Brian Chesky’s new playbook

Brian Chesky is the co-founder and CEO of Airbnb. Under Brian’s leadership, Airbnb has grown into a community of over 4 million hosts who have welcomed more than 1.5 billion guests across over 220 countries and regions. I had the privilege of working under his leadership, so it is a great honor to have him on the show. We discuss:
• How Airbnb has shifted their thinking on product management
• Why bureaucracy happens in companies, and how to avoid it
• The importance of founders diving into the details
• Why Airbnb moved away from traditional growth channels and what they are doing instead
• Airbnb’s newly released features
• How and why Brian encourages his team to set ambitious goals
• Why he says he still has a lot to prove
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Brought to you by Sidebar-Catalyze your career with a Personal Board of Directors: www.sidebar.com/lenny/?... | Jira Product Discovery-Atlassian’s new prioritization and roadmapping tool built for product teams: atlassian.com/lenny/?... | Eppo-Run reliable, impactful experiments: www.geteppo.com/
Find the full transcript at: www.lennyspodcast.com/brian-c...
Where to find Brian Chesky:
• X: / bchesky
• LinkedIn: / brianchesky
Where to find Lenny:
• Newsletter: www.lennysnewsletter.com
• X: / lennysan
• LinkedIn: / lennyrachitsky
In this episode, we cover:
(00:00) Brian’s background
(05:18) The current structure of product management at Airbnb
(09:21) How fast-moving companies become slow-moving bureaucracies
(12:20) Brian’s thoughts on performance marketing
(13:50) Airbnb’s rolling two-year roadmap
(15:30) Brian’s journey as CEO in a growing company
(18:34) Best practices for A/B testing
(20:30) Who inspired Airbnb’s new direction
(23:18) The first changes Brian implemented at the onset of the pandemic
(24:51) Why founders should be “in the details”
(30:15) Airbnb’s marketing, communication, and creative functions
(31:38) Advice for founders on how to lead
(34:15) Tips for implementing Airbnb’s business methodology
(38:48) Airbnb’s winter release
(41:47) Why Airbnb no longer has separate guest and host teams
(42:38) Brian’s thoughts on design trends
(45:36) The importance of empowering hosts with great tools
(45:57) How setting ambitious goals improves team performance
(50:05) Tips for preventing burnout
(56:02) Tips for personal and professional growth
(58:19) Why Brian says he still has a lot to prove
(1:02:58) Paying it forward
(1:05:03) A fun fact about Brian
(1:09:26) Airbnb’s origin story
Referenced:
• Localmind: www.crunchbase.com/organizati...
• Config 2023 in review: www.figma.com/blog/config-202...
• Why Founders Fail: The Product CEO Paradox: techcrunch.com/2013/08/10/why...
• Hiroki Asai on LinkedIn: / hiroki-asai-a44137110
• Jony Ive on Crunchbase: www.crunchbase.com/person/jon...
• Charles Eames: en.wikipedia.org/wiki/Charles...
• Airbnb 2023 Winter Release: news.airbnb.com/en-in/airbnb-...
• Airbnb 2023 winter release reel: x.com/bchesky/status/17222438...
• John Wooden’s website: coachwooden.com/
• An 85-year Harvard study found the No. 1 thing that makes us happy in life: It helps us ‘live longer’: www.cnbc.com/2023/02/10/85-ye...
• Sam Altman on X: / sama
• Alfred P. Sloan: en.wikipedia.org/wiki/Alfred_...
• Bob Dylan quote: quotefancy.com/quote/950807/B...
• OpenAI: openai.com/
• Michael Seibel’s website: www.michaelseibel.com/
• Y Combinator: www.ycombinator.com/
• The Norman Rockwell Museum: www.nrm.org/
• Rhode Island School of Design: www.risd.edu/
• Joe Gebbia on LinkedIn: / jgebbia
• Nathan Blecharczyk on LinkedIn: / blecharczyk
Production and marketing by penname.co/. For inquiries about sponsoring the podcast, email [e-mail].
Lenny may be an investor in the companies discussed.

