, the less it matters. And some of the most phenomenally good startups, if you were really pedantic about it, the TAM would be like tiny. Like the TAM of Uber would be like nothing, right? Like how the TAM of Airbnb would have been nothing.”
Dalton Caldwell Apr 18, 2024 ▶ 29:40 Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (YC)
Apr 18, 2024 neutral
Opinion
Caldwell: Airbnb founders' decision to keep going was purely irrational
“When they probably should have shut down like three or four times before they got into YC. It objectively wasn't working. They were basically ruining their lives. They were disappointing their parents. Everything was wrong. And it was a purely irrational act f…”
Dalton Caldwell Apr 18, 2024 ▶ 7:32 Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (YC)
Apr 18, 2024
Insight
Caldwell: Founders should pivot when out of growth ideas, not before
“Like if it's not going well and you're out of ideas, that is usually a good time to pivot. But when there's a, you know, you have like half a dozen or a dozen really good growth ideas that you haven't tried yet, try them, right?”
Dalton Caldwell Apr 18, 2024 ▶ 18:19 Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (YC)
Apr 21, 2024 positive
Opinion
Kapoor: Airbnb and Pinterest led tech by differentiating on interface design
“Companies like Airbnb and Pinterest Were leading an industry, and they were leading not just because they, like, built technology and made it accessible, but because they were really using the interface layer to differentiate.”
Mihika Kapoor Apr 21, 2024 ▶ 1:07:40 Vision, conviction, and hype: How to build 0 to 1 inside a company | Mihika Kapoor (Product, Figma)
May 26, 2024 neutral
Assertion Not checkable as stated
Rachitsky: Airbnb reduced logout churn by extending session lengths
“The logout example is interesting at Airbnb. We found the logout was actually causing a lot of churn also. And the, but they went there initially they went with the simple solution of Just extend the session logout link instead of like a week, make it two week…”
Lenny Rachitsky May 26, 2024 ▶ 1:25:14 Unorthodox frameworks for growing your product, career, and impact | Bangaly Kaba (YT, IG, FB)
Jun 9, 2024 positive
Assertion Supported
Rachitsky: Roughly 70% of Airbnb growth is driven by word of mouth
“Something like 70% of Airbnb growth is word of mouth. And frequency of use is actually really low. It's like once or twice a year.”
Lenny Rachitsky Jun 9, 2024 ▶ 35:51 Lessons from a 2-time unicorn builder, 50-time startup advisor and 20-time board member | Uri Levine
Jun 27, 2024 negative
Assertion Supported
Y Combinator hated Airbnb's original idea and tried to change it
“Like we hated their idea and Paul tried to get Brian and Joe and Nate to change it.”
Jessica Livingston Jun 27, 2024 ▶ 22:15 The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of YC, author)
Jul 7, 2024
Disclosure
Maples: Floodgate passed on Airbnb thinking nobody would stay with strangers
“I mean, if there's one piece of goodness about us passing on air bed and breakfast design, Ann and I were like, man, you know, nobody's gonna want to stay in a stranger's house. That's crazy.”
Mike Maples, Jr. Jul 7, 2024 ▶ 28:54 Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Partner at Floodgate)
Jul 7, 2024 positive
Assertion Not checkable as stated
Maples: Airbnb succeeded by combining online reviews, Facebook Connect, and 2008 crisis
“They benefited, I think, from a couple of things. One was the proliferation of customer reviews online and people's trust of reviews as a substitute for trusting the brand of a hotel. But then also Facebook connect made it possible to pass people's profile inf…”
Mike Maples, Jr. Jul 7, 2024 ▶ 24:23 Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Partner at Floodgate)
Jul 7, 2024
Disclosure
Maples: Brian Chesky offered an Airbnb seed investment at a $1.5M valuation
“I think he offered me a chance to invest in a 1.5 million dollar valuation.”
