Uber Is Coming for STR. Airbnb Has an AI Agent Coming.

0:23Good morning. Happy Monday. This is Brandi Canale. I'm here with Jamie Lane and Michael Golden. And we are together for the first time in like two weeks. I've missed you guys.

0:35Michael Goldin: We are in the midst of the fall conference circuit schedule. And next week will be no different. And the week after that, the week after that. And I'm going to immediately have beef with Jamie, for those of you watching, because how did you get Skiff merch? For the listeners, Jamie has a Skift hat on, and I was also at Skift Global Forum all week, and I am merchless. Tell me. I've wanted one of these hats since before GMH became part of Skift, and then I saw an opportunity to get one at the Global Forum, and I seized it. So I want to thank John Ahn for helping me secure this hat. Okay, shout out to John.

1:20It was great to see him.

1:21Michael Goldin: Can you help Brandy and I secure that? This feels, I feel gypped, but it's been a crazy two weeks. I've gotten to see both of you guys in person, which is great.

1:34Brandreth Canaley: Michael, you and I had quite the stint in Madrid, which was really fun at Gastival. And then Jamie, I got to see you in New York. So how are you guys feeling? We have a little bit of a lull before the conferences pick up again.

1:48Michael Goldin: Yeah, it's super exciting. And on a personal note, I've joined Kismet. Yeah, that's public now. It's public now. We're the infrastructure connecting vacation rentals and hotels to the LLMs. So very relevant topic for the entire year, 2026. It couldn't be more relevant. And I applaud you for, in our great debate, you have literally put your money where your mouth is in terms of your bet on how agentic bookings, how AI layer is going to change by betting your career on this change. You make it sound so serious. I know. I was like, well, that sounds pretty honest. Look, it's the topic that everyone's talking about.

2:38Michael Goldin: It is moving extremely fast. All the CEOs at Skift were talking about it. At Guest Eval, literally had someone tap me on the shoulder and ask if they could search. I could search on my GPT for their properties if they'd be found, having no clue that I was a part of Kismet. So it's an exciting time. We are at the forefront of everything that's coming out. we're seeing we've seen a muse booking come through over the weekend so seeing a gentix search converting into bookings is also really cool and it's so so early i'm still not sold on muse but can we talk about that a little bit before we get into the stories because we we discussed muse what three or four weeks ago we we largely dismissed it because it wasn't great at travel.

3:33And now three consecutive weeks, it's been number one and downloaded app in the app store. It caused a collapse in the values of the major OTAs because of how the market, at least Wall Street sees the sort of search layer changing in terms of travel. And Brandy, how many times was Instinct and Muse mentioned at the global forum? I think every single question or interviewer from Skift, every single CEO mentioned the two of them at least a few times during the conference. Yes, you're right. They did. And then I don't know how I've become like

4:16Brandreth Canaley: the cynic on the show, but that is not to say that I don't think that there is going to be a revolution in the way that we plan travel and the way that these agents help us. But the fact that like an app is number one in the app store a couple of weeks in a row, I don't think is relevant in the grand scheme of, of, of everything. Right. And same, like, I think it is crazy that an app shoots to number one for a couple of weeks and it tanks the valuations of these enormous companies. Like it's all just so finicky and fickle. And it's like, we are talking about very long cycles here of like just of, I don't know, these institutions.

4:54Brandreth Canaley: So I, um, to me, that's just, it just, everything's just seems a little silly that, you know, an app store being number one can like collapse value. But, um, I do think it's interesting. I was, I hadn't heard of instinct before skift. I mean, I feel like in the last three weeks, so much as how backwards hat, Jamie. Oh, we got Brat Boy Jamie on the pod now. Watch out. But it's, yeah, it was really crazy to go from like, oh, we don't know if this is going to be anything to now everybody at Skift was talking about both of these agents. So yeah, interesting times. Have you given in to Muse yet? either of you oh i have um just playing with it i've played with it i haven't given it any permissions yeah i i bought i bought a new dress shirt on muse yesterday just to see how the entire flow could work in the end of like help me find something and then put it in the cart and check out um and it it worked i assume it's going to show up on my doorstep but not on amazon though not on amazon i love that they were like it's all about security and definitely not any of our ad revenue i mean the thing is both could be true but um i don't think that that was like

6:18Michael Goldin: the main reason yeah so i'll i'll take some of the skepticism on like is muse the answer i i don't know i think i've got a healthy dose of skepticism uh as well but Siri is going to come out with one. ChatGPT is going to come out with one. A personal agent in your pocket is going to happen. And it seems to be happening faster than we might have thought. You know, how much people let it do and how much people know how to do with it is one thing. But, you know, the curve of adoption is absolutely insane with all of AI.

