ChatGPT Checkout Retreat, Expedia Reset and UAE STR Cancellations

On this week’s Good Morning Hospitality, A Skift Podcast, Wil Slickers, Brandreth Canaley, and Jamie Lane break down the latest headlines shaping travel and short-term rentals.

They start with OpenAI walking back plans for in-chat checkout in ChatGPT, a move that shifts the platform back toward discovery rather than transactions and eases pressure on OTAs like Expedia Group and Booking Holdings (NASDAQ: BKNG).

They also unpack comments from Expedia Group’s CFO about how the company has “radically changed the direction” of the business with new performance metrics and strategic priorities.

The team then looks at cancellation trends hitting vacation rentals in the United Arab Emirates, where regional instability is beginning to ripple through bookings, before diving into analysis on whether Airbnb may need acquisitions if it truly wants to “own the entire trip.”

They also highlight Breezeway’s recent funding news following the bonus interview with Jeremy Gall released earlier last week.

Watch This Episode

Vacation and Shoutouts

Good morning.

Happy Monday.

Good morning, you two. How are we doing?

I’m fantastic, because I’m on vacation.

On vacation, but still doing the morning show. I love it. I love the commitment.

Yeah, I figured after last week’s technical nightmare, I owed it to you guys to come on the pod.

Yeah, that was crazy.

You got a lot of having a PC for work, right?

I hate it so much. I hate it deep within my bones.

But especially since Michael’s not here, it would have been a lonely episode if it was just me and Wil.

Yeah.

Yeah. Jamie, what do you think the episode would have been like? Do you think it would have been a lot of just me asking you for more data, or do you think we’d have had maybe some banter on some disagreement points?

Fight, fight.

We could have gone in different directions.

It’s been a dark week in terms of economic data, and we could have gone way down the hole of how bad things are right now, or just have a deep philosophical debate on the impact of Airbnb and AI on the travel industry.

Good thing I’m here to keep it light.

Yeah. You guys already saw my thoughts in the private chat earlier this weekend. So I think yeah, it definitely would have gone a dark, dark rabbit hole.

Before we jump into things, I want to give a shout out to Stay Montana.

They’re the operator that I’m staying with here in Big Sky. Really great experience so far. It’s really cute.

The owners of the home, their daughter Ella, who’s 14, has made little cookies that they leave for all the guests, and it has her recipe on the back.

So they’re creating the next generation of vacation rental owners and operators, and I love to see that.

Love that. Love that. Hospitality in action.

I love that.

Yeah, definitely.

I’m also jealous that you’re in Big Sky. I’ve been wanting to go to Big Sky for a while. It sounds incredible.

Very excited.

We’re here for an entire week, so pretty pumped. The snow is, I mean, there is snow. It’s not great snow, if I’m being honest.

But we booked this trip like eight months ago, so we’re here. And I mean, there is snow and the infrastructure. Big Sky just invested over $100 million in the resort in the last couple of years.

So the infrastructure is fantastic. And I mean, the scale and scope of what you’re looking at on the mountain is unparalleled. So I’ll deal with some mashed potato-y snow with low coverage to just have the experience.

Yeah, let’s say welcome to the club.

Same in Colorado, same in Utah, same in all the snow states. But we got a good amount of topics for today’s episode.

3:10

Industry News and Acquisitions

And I guess the first one, we got to give our friends at Breezeway a big round of applause and kudos for their recent investment round. I did talk to Jeremy Gall last week on the pod, and we did a bonus episode.

And I did clarify with him, it is a bonus round, or not bonus round, sorry, bonus episode. It is an investment round, not a acquisition. So I did ask, because I was like, are we going to see Jeremy disappear?

Like, what’s going to happen? So they’ve taken funding in the past, but just never really announced it. And this one was big enough to really kind of make them go, you know what, we should kind of spotlight this a little bit.

So yeah, you have to highlight all that hard work, and it’s exciting as a Breezeway user to see what they’re going to do with that money.

I know.

