Learn what drives traveler booking decisions and how to improve visibility and increase vacation rental demand.
What’s in this episode
Building a great vacation rental operation takes far more than adding doors or chasing occupancy.
In this episode, Tim has a candid conversation about what makes excellent operators stand out with guests Alex Husner and Annie Holcombe, the expert voices behind “Alex and Annie: The Real Women of Vacation Rentals” podcast.
Alex and Annie reflect on how they each found their way into the vacation rental industry and what’s evolved in the sector. Together, they unpack some of the biggest challenges facing property managers today, including the temptation of growth, the pressures from a competitive market, and the complexity of managing an ever-expanding tech stack.
Listen to the full conversation for their insights on branding, distribution, AI, and why smaller operators need a strategy over scale.
Read the transcript
[00:02:11] Tim Rosolio I mean, I've known about you guys for years, probably long before we met, you know, your sort of names and faces in the vacation rental industry. But the interesting thing is, like, when you're little, you didn't dream of being like, oh, I'm clearly gonna work in vacation rentals, right? So maybe tell us, like, how did you get here? How did we all end up in this industry? When I was, how did you get into the vacation rental industry and what's kept you here?
[00:02:43] Annie Holcombe So, I actually was a gymnast, and I thought I was going to go to the Olympics. That was my dream. I had actually gotten injured and ended up having to stop doing life for a while. And when I got back into doing life, because I had to have some reconstructive surgery, I had, I started working at a front desk at a hotel, and I loved it. I realized hospitality was where I needed to be. And so a couple of years after, you know, being in hospitality, I was working for a company that was managing hotels, and they morphed over into vacation rentals. And that was how I got into the industry. I was doing, helping with growth and business development and talking with developers and talking with homeowners associations and talking with owners. And I just realized, like, it was just a really cool industry. So, this was like in the late ’90s before it was really a big thing. And I was in the Panhandle of Florida, which is a very large market.
[00:03:26] Tim Rosolio Vacation rental capital of the world.
[00:03:28] Annie Holcombe Exactly. I mean, outside of Orlando, it's the second biggest in Florida, but I think I just got hooked on it, and I had tried to leave twice, and then just, it draws you right back in. I think it's the people, it's the stories, it's the honor of being part of people's experiences, whether it's the first time to go to the beach or the last time. It's just an honor to be part of that. And I think for myself, it tugged at my heartstrings and kind of like what gave me passion and drive was just connecting with people. And so I just never left.
[00:03:56] Tim Rosolio Good place to be. How about you, Alex?
[00:03:58] Alex Husner I'm going to tell a story that actually you don't even know, which you've heard, just about all of them. You know, I'm from New Hampshire. I grew up in New Hampshire, so this is...
[00:04:05] Tim Rosolio Homecoming for you.
[00:04:05] Alex Husner It really is a homecoming for me. But when I was little, I dreamed of being a broadcaster, and my dad has videos of me. There's a tradition in Conway, New Hampshire, which is maybe, I don't know, a half an hour from here, where they do this duck race that they put these rubber ducks at the top of the waterfall, and they all go down the river, and my dad would take me every year, and I'd pick ducks out of the river. Totally ruining their chances, but I would interview the ducks about the race that they were in. And so my dad said, when we started the podcast, he was like, this makes perfect sense. Like, this is always what you want to do. But how that ties into vacation rentals, I was in Myrtle Beach, moved down there, another vacation rental mecca, got started with Condo-World, and was there for 13 years, and had an incredible career with them, and just saw the impact that, you know, being part of company that really gives you that opportunity to grow and just seeing how much could still be done within the industry of what we were building and what else was out there. And it's a very close-knit community. And it's just, you know, I can't imagine working in another industry because I would miss all my friends so much, to be honest.
[00:05:16] Tim Rosolio Yeah. It is cool how we get to, you see a lot of the same folks, and they're typically sort of hospitality junkies like us, and you build friendships over time, which is really fun. I think I can certainly attest, you know, when Expedia executives, when they start getting in front of the vacation rental crowd, they're like, this is a different field than in the other industry.
[00:05:40] Alex Husner Not as buttoned up.