6:57Brandreth Canaley: Yeah, I think in a year or two, this might be a totally different landscape. But it was an interesting thing that Brett Taylor, who is the chairman of the board of OpenAI and the CEO of Sierra, said that AI adoption is going to happen a lot slower than everybody is talking about right now. And his point wasn't about these chatbots coming out, but the practical uses for a lot of businesses and he gave like a flower shop example of like you might be able to help their ai might help their you know accounting or their automation but like it's not going to be making the bouquets of flowers for them right and so there's like this i think in brian touched on this to brian chesky in his topic or you know his session that kind of the silicon valley tech world is in this bubble where it's like they there is like a bigger the broader world isn't necessarily on the same page of adoption right now.

7:56Brandreth Canaley: But that could change in two years. Like in two years, every single person could have just the AI agent, like their preferred, their muse or their clod or whatever they're going to call it. And, you know, that'll just be standard.

8:10So, yeah, I mean, maybe and maybe this is a good lead into our first topic of and Michael, you shared this great article on sort of outlining and how Muse instinct these chatbots could sort of change the booking layer, change the entire path. And one, it starts with what you've been arguing since the beginning of the year around, and if the Muse agent can just connect into a properties direct website that's going to disintermediate the OTAs. And that could, and even 5 % of bookings could kill their growth for the next few years, which is, I think, largely what the market was reacting to. But there also becomes this other argument and it's really relevant for Uber, maybe booking and Expedia on ads being a major driver of growth for these platforms.

9:19So you mentioned it, Brandy, that Amazon has banned Muse, I assume they've banned Instinct or some of the other ones of shopping on a user's behalf. Essentially their entire profitability growth in these past two years has been outside side of AWS has come from ad sales. So if all of a sudden the average user is using Muse to go onto Amazon and buy their toilet paper, they do not get served ads. They do not add. And I think I go to Amazon and add one or two things and end up with five things in my cart. How does that happen? And they're very good at serving me things. I'm like, oh yeah, of course I want that.

10:12I need it. It's not I want it. I must have it. I need it. I must have it. Yeah. And so it makes sense on why Amazon might care about it. But when you're going to book travel, like I go and book a trip to Puerto Rico I have coming up. Like I know I'm going to book a hotel or a short term rental and there's not all these add-ons that people are, I'm sort of expanding my share of wallet. Like, of course, I'm booking wants me to add a flight, add an experience, add all these other things, but ultimately I'm there. They're really not. And then, um, yeah. So, uh, and they see like if they're actually serving that layer, um, uh, well, so So Expedia is partnering with Muse to give a real-time API to the booking information.

11:09They can have that, and they could be the pipes to make that work. Yeah. Well, I think we have the first main story.

11:18Brandreth Canaley: It has to do with Uber today, and it is really all based off of Dara's session at Skiff Global Forum, which is great. If you haven't had a chance to go and listen or watch the whole video, you can do so the link in the show notes or on skip.com. But it was one of the first interviews that was done and it was really good. But so kind of removing the agents for a second, you have Uber, you know, kind of laying, setting the table for the amount of data that they have, the amount of activity that they have, all of this inventory, all of these, you know, drivers and couriers and all this customer data.

11:53And then you have the hotel of it all.

11:57Brandreth Canaley: And so kind of like one of the themes of the week was like Uber and Airbnb are coming from different directions, but hotels is like the meat in the middle that they're all trying to get after. And it's, you know, Uber has the, I'm sorry, Expedia integration. So you're going to be seeing if you're a short term rental operator, your verbal listings are going to be appearing there and everything. And so is this, are we closer to the connected trip now that Uber is in there? and like, is Uber going to be the one to do it? They were talking about how, you know, people think of Uber as like your instant, like your food, the ride that you're getting, not necessarily where you're looking long-term to book travel.

12:33Brandreth Canaley: And I'm curious, Jamie, if you think that people can change their minds and their booking behavior. Yeah. I think one of the metrics he might've mentioned was like that 80 % of the bookings were coming from Uber One members. Yeah. Are you an Uber one member? I'm not an Uber one member. Uh, but I think if I was like, just like all these different ecosystems I'm part of, like if all of a sudden and the Uber one benefits for booking a hotel are massive. Uh, so I would like, I think it's something like 10 % back. If I book a hotel that I could then go use on Uber Eats or other forms of spend that I do through Uber.