Will, thanks for throwing me under the bus with the hard question too for Jeremy.

Yeah, he was like, yeah, thanks for the softball, Jamie.

I was like, look, we’re all thinking it. I’m just going to put Jamie’s name on it, because it was your question. You did have a great question.

I was glad you asked it in the group chat, because I’m a little rusty with my interview skills.

I haven’t done a lot of interviews lately, so it’s more of a, give me some hardball questions that aren’t easy that everyone would just be like, okay, we kind of expected that. Yeah, that’s good.

But to not tease it too much, we will got in deep on like how AI point solutions could impact their business.

Like they’re really building the operations platform and it feels like they’ve got a big lead, but there’s a lot of competitors sort of nipping at their heels, building great AI solutions that take certain pieces of the operation pie, but not build

the entire solution like they’ve done. So can they continue to innovate enough to be the dominant player? I think is a big question.

For sure. And the one thing that they do have against those competitors are nipping at their heels is the data. They have a crazy amount of data.

If they could utilize that appropriately, I think they’ll do really well.

Well, and they’re so entrenched in so many of our businesses. I think they are like the leading software. So you have like the cost, the pain of switching and all like that.

So if they can kind of, you know, shore up some of the things that operators are looking for, a lot of more automations, I think that they’ll maybe something I’ve suggested in the past.

What’s your wishlist, Brandi?

Well, there’s, I mean, again, capacity-based housekeeping, like auto-assigning based on geographical location, you know, that kind of thing. So, yeah, I’ll just keep shouting it into the void until someone does it.

Remains sticky, Breezeway, remains sticky. That’s all I gotta say. Well, speaking of bonus episodes and content, we have another episode coming out tomorrow.

So Brandi, do you want to lead us in?

Yeah. So tomorrow, we have a bonus episode with former Romy CEO, Andreas King-Giovanis and CFO, Iskander Karimov. The three of us were running Romy for the better part of 10 years.

And we have a special kind of episode to talk about our acquisition and everything like that. So it’s part news announcement and part announcement, and then part a retrospective of the company that we built.

And I think a lot of people listen to the show have built their own businesses. So I think people might be able to relate to some of the highs and lows that we went through.

100 percent. During the recording of it, I was behind the stage monitoring the recording, and I was laughing and smiling because like it is kind of crazy, 10 years of what you guys built.

And this would be one of the many acquisitions on the show, that one we’ve covered, but also like that’s happened with any of us on the show that I co-host. So it was actually really cool to go down that memory lane.

And I remember the first hearing of you guys and meeting you, I think like early COVID, thanks to our friends at Good Old Noise Aware, and now REST. And it was a lot of good moments, I would say. It’s just from thinking back of when we all first met.

Definitely.

And it feels good to be able to like say it now because this happened in August. And so I’ve just been like, yeah, like we’re still, we didn’t, I didn’t quit.

Yeah.

It’s like, everyone’s like, wait, Brandi, why are you announcing the acquisition post-Statera?

Yeah, exactly.

Yeah. That makes sense. And shout out to our other amazing co-hosts on the GMH Hotels episode who’s tuning in live on LinkedIn, Steve Turk.

He said he’s excited to listen to the episode tomorrow. So it’ll be a good fun bonus one for all the GMH listeners. But moving on, we do have some great topics that I would love to jump in with or jump into.

8:19

Expediaʼs Strategic Turn

So let’s begin. This first one, I think we’re going to go with Expedia. Expedia has basically said they’ve radically changed the direction of the company, which is true.

We’ve talked about on the show. But I think maybe kind of what Brandy and Andreas and Iskander were doing is going down a little bit of memory lane here and talking about when they were super bloated, lacking direction, lacking vision.

Now, the company has obviously made what seems to be a complete 180, obviously with their B2B platform, hugely expanded and taken off.

Arianne Gordon’s leadership really steering the direction and there’s been a ton of layoffs, so I’m going to open the floor.