[00:05:41] Tim Rosolio Yeah. It's not as buttoned up. At the same time, they notice the passion that everybody has for the category. So, it's an exciting place to be, right? I mean, for me, I always say the hotel business or the airline business, that's very developed. In vacation rentals, especially with the online portion of it, we're still kind of in the second inning, right. There's still the opportunities to move big mountains. So, there's a lot of change that's happened. There's a lot of changes that's coming. But I'd be curious if you two have noticed, is there anything that like has remained the same throughout all of this? If you started in the ’90s, you probably were at a time where, I don't know, people were mailing checks, people who are looking through...
[00:06:28] Alex Husner Faxing?
[00:06:29] Tim Rosolio Yeah. Through catalogs. Bookings were happening, I guess, over the phone. That's a very different time in terms of the booking process. But in terms the hospitality and customer care and stays, what are some of the things that you think remain constant?
[00:06:44] Annie Holcombe I think it's the purpose that people are traveling for. When you go to a place like this beautiful house in New Hampshire, you're going there to be with your friends and your family and kind of just have that experience that you don't get in your day-to-day lives because everything is just so fast-paced. So, I think that that's never gonna change. People are still gonna want to have those connections. And again, like I said, whether it's the first time that you're taking an infant to see something or it's grandma's last trip. I mean, it's everything in between, and it's all those experiences, and those emotional bonds that happen that that is always gonna be part of vacation rentals that you don't get at a hotel, and you're never gonna get that at a hotel. Not that people don't have experiences at a hotel, but there's just an emotional connection you can have in a vacation rental that you can't in a hotel.
[00:07:28] Tim Rosolio Part of us, the togetherness. And that's also like, I hadn't ever thought about this until you mentioned what you just said is like, there's almost like a circle of life, like element to vacation rentals.
[00:07:39] Annie Holcombe It totally is.
[00:07:39] Tim Rosolio Because it's something that many people do their entire life, literally from being children and being the kids that are in the basement, ruckusing with toys, and then maybe you get a little bit older and you're the ones that are hanging out by the fire, and then someday maybe you're bringing your children. I mean, it's a very special category, and because you're staying together, it's just different than the hotel.
[00:08:02] Annie Holcombe Absolutely.
[00:08:02] Alex Husner Absolutely, absolutely, yeah.
[00:08:04] Tim Rosolio How about you? What are your thoughts on what's stayed the same?
[00:08:07] Alex Husner What stays the same, I mean, honestly, I would answer the same thing. I think what has changed, I'm going to spin the questions a little bit, that's the same, but what has changed is that the brands that have done really well over time with still being able to deliver that experience, but still stay relevant in the world of where OTAs are dominate a lot, are the brands show the memories of the guests, that they really, I mean, they're not just showing the properties, but they're showing how those memories are actually made and the impact that it makes on those families and those travelers.
[00:08:36] Tim Rosolio You know, we as a platform, you know, we encourage property managers to build a brand because that's a brand that we can showcase on Vrbo, and we cannot just tell about the home, but we can talk about the consistency of experience that you saw when you were at Casago, you know?
[00:08:55] Alex Husner Yeah, yeah, yeah.
[00:08:55] Tim Rosolio Lot of what you guys do in your consulting work these days, though, is trying to figure out, like, how the hell do I make this scale? So, like, what are the tips and tricks for property managers for how they do that? What are, like, what are the nuggets that you say, like, you must do this well?
[00:09:10] Alex Husner We've noticed over the last few years, it's been growth at all costs. And people coming into this, they saw this as this huge opportunity to get rich quick, as we always say. And then they realized, this is actually a much harder business than I thought. And they go into it sometimes thinking, I'm fixated on the number of doors that I have. I have to get 50 more. I need to be at 200, I need 300. And you look at the legacy companies that have done well and are still standing the test of time. That was never their mentality. I mean, they grew over time, and they might have, you know, acquired other companies and grown organically, but they were trying to build a good business at the core. I mean a lot of these businesses are family-run businesses that are passed down to generations. So, it wasn't as like, you know, fierce as terms of making decisions and scaling so quickly. For people that are trying to grow, I think you have to really think about what the end game is, and what you're trying to build, is it a legacy business? Is it business that you're gonna sell? Whatever that is, but then, you know, look at how you're building it with the people and the tech that are gonna support it in a meaningful way. And sometimes growth doesn't look like overnight. Sometimes it looks like a year or two years longer than you thought.