13:17So all of a sudden, I have a huge incentive if I'm an Uber One member to start booking my travel. And ideally, they're connecting it through. And Rafat talked about having that Uber show up right as you're walking out of baggage claim and just the seamless experience that we all want in the future. and their ability to deliver that becomes exponentially more likely if they know where you're going, they knew the flight that you were on, they just know so much about you and can schedule everything to happen for you. Yeah. You know, I have to admit, so I accidentally had Uber One for a long time because I signed up for it to get discounts on Uber Eats.

14:02Brandreth Canaley: I use Lyft because I get like 10 times points or something like that with my credit card. Um, and ecosystem got me like, I only use, sometimes I use Uber when I'm in New York cause it's cheaper, um, or internationally, but it was like, it never in a million years would have occurred to me to look at a hotel on Uber. But now I'm like, that is really interesting. And I think I'm curious if this happens to anybody else, but I have a little bit of like ecosystem fatigue, like which one of these ecosystems, what, where's my natural habitat? You know, like I, I don't like, do I live in Airbnb and book all my hotels in there?

14:44Brandreth Canaley: And then I'll have, you know, my vacation rental and short term rental people yelling at me to book direct. Then do I live inside of Uber? But now I have to change from Lyft. Do I live inside my agent? Like who is, who is getting my attention? Yeah. And you would, if you're having that fatigue and with a strong incentive, I'm sort of fundamentally like to go direct. Like, and is that going to, and that's why these OTAs have such strong value. And why does, and booking ecosystem so valuable? It's genius. It's the rewards. It's, I'm sort of what they've built around that, that keeps people in the ecosystem.

15:29And so even if, and Muse Instinct build out this layer that they're booking on people's behalf.

15:40The sort of upside case for booking is you already have all these people that are embedded in their ecosystem and the agent's just going to keep booking. And it really doesn't matter what the front door looks like. It's still going to all go through that layer that the consumer wants.

15:55Brandreth Canaley: Well, an interesting point. This is actually from an article that Michael sent to the group chat that I think last week, but about the kind of the component about Muse that I didn't really think about was the WhatsApp of it all and how that is just going to be like a whole plugin. Cause for me, Muse has just been trying to get me to use it via Instagram, which like I'm not going to do. Um, but if you are most of the world who uses WhatsApp, um, then I can see that becoming a really easy way to suck people in because it's already in this app that they use all the time. It has all of their, which like, this might be the scary part.

16:30Brandreth Canaley: It has all of your personal conversations that you're having with people. But like, it's, it's how, how are you communicating with the hotel or the host that you're going to stay with, you know, whatever your plans are. So I think that's, that's really interesting. And Dara also was talking about the leverage that all of these kind of all the suppliers have right now or could have. And that I think might be the layer of friction that we have right now. I don't know how long it will take to solve that, but can these agents really get to the product that people want right now? And so that's the layer that I think right now is causing the most friction.

17:11Brandreth Canaley: Although Michael was saying that they had a muse booking, but that's one booking. Not to yuck his yum, but is that a sustainable path forward?

17:19Michael Goldin: Yes, it absolutely is.

17:26Michael Goldin: Is it a sustainable path forward? I only caught a piece of this. My internet's giving me fits. I apologize, everybody. We don't know. Everything's moving so fast. But we do know that the AI world is here. And if you aren't discovered and booked, then it's going to end up in Jamie's thesis, which is all back to the OTAs. We think there's a powerful capability to be able to pipe into all of the different agentic searches and then ultimately give them, the agents, the tools to make the reservations. Yeah. Well, you've bet your entire livelihood on it. Heck yeah, I have. So, Brandy, on Wednesday afternoon, we were told about a special guest coming to present at Skift.

18:26And I didn't think there was going to be someone that could really one-up Brian Chesky sort of closing out the day. But we had Prince Harry, the Duke of Sussex. Yeah, you really nailed that. Great job. come and present. And one, I never thought I'd go to a travel conference and see royalty outside of the major OTA CEOs. Yeah, I mean, the fact I was 10 rows away from Prince Harry, I was like, this is crazy.

19:03Brandreth Canaley: Young Brandy would be freaking out right now. I had such a crush on him when I was growing up.