Now, layoffs is good thing. No, I think we’ve been talking a lot in the last year about Expedia’s doubling down on the B2B sector and Gordon is a huge reason they have some clarity.

I think about your own business when you try to change direction or change focus and how difficult that might be in your small to medium-sized business, and then you think about what that entails to take a public company that is still by a lot of

metrics successful. Then trying to turn it around when it is so big, you have to have leadership changes, you have to cull a lot of people, unfortunately, and it also, there’s a lot of scary economic news around jobs, but sometimes these layoffs can

For sure.

While we were saying before we went live on the show, you and me talking about going from our own startups to then now more corporate business, it sometimes can feel like, yes, you move fast, but it’s also there’s a lot more bureaucracy and things to

go through, and maybe a certain approval route that you have to go, and it can feel like things slow down and get caught within its own system, I guess, right? Like as much as Skift likes to proclaim they’re still a startup, we’re over 100 employees

Big leagues now.

It is, and it’s like, look, we got to be real in some shape or form, where it is a corporate structure, and sometimes with corporate structures, there could be too many cooks in the kitchen versus when you’re a startup.

It’s like you and me and one other person, maybe if we’re lucky to have a third on the decision-making. So it’s like, okay, you get to have that leanness and that agility and speed.

But yeah, I think in this term, layoff could be good because they get to avoid some of that.

Well, and 11 minutes and 19 seconds in, I’m going to mention AI for the first time. But that also is a big part of their strategy.

They’re saying like we’re able to slim down some of these teams because of the machine learning that can help us with our product and all this. We’re going to talk later in the episode about the different chats and the transactions in chat.

But AI is helping these big companies, and that is also going to see them trimming down, becoming more efficient, hopefully. Hopefully, coming out with some cool… A lot of this is what is on the back end for the company.

How are we maximizing our shareholder value? It’ll be great to see once some of these ideas and once these changes are really maturing within the company, how we as customers see the benefits of this.

Do you think Expedia will ever lower their commission because they’re just making so much money? They’re like, actually, now you get a 10% commission.

One can only hope.

And Expedia and Booking both talked about it. They’re both growing their supply, growing their bookings 10% plus in 2025, and they’re keeping their expenses and flat to even declining in some areas. So those efficiencies are coming.

And it’s great debate right now on are these efficiencies going to impact the overall economy in terms of we don’t need all these people to do the jobs anymore, or are these benefits just going to compound?

Everything can get cheaper because we can all do it more efficiently and bring down those fees. Then Brandy’s business gets more competitive and better margins, and they can hire more people and expand more ways.

So I think as an investor, you like to see it that they’re expanding their margins, they’re growing. But as a worker at maybe one of these companies, if you’re one of the ones getting laid off, it’s not so great.

Yeah. No one who’s gone laid off is like, wow, thanks guys for your really positive spin on me losing my job. But I think this is like the broader conversation is how AI is transforming all of that.

Yeah.

Well, in the top of the episode, Jamie, you kind of mentioned it kind of got a little dark this weekend.

13:39

Economic Data and Travel

As the job report was announced, we have more updates on the Iranian war happening. So with oil is now over $100, which last week when we recorded on Monday was at 65. So that’s great.

Can’t wait for that. As a guy who drives a car that needs premium gas, but yeah.

Toyota’s for the win, baby.

Yeah. So let’s go in. Give us some updates that happened on Friday.

And then also I know we have some UAE data updates as well. So we’d love to give you the money.

I won’t dig too into it, but it was definitely a job report that was not good. Economy lost 92,000 jobs in February. A lot of that was in leisure and hospitality, down 27,000 jobs.

I’ll blame some of it on the weather. And there are seasonal impacts of if people don’t hire. We had a warm winter last year, it was definitely colder.

I already hear in a lot of the ski resorts, they just did not hire as many people because they didn’t need to open up the back bowls or something like that. So, yeah, definitely some weakness there. Last three months, we’ve averaged 6,000 jobs.