[@adamrossProduct]

These Apple-centric practices and organizational approaches are becoming increasingly commonplace, especially in those companies trying to reinvent themselves as tech forward. I’ve practiced product and I’ve practiced various forms of marketing, and there were plenty of times where I was practicing product marketing without having a name for it. This idea that the connective tissue between the street/users and the engineers/designers is a function of the core skills you might need to sell something to someone feels like a productive way to reinsert qualitative rationality into a tech environment dominated by quantitative reasoning. So it’s helpful to hear Brian talk through his current rationale for adopting these practices and principles. Two minor critiques; Lenny it’s time to adopt a POV and push back on these folks you are interviewing. Many of them are constrained by their valley environments. For example, you asked (rightly) about work-life balance. Brian starts to address this question with empathy for how his lifestyle at 42 years old allows for a unique approach to managing this balance. But he never diverges from this thread of viewing work-life balance through the prism of his own lived experiences. Pushing back would have been appropriate, and perhaps necessary to help him understand the root of why people ask questions like this. This leads to one last critique; I would imagine working for Brian is an engaging, meaningful challenge. But what does that really mean for someone? What’s an example of how his approach has driven people away from Airbnb? It’s not a bad thing, it’s just actionable information so if we find ourselves reporting ti leaders with similar philosophies, we can be proactive. Product is an inherently unsafe role, but your podcast sometimes feels entirely too safe for the leaders who participate. We shouldn’t treat everything that comes out of these folks’ mouths as gospel.

[@producteawithleah]

I considered for a second inviting Chesky but with the condition that it's not gonna be with cushion gloves.

[@LennysPodcast]

Adam, thank you for the super thoughtful and spot-on reply! To your point, I wanted to ask these *exact* same two questions as follow-ups. But knowing we only had about an hour together, and also how much Brian has to share for each question (i.e. first answer took 10m lol), and that I wanted to get through other topics, I decided to keep moving vs. get deep on a topic or two. Tough call for sure. I'm going to bring on another senior Airbnb leader who'll have more time, and I plan to drill deeper into some of this stuff further.

[@tanyatango4197]

Thank you adamrossProduct for this response. Exactly my thought. The way Lenny, you opened the episode (could you have imagined you would be on my podcast) and facial expressions at certain points makes me believe you know the realities of working with leaders like this. Not pushing back or challenging them on their very one sided, techbro approaches to running companies, clearly completely oblivious to the impact it has on others life experiences is dangerous. 1 hour is a plenty if time to do so. How many rookie leaders might walk away with these tough boss philosophies as holy grail after this? Given the way Linkedin is going gaga over this episode. It is disappointing that time and again this brand of leadership gets glorified. First it was hardcore twitter by EM, now this guy, in an environment where the power equations have already gotten skewed heavily on employer side, more such leadership emerges tech will become a place for only one dimentional workoholics who want to believe they are changing the world with their websites and apps.

[@tanyatango4197]

​@@producteawithleah you seem to have a different perspective on leaders like this than hailing them as someone who deserves to be at top 10 great leaders. Isnt it worth spilling the tea to create some balance?

[@producteawithleah]

@@tanyatango4197 i mean I would but i highly doubt that he would come on :)

[@lolajiang4946]

Lenny I've been binge watching your shows. They are so insightful and educational. Keep up the good work!

[@amirbakhshi6696]

Thank you Lenny what a great episode, 10/10! Leaders are in the details, Brian Chesky!! Love it!

[@coderabsolute9583]

This is one of the best podcast you hosted, Lenny! Thanks!

[@Textras]

Always great insights from Brian, great interview.

[@user-uo8px5ly1l]

This is the guest I anticipated most! Thank you, Lenny, and congrats🥳

[@Divicati]

This is gold, thank you both.

[@victorchibacu7128]

Love the kitchen analogy between marketing and engineering! Great stuff ✨

[@harfreeka]

this is one of the greatest and best podcasts I have listened to this year.

[@earlytoarrive]

Lenny - thank you 🙏

[@doitinpublicshow]

Brian's energy is unmatched. So much gems here!

[@incyphe]

What an intense interview. Thanks!

[@avazbek]

Great talk Lenny, thank you for what you're doing. It's a geeat source of knowledge and inspiration. Keep it up!