Mike Maples, Jr. Jul 7, 2024 ▶ 35:59 Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Partner at Floodgate)
Jul 7, 2024 positive
Insight
Maples: Pitch slide one should explain what a startup does in plain English
“Slide one, you say what you do as if I literally know nothing. So it's not, we're Airbnb, we're a marketplace for unused residential housing space. Bad. But you'll get advice that says to do that because VCs think marketplaces are hot, residential real estate'…”
Mike Maples, Jr. Jul 7, 2024 ▶ 1:21:48 Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Partner at Floodgate)
Jul 14, 2024
Insight
Rachitsky: Rotating teams across different metrics is highly inefficient
“Rotating between different metrics is so not efficient because you get good at, we're going to move this metric and your team's like, cool, we totally understand this lever, like cancellation rate. We've become really smart at cancellation rate. And then three…”
Lenny Rachitsky Jul 14, 2024 ▶ 54:21 Building a world-class data org | Jessica Lachs (VP of Analytics and Data Science at DoorDash)
Aug 4, 2024 positive
Insight
Infrequent user behaviors require rigid product frameworks to build empathy
“This on average in the U S is, is something people do once in seven years. You know, I'm sure the average had opened doors, something similar. And so it's a little bit harder to like be a customer. I took Uber every day, probably used Airbnb a number of times …”
Brian Tolkin Aug 4, 2024 ▶ 33:06 Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber)
Aug 22, 2024 neutral
Assertion Not checkable as stated
Lenny Rachitsky: Airbnb employs at least 100 people just to optimize pricing.
“I think it surprised people to learn there's like at least a hundred people at Airbnb just working on like pricing, optimizing pricing recommendations.”
Lenny Rachitsky Aug 22, 2024 ▶ 50:37 Succeeding as an introvert, building zero-to-one, and PM’ing your career like a product | Deb Liu
Sep 1, 2024
Insight
Companies should never directly copy another organization's operating model
“I don't think You should copy another company's ways of working. Like the reality is it is How a company operates is so unique to the founders, to the leadership team, to all the employees and the domain, potentially the moment in time”
Vlad Loktev Sep 1, 2024 ▶ 1:14:32 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 negative
Insight
Scaling teams often fall into the trap of focusing on external dependencies
“What I've seen as an organization scales, people transition from saying, I can do X. And they transition to saying, Can the other team do Y so that I can do X? And I think that's a very dangerous place to be because at the end of the day, like you just need to…”
Vlad Loktev Sep 1, 2024 ▶ 12:09 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024
Insight
Impact in hypergrowth companies depends heavily on daily psychological self-regulation
“Oftentimes it's about also like being able to be impactful at a company that is in hyperscale and is growing quickly. A lot of it is actually just psychological. So it's not like there are these like core skills that sure, like you gotta have some baseline ski…”
Vlad Loktev Sep 1, 2024 ▶ 24:09 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024
Insight
Employees not working on top company priorities should find different jobs
“If you find yourself in a situation where you're not working on a top priority of the company, like you should probably get a different job because it's at the end of the day, you're spending so much of yourself and so much time at your job. You might as well …”
Vlad Loktev Sep 1, 2024 ▶ 9:02 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Assertion Not checkable as stated
Airbnb required back-of-the-envelope impact math for every single product project
“Every single project that we worked on at Airbnb We did back of the envelope math with assumptions. To help us understand the impact that something would have. And you needed to at least, now those assumptions could be completely crazy and could be very challe…”
Vlad Loktev Sep 1, 2024 ▶ 12:38 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Insight
Mission alignment and raw horsepower matter more than domain expertise
“Basically, mission over domain expertise, mission over skills. I think that if you have like a raw, like that raw horsepower, and you're deeply, like, you just love the mission so much, you can build whatever skills are necessary for the job.”
Vlad Loktev Sep 1, 2024 ▶ 1:00:55 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Insight
Brian Chesky's leadership growth stems from directly consulting domain experts
“And a lot of his like secret sauce is not being afraid to ask people for help who are experts in the thing that you're trying to learn.”
Vlad Loktev Sep 1, 2024 ▶ 29:43 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Assertion Supported
Airbnb's PM-to-PMM shift primarily served to offload project management duties
“So I would say the rebranding of Product manager. It did do some important things like shed project management and establish an entire function that focused on, on making sure things are moving in their, like the right direction from a project perspective. And…”
Vlad Loktev Sep 1, 2024 ▶ 1:24:10 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Insight
Employees with grounded conviction should not self-censor or hesitate to challenge leadership
“If you have a strong view after you've really grounded yourself in the truth and you feel like you've done your homework and you've asked all the questions, if you still disagree, if you still feel like we're going in the wrong direction, don't be afraid to po…”
Vlad Loktev Sep 1, 2024 ▶ 18:24 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024
Insight
Great teams are built by assembling complementary skill spikes rather than generalists
“Instead, what I've learned over time is instead of trying to find people that are good at everything, you need to look for people who spike on specific things and then add them to a team with different spikes. So there's no single person that is like spikes on…”
Vlad Loktev Sep 1, 2024 ▶ 31:04 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Insight
Leaders in fast-growing companies need direct reports to surface uncomfortable realities
“Large companies, things are growing. Lots of things are happening as a leader. You miss so many things. And so Hearing actually what's happening and the reality of what you're dealing with. It was just so, so helpful.”