[00:10:19] Tim Rosolio I mean, especially as private equity gets involved, I think there's a lot of dialog that's out there about, like, what's the race to the exit. But if you were to like talk to, like, some mutual friends of ours, like Tim Cafferty or Miller Hawkins, they'd be, like, when I started this, I wasn't thinking about how I would exit. I was thinking about...
[00:10:36] Annie Holcombe How to feed my family.
[00:10:37] Alex Husner Yeah.
[00:10:37] Tim Rosolio How to feed my family, to employ people in my local location, and to deliver great experiences. And along the line, both of those guys and a lot of other people have made some money, but it wasn't, it wasn't about how do I get to this exit.
[00:10:50] Alex Husner Unicorn.
[00:10:51] Tim Rosolio This exit lane. What else do you see in your consulting work?
[00:10:55] Annie Holcombe So, I actually work or focused on working with the smaller operators. And what I saw from being at different companies was that the smaller operators, especially post-COVID, weren't getting good information. I'm not going to say that it's wrong, but it necessarily wasn't setting them up for a long-term success. So, they weren't going into it with a strategy. They weren't going into it thinking, like, I need to have a brand. I need to have an ethos for my company. Like, I need do all this stuff. So, I think I talk a lot about distribution. You know, there are some people that have just, you know, they've grown and they've scaled and great. And they did this, you know, growth at all costs. And then all of a sudden find themselves 200 properties with no website, only using one channel. And they're calling their...
[00:11:36] Tim Rosolio We're using Vrbo, right?
[00:11:37] Annie Holcombe Of course, of course.
[00:11:38] Tim Rosolio All of their bookings come from Vrbo.
[00:11:39] Annie Holcombe All of their bookings come from Vrbo.
[00:11:41] Tim Rosolio Perfect. Continue what you're doing.
[00:11:41] Annie Holcombe A 100 percent occupancy. But that's not the case with everybody. So, I think it's just that people get into the operation, and all of a sudden they're five years into it and they're, like, oh my gosh, what am I supposed to do with it? So, I try to, I wanna get these people when they're entering this space, and they are 10 units in, and they are thinking, okay, well I do wanna grow to 20 maybe this year, and maybe 50 next year, but what do I need to do to take those next steps? Well, so to me it's like, are they using every tool that Vrbo can provide for them? Are they using the breadth of the Expedia Group? I mean, having worked at Expedia, I know the power behind that. And so you have all these channels that do have depth and breadth that you could use. And so I think sometimes people forget that there's a lot of options out there to be mindful of it. Do you wanna attract new owners? Well, there's, there's different channels for that. Do you want to go into new markets? There might be different channels for that? We talked about international business. Like, where is that? You know, Vrbo can help with that. And so, I think that people don't think of those things they're thinking, how many units can I get? How much occupancy can I drive? But they're not thinking, like, how am I gonna do all those things together? And so it's just trying to grab them in the very beginning to make sure that they have access to information through, whether it be VRMA through the association or working directly with their Vrbo rep or their other channel rep to get that information and understand exactly how it impacts their market, because all markets are different. There's that going back to kind of, you know, your comment about where vacation rentals are compared to hotels and, you know, we are in a very early stage. And I think that if you're in the early stage, you can be more thoughtful about it, but we're also in a situation where there is no norm. Every market is so inherently different, which puzzles the hotel people, because they can say every Marriott is the same wherever you go. Every Hilton is the, the same wherever you go, but that's not how vacation rentals are. Every one of them is its own little property, its own hotel.
[00:13:28] Tim Rosolio I mean, let's face it. There's really no standards.
[00:13:32] Annie Holcombe Which is a whole different conversation.
[00:13:33] Tim Rosolio Well, that's, and that's the opportunity.
[00:13:35] Annie Holcombe Yeah, absolutely.
[00:13:35] Tim Rosolio What I was thinking about as you were saying that was, you're saying that some of these companies that are newer, they don't have a strategy.
[00:13:46] Annie Holcombe You did need one. You just had to have a bed and a room and you were good to go.