That is not good. We should be growing about 100,000 jobs right now. So we did see the rate tick up as well.

And then you mentioned gas prices now up to $100 a barrel. That’s now $35 increase over the past week. And rule of thumb is every $10 increases gas by $0.25.

So we’re looking now at about a dollar increase in gas prices as expected from the recent rise in oil prices. And then we’re continuing to watch what’s going on in the Middle East.

We are still seeing broad-based cancellations throughout the region as people look to change their travel plans. In the UAE alone, last week, we saw 90,000 nights cancelled. That’s up from a typical week of about 19,000.

So the chart up. Yeah, sure. So that’s up almost 4,000 or 400% year or week over week.

Gross nights booked, the flip side, nights booked were down 30%. So we do see some bookings from those people that are sort of displaced looking to stay longer just because they have to, they can’t get out.

But generally what we see in conflicts like this is lasting impacts from just people not traveling to that area anymore. And that’s going to have compounding effects. So not good right now and across the Middle East for bookings.

So this is UAE, this is Saudi Arabia, this is Jordan, Israel. This is not minimal in terms of its impact that’s happening throughout the Middle East.

Yeah. So when we were thinking about the gas prices and everything, I learned a tidbit about jet fuel that they basically have just in time production. So there aren’t reserves of jet fuel because of how it has to be, it can’t be stored.

So last week I have a vacation in the end of May coming up and I texted the group chat and I was like, if you have not bought your tickets yet, you need to buy them like immediately because it’s going to get really crazy once that starts to.

So it’s interesting if you have a vacation coming up that requires planes, maybe today, book those flights.

Yeah. Go ahead, sorry.

No, I was just going to say, I mean, this is one of those ripples that you don’t see coming. So how is it going to impact domestic travel? How is this going to impact people coming to the United States for the World Cup and to Canada and Mexico?

So this is going to be something that we’re obviously tracking for the rest of the year.

Yeah. Our company, Retreat, was supposed to be in Jordan this year in May. I doubt that’s happening.

And on our Skift Travel Podcast with Seth and Sarah, we had Gordon Smith, who’s our airline editor, on the show this week and or last week.

18:02

And he was talking about, you know, people that have had to now like, I forget that I’m geographically a little bit challenged, so forgive me.

But basically, if anyone was going to be crossing over, you know, UAE Middle East area, they have to go the long way around now just to get anywhere because of the conflicts, you know, airspace is closed, all these things.

So not only with Brandy’s comment on the jet fuel being not able to be stored and has to be like in production in terms of on demand, now it’s also going to be probably more expensive because not all of that, but because they also have to go a lot of

Well, you also think those a lot of the like Dubai and Qatar, those are like Doha, those are major international hubs for transfers over to Asia.

But that’s every time I’ve gone over there that we’ve flown through one of those airports. So that’s, yeah, it’s going to be a lot of disruption, a lot of disruption for sure.

Yeah, it’s going to be fun. Can’t wait. Can’t wait to update.

Sarcasm for anyone else.

Yeah, yeah, for anyone that knows me, you know I’m being 100% sarcastic.

So this one was a fun topic because this has been on the show.

19:16

ChatGPT Transaction Shift

We’ve discussed this quite a few times in terms of ChatGPT, rolling out direct bookings, and all these other things in terms of advertising on the platform, especially for travel and really take on the transaction.

But, excuse me, sorry, I’m forgetting where my article link is. But ChatGPT, Bails on Transactions, is good news for Expedia and for booking.com. Give me your guys’ takes.

I thought that this was going to be a really cool feature.

And there was also some implications for not just the big OTAs, but potentially being able to create your own app and have those in-app transactions.

And I don’t know, but I think this speaks to the, you know, the article talks about this, but just user adoption is not there.

So are these, you know, is ChatGPT going to focus a lot of effort on something that isn’t showing a lot of promise right now, versus, you know, investing in another part of the product? And then they can always come back to this.

