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John Richards
Welcome to The Architects of Travel. I’m John Richards. This is a show about the people building the future of travel—developers, founders, and innovators creating the platforms, APIs, and products that power how the world explores. The Architects of Travel is brought to you by Nuitée, the company behind liteAPI, the world’s only open hotel and travel API, with real-time rates and availability from more than two million properties worldwide. Start building the future of travel today at liteapi.travel. Today’s guest is Sam Shank, founder and former CEO of HotelTonight. Long before mobile booking was the norm, Sam and his team were betting that people would one day be comfortable booking hotels from their phones. That vision helped turn HotelTonight into one of the most successful travel startups of the mobile era, culminating in its acquisition by Airbnb. In this conversation, Sam and I look back at the early days of building a travel startup, the challenges of creating a new category, and the hard lessons that come with scaling a company. We talk about why focus becomes even more important as a business grows, and why distribution has always been one of the biggest factors separating great products from successful businesses.

That thread runs all the way from the early days of mobile apps to today, as AI once again reshapes how travelers discover and book experiences. Sam shares his perspective on what founders should be thinking about in this new era, why distribution remains as important as ever, and how AI could transform the future of travel. All right, let’s jump in.

Hello everyone! Today I’m excited to announce we’re joined by Sam Shank, Co-founder at Stand, advisor, and angel investor. And importantly for us today, we’re going to be talking about him as the former CEO at HotelTonight. Successful exit to Airbnb. I mean, incredible story, Sam. Thank you for coming on the podcast.

Sam Shank
Oh, great to be here. Thanks for having me.

John Richards
Let’s start there. What in the world gave you the idea to found HotelTonight and kind of jump into the travel industry?

Sam Shank
Yeah, I actually jumped into two companies before HotelTonight, and I was combining a personal interest in travel with my interest in building internet companies. I sort of naively thought that it would be very easy to build something slightly better and disrupt things, and I realized very quickly that it was going to be very hard, especially around doing something that got a lot of distribution. I think that’s ultimately the hard part of building an internet travel company—getting in front of customers is hard. Probably even for an internet company in general, getting in front of customers is very, very hard. So the first two companies, you won’t remember—they’ve sort of gone their own way, but I learned a lot. And it also gave me insight into where the world was headed in online travel, and the booking window was getting shorter, and mobile bookings in particular were growing very, very quickly.

But it was only like one or two percent of overall hotel bookings—I think it’s now like 70% or something. I looked at the App Store on my iPhone 1, which I was enamored with—I loved the App Store—but every travel app had like one star or two stars, right? They didn’t do anything interesting and novel the way the other categories did. And I said, wait a second, if you built something mobile-first, which is what it’s been called—what would that look like? What would it do differently? Could you build a brand here? So I did a little sketch that’s hanging in my office today, on a whiteboard, and a little back-of-the-envelope thing, and I was looking at that and I said, you know what?

That’s actually a pretty good idea—to build a very simple app for getting a same-day hotel room in just a few taps. At that time you couldn’t do that. It was very difficult to find a same-day hotel room, and they weren’t discounted, which to me was also a missed opportunity, because hotels with empty rooms don’t make any money. They expire, but they’re not a deficient or defective product—it’s the exact same hotel room as any other. So I was thinking about that, and I looked at it and I was like, yeah, that’s a pretty good idea. Maybe I should pivot this company into it. And I was like, maybe this is actually a separate company.

And then I was like, maybe, just maybe, this can change the way that some people travel by making people more spontaneous.

John Richards
I mean, that’s such a bold vision at that point, when no one else is doing it. So what did you look to once you kind of mocked that out? Did you start looking at, well, how am I going to have these conversations with hotels? Or did you go first straight into, let’s build this app and see if it’s possible, and we’ll figure out that aspect later?

Sam Shank
I had so much confidence in what this was, and that this was the culmination of a lot of different threads coming together. I think that pattern recognition was something that gave me a lot of confidence. So for me it was inevitable—I was like, if I’m not going to do this, somebody else is, so I might as well do it. I laid out exactly how we would go about doing it, how we’d roll out in different cities. I was lucky to be reconnected with a friend, Jared Simon, who had a bunch of experience signing up hotels, so he built that side of the business.

