Airbnb CEO Brian Chesky on AI Strategy & New CTO, Microsoft’s Anthropic Deal | Jan 14, 2026

0:13Welcome, everyone, to the information's TI TV. My name is Akash Paswitcha. It is Wednesday, January 14th. Today on the show, I am talking to Airbnb CEO Brian Chesky about the company's new chief technology officer that he announced today. I'm also talking to him about the current state of Airbnb's business, where it's going, and how he is integrating AI. We'll then get into some exclusive reporting from the information around Microsoft's growing relationship with Anthropic. It is Wednesday, which means it is time to discuss our weekly finance newsletter. The topic for today, how one new tech bank with a name plucked from J.R.R.

0:53Tolkien's Middle Earth is trying to shake up finance. Excited for that conversation. And we will end with a segment about how a new proposed billionaire tax in the Golden State may or may not impact Californians' desire to leave the state. It is a fun show, so let's get right on into things. Airbnb has a new CTO. The company said today that Ahmad al-Dali, who previously was a top AI executive at Meta, is taking the job. I sat down with Airbnb co-founder and CEO Brian Chesky to talk about how he plans to further integrate AI into the Airbnb platform and how he's thinking about the future of his business as the stock has basically been flat over the past few years.

1:37I also got some details about the current state of Airbnb's experiences, services, and hotels business lines, which he is betting on to re-accelerate top-line growth at the company. Here is that conversation. Brian Chesky, welcome to TITV. It's great to have you here. Well, thank you for having me. So, look, you wrote a memo to employees introducing Ahmad al-Dali as your new CTO. and before we get going, the first thing that jumped out to me was that you wrote, he grew up in Winnipeg, Canada, one of the coldest places in the world. And I just wanted to share, I was also born in Winnipeg, so I can confirm.

2:18Is that, can I confirm that? Oh, it's true. I mean, it is cold, but. The coldest place I've ever been was Calgary. I got off the airplane and Calgary with a jacket. My friend picked me up and gave me a jacket to put over my jacket. And I've heard Winnipeg's colder than Calgary. They have to plug in their cars at night. That's how cold it is. But it's a great hockey town, and I know you're a hockey fan. I love hockey, and I grew up in a place not quite as cold as Winnipeg and upstate New York, but it was kind of near Buffalo. So kind of familiar with snow and cold in hockey. There you go. Great.

2:50Okay. Well, let's get into it. So I want to understand how a mod fits into your vision for AI at Airbnb, because you've said publicly that you want Airbnb to be the real world connections app in an AI world. You've also talked about how models will become commoditized in the long run, will become something like electricity. And you're already using AI in many of your customer service tools on your platform. And so the question I want to start off with is, how is Ahmad going to help you extend AI throughout the rest of the company? I mean, three things. Number one, you know, the most fundamental thing is AI is this great workflow technology to make everyone more efficient doing their jobs.

3:36And I think, obviously, software engineering is being revolutionized to AI. But basically, every single function of company, from legal to finance to design to marketing, could be benefited from AI tools. So I wanted to be one of those companies that started before Genove AI where we're not an old school company. We're a new school company, and we're using the latest, greatest tools. That's number one. That's just fundamental. Number two, a lot of people talk about agentic AI, and one of the most common use cases is travel, a travel agent. We decided to start with the hardest part of AI with Airbnb, which is customer service.

4:10And so now 15 % of our, you know, we were able to reduce our contacts in English by 15 % by having the AI do customer service. That's really, really hard to do. It's one thing to say, where should I travel? It's another thing to say, I'm locked out. Can you help me? And so we want to take that customer service agent and bring it up funnel. And ultimately, you know, I don't think we're going to live in a world where you just use one agent, one chatbot to do everything. I don't think you're going to want a thousand agents that just like you don't want it. You can't have a thousand friends. You don't have just one person in your life.