There’s a whole section of this industry that is, you know, there’s so many people that are so all in on AI, but then it’s like, what is the general, like, who’s going to be like, hey, ChatGPT, book my trip end to end, you know, like that kind of

Well, Adriana Lee, her last week, I mentioned her feature, it didn’t come out yet, but it came out last week, and the title is truly, you know, travel is building AI for a traveler that doesn’t exist.

And so it’s like, the travelers don’t want to hand off, like they’re still in the, like, yeah, inspire me, give me some ideas, but I want to book the trip. I want to make the transaction. I want to be the one that makes the decision.

I’m not going to have AI do that for me. So I think that sentiment, like to what you just said, Brandy, is 100% true. Like, yeah, you can be all in on AI, but how realistic is this right now?

Glad Michael’s not here because I don’t need to say I told you so.

You know, we could have it now is immortalized.

Don’t worry, I’ll clip this and I’ll send it to him.

But I never thought they’re going to be able to pull this off.

Like, yeah, it looked cool. It could have been cool.

But to think that ChatGBT or any of the LLMs were gonna disintermediate the actual process of booking, that they’re gonna somehow go out and aggregate all this inventory that could be directly bookable or integrate with all these direct booking sites

or make it bookable across the platform, like was gonna be a very tall order. And then put at risk all the potential advertising dollars that booking.com, Expedia, Airbnb and all the OTAs would actually end up spending on their platform to make sure

that they are the platform that’s chosen, like just, especially when they’re trying to figure out the revenue model and moving to advertising, just I never made sense to me. So I do think they’re gonna be pushing heavily into these integrated apps.

And they talked about it, of getting booking.com to create an amazing app within the LLM to give you that booking experience, make it seamless, let you build your travel itinerary, suggest the top 10, top 5, top property to then book and make it

seamless. You’re just doing it through booking.com. They’re gonna get their commission. They’re gonna pay for being that option.

And everyone’s happy and the ecosystem keeps moving.

Yeah, Paul was commenting that one of the big setbacks with a lot of AI ideas is that it doesn’t actually improve the end user experience at this point. We are still so in the infancy of this new era. So that’s a great point.

We have to start seeing, the average person who isn’t paying attention to the tech news or what’s going on has to be like, oh, this actually really does somehow meaningfully improve my experience.

The money component, I also, and this is just my personal opinion, but there’s something about like, no, I want to be the one that presses enter, that like, to me, it’s already like a little shady sometimes that my credit card number can

auto-populate because I haven’t saved like Google Wallet or whatever, because it just feels really ten, like it feels like someone could just come in here and grab this. So I don’t know if I want Claude or Chat GPT being like, now we’re going on a

shopping spree. Did you want 12 days at an Amman? Yes. Non-refundable.

I also saw a post a couple of weeks ago before I deleted social media off my phone, but it was, I think, 250% increase of uninstalls of Chat GPT once they announced a defense contract with the United States.

I was like, all right, yeah, I would do that too. That makes sense. I’m in that same boat.

I wouldn’t want that information with them. Chloe on YouTube mentioned that planning the trip is her favorite part of traveling. I want to let AI do that for me, even if it would save me hours of endless scrolling on OTAs.

A great example is, I want to go for these dates like what are the best flights, or what’s the best use of my points?

Or, you know, kind of… Yeah, and kind of figuring out, I mean, some of the financials or the logistics or, you know, all of that, I think, are great uses.

And this will continue to evolve, but in its current state, this is what the AI companies want us to be thinking that they’re at a level that they’re not quite yet.

Well, back to the kind of main article though, this was a heavy push, I thought, from chat in the, you know, maybe what, a month ago?

Like, this wasn’t very long ago where they were like, yeah, we’re gonna push this movement into, you know, taking care of the transaction or the checkout process. So I’m curious to see what changed. Why did they take this hit from a value standpoint?

Jamie, you mentioned in our private chat that this was a big hit for their evaluation. So something obviously must have changed, but I’m curious why, because they seemed pretty bullish. And to now walk it back, it’s like, all right, who paid you?

