DARM 2025 Fireside Chats: What the Industry Is Finally Saying Out Loud
This episode was recorded live at DARM 2025, right in the middle of the event, while the conversations were still unfolding and the energy was still fresh.
Alex & Annie sit down for two fireside chats with Alex Cisneros (StayTerra) and Dennis Goedheid (Casiola) to talk through what’s showing up in the industry right now, and what operators are being asked to decide even when the path forward is not perfectly clear.
If you were at DARM, this conversation will likely put words to what you were feeling. And if you weren’t, it offers a clear window into the discussions that mattered most this year.
What you’ll hear in this episode:
1️⃣ Why StayTerra targets reputable, community‑rooted operators
2️⃣ Where centralization helps, and where local teams must stay empowered.
3️⃣ Why multi-brand scale starts with getting data into one place
4️⃣ Why loyalty is still tough to crack in vacation rentals.
5️⃣ A more grounded take on luxury: less formality, more ease.
6️⃣ How Casiola is building growth through partnerships and ambassadors.
7️⃣ AI guest service that anticipates needs and raises expectations fast.
8️⃣ The next challenge: being discovered when AI gives only a few options.
Connect with Alex Cisneros:
LinkedIn: https://www.linkedin.com/in/alexjcisneros/
Website: https://stayterravaca.com/
Connect with Dennis Goedheid:
LinkedIn: https://www.linkedin.com/in/dennisgoedheid/
Website: https://www.casiola.com/
Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).
👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.
Considering an exit strategy?
#vacationrentals #shorttermrentals #DARM2025
00:00 - Live From DARM: Setup And Guests
01:31 - What State Terra Buys And Why
04:46 - Centralizing Finance, Data, And RevOps
09:05 - Choosing Markets, Brands, And Cross‑Sell
13:18 - Brand Strategy, Loyalty, And PE