4:43And so I do think some specialization will benefit and not too much specialization. What we're going to specializing in is traveling and living. If you want to travel or live somewhere, you're going to go to Airbnb and we're going to be able to use the same models as the Frontier Model companies because we can license those models. But we're going to specialize. We're going to tune them and train them for our use case. We're going to design these really great interfaces that married Airbnb's design with Frontier Technology to be able to help you travel and live anywhere. The other point I'll just say is a very small percent of Airbnb is the app that you see in YouBook.

5:20A large part of Airbnb is managing 5 million hosts, having 5 million hosts in our community, handling over approximately$100 billion, going through our app in nearly every country in the world, trying to keep people safe every night, handling tens of millions. What are some of the things that you could see AI automating on that vector of working with the supply? Well, creating a listing is probably the most obvious one, right? You can, in the future, basically just add your address or even just say, my current location is I'm home. We can then scrape an MLS. We could basically create your listing for you.

5:58If there aren't photos, you could take photos. AI could use computer visioning to then take the photos, write the description. it could verify the amenities exist at that property. So creating a listing would be significantly easier. That's just one example. There's like dozens and dozens of examples like that. And so I wonder how you think about ROI in this AI area. Is it quantifying time savings either for your own workforce or for the people who are putting their homes up to be listed on the platform? Is that something you quantify? Do you think about increasing revenue if you're getting more bookings, being able to use a chat interface?

6:37I mean, how do you quantify ROI for AI? Probably three things. First is just being able to move faster and deliver more features. For example, if every engineer is using AI tooling and you create like double the efficiency, then you can essentially ship features at twice the rate and that will, of course, lead to a lot more growth. So that's on the tooling. On customer service, you can reduce customer service contacts. That, of course, if an AI agent can essentially handle a ticket, that saves a lot of money in the workforce. But also, if it can respond faster, you can recover the customer and pass the savings on to the customer.

7:13The third thing is just essentially making it a better store for you. So making it easier to find the right booking increases conversion of supplies. So as conversion increases of traffic, revenue goes up. So shipping features faster, reducing customer service, increasing revenue by increasing conversion. Those would be kind of like three really big ROI metrics. Again, there's probably dozens. Those would be probably the three most important. So it leads me into sort of a broader discussion I wanted to have with you about the business at large. I mean, if you look at the growth trajectory for the business, you guys have no problem with profitability.

7:49It's very strong there. Growth is decelerating and the stock has very much been flat. And the solution to this, you've said, is experiences, services, and hotels in the long run could be multibillion-dollar businesses. Where are those businesses right now in terms of revenue? One thing I want to say is growth had been decelerating, and now it's re-accelerating. In our most recent Q3, we showed acceleration from Q2. We haven't reported a Q4 results yet. But I'm very optimistic. Q4 was guided to 7 % to 10 % around the same as the current quarter, right? Yeah, and I can't obviously comment on the results.

8:27Our earnings call is in, I think, four weeks. But we are optimistic that over the coming years, we'll be able to accelerate growth in Airbnb. And how are we going to do that? A few things. Number one, creating new businesses. So you asked about experiences. Experiences, we are really optimistic, could be a multibillion-dollar business. Services. There is no Amazon for services. Whether you want a chef or you want a personal trainer or masseuse, We think that could be very popular for travelers and eventually locals. Hotels. People don't realize how big the hotel industry is. Google and Meta are essentially advertising companies.

9:01They're in the advertising industry. The advertising industry is smaller, I believe, than the hotel industry. So we do not need a large market share of hotels to have a huge business. Hotels will absolutely be a multi-billion dollar business. One example, there were over 400 million searches for New York City on Airbnb last year, 400 million. Airbnb is essentially banned in New York. Adding hotels, we can make quite a bit of revenue in New York. So there's a lot of these businesses. And what we want to do is release more and more businesses every year. So we think there's a lot of growth of those new businesses.

9:33But in our core business, just one more comment. 70 % of our business and our core business is in only five countries, U.S., Canada, Australia, U.K., and France. There's a couple hundred other countries in the world that can still grow in our core business. So there's still a lot of growth. And for that reason, I think we can reaccelerate. So I'm just trying to get a picture of where those businesses are right now. I mean, we look at experiences. I mean, how much revenue is experiences generating for the company right now? They're all very, very early. We don't report on a segment basis, so I can't share what those are.