[@asfandiyar5829]

Thanks for this awesome podcast. Really eye opening for someone who is pursuing a career as a start-up founder. Makes you question what is actually important.

[@TDSkj80]

Lenny - Your podcast is AMAZING! I only wish I had found it long ago. Brian - Thank you so much for sharing your wisdom. So generous of you!!!

[@semerda]

Lenny, what an amazing interview! Packed with valuable contrarian advice. I've always held the belief that everyone in a company should become a product expert. Limited knowledge makes selling or building challenging. Bravo on the outstanding interview!

[@MikeWilliamsYoroomie]

What an incredible chat and so many great takeaways from this episode! Brian has led the way for us in the world of marketplaces and this is a great example of how he's continuing to do so. Thanks for the awesome episode Lenny.

[@iqbalhape]

Tons of gold, wisdom per words rate is so high. Thanks Lenny and Brian, I jotted down so many things I'm discussing with my team asap to re-evaluate how product & marketing works

[@lililiu8446]

Brian is a great teacher❤

[@beibeihu4992]

I really LOVE this episode. Brian Chesky is a deep thinker and who always articulate the thought so clearly and strongly. I have learnt so much!

[@JamrockVybzTV]

This podcast is among the greatest I've listened to this year.

[@user-rp6mc7sw9y]

One of the best podcasts, I have ever listened. Thank you Lenny! Thank you Brian! Bless AirBnb!

[@HelenSpryker]

Finally an episode where there is a much more focus as well on Design. Finally someone speaking about how important design is as well and not thinking PM is the be all and end all. Great talk on the details

[@alirazarizvi-34]

This was incredible. I mean this had so much knowledge and wisdom being imparted, might have to watch twice to absorb it all.

[@HeyDanHay]

I woke up in amazement to see this posted and sent to my email! This is an incredible interview and must have been so cool to do.

[@sandratubale-dingal3005]

Love this conversation!

[@user-iq3ti1yh6c]

Amazingly honest, straightforward conversation! Thank you!!! I wish the speaker TO Take A VACATION. He needs rest!

[@rupesh-qq5rl]

So thoughtful questions Lenny, And Brain is the most thought leader of this generation.

[@acupofwhat]

To be honest, there's just an incredible amount of self hype in the tech industry. There are just as talented people as this guy in my own team, perhaps even wiser and smarter...

[@Skarredghost]

Amazing interview, very inspiring. Thanks for sharing it!

[@sg.2101]

This is the best episodes ever. I had this in my watchlist but only coming back to this. This jjst blew my mind.. A detailed teardown on twitter is coming very soon ❤

[@Calm_passion]

Hi Lenny , Thank you so much for this interview! So grateful that I can listen to this from South Korea! Amazingly thankful

[@set_app]

Pure genius. Loved watching Brian think on the spot to these trying questions. Very well conducted interview 💥🚀🤙🏻

[@raducrv1]

Seriously, 7000 people and you get down to identifying what blocks each individual. You're a super human :))

[@davidoshinpodcast]

Lenny Thanks for this

[@joshuaadickerson]

Companies don't get what PM means and use them as EMs and Design Managers. Then they make actual EMs and DMs feckless "people managers". This is my favorite podcast you've done as it's something I've been preaching for a long time.

[@GoesByStrider]

And there it is. Here is what I suspect will become a historic recording, similar to the famous Steve Jobs interviews of the past. He has identified much of what I've felt is wrong with tech for so long. Specially in regards to how they've become so driven by internal politics. This was much needed. Makes me optimistic about the future. Thanks, Lenny.

[@yanfranca8382]

One of the greatest CEOs alive - and one of the most charismatic as well.

[@hannahyingzi]

No doubt

[@acupofwhat]

Not the worst CEO for sure... but man wipe your mouth

[@hovgrig]

Thanks for a great work Lenny 👍I'm not driving without your podcast on anymore.

