The Ledger

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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
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)
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)
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)
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)
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)
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
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)
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)
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
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
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
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)
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
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
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)
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)
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
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)
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
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
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
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
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
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
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)
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
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)
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
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)
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)
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)
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)
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)
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)
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)
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)
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)
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
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
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
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
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
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
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
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
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)
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)
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