I focused on the product, the marketing, the press, and the fundraising side of things. We were also lucky to have Chris Bailey, who was the CTO of the second company that I started, build the app and all the web interface behind that powered it. We did all of that in ten weeks—we just sprinted to build the MVP. We barely got it out there with a handful of hotels, but it gave enough signal that we immediately got a very strong reaction. People were sort of waiting for, like, what can my great iPhone do in the travel category that it couldn’t do before? We solved that unmet need that people may not have even been able to articulate. And we definitely filled a gap for the hotels. I remember it was at the Gramercy Park Hotel, it was Fashion Week in New York, everything was full, and there were all these celebrities at the hotel. I walked downstairs and I was like, hey, do you have any rooms tonight? And the front desk manager said, yeah, we always have like four or five rooms that we can’t sell no matter what. And I was like, huh, that is opportunity. That was another signal.

But we just went for it, because there was a lot of conviction. And with an app, there’s no way to do a smoke test—you’ve got to go through the App Store approval process, and it has to work before they approve it. So that was our way of doing it: we spent about, I don’t know, maybe 500 grand to get the app launched. That was mostly our salaries and the team’s salaries to get it launched. And that was our MVP.

John Richards
Wow. Now, how did you kickstart a growth curve for something like that? You’re getting into the App Store, you’re doing something different, but how do you get that momentum flowing when you’re starting out and you’ve just put it out there? As you mentioned, it’s hard to advertise in that space—so what did you do to get that early adoption?

Sam Shank
We were so early—it was just after Instagram and Uber launched. But there was no mobile advertising ecosystem. You couldn’t buy mobile download ads, app download ads, on Google or Facebook—all of that came years later. And our marketing budget was like a hundred grand, so we didn’t have the ability to buy our way into it. We had to do things the old-fashioned way, which was a lot of earned media. I had built a lot of press contacts through the first two companies, and I told the story of why what we were doing was different and better, and how this fit into where the hotel industry was going, and sold a bit of the future. So it was a very compelling story for the industry, and a compelling story for the consumer.

So I spent a lot of time on press. We also developed a great relationship with Apple, who was also looking for new things that would get people to buy the iPhone and download apps. We were promoted quite a bit within the App Store. And there were these rankings back then that were a lot more important—like top travel apps—that sort of motivated me to go into this business in the first place. There were times when we were the number one downloaded travel app. It was like three of us sitting around high-fiving, like, we’re bigger than Google Earth on those days, right? So a lot of it was the luck of fortunate timing—we were in there early, before even Expedia had an app at all, but not so early that there were only a handful of people on the iPhone. So we sort of lucked into the sweet spot.

John Richards
I love it. Now, for other folks out there who are maybe at that stage—they’ve got an idea, they’ve mapped it out, they think they’ve found a good pattern that fits, and they’re trying to figure out how to get to that next level—what would you recommend for them? I’m hearing you talk about the importance of relationship-building and partnerships. Is that where they should be focused? Are there other areas, especially in the travel space, that were uniquely important in those early few years?

Sam Shank
I think in online travel, if it’s a consumer product, it really comes down to thinking through distribution—do you have an insight on distribution and a distribution advantage? One way to think about HotelTonight is that it started with the distribution insight that the App Store was going to be a place where brands and companies were going to be created. Then we figured out what we would build for that. It wasn’t that I woke up one day and said, I want to build a last-minute hotel booking app—that app came out of the insight that this was going to be a great way to distribute a product and build a company and a brand. So deconstructing it a bit, I’d recommend entrepreneurs think through their distribution first.

What is that insight that you have? Is it agentic search optimization? Is it building tools for agents and MCP server aggregation? Is there some insight there? That’s the area I’d gravitate to now, and then you can build a product around it in much the same way. I think OpenClaw is one of the best examples of that recently, where there was just a lot of interest in the open source community for these types of tools. I think he tried 10 or 11 times before OpenClaw was the one that really broke through. So: think distribution.