Vlad Loktev Sep 1, 2024 ▶ 4:11 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Assertion Not checkable as stated
Airbnb intentionally slowed product velocity to fix declining quality
“The quality like of what we were releasing kind of suffered because we were just push, push, push, ship, ship, and people were shipping across the board. And I did feel as a leader, like I wasn't proud of some of the things we were shipping. And so I appreciat…”
Vlad Loktev Sep 1, 2024 ▶ 1:19:38 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Insight
Embracing employee skepticism disarms pushback to contentious decisions
“There's just something very disarming when you embrace the questions, you embrace the negativity and you have an open mind that maybe there are some things that you missed and some things that you didn't consider.”
Vlad Loktev Sep 1, 2024 ▶ 22:33 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024
Disclosure
Loktev explicitly warned Airbnb candidates about chaotic pivots and weekend work
“It's like the anti-sell, sell where I will share the worst day or what I think you will think as a candidate, what the worst day would be at Airbnb, and then still ask you if you want to join the team. And I would basically tell people, we're going to work day…”
Vlad Loktev Sep 1, 2024 ▶ 53:42 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024
Insight
Company core values should be descriptive of reality, not aspirational
“Something they learned about core values that I thought is really interesting is they shouldn't be aspirational. They should be who you actually are. And so there's a period where the founders are like, we're not actually amazing at this thing. So let's just r…”
Lenny Rachitsky Sep 1, 2024 ▶ 1:11:53 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 neutral
Insight
Hypergrowth repeatedly breaks leadership processes, forcing constant reinvention
“The process breaks, how you hire breaks, how you spend your time breaks, the projects you work on, everything breaks. And you gotta reinvent yourself.”
Vlad Loktev Sep 1, 2024 ▶ 29:15 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 1, 2024 positive
Assertion Not checkable as stated
Airbnb blocked promotions for high-impact performers who lacked core values
“At Airbnb, we had core value interviewers up until, I mean, my entire tenure, basically, even when we had thousands of people already at the company, when we were hiring people, everybody had to pass core values interviews. So it was very ingrained in how we h…”
Vlad Loktev Sep 1, 2024 ▶ 1:10:19 Embracing chaos, inquiry over advocacy, poking the bear, and “impact, impact, impact” | Vlad Loktev
Sep 5, 2024
Disclosure
Airbnb used nights booked, not revenue, as its North Star metric
“At Airbnb was, our North star metric was Knights book. And so it's similar to Amazon. It's not like the money Airbnb made from bookings, but it's like Knights booked. And it was really, and basically every experiment we ran is like, is this increasing nights b…”
Lenny Rachitsky Sep 5, 2024 ▶ 1:22:40 The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”)
Sep 22, 2024
Assertion Supported
Rachitsky: Airbnb created fake desk-sharing service 'Airbrb' for April Fools
“At Airbnb when I was leading a lot of the April Fools jokes year after year, and one of the best ones we did was we launched, it's basically we did the opposite of what you did. We launched Airbrb, which was a desk sharing service, and we made like a whole lau…”
Lenny Rachitsky Sep 22, 2024 ▶ 1:14:02 Becoming a super IC: Lessons from 12 years as a PM individual contributor | Tal Raviv (Riverside)
Sep 29, 2024
Assertion Not checkable as stated
Airbnb defined true search intent by tracking users who searched with dates
“The Airbnb example is exactly the way we did at Airbnb is we looked at people that are searching with dates as intentful users, and then how many of them convert to a booking.”
Lenny Rachitsky Sep 29, 2024 ▶ 20:47 How marketplaces win: Liquidity, growth levers, quality, more | Benjamin Lauzier (Lyft, Thumbtack)
Jan 5, 2025 neutral
Assertion Not checkable as stated
Rachitsky: Airbnb co-founder Joe Gebbia resisted process until chaos forced adoption
“He was very anti-process at the beginning of Airbnb. He's like, we're not going to have a process. I hate process. We're going to run. That's the big company stuff. And then it just, It's chaos constantly. And then eventually it's like, okay, we need to have u…”
Lenny Rachitsky Jan 5, 2025 ▶ 47:48 Scripts for navigating difficult conversations | Alisa Cohn (executive coach)
Jan 16, 2025 positive
Disclosure
Rachitsky: His creator income far exceeds his past Airbnb PM salary
“I make much, much more than I made as a product manager at Airbnb. And also it's a lot more, it's a lot less stressful.”