You know, that’s what goes through my head. But…

The tin hand comes out.

Yeah, and what goes through my head is like, they are getting crushed right now by Claude and some of their other competitors. Like the models from Jim and I are incredible. The tools from Claude are incredible.

They need to focus on their core of what they do best and make sure that they are the tool for consumer, for enterprise, that their models are top and maybe moving into and competing outside of their core might not be the best use of their resources

Well, I mean, coming back to our earlier conversation about companies regaining focus and it’s kind of like, let’s get back to the basics.

Let’s focus on what our core offering is. And also, it is crazy how much better Claude is. I just started using it like two weeks ago.

I was like, this is significantly better.

Okay, question. As a guy who only uses ChatGPT right now, it’s trained on all of our data from transcripts of the podcast to all the things. If I move over to Claude, how hard is it going to be to train up that son of a gun?

Am I going to be spending days like prompting like, you idiot, why are you giving me this BS answer? That makes no sense.

I highly agree with that.

I switched over. I spent all weekend playing. I’m obsessed right now.

For our live viewers and listeners, I want to know what AI model are you using?

Why do you like it? What made you switch if you did switch? I want to know.

I want to know.

Also, we’ll be curious how people are using this for travel, because we’re talking a lot about hypotheticals and what some data is showing. But if you’re listening, how are you using this at all? And have you had any success stories?

Or if things have tremendously backfired, those would be more fun to hear. So let us know.

Very good. I don’t know who this is, but LinkedIn user says it’s quick. So I was like, all right, cool.

Good to know.

I’d say to one of your points though, Wil, you can still tell though when someone is just copying and pasting out the thought of Plot or ChatTPT and not putting their own thought into it, just taking the generic answer.

It’s like, maybe that’s better than what they would have come up with on their own.

It levels everyone up a little bit, but those people putting, and to your point, I need all the context of everything I’ve been doing for it to actually get a good response. It takes time, it takes effort to get really good work out of it.

Yeah, 100%. Just a couple of quick comments that came into the show. We had Jackie say, chat GBT, or she’s on chat GBT, might switch to Cloud after this.

Another LinkedIn user said, Cloud is the best, easier to train up.

A lot of Cloud fans in the house.

Sounds like we have a majority of wins over here. Sounds like it. Well, this has been a fun episode.

I think this is a great topic, a lot of speculation, a lot of good insight. It’s been cool to also revisit topics that we’ve been talking about for the last couple of months, and see how this evolved so quickly in the last quarter.

I know there’s going to be a lot of that to come still, but as Michael is out on spring break with his family, what do you guys have this week that you’re looking forward to, or are you guys going to go on?

I’m on vacation. Yeah, I’m literally looking outside at the mountain right now. It is gorgeous.

The sun is coming up and shining on the peaks. Oh my God, it looks so pretty.

Well, I am excited that we did get it. We got an hour stolen from us, but now that we get 7 PM sunsets, which is nice.

Yeah, it’s not going to be as crushingly depressing at night.

Jamie, what about you? What’s going on?

Yeah, I’ve got my AirDNA team all in Atlanta this week for our Data Science Opsite. We’re building some fun stuff. Lots to announce coming up soon, but it’s going to be a fun day of our week of building.

I love it.

Are you guys doing a hackathon type of approach?

We’re going to have a day and a half of hackathon, some planning, some strategy, some fun, all mixed together.

All mixed together. It’s a good approach. I like it.

Well, for all of those who are tuning in, thank you so much for participating live or listening on the audio version of the show.

Don’t forget that we mentioned at the top of the episode, we have a bonus episode coming out tomorrow with Brandy hosting her own special on the show with Andreas and her former CFO, Iskander, at Romy as they announce their acquisition by Cozy

Sweets. And then of course, our GMH Hotel episode coming out this Wednesday with Sarah Dandishy and Steve Turk, who always bring that early morning energy. We love to see it, but until next time, we’ll see you all again next week.