And then product later. If you have a product—even if it’s better, even if it’s really interesting—it’s got to be like a thousand times better than anything else out there for it to get viral activity, especially in travel, where you only use it a few times a year. The most recent example of something that really took off just because it was great, without distribution, was ChatGPT. And it’s hard to think of the one before that, that just took off. So the “build it and they will come” approach really rarely works—it takes a lot of other insight, timing, grit, and being early in some way of getting a product out there to give you tailwinds.

John Richards
So you moved forward with that and hit the more mature aspect of HotelTonight as it started to really grow. How did your perspective and what you focused on change as you got closer to the exit to Airbnb? For groups out there who are starting to be in that spot where they’re getting traction and now looking to move to the next step—did your concerns and focus change, or was it still really just doubling down on what was working, staying one-minded about where you were spending your time and effort?

Sam Shank
It’s a great question, because there’s always a ton of tension between staying focused and also planting enough seeds that you don’t get boxed in by what you’re doing in the first place, while making sure you’ve got enough growth vectors. That’s the tension—it’s one of the biggest challenges of leadership, pointing people in the right direction but not in too many directions. I don’t know if I got it right, but what we did was stay focused on what we were doing. We did geographic expansion, and then we planted seeds around expanding beyond the same day—first into one week ahead, that last-minute window, and then ultimately into several months ahead—moving toward a full-service online travel agency that had a specialty and roots in same-day hotel booking, but also allowed you, for certain use cases, to book early.

So that was the trade-off we had, and there was tension there—how much do we still focus on the core versus how much do we focus on the new growth area? I think the other area I spent a lot of time on that was really important was building the right team for the company at each moment of our growth. Having the right team allowed us to do both—focus on the core and not lose that advantage, but also expand beyond it, because I felt we were reaching a saturation point on the core, or I didn’t want to reach one. I wanted to make sure we could continue to flourish and find new veins of gold to go mine.

John Richards
I love it. So you mentioned having some experience previously in travel—you didn’t come in completely blind to the space. You knew the space and then identified this. But was there anything, as you were building this, that was a unique challenge or a unique benefit of working in travel specifically—something you don’t see as much, or at all, in other markets? Because you do investment and advising across different kinds of companies, are there certain travel-specific things you’re always paying attention to when you’re looking at a business in the travel sector?

Sam Shank
In addition to distribution, which I mentioned, I’m always also looking at frequency of use and repeat customer behavior, which is really hard, because this isn’t something that a lot of people use multiple times a day, or even a week, or even a month. Having a repeat customer, though, is wonderful because of the economics of that customer and their loyalty—it turns into much more recurring revenue if they show up directly. It’s very hard, but we certainly focused a lot on that. Not every customer, of course, is going to come back. So that’s on the consumer side. On the hotel side, I look a lot at alignment with the hotel’s goals.

That’s going to really help with the sales cycle, help with retention on the hotel partner side, and also get you the best inventory—whether it’s inventory for the ski industry or the activities industry. Inventory quality, both in availability and pricing and selection, is also important. Just signing a property or a partner doesn’t mean you’re going to get the very best from them—it requires a lot of work, a lot of product development too, to encourage and reward the right behavior. In the industry, there’s basically carrots and sticks to get your hotel partners and supply partners to do the right thing for a marketplace. We focused a lot, almost exclusively, on the carrots, and that made for much better long-term partnerships.

John Richards
It sounds like an industry where you’re often thinking long-term, whether that’s repeat customers—but realizing it’s not a daily thing—or building strong relationships with hotels, making sure you don’t get an advantage now but ruin the relationship long-term. That really seems to play a part. Now, I’d love to pivot to the world we’re in now. As you look at what you did and the space we’re in now, what are the big changes you’re seeing? Obviously AI is starting to impact this—if you were to try and launch the same business today, would you think about it differently, or would you even say that moment’s passed and you’re looking at very different patterns now, maybe in the AI space or a whole different area?

Sam Shank
It would certainly be very hard to launch a mobile app these days and stand out and get any attention—even a few years after we launched, it became a very different marketplace. Every conversation now is related to AI, and it should be, because it’s so magical and transformative and powerful. What’s still up in the air is how it changes distribution for B2C bookings. If you look at some of the trends in other verticals, SEM traffic is definitely waning. It’s still incredibly lucrative, but a lot of results are better solved by an AI set of answers than a set of links out to a website where you then have to click around and find the answer.