[00:13:51] Tim Rosolio Somebody was willing to do that based on where we were with demand volume and supply volume. Now, I would actually argue, I mean, all the data I look at indicates that we had the demand bubble during the pandemic, and then it actually created the sense that this was perhaps easy, and that this could potentially be like the get-rich scheme. And we're actually now in a little bit of a supply bubble, because you had all the supply that came on. And even though industry is growing, it hasn't grown at a pace to fulfill the expectations, the expectations of all those people that came on, which is I think why we're ripe for smart people like you to level up some of these folks that need support and are doing this right at scale and actually need a strategy. Because I am of the opinion in this category right now, the volume of supply you have is a total vanity metric.
[00:14:45] Annie Holcombe Yeah.
[00:14:46] Tim Rosolio That's for OTAs and that's for property managers. It's a matter of, do you have enough selection that will be fulfilled? And when in fact it is fulfilled, the experience is amazing and creates a sticky traveler. And for me, I think most markets, most markets are probably oversupplied right now. It's really about, do you have the best homes and the most consistent operators?
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[00:15:36] Tim Rosolio Another thing I'd like to dig into, just as you were talking about some of the tools, like how do you guys think about the different technology that's out there? Software, CRM, owner relations, like, what are you seeing in the tool space?
[00:15:52] Alex Husner There's way too many. Yeah, it's very fragmented. And I think we've been trying to solve for problems that we've created over the years. And I mean, you look at a property management system at its core is really, it's not a PMS, it's a BMS, it's a booking management system, right? It doesn't really manage your business, though. I mean, it's managing the bookings. And so because of that, you've got to have all of these other bolt-ons and other things that have to be part of it because it's gotten so complicated as an industry. But I think a lot of managers, I mean, they're looking at their tech stack and it's, like, you know, our margins are already small. And when you've got to pay a dollar a night here or three dollars here, or a percentage on this and that, it's just, it really, really adds up. And you can't go to VRMA and walk around the trade show and say, yep, I'm gonna do this, this, this, because by the time you get home, like, there's nothing left at that point.
[00:16:43] Tim Rosolio Oh, your margin's gone.
[00:16:44] Annie Holcombe Yeah, exactly.
[00:16:44] Alex Husner It's gonna drive your team absolutely bonkers. So, we have a lot of managers that come and look to us to ask, you know, what are the best systems? What's the best type of tech stack that's the leanest tech stack that I can have to operate the most efficiently, to be the most profitable? One of my clients is Boom, which is an AI property management system, which is AI at its core. And the mission of that is to really consolidate so that you don't have to have all these other tools, because when the AI has access directly to everything going on in the business, it can actually execute on your behalf, too, versus some of the bolt-ons. And I think, you know, AI has become a buzzword, but it's not even a buzzword anymore. It's just, it's day-to-day, and everybody needs to accept it, and it should make our businesses easier. But in a lot of cases, I think it's making it harder for companies because they're trying to add it into things that some of these systems were built many, many years ago, and the AI is not going to help.
[00:17:38] Tim Rosolio Yeah. It creates some complex, almost like overly complex decision making, right? Because there's certain things that are available in the core PMS. Then there's things that you can partner with. And then there's probably an evaluation of like, what, like, like what do I actually not really need at all? Can I operate a profitable and successful business without this thing?
[00:18:00] Annie Holcombe It's like that shiny penny, you know. It's like this, I got to get this 'cause it's the newest and that's the latest and that is the greatest, and the AI is a great example. The number of people that I have in my inbox that want to show me their new AI tool on a weekly basis is just mind numbing. And when I go and I look at what their tool is or what their background is, they were a banker six weeks ago, you know. And so it's, like, if you're not in this business, you know, it just goes back to like, this is a unique business, and you have to understand the uniqueness of it, and how operations exist before you can really provide somebody with a tool that's gonna help them, but there's just so many out there that people just flash, and they think they have to have, and so they find themselves, like Alex said, with so many bolt-ons that they don't necessarily need, because they might not even be using their PMS to its fullest extent, because they haven't asked the questions, and maybe the rep that they're working with or maybe that they are small and they don't have a day-to-day rep, they have to know what to ask. And I think that's for me from the Annie & Co. perspective is helping them know the questions that they need to ask before they get too far down the road and find themselves buried under. I think it was Lino Maldonado called it the Jenga tech stack.