10:08But I would say that experience is a little ahead of services, service a little ahead of hotels. and I think each of them will take a few years. Like we basically put a horizon of three to five years for these to be multi-billion dollar businesses. But Experiences is the one most likely to hit a billion dollars in your mind first in terms of revenue and contribution to the business. That's interesting. Maybe not. It's the furthest along because it already existed. And so there was already a higher revenue base. That being said, the TAM, the Total Adjustable Market Hotels is the largest obvious one.

10:42And then services is super binary. Services could be a medium business or a massive business. And the real question on services is whether or not locals book service in their own cities. If they don't, it's a good business. If they do, it's a hugely successful business. And I wonder what you say to, I mean, we've had other travel entrepreneurs on the show, and we've talked a little bit about experiences and services. And the challenge that they have talked about is that it's hard to get people. Services is a bit separate from booking hotels or booking a trip. I mean, it's almost a category on its own.

11:21And you've talked a little bit about how you segment customers in Paris and L.A., people visiting, people living there. But what's the biggest challenge right now getting people to, A, offer services? I mean, is it a supply issue? Is it a demand issue? What's the bottleneck right now? The bottleneck is absolutely not supply. We're inundated with supply for people requesting services and experiences. And I presume that that's only going to increase. I mean, I can't predict what's going to happen with AI, but with more and more jobs being automated, I think more and more people are going to go to the service industry.

11:56And I think the vast majority of hosting opportunities aren't going to be automated AI. So I think that increasingly people are going to be looking to Airbnb to become hosts. I think the bottleneck is awareness that we have services, awareness that we have experiences, that you can trust that they're high quality. So it's really just a matter of people being exposed, using them, and then word of mouth increasing. Experiences are going really, really well. In Paris, for example, we decided to focus on Paris for experiences. That is growing very, very quickly. So if you type in Paris and experience, you'll see that's what I think a future marketplace can look like.

12:29One thing that's surprising is that Parisians are booking experiences in Paris. That I wasn't expecting. They're working really, really well. On services, we really focused on Los Angeles. You type LA, you'll see a really robust store for services. It's working in LA. So we're now bringing it to cities all over the world. We just launched grocery stocking and airport pickup. Those are working out really, really well. So you get to an Airbnb. We have an integration with Instacart where you can have groceries stocked in your fridge. That's very convenient. And then in Europe, Uber is not always allowed in an airport.

13:01It's really hard. So we worked with some local companies in Europe to be able to do welcome pickups where we do this really simple integration. The driver has flight information. They can pick up the airport and take it to Airbnb. As you think about getting the revenue growth rate up to that 20 % mark that you've said that you hope to get the business to, I mean, advertising is one easy way. If you sell ads, that's one way you could sort of juice the revenue growth. Why not just start there? I think advertising is another multi-billion dollar business. It's at least a billion dollars. And so the question is, why not start there?

13:36Well, the reason not to start there is, number one, it's not the most perishable opportunity. I love this Jeff Bezos framework that you can do anything, but just start with the things that are most perishable. And I think the most perishable things are going into new service categories. I think there's a real opportunity for us to do that. The second thing is there's the old model of ads within search results pre-AI, like the Google model of adding ads. But we are now going to be living in a world of AI search. And so we want to design ads for an AI native search world. And no one's really figured out how to do that.

14:08And we might be one of those people to try to figure that out. So we don't want to create ads for the old world. We want to create an ad unit for the new world. So we're waiting to get AI search right before we think about doing ads. How do you think that plays out? You come from a design background. I have so many questions for you about what designing a good customer experience looks like with advertising, which is the way that a lot of these platforms are going to have to generate and monetize more revenue. What does a good customer experience look like from a design perspective with ads? Talk a little bit about that.