For hotel booking, that could be very disruptive, because it means some of those “what’s the best hotel for me” type questions that are now answered by going to an OTA and doing some sorting and filtering could instead be answered in a self-contained way, through an AI that knows where you’ve stayed before, what your general preferences are, and has context on why you’re going on the trip—and can do all of that work for you in a far more elegant and efficient way than doing it yourself. That poses a lot of threats for the incumbents and opportunities for new folks. So that’s what’s exciting. I know there’s something there—I don’t have a strong point of view yet on exactly what that is, but it’s certainly something I’ve been watching for quite some time, and I’ve got more opinions on how the incumbents are going to be hurt than on what the opportunities are for the new entrants.

John Richards
On that—and hopefully I’m not repeating the same thing—but I’m curious: there are a number of folks trying, but it feels like no specific AI booking portal has yet become the thing. HotelTonight became recognizable for solving that first and being the one to step in there; we don’t yet have, at least in my opinion, a single group that’s clearly driving that space. I’m curious if you have thoughts on why we don’t see a dominant one yet. I know lots of folks who are in the process of creating cool ideas in this space—maybe one of them will be it. But any thoughts on why there isn’t a leading AI booking product yet? Do users need to get more comfortable with it? Does it need to bring more value than just being AI? Maybe AI isn’t quite there yet. Any thoughts on what needs to change to really dominate in that market?

Sam Shank
There are a lot of great companies doing really interesting things there—the founders of Kayak are working on something I’m excited to see. I think the biggest answer to your question is: it’s early. The AI is getting better, and connecting with live inventory has been a challenge, so there are solutions and opportunities there, but it takes time to build these things out. So that’s one piece. The other is that AI, unlike the App Store or one of the big platforms before—Google and SEO—doesn’t come with built-in distribution yet, and I don’t know exactly what that distribution will look like. OpenAI just announced an ad product. So—

John Richards
Yes, it’s funny. We’re talking about this like the day after that.

Sam Shank
Yeah, exactly. There are things happening, so it’s important to be—I don’t know, I think with HotelTonight we were positioned to take advantage of that opportunity, and that’s why we were able to do it in ten weeks. We were sort of positioned for luck. And I think a lot of these companies are positioning themselves for when there’s a tectonic shift in how people find services beyond Google, especially AI-native services, so they can be there and really grab those opportunities.

But I do think that because AI itself—ChatGPT is really a self-contained experience, unlike the App Store, unlike Google, unlike the web when that was coming out—it presents some challenges to building new services, because people just don’t go and find new services through ChatGPT. So I think we’re going to have to see if new opportunities emerge from the big players, or we’ll have to get more creative, or the services themselves will have to become 10x better than just asking itinerary-planning questions on ChatGPT, which is what happens a lot right now anyway.

John Richards
I love that this has come full circle, where your watchword has almost been distribution, and now it’s about where the distribution is inside of these—and whether that’s going to be native or come from outside. Fascinating and wonderful insight that I’ll be thinking about even after this. I want to come back to a point you mentioned earlier: the disruption that will happen, especially once something gets nailed in this space and distribution really lands. What do you see happening to our current model of a few large online travel agencies? How do you think that’s going to shake up as we move to more AI-first interactions?

Sam Shank
If you imagine a world that looks like the movie Her, where everybody has an amazing—hopefully not fully sentient—but an amazing, essentially executive assistant. You give it that query, like, hey, book something for me for that business trip in Chicago, even though I haven’t been to Chicago in years. It’ll look around the web, know me, and pick the right hotel. Within that hotel, it’ll figure out what the best price and booking option is, based on price, cancellation policy, room selection, et cetera, and make all those choices without me having to spend the time to do that. It’ll do that not just for people who can afford it—it’ll do it for everyone. In that world, all of the OTAs become just another source being looked at by the AI, by my assistant, to find the best thing for me. What’s also interesting is that a lot of OTAs exploit a bug in the human brain, which is that we think if something’s rank-ordered, the one at the top is somehow better.