[00:19:03] Alex Husner Yeah. Leaning Tower Attack.
[00:19:04] Annie Holcombe The Leaning Tower attack, yeah.
[00:19:06] Alex Husner And one thing I wanted to add to that, too, I think when you look at the U.S. markets, the legacy vacation rental markets, the Myrtle Beach, the Panama City, the Outer Banks, Roy, my boss at Condo-World, used to always say, it's like monkey see, monkey do. So, if my competitor is doing it, I'm interested and I'm going to check it out. But if they're not doing it yet, we're going to wait and see, you know. And that's very much still the mentality in a lot of these markets of, like, we are going to keep what we have, but we're gonna wait until somebody else does it, and then if they do it, then we'll do it. You go overseas, and that's very different. I think internationally, property managers are much more open to trying things, but their tech stacks over there have not gotten outrageous like they have in the States. So, they're trying to solve problems from a more holistic approach, I think, which that's been interesting in my work of just seeing the conversations of, they're like, yeah, let's sign up, let's do it.
[00:19:53] Annie Holcombe There's some extremes on both sides of it, but I think as a whole, people don't really think what that tech stack's gonna do to them in the long run.
[00:20:00] Tim Rosolio Yeah, so that's on like a lot of, like, the efficiency side. Let's talk about growing top line. I mean, Annie, I mean you're sort of an industry veteran. Even including your time of Expedia really understanding, like, the power of B2B and channels. We're making a big deal about putting vacation rentals into B2B. From your experience of seeing how inventory in the hotel space, you know, initially, it was probably basically, like, well, you had direct and you had Expedia and Hotels.com and maybe Priceline.
[00:20:32] Annie Holcombe Yeah.
[00:20:33] Tim Rosolio But now, inventory is a lot of places, hopefully relatively seamlessly. What's the vacation rental journey to get there?
[00:20:40] Annie Holcombe So, it's interesting, we were talking earlier about, like, sports travel. And so I was in the Panama City Beach market years ago. There was, I worked at a convention property that we had torn down and built. We had hotels and we had, vacation rentals were coming online. And so, I had done the sports market because nobody wanted to work the sports markets. They're like, it's moms, it’s baseball teams. They, you know, they make everything dirty. They're loud, they're, you know, whatever. Well, when I got condominiums and vacation rents, it was like literally adding rocket fuel to my sales. There's a gentleman in our community. They called me fast-pitch Annie because I worked with a fast pitch baseball or softball teams. We sponsored every event, but they wanted that. They needed the washing machines. They needed to be able to, you know, get dinner together so they didn't have to go out to a restaurant, because it was expensive because of these, these travel teams are going to an event every other weekend.
[00:21:26] Tim Rosolio It sounds like kind of a racket. I'm glad I don't have, like, a child that does this because...
[00:21:31] Annie Holcombe Yeah. My son didn't do it, but I was a gymnast, and we traveled a lot, too, and that alone is like there's just so much value to it. So, like going back to, like, from the Annie & Co. perspective, it's talking to somebody like understanding their market, and then with the business, it's, like, what businesses are in your market that are bringing people in. Panama City Beach is a great example at this point. We're rebuilding from a hurricane from 2018. Our Air Force base was destroyed, so they're rebuilding it. It's going to be the base of the future, so it's got a lot of people coming in from construction. They're there for months at a time. You're going to have to do your laundry. You're not, laundry mats aren't a thing anymore. I mean, you want to have a place to work. You want to have a place to relax. So, I think that overall vacation rentals serve a great purpose in the business. Are they for someone that's going into a market for two nights? Probably not. But if you're going to be there for a week, two weeks, you know, you're there as a remote business for a while, it makes perfect sense. So, to me, it's like, you know, I say this all the time, the hotels are entering the space. They're doing it. What Marriott Bonvoy did with the homes and villas product, I mean, they knew that they were losing people to the vacation rentals from their platform. They were losing that loyal hotel guest. And so they understood that. So, I think that there's a synergy for these two pieces to work together better. But from business perspective, people are gonna continue to wanna bring their families on these trips and extend and make it that bleisure trip that used to not be a thing, because it was you went on your business trip, you had to come home to be with your family or that was, you know, your business maybe didn't allow for that. But I think trying to find work-life balance has, you know, bled over into this. So vacation rentals absolutely need to be in the business sector.