14:47Let me just back up and say something about the whole ecosystem of consumer, then I'll talk about ads. I don't think, generally speaking, people have figured out how to make money on AI consumer. I think AI enterprise is going really, really well. On the board of Y Combinator, the vast majority of startups are enterprise. Very few companies are applying for consumer. And I think what we've seen is it makes sense. Models, the queries are fairly expensive, but you can pay for them with enterprise. I think with consumer, there have to be one of three models to make money consumer, either advertising, paid subscriptions, or essentially e-commerce transactions.

15:25I think Airbnb is one really good model because we have a very high-tick dollar, so you can make a lot of money in every transaction. So we can afford to invest quite a lot in AI from a transaction increase standpoint. If it increases conversion, that's great. I think advertising, though, is probably inevitable for a lot of chatbots. And then the question is two questions. One, does the company optimize for engagement or not? Two, do people distrust the results if ads are delivered? So in Google search results, I never distrusted Google search results because the ads were on top. I said, okay, well, those are ads.

15:58They're clearly ads. The things below them are what Google suggests. So we never distrusted it. With AI, it's really important that the questions, people no longer distrust the veracity of information. And I think that's a design challenge. and how I would solve that, I haven't totally, we're in the middle of figuring that out. But I think that's the biggest problem. The second, which is not our problem, we don't need to optimize for engagement. But I think it's really, really important that a company's North Star is user experience, not engagement. Because when engagement's the North Star, then I think suddenly the company becomes the customer.

16:31So I think it's really important for a chatbot that people trust the chatbot. And so therefore, you just have to make sure that it's not compromised at all. Would you ever integrate more with OpenAI? Absolutely. I say that knowing that you're friends and knowing that you've said that the models aren't there or maybe the interface is not there yet. They're not there yet, but I think they'll get there. And when they get there, we'd love to integrate. Listen, like other travel can be decided to like integrate with chat GPT. And I told Stan, we don't need to be the first. We just need to be the best.

17:04I don't need a race to it. The SDK, like three things. Number one, it was a little bit hard to discover Airbnb in the chatbot. Now it's becoming more easy. You didn't have to install it. Number two, there was a lot of latency. So it took many, many seconds to load. Three, 90 % of people when they book an Airbnb, they send a message. They have to verify their identity. So there were just some interface things we needed to be able to do an integration. But we are absolutely interested in showing up in ChatGPT and Gemini and others. I don't think they're an existential threat at all. I think two things can coexist.

17:40I think what can coexist is we can win from specialization, but also some people are going to start their travel inspiration at chatbots and they can continue it on Airbnb. So I think both can coexist. And as long as your experience is great, we will do it. But we're not one of those companies that wants to be the first to integrate. We want to be the best integration. Right. I want to ask you quickly before you go, Brian, there are a lot of budding entrepreneurs in our audience that look up to you. If you weren't building Airbnb right now, what business would you be building? I would do something with consumer AI.

18:15I don't know. I mean, I could give you a bunch of categories that I think are really interesting. But right now, again, I'll just say this. A lot of people are afraid to create consumer AI companies. When I joined Y Combinator, almost every company was a consumer company. The App Store had just launched, and everyone was making apps for regular people. Now, almost every single person is creating an enterprise AI company. It makes sense, but the vast majority of the economy is not gonna be enterprise, it's gonna be consumer. The biggest companies in the world are gonna be the companies that touch the most lives.

18:48And the companies that touch the most lives daily living are gonna be consumers. So my advice to entrepreneurs is don't be afraid to start a consumer company. It's possibly harder. It's a little more of a hits business. It's more marketing than sales, a little harder to control. But don't be afraid of it because AI has not changed daily life yet. And it won't change daily life until a proliferation of consumer apps come. Now, what would they be? I think health is interesting. I think education is interesting. I think e-commerce is really interesting. E-commerce is a great business model, right?