Lenny Rachitsky Jan 16, 2025 ▶ 26:29 How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor)
Jan 19, 2025 neutral
Disclosure
Rachitsky: Much of Airbnb's flow was guesswork, not tested optimization
“What made me realize this back in the day was thinking at Airbnb, especially thinking about people looking at our flow and being like, this is, they got it all figured out. We're just going to copy what they've done. Cause they're so thoughtful and have tested…”
Lenny Rachitsky Jan 19, 2025 ▶ 32:39 10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey)
Mar 16, 2025 positive
Assertion Not checkable as stated
Rachitsky: Airbnb personality testing showed quiet PMs were just as successful
“We did a test of all the PMs at Airbnb while I was there, like a personality test, and it's interesting how it was all over the map, and there wasn't, like, you need to be this, like, energetic, charismatic person. You could be just a thoughtful, quieter perso…”
Lenny Rachitsky Mar 16, 2025 ▶ 59:39 The hidden power of introverts: How to thrive without changing who you are | Susan Cain
Jun 12, 2025 neutral
Insight
Baxley: Meta Is Still a Startup, But Amazon Is Not
“I had this other theory that a startup is still a startup until the founder moves aside. So by my definition of even meta is still a startup in a way that Amazon's not. And, you know, an Airbnb is still a startup in a way that Pinterest is not because Ben's mo…”
Bob Baxley Jun 12, 2025 ▶ 12:28 35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
Jun 12, 2025 neutral
Opinion
Baxley: Google and Amazon Do Not Compete on Design Like Apple
“And Apple does, Airbnb does. I don't get the sense that Google does. And I don't get the sense that Amazon does. And that's not a critique on them. I don't think that those organizations are competing on design in the same way.”
Bob Baxley Jun 12, 2025 ▶ 17:00 35 years of product design wisdom from Apple, Disney, Pinterest and beyond | Bob Baxley
Jun 15, 2025
Assertion Not checkable as stated
Rachitsky: Joe Gebbia urged an Airbnb designer to build something entirely unseen
“There is a big launch coming up and there was a designer sitting at late in the office, trying to read, update the website to include this new product. It was a launch of Airbnb neighborhoods, like, I don't know, 10 years ago. And he's, and she was just like, …”
Lenny Rachitsky Jun 15, 2025 ▶ 46:22 How to build a team that can “take a punch” | Hilary Gridley (Head of Core Product, Whoop)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 6:14 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 37:24 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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 Conley Aug 3, 2025 ▶ 24:35 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 positive
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…”
Chip Conley Aug 3, 2025 ▶ 55:28 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 9:16 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 26:11 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 negative
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…”
Chip Conley Aug 3, 2025 ▶ 16:12 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 6:42 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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 Conley Aug 3, 2025 ▶ 50:04 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 13:05 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Aug 3, 2025 neutral
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.”
Chip Conley Aug 3, 2025 ▶ 9:40 Brian Chesky's secret mentor who scaled Airbnb (after dying 9 times & building a hotel empire)
Sep 28, 2025 neutral
Assertion Not checkable as stated
Rachitsky: Airbnb's Superhost program made hosts happy but moved no metrics initially
“Interestingly, it made hosts really happy like you, just like, I want to be super host. I don't know why, but I want to be a super host. It didn't actually move any metrics, which is interesting. Might have changed over the years, but it was an interesting, in…”
Lenny Rachitsky Sep 28, 2025 ▶ 21:04 A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype)
Mar 12, 2026 neutral
What-if
Rachitsky: Without the newsletter, I likely would have started a failed company
“I'd probably find another company to start and I probably would have failed considering most startups fail. So I'd probably be in this like, oh no, is this thing a thing I should be doing? I'd be in a, on the struggle bus of startup life probably. And then pro…”
Lenny Rachitsky Mar 12, 2026 ▶ 7:03 A behind-the-scenes interview with Lenny Rachitsky on building his newsletter and podcast
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