[00:23:06] Tim Rosolio I'm actually thinking more from a perspective of like then, like also distribution. Like, if we're trying to access that business traveler or that travel sports parent, like, how do we think about getting these vacation homes distributing more broadly to get more eyeballs on perhaps more people that aren't, or they're looking for more than the annual beach bash.
[00:23:28] Annie Holcombe Yeah. So, you have to, I mean, you have to work with the channels that can get you in front of that. So, like, I mean, there's, you know, the American Express Travel Agencia being on GDS is really important. I think that again, a lot of property managers and a lot of hosts, they don't know that that exists. So for me, it's like educating on, like, what does your market look like and what kind of businesses can you tap into that are bringing people there. And that's the channel that, you know, whatever channel they're booking through. Because it could be a travel service. It could be, you know, a lot of it is with travel agencies through GDS, that type of thing. So, I think that's what you're getting at is more, like, yeah.
[00:23:59] Tim Rosolio Hundred percent, yeah, because in my mind, it's, like, with all the hard work that we've done re-platforming, that enables us to think about vacation rentals beyond Vrbo. And I mean, I'd be curious to hear how you're thinking about in Myrtle Beach, the most traditional of all vacation rental markets, where the vast majority of the bookings are the annual beach bash.
[00:24:23] Alex Husner Right, right, yeah.
[00:24:24] Tim Rosolio You have some experience with, like, the DMO and the Chamber of Commerce. Like, how are you guys thinking about bringing in new travelers?
[00:24:29] Alex Husner You read my mind. I wanted to go with it. No, I was just going to say that I think, you know, the onus is also it's really on the DMO, and these situations, especially when it comes to sports tourism, because typically those fast pitches of the world, those different groups, they're starting at the DMO level. And it's really those are the conversations that to me make the most sense of how do we make sure that those organizations know, there's more than just typical hotels to book when you and the benefits of that, right? But we just had an episode that aired recently that we talked about, you know, DMOs and short-term rentals working together. Myrtle Beach is an example of a market that works very well together. Panama City Beach also. There are many markets that it does; the vacation sector is not as welcomed, because there's more hotels that really don't want them to be part of it. So, you know, it is a market-by-market type thing, but we are both from markets where we've seen it done successfully. And when these organizations come to Myrtle Beach, they're gonna see the destination, and they're going to think “I want to come back here with my spouse” or “I want to come back here for a girls’ getaway.” And that next trip might be at a hotel, you know, or vice versa. So, it's like, it really, you have to look at it from, like, the broader scale of you want more people coming to the destination. We want them to see the vacation rental product. They might not stay there every single time, but that's okay. You know, it's about awareness.
[00:25:43] Tim Rosolio Yeah. And then magical things happen, 'cause it's my understanding in Myrtle Beach that there's, like, Canada week or something like that, but you're in Myrtle Beach.
[00:25:53] Alex Husner And they swim in the ocean in March. It's crazy, but they're fine with it.
[00:25:57] Annie Holcombe At Panama City Beach, there's a prom for our snowbirds. Like they have a, they have like a Valentine's Day prom for the Canadians, yeah.
[00:26:03] Tim Rosolio Oh my god. That might be a conversation we need to learn more about later, because it sounds like a whole thing.
[00:26:10] Annie Holcombe It's probably a whole thematic episode.
[00:26:13] Tim Rosolio What's the one thing that you need in a vacation rental to stay? And it probably depends on the type of trip.
[00:26:19] Alex Husner I like to stay at places that are nicer than where my home is, to be honest. Like, I want to stay somewhere that is different and unique and gives me a different feeling than what I have at home. And I have a nice house at home, but, like, I want to stay in a place like this, that this is a completely different experience than where I live. There's water, we're on the waterway, but this is on a lake. And like just the architecture here is, like, it just gives a very different vibe to it. So, I like to stay places that just gives me a very different feel.