[@aliyaismailova6897]

Amazing podcast! Love it! It is interesting how right after Brian told about too many unnecessary A/B tests you get an ad about experimentation tool 😄

[@sezaiburakkantarci]

Brian is one of my heroes, with his relentless chase for what he calls a "seven star experience" for his customers. From Paul Graham, to Brian, to us, to forward generations: "All you have to do is get 100 people to like you." Thank you so much Lenny. This was a delight. 💫

[@user-bn4jk8gn1k]

wow, talk to Airbnb hosts, he's not that popular.... he never listens to anything we ask for. Did we ask for Categories? no. did we ask for this Listings tab? no..... it's true the ABB dashboard is the best in the biz, but there are still many gaps that we've been asking for, for many years. Every time they release new features we all groan, wondering what will be broken this time.

[@Hermon_nz]

Man the value in this is insane!!! Thanks

[@CoreyONeal]

"Every leader should be an expert in what they are leading. There should be no people managers in the company... meaning, you're only responsibility is people [and] not the work, not the domain. " 👏👏👏

[@SanjayNegirocks]

I'll have to listen to this 10 times

[@JohnRodrigues.]

I was there in that room. Brian is a great leader, I look up to him.

[@MalikaYunus]

Lenny has such a kind, considerate presence. Airbnb was lucky to have you!

[@LennysPodcast]

Well that warms my heart!

[@MalikaYunus]

@@LennysPodcast I only just discovered you, but after a few episodes, I can see why you make a good podcaster. You are inquisitive while making the guest feel at ease. You seem like the type of person who brings a lot of value while staying humble. That’s why I said I think Airbnb was lucky to have you. You’ve gained a follower! Keep up the good work :)

[@Alex.kantrowitz]

Great stuff Lenny, awesome interview!

[@LennysPodcast]

Thanks Alex! And thank you for indirectly helping make it happen!

[@MrNeverNeverhood]

Great talk

[@alexeyhimself]

It felt to me like Brian read SVPG's "Inspired", "Empowered", "Loved" and even a last draft of "Transformed" books and decided to make it all and at once! 😅 Fantastic interview, Lenny! 👏I agree on every word Brian said! Very impressed with this CEO and now I am even more proud to be an Airbnb customer! 💪

[@whattimeisitnow124]

The exact opposite. He says he's dictating a 2 yr roadmap with 6 month launches. How is any of this what Cagan talks about??

[@alexeyhimself]

​@@whattimeisitnow124 a company with thousands of employees can't exist without roadmaps and planning. That's normal. And as I know what Marty says about roadmaps is that they are fine by their nature, but the problem with them is that they often made at a wrong time: before we addressed the risks. And what I've heard from Brian in this interview is that Airbnb actually changes their roadmap: yes, they have it, but they adapt. I don't see any contradiction: they have roadmap, they keep it flexible, they tune teams with new principles. My comment was about a huge volume and deepness of changes Brian makes in an organization. I am very impressed! And as Marty says, "transformation starts from a CEO". Will look forward to see the results that will follow in Airbnb!

[@yoongjason]

Terrific conversation. Brian's actions are an excellent example of a CEO real-time fighting off Day 2. Well done Brian. I also noticed a few Amazon head nods: 1) Bias for action 2) Single-threaded focus 3) One-way vs two-way door fast decision-making 4) Dive deep (Leaders operate at all levels, stay connected to the details, audit frequently, and are skeptical when metrics and anecdote differ. No task is beneath them)

[@Patrick-vq4qz]

This guy is so on target. I would like to work for and with him!

[@kseniaapolonskaya5933]

Well that episode turned me into Brian's fan. You can tell he has been thinking about these themes deeply, and it was so very interesting to follow him on this journey of re-inventing his company and himself as a founder.

[@KazzyOfficial]

47:02 First principals thinking breaking things into components

[@_peterferguson]

Damn having Brian on is huge congrats

[@thibaultpaul4571]

amazing

[@chetansingh4047]

Cool Interview. But Lightning round is missing. It would be great to hear the mindsets of these guys on those questions who see organization from the very top and also from inside.

[@ankurmadan99]

How would you scale when CEO reviews each project at a regular cadence and every decision comes top down?

[@Hubforce]

How do you think the buying process in b2b SaaS will change in the coming years?

[@travelclassinternational]

Awesome🔥 I keep scrolling back through the video as I struggle to keep up with Brian's thoughts. However, if you slow down the playback speed, it seems like listening to a drunk person 😃

[@Wealtharch]

Thanks for the great interview Lenny. Brian is my favorite CEO. Compared to other great CEOs, he seems to be willing to be interviewed more than the others. Why do you think that’s the case?