19:20We talked about there's not a lot of business models for consumer AI. E-commerce is a business model. So these would be really obvious spaces. Right. All right. Well, Brian, I want to thank you for coming on the show. We really appreciate it. It was a great discussion and hope to have you back again soon. I hope to. I hope this is the first of many interviews. Great. Well, that is Brian Chesky, the CEO of Airbnb here on TI TV. Thank you very much.

19:48Okay. Microsoft is growing its relationship with Anthropic. New exclusive reporting from the information today reveals just how much Microsoft is spending on Anthropic. I want bring on Aaron Holmes, one of the reporters on that story, to talk about what we've learned. Aaron, welcome back to the show. It's great to have you here. Thank you for having me. So what did we learn about Microsoft's work with Anthropic? Yeah, so I mean, over the past year, we've seen Microsoft and Anthropic get a lot closer, even though OpenAI remains Microsoft's most important AI partner and provider. And specifically, that's looked like Microsoft becoming one of Anthropic's biggest customers, spending on track to spend more than$500 million annually on Anthropics models.

20:33And we've also learned that Microsoft is now incentivizing its salespeople to sell Anthropics models on Azure, just as much as it incentivizes them to sell OpenAI's models. And beyond that, I think Anthropics is also starting to even get more involved in helping Microsoft build products that use its models. So across the board, these companies are getting a lot closer. Now, you reported that Anthropic is on pace to spend$500 million annually with Microsoft, and that would make it one of Anthropic's biggest customers. Did I have that right? Yeah. Anthropic is spending the money on Microsoft. No, Microsoft is spending the money on Anthropic.

21:14Yes. Microsoft is spending$500 million annually on Anthropics models. At the same time, Anthropics did commit earlier or late last year to spend billions of dollars on Azure cloud services. So the money is going both ways. But yeah, I mean, the money that Microsoft is spending on Anthropics is pretty significant for the startup. Anthropics projected that it was, you know, going to make in the realm of$7 to$9 billion in revenue last year. So this is pretty significant that it's getting this much from Microsoft. Now, one of the questions I wanted to understand here is what types of models is this?

21:51Because Microsoft obviously has an expansive suite of products. Are these coding models? Are these large language models? What are they buying from Anthropic? Yeah, so as of the$500 million annualized figure, Most of that was coming from coding models, which Microsoft was using to power AI agent coding features in its GitHub Copilot software. And since then, the amount that Microsoft is spending has actually probably grown a lot because they've started to also add Anthropik models to other AI products like Office 365 Copilot and Security Copilot. So at this point, it's really across the board that Microsoft is using different Anthropik models for different types of AI products.

22:36Is Anthropic reciprocating? Are they spending with Microsoft? They are. So they, you know, Microsoft also invested$5 billion in Anthropic in September. And around that time, Anthropic said that they would commit to spend several billion dollars on renting cloud servers from Microsoft. And they also said, you know, they might contract several more gigawatts of cloud server space in the coming years. Although it's hard to know exactly what that means. But yeah, basically both of the companies have now become large customers of one another. And who do you think has the leverage in this relationship?

23:16Yeah, I mean, with all of the ways that money is changing hands back and forth, it's a little hard to say who's benefiting more. But I think my take is probably that Anthropic is getting the most out of this right now because they really want to grow their enterprise business and getting access to customers of Microsoft's Azure cloud service is a way to massively expand their potential universe of customers. At the same time, Microsoft does already have access to reuse OpenAI's models for free. So it maybe doesn't need Anthropic quite as much as Anthropic needs Microsoft. But regardless, it is obvious that both companies are benefiting a lot from this partnership.

23:57And I want to end off with a chart that I would encourage people to look at in the story. You basically mapped all the ways in which the AI model companies and the cloud providers and companies like NVIDIA and Meta, the ways in which they are doing deals with each other. And it's a great matrix. My takeaway from that is everyone's working with everybody. My question for you is, is that inevitable? Do you see it as a risk? What do you make of that? Yeah, I mean, I think in some ways this was inevitable, especially when you look at cloud providers like Microsoft, Google and AWS who want to have customers on their platforms using all models and they don't want customers to have to use a different cloud provider to seek out different models.