[00:26:45] Annie Holcombe I like the experience. I think that, you know, again, getting out of what your normal comfort zone is, trying something different. We've been able to, Alex and I through the podcast have been able to travel to Europe a little bit the last couple of years, and just to be able to, you know, I stayed in, actually, a property in Milan. We got to be in a residential, like, in a building with other people, like, that were Italians and, like, kind of live their life, like, vicariously through them every day, and, like, get recommendations for restaurants and where to go. And I think there's just something in a hotel, you know, you depend on the concierge. You're not running into somebody that lives in the building that can say, like, yeah, don't go to that restaurant, you need to go to this one, or don't go to this museum at that time, go this time. And so that's what I want, is I wanna come away with some really core memory that I won't ever forget.
[00:27:27] Tim Rosolio Yeah, it certainly makes it different. Well, you know, one of the things I really love about this house is, and you guys talked to David, like, the guy's an MIT professor, and he's very tech-oriented. I think it's cool that when I walk in this house, like, it's got, like, nice technology, but I don't feel like I'm in, like, an episode of the Jetsons. There's no, like, talking refrigerator or anything like that. I think everybody in this category is trying to balance power of technology, convenience of technology with human touch. Is there anything that you guys have seen in your consulting work that sort of threads the needle there?
[00:28:02] Alex Husner I think with AI, things are going to change a lot. I mean, a human touch is really evolving as far as, like, what that really means, whether we like self check-in or checking in at an office. And I was actually surprised that you said you like checking in, you like to go.
[00:28:20] Annie Holcombe I like people.
[00:28:21] Alex Husner Yeah, and I do, too. But at the same time, if I've been traveling, I wanna get to the property. I'd rather be able to get in. So, I love the convenience of just being able to get into the property. But at the same time, I think the main thing is, for me at least, is the human touches. I wanna be able to get information as I need it. I don't wanna come into this house and have to read manuals because the technology is so complicated that I don't even know how to turn the lights on. Like, I just, I want it to be intuitive. But I think where AI is starting to come in, and we've seen this in clients that we work with, that the AI is getting so good conversationally that it's becoming, people think that it's better than a human, right? And one client that I know of in Sweden, their AI agent has been asked out to coffee, or lunch, or dinner, 11 times in the last three months. And that never, he said that has never happened when they had real people answering.
[00:29:14] Tim Rosolio Is that like the movie Her?
[00:29:15] Alex Husner I know, like that, right?
[00:29:16] Tim Rosolio What's going on here?
[00:29:17] Alex Husner Exactly. This is a little weird. Exactly, and I think at that point, that's maybe when they reveal like, oh no, like Sophie is actually, like, not real. But people go back and forth with it, and you're getting so much more thorough information that, you know, the human touch is kind of evolving into people wanting information when they need it in a way that's going to answer their questions before they have to keep asking more and more and more questions.
[00:29:39] Tim Rosolio It's going to be amazing how it all, how it all evolves, and it's a great example of useful technology. Let me ask you, though, do you ever, like, check in to, like, a fancy hotel? Like maybe you get in, you see the shower and you're, like, I don't even understand how this works. This is too complicated.
[00:29:56] Alex Husner All the time. All the time.
[00:29:57] Tim Rosolio Whatever happened to just, I turn this and I pull that and the damn thing's on. I digress.
[00:30:02] Annie Holcombe Have you ever stayed in any of the technology-forward properties in Vegas? They're notorious for that.
[00:30:07] Tim Rosolio Tell me more.
[00:30:07] Annie Holcombe When they first opened, they had like a touch pad, and it would do the curtains, and do the lighting, and everything. It was crazy, but it was, like, they don't tell you how it works. It's just like your room has a master control. That's all you get when you walk in. So, you're pushing buttons and all of a sudden, like, at 3am, all the curtains open up because you had no idea.
[00:30:26] Tim Rosolio This is Vegas. I don't need that right now.
[00:30:27] Annie Holcombe I definitely don't need that, but I think it is. I think the technology piece of it is really important, and it can help demystify some of the things that have to be done in the business. But I am an emotional touch person. I'm a hugger. I like to see that, and I like to see people, and I'd like to feel.
[00:30:43] Tim Rosolio Do you think you'd ask out the AI bot?
[00:30:45] Annie Holcombe I might.
[00:30:46] Tim Rosolio All right.