[@LennysPodcast]

I think in part because he's trying to change how companies operate, based on his recent experience

[@tddtv]

All good, as long as you have sustainable pace built into the culture. All this motivation, etc. sounds wonderful to many, but make sure you're not burning out your employees. Go well. Small steps. Take Breaks. Slow down to go faster (build in quality, don't ship shit) when coding and designing. People shouldn't live their life and all hours for a company. Sustainable pace.

[@cliosight]

Is it safe to approach someone for mentorship or investment without knowing them well?

[@shotokankjs]

He just applied theory of constraints as Eli Goldratt stated in his book the Goal.

[@X-Dime]

Amazing! Just... Amazing!!!

[@benjaminajah4726]

From the elevation speech to the end, i knew this will be a greet video

[@amrmohallel]

This might be the best podcast i ever watched

[@withfirapp]

The culture is what happens when you are not in the room and the brand is what people say when you are not in the room.

[@TDSkj80]

Genius

[@basieniaa]

This interview seems to be the first one I find challenging to watch on your channel. Even if they were to replace half the team with ex-Apple employees, it might not address the larger issue that Airbnb seems less relevant now. My experiences with Airbnb have often involved shady and overpriced offers in various locations. Personally, I haven't come across anyone who has used it and could recommend it, and I suspect this should be the main challenge for the company.

[@vix182]

Yeah your personal experiences > Airbnb just posted record growth in bookings (113 million, up 14% YoY)

[@IZSIN222]

@@vix182I get that but I also agree with him

[@SuruLereinLasGidi]

where in the video does Brian list 3 things key to success -execution, product and ?

[@yunjieyao8058]

I cried at the end of this episode. Amazing interview, thanks Lenny and Brian

[@chxu]

No, you didn’t.

[@officerjimlahey]

You cried? LOOOOOOOOOL

[@vgurbuxani]

Having worked at both Apple and Google. This is an exact copy of Apple and it works great for hardware to software full stack integration. This is a load of crap to do bottom up thinking, which is what Google does extremely well. This is great for Brian which means it’s just top down tentpole projects run by Brian Cook, who’s no Steve Jobs. For a pure software startup, what Brian is doing is going to fail. Look at Apple Maps when it first launched, iTunes, Numbers. Name one pure Apple software product that doesn’t require Apple hardware to be good. You can’t, this is a great time to short Airbnb and build a more affordable airbnb. They just rent unused space in peoples houses! Not a iPhone!

[@goneballistic]

I completely agree with this. There is some good ideas here but having lived this exact structure, it fails over time. I look forward to the podcast in a while where they are like "oh that didn't work. Turns out the Product people spent all their time running projects and writing marketing content"

[@user-kg1od9es5d]

lol I said this to a friend - airbnb is dead. It starts from the top with leadership. Cant be bothered to go into detail for simpletons [not you] who don't get it.

[@jordan5253]

@51:35 is a bar 🔥

[@MrBjornHarvold]

I want what Brian’s on if that’s what it takes to run a billion dollar biz

[@tsengalbert2020]

Lenny I'm curious: when the CEO is very hands-on in the product decisions essentially the role of product managers is gone. But is that to say there are no more product people at Airbnb anymore? He mentions there is still a small group of senior experts but where do the delegation occur? How do you keep senior leaders from feeling powerless in terms of product decisions?

[@goneballistic]

he basically still has product people, he's just moved the actual project managers out, and added product marketing to the product manager role. There are still product managers but they are split focus now. It's not workable long term. The product people get swamped doing marketing stuff and you become customer and engineering driven, which often leads to inconsistent delivery and you can't attack larger long term goals. You need someone looking at the big pictures and keeping the product focused on company drivers.

[@AnyelinaL]

I don't see airbnb will do great in the future. Countries in Europe, and cities like New York, are implementing new housing restrictions and penalizing home owners who do short term rentals with Airbnb. Most probably some other countries will follow because this is causing housing issues to people who live in the cities and are having trouble finding reasonable housing for rentals. Airbnb has paid already fines in some countries already. Also, the rates with airbnb have increased so much, with ridiculous cleaning fees and other fees, that it's actually better in many cases to go to a hotel. At least you don't have to pay extra for cleaning, and it's even included breakfast.