Even if we’re presented with information framed as our picks, or defaults, not based on any other criteria, we think it’s better. It turns out that a lot of that is based on how much they’re paying, which has nothing to do with the benefit for me.

John Richards
Yeah.

Sam Shank
So what’s great about having an AI executive assistant is it can look at, say, all 500 options in Chicago, instantly and neutrally, and not think about rank order at all. It’ll exclude that concept and instead look at other criteria to determine what’s best for me. That’s hugely disruptive, because a massive amount of the profits of OTAs come from the advertising portions of their business—placement fees.

So I do see a ton of disruption there. That doesn’t necessarily lead to opportunity for new entrants, but it does create a lot of disruption. I think it’s very good for the hotels themselves, who are paying quite a bit right now to be seen on OTAs—when that playing field is leveled, they can be seen at the same level as everyone else, and they can compete on what they do best, which is quality, amenities, reputation, reviews, and good pricing and value. So it really levels the playing field.

John Richards
Fascinating. Excited to see what happens, and a little terrified at the same time, with all of this world changing. But I love that we’re going to see how that plays out for the hotels—small boutique hotels that maybe aren’t as recognized, moving up in the rankings and finding an audience where they’re delivering something that other folks were able to cover over just by spending. That’ll be really cool to see.

Sam Shank
Yeah, and it also won’t be the same right hotel for everyone—the number one hotel for me will be different than the right number one hotel for you and everyone else. So it also levels the playing field for people to appeal to a very specific audience. I think we’ll see a lot of that too—for someone who’s interested in a particular type of area, stay, or experience, that hotel will start specializing in it and getting a lot of share of business from folks in that cohort of customers.

John Richards
I love it. Before we wrap up, I want to ask you—thank you for coming on as an advisor at Nuitée. Why did you get involved with the company, and how do you see it positioned in the current market?

Sam Shank
It’s a thrill to work with the company. It’s such a wonderful team. I was first attracted to the team, and Med, the CEO, and just the drive and ambition of everyone. I was also very attracted to the solution—this idea of a single API to access 200 different inventory sources simultaneously, with great content, would have solved a huge problem at HotelTonight. We had a team in Berlin—they did great work. I think there were about 10 people bringing in three data feeds, normalizing them, choosing the best content. I think we did a pretty good job given the limited resources we had.

But it was still a lot of hard work, and being able to tap into all of that with a single interface would have been a huge accelerant for our business. So I was fired up just to hear about it, because I knew it was solving such a big problem—I had that problem myself. As I looked more into it, I saw the ambition and the technology advantage the team had built. This is, I think, the ninth year of the business, so it’s a nine-year overnight success. Thinking about where this business can go is very exciting.

John Richards
Well, we’re very thankful to have you and your insights to help us as we’re navigating the space, so thank you. Before we wrap up, anything you want to shout out or promote, or where folks can follow up on your current ventures?

Sam Shank
I post on LinkedIn, just at Sam Shank, and also on X—a little less active there, but you can follow me on X as well, at Sam Shank. I post about a lot of different things, including hotel distribution, and some other areas I’m fascinated about, including electric vertical takeoff and landing aircraft, and all sorts of things I’m thinking about.

John Richards
Well, thank you. I’ll make sure to have links to both of those properties in the show notes. And thank you so much for coming on—this has been super informative. Thanks, Sam.

Sam Shank
Thank you, John. Great to be here.

John Richards
This podcast is made possible by Nuitée. Through liteAPI and its white-label platform, Nuitée helps startups, travel companies, and developers seamlessly launch booking experiences. Whether you’re building a new travel app, adding hotels to an existing platform, or experimenting with new ideas in travel technology, learn more at nuitee.com. Thanks for tuning in to The Architects of Travel. I’m your host, John Richards. This show is a production of TruStory FM, with audio engineering by Andy Nelson and music by Captain Qubz. You’ll find all the relevant links in the show notes. If you’ve enjoyed the episode, please take a moment to follow the show and leave a rating or review. It really helps others discover it.

Join us next month for another conversation about building the travel future right here on The Architects of Travel.