[00:30:46] Annie Holcombe I mean, no, I wouldn't ask at a stranger that way, but we're gonna find a balance in it. I think it started to, like, swing where it was, like, technology was taking care of everything, and people were so dependent on the technology to handle the check-in and handle the reservations and handle all this. And yes, AI is gonna be able to answer questions that come up, but I still think at the end of the day, we're human, and we want to have human interaction. And if we start to feel like it's robotic in nature, that, you know, that just, to me, takes away, like, the whole experience of one of a vacation. I couldn't go stay in a hotel and get that.
[00:31:17] Tim Rosolio Digging in like a bit more, though, like you mentioned, though, that you, like, you like going and picking up the keys at the centralized location.
[00:31:23] Annie Holcombe Yeah.
[00:31:24] Tim Rosolio What do you like about that?
[00:31:25] Annie Holcombe I like to have a solid key. You know, you're checking in at night, and the battery pad has died because they didn't, you know, they didn't know it was running out and they weren't taking it, and you can't get in, and you can't hold to somebody like...
[00:31:34] Alex Husner Then you sleep on the porch.
[00:31:35] Annie Holcombe Right, and I mean if I had a key, I could get in.
[00:31:37] Alex Husner It's interesting, too, because it's like, I can't even remember actually the last time that I got a hard key at a vacation rental. But in my history at Condo-World, when you would walk into the building, we had a wall of keys that was as long as this. And they were all, yeah, what could go wrong? Exactly. But that's just how it was at that time. And during COVID, when guests couldn't come into the office, we had the unique situation that our office was a huge raised beach house style office building. So, we created downstairs, like a Chick-fil-A drive-through check-in. And guests still love that. We got the best.
[00:32:09] Tim Rosolio That's kind of fun.
[00:32:09] Alex Husner It was, it was.
[00:32:11] Tim Rosolio Did you have waffle fries or was there any snacks?
[00:32:15] Alex Husner No snacks, no snacks, but it was a well-oiled machine, and guests, we got the best reviews that summer that we had to do it because people were, like, amazed that we were able to pull that off. Meanwhile, the competition, people are still having to wait, you know, in the sun on a Saturday in July for an hour outside waiting to one person at a time to go in to get their key.
[00:32:32] Tim Rosolio So, you know, we've moved on from that, thankfully. That's probably a good stopping point, but thanks so much for joining us here and for being amazing stewards for our category.
[00:32:45] Annie Holcombe Thank you.
[00:32:46] Alex Husner Thank you for having us and all the support. Yeah, you have a great team. It's been a lot of fun.
[00:32:50] Tim Rosolio Yeah, shout out to the partner success team, which does such an amazing job for everybody. Good things to come.
[00:32:57] Alex Husner Yeah. Yeah. Sounds good. Thank you.
[00:33:00] Tim Rosolio Thanks to Alex Husner and Annie Holcombe of the Real Women of Vacation Rentals podcast for stopping by the pod. And of course, thanks to David Rose and Lakefront Escape on Squam for hosting us for the conversation. To see a full listing of all of Vrbo's vacation rentals of the year, including Lakefront Escape, visit the link on the description. And stay tuned for more Powering Travel, and go back to listen to previous seasons you may have missed. To get updated when new episodes are live, be sure to follow us on Spotify, YouTube, Apple podcasts, and anywhere you listen and watch your favorite podcasts. Thanks again for listening to Powering Travel, brought to you by Expedia Group.
Meet the experts
Tim Rosolio
Tim is a subject matter expert in vacation rentals, and he oversees work across key projects and initiatives at Vrbo. In addition to years of experience in the business, Tim understands what Vrbo hosts need because he is a host himself. He also previously worked on the Expedia for Business Strategy & Transformation team.
Alex Husner
Alex is a vacation rental industry leader, fractional CMO, and co-host of the award-winning “Alex and Annie: The Real Women of Vacation Rentals” podcast. After 10+ years growing Condo-World and then Casago, she now advises vacation rental companies and tech brands on marketing, positioning, brand visibility, and revenue growth.
Annie Holcombe
Annie has worked in hospitality and vacation rentals since 1992 — with tenures at Expedia Group and Marriott — before launching her consultancy, Annie & Co. In addition to co-hosting “Alex and Annie: The Real Women of Vacation Rentals,” she helps property managers and tech companies build real growth strategies.
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