[@santiagopuentep]

That's not what's causing housing issues. Those european countries and new york are implementing socialist policies (politicians controlling the market). Telling the citizens how to rent their own properties is not only immoral, but it will crearte more housing problems. New York and those countries are going downhill.

[@alexself3097]

Airbnb decentralizes the revenue for one of the biggest industries in the world. It’s a business for the people.

[@acupofwhat]

Key takeaways; Lead w/ self confidence CEOs must be CPOs Don't apologize for how you lead Managers must know & understand details Delete useless hierarchy layers

[@bertobertoberto3]

Deep

[@fmiraftab]

lenny - this was i think ur only podcast where u allowed the speaker to get on his soapbox. A bit of feedback - continue to reign in the discussions to ensure folks dont suck all the air out the virtual room

[@sidelnie]

Fantastic interview...It's a little sad to see Brian's graying hair as I always thought of him as a young startup founder. I think Brian to should leave AirBnB and start another company. I think he should tinker with business concepts that drive strong emotional connection and put smiles on people's faces. Airbnb is great at driving economic value to hosts and guests but I think Brian is craving to do more. I might have to be outside of AirBnB. Best wishes and good luck Brian!

[@99CaNdYfLiP99]

3:47 4 minutes introduction wow

[@pcaso]

People having depth of topic talk fast as the signals can be processed faster.

[@BigDataLogin]

cool

[@Sece1]

Lol. Glad to hear that a ceo openly speaking about the issue of PMs don’t know shit about their products at least in last 3 companies I worked for..

[@krishsubramanian9703]

I agree with the new direction and what prompted it. However, the 6-month release and Program management are not desirable for a company trying to reinvent itself. Many big corporations take directions from marketing and become feature companies rather than solving real customer problems. The designer and engineering team will take direction from marketing that have its own wishlist. The less said, the better about the Program management function which is fundamentally interested in status collection rather than being part of a customer problem-solving session.

[@Simbreaker603]

Good interview. but why does he touch his face every 10 seconds

[@Nunya-lz9ey]

Probably coke

[@flying_macaw]

Good observation

[@Didi38]

I think his mind is a little overstimulated.

[@muriloams]

My gosh, there is so much room for CEOs and leaders out there to misinterpret what Brian is advocating for. It’s going to be a mess until they get there. It is definitely not less product management but better empowered product managers and teams and also one single clear cohesive product vision and strategy. Not one vision and strategy per BU.

[@nat.serrano]

He’s a great speaker, he should speak more often .

[@sohambhatia]

Sheesh, Sam comment at end was a bar

[@nyongyi]

When Chesky talking about bureaucracy, didnt amazon went through exactly same situation? 🤔 Then Amazon leaders created single threaded teams (which is basically horizontal team) to try to eliminate all that bureaucracy, politic and MAINLY dependencies. Seems like Chesky just want top down more features fast as possible, not that I'm saying is a wrong thing to do.

[@andrewhannebrink56]

Bro literally says rizzdom at 102:57. Rizz god no doubt.

[@satoriasimov9169]

Brian 🫡

[@SuperKillaki]

This is refreshing. There are so many stupid sub-functional teams and names with overlap. Simplified org structure ftw.

[@chips-n-salsa]

Brian is saying what Marty Cagan has been saying for years with a lot of CEO fluff in the middle.

[@99CaNdYfLiP99]

1:26 near the top??? OK, who's on top?

[@maximilliansbabo2099]

5 mins till the video starts…

[@majedaleisa]

I don't understand how a software company with a single product (airb&b) has 7k employees. Why?

[@flying_macaw]

7k includes the person who verifies the listings in each city and their extensive customer care team for each geography as well

[@Didi38]

There are milions of Hosts and milions of guests using Airbnb every day around the Globe. All that need to be managed and assisted.

[@taktischekartoffel]

The juxtaposition of the comments here vs reddit. 😂

[@Thejimc72]

Maybe good for the CEO, but as an employee, this sounds like a nightmare

[@LithicMetals]

Great to listen to, but hard to watch.