19:11but I got a lot of questions. I know this was on the list, but like, why was he there? What was he talking about? Yeah. I actually thought it was a great message. How did it resonate with you? Yeah, it was great. So the kind of con,

19:25Brandreth Canaley: the backdrop to all of this is that it was UN week in New York. So he was there. I mean, obviously not just for skip global forum. He was there also presenting at the UN and other or climate related things, but really talking about, um, we'd like to try basically our responsibility to improving or our stewarding of the areas that we go and travel, which I thought was really important. And, you know, we, I thought that was a really good message. And how do you get people on board when you're just focused on the bottom line? Um, and I thought that was interesting because another, I forget which conversation it was, but someone earlier in the day was talking about how the sustainability movement and like people say that they're willing to pay for the extra whatever at the hotel to make it be sustainable.

20:15Brandreth Canaley: But then in reality, that never happens. And so he was talking, you know, when we go to these communities, you're spending, you know, you're using so much more water, electricity or whatever. So what are you as a travel company doing to be stewards of the places that you're, you know, using basically. So I thought it was a good message and he was a good, great get for Skift.

20:36Michael Goldin: Oh yeah. Am I just living under a rock? I had no idea that he was involved in anything travel oriented. Yeah, he has, but I had never, I mean, I'd never heard of this company, but that, um, but it's like, but he's involved in a bunch of stuff.

20:50Brandreth Canaley: He has a, uh, travelist is the name of the company and he is involved. I knew he was involved in a lot of climate related things. So this isn't really surprising. And he had spent a lot of time in Uganda, I believe it was. And so it like that was kind of the draw that he had spent so much time going there. And then that's, you know, how he got involved. So I thought it was a great message. He had he had a nice speech that wasn't too preachy, I thought, because I mean, some people can be super preachy and kind of recognizing the place of privilege that he obviously comes from he's a prince um and then no uh but then and then there was a great interview with sarah coppitt after so i um yeah i thought it was great it was a good surprise celebrity

21:34Michael Goldin: yeah that's can we get him on the show about as big of a celebrity as possible will yeah schedule him for next week we can we can yeah we'll do it um well so our our this second topic

21:48Brandreth Canaley: for the show is we couldn't obviously mention Skip Global Forum without Brian Chesky. But I thought a really interesting end to Dara's segment was advice to Airbnb, which I'm sure Brian is taking to heart, but about cutting, killing what's not working. And if Airbnb, I don't know, we've talked about a lot of Airbnb's launches, so I'm wondering if that's going to resonate with him. But Brian's big commitment was launching an AI agent in 2027. I don't think this is a big surprise, but was curious your takes on on this news, if you were shocked. But about this. I wasn't shocked. I'm surprised they haven't released one yet, given that and bookings got theirs.

22:36There's Expedia just bought one. And Muse, all these, and GrokBot, all ChatGBT, they've all built agents around travel. Travel's one of the most recognized use cases of these agents. And I'm not sure if it was in Wall Street putting pressure on if you're not going to do it like someone else is and they're going to eat your lunch because consumers want it or that they really think that they have created something new. And Brian's talked about for the past two years, they doesn't think chat interface is going to be the agentic way to book travel. And he said on stage that it's going to move beyond chat and be something new and innovative.

23:25So I think I'm on the edge of my chair. I'm wondering how they're going to innovate on this. So excited to see what it is, but I'm given their releases over time and the success of those releases. I'm not, I don't have high confidence that they're going to revolutionize the way we book from it. Yeah.

23:52Michael Goldin: And there was an exchange between him and Francis, the Sonder founder in Odessia. I think I pronounced that right. uh the it was an interesting back and forth uh about travel and an agentic travel search and i don't know i i saw what dara said with uber i'm sure you guys covered that while i was fixing my internet but i'm a lot more in his camp there's there's going to be lots of different flavors of agents that people like and want to use i don't know why anyone would have different a myriad of different agents for different, I don't know, personal search. Yeah. An investor earlier in the day, whose name is escaping me, was asked if it was like a rapid

24:43Brandreth Canaley: fire round. And he was like, would you invest in an AI travel planner? And without hesitation, was like, no, no additional context. And in my notes, it just says no parentheses, LOL.

24:59Michael Goldin: Well, yeah, they've got a great brand with a lot of travelers and a lot of loyal travelers. They do control a good amount of inventory that's exclusive to them. So they have that playing for them. But I would bet on the market versus them specifically. But Chesky's proven us wrong before. and he had a big ask brian for all the other companies out there they're like build us an sdk let us build the user interface that we think travelers deserve within your chatbot like if chat to bt you want to have a chatbot that does bookings on airbnb like let us build what that interface is going to look like.

25:53Like if you call Airbnb, we're going to serve the photos. We're going to serve the experience a way that's going to be in a rich version that's going to convert those users through the funnel. But essentially what's available now, they're just sort of, you use Muse and it's, I'm pulling up the browser. It's trying to do it on your behalf. It doesn't. And what's happened has not changed the fact that it's still a terrible experience to use moves to book travel. And like it is if it is going to move to the agentic layer like that. um airbnb and others or airbnb in particular they're like they've spent so much time on their app and they're able to do that because apple built an sdk so people could build apps within their ecosystem and that it needs to move to that point where all these companies can build what that UI looks like for the user.

26:54So kind of slight pivot from this to the host side,

26:59Brandreth Canaley: because Airbnb's pro host forum was happening at the same time. Now, a component of the AI agent that has come up is like, obviously, all of the content in your listing is going to become increasingly more important, because it's not you're not depending on a human's eyeballs to catch something that might be relevant to them. You have to make everything in your listing relevant to the chat or to the bots, right? And, or the agents. So I feel like bot has like a negative connotation now, but to the agent. And one of those things is reviews. And so I think on the host side, we've been complaining about the review system for many years.

27:41Brandreth Canaley: And now those reviews are going to like the agents are going to have so many like infinite context of your Airbnb listings to look at all of those reviews and maybe pick certain things out. And I know that at the pro host conference, that there was a lot of very vocal feedback, how we host can be like extorted for reviews, which we've talked about certainly in the past. And now like, that's just the pressure on reviews is going to be, I think even more extreme, which as a host is really it's just disheartening, I think.

28:16Michael Goldin: It's two-sided. It's not just the reviews, but also how you answer and respond to the reviews. So Will Reynolds at Gesteval went through examples of this. Agents can see if people are complaining, but if you don't respond and say, we've fixed it, we've taken action for it, we've refunded, whatever, that's actually good data to the pipe back in. That shows trust. That shows responsibility. So it doesn't have to be a net negative when a bad review comes in. You can actually spin it, especially for the agents, as a net positive. This guest is extorting us. They actually destroyed the place. These people never have these people stay with you.

28:58Michael Goldin: And Brandy, you touched on something that was, I think really key, which is direct booking sites often have better data than an OTA listing site. And that is a key differentiator for agents finding your property through the LLMs or whatever, because you can have more answers for them there than the OTAs have access to. So it is an an important call out. Um, I suspect the OTAs will find ways to pull more and more data. Yeah. That's what I, my next, my next question is like, how long do you think it's going to take for that? Like to be leveled, you know? Yeah. I mean, some of that's up to what you give them, right.

29:46Michael Goldin: It's all permission. So, yeah.

29:48Brandreth Canaley: Well, I also think about like booking.com for example, where, I mean, this could have changed, but you can't choose the order that your photos are in. and which is great or you can't and you can't write any of your content like it pulls and creates your content for you so I mean I always hated that when I was in charge of doing our distribution many moons ago but it's just interesting to see how many of these kind of like fixed qualities of the OTAs that they've had over time how like if any of these things change as they shift all of their content to be readable by these agents slash bots. Well, it's been an interesting couple of weeks.

30:28I'm glad I got to see both of you guys in person, but I'm glad to see both of you guys here on the show on a Monday morning.

30:36Michael Goldin: And again next week at Verma. And again, yes. Jamie just showing off all his merch. But yes, it'll be great to be at Verma. If anyone, if any listeners are going to be there, let us know. It was so great to see so many listeners, especially at Guest Evolve. Shout out to Margarita in Lisbon. She came up to me and was like, oh, I listen all the time. So thank you to our European listeners. It's great to hear that you guys are tuning in. So yeah, if you're at Burma, let us know. Anything else on the docket for you guys this week? Yeah, and come say hi. We love saying hello to the listeners. For our European friends, I'll also be at VRWS in Lyon next week.

31:17So I am really excited to see the plane that is going to be getting us from Nashville to Atlanta to Paris to Lyon and how many of the Verma crowd is going to be making that migration east. You'll have some friends.

31:37Michael Goldin: Oh, yeah. A lot of vendors on that plane. Oh, I bet there will be. Amazing. Well, thanks everyone for listening, for tuning into the live show, and we will see you all next week.

32:12Thank you.

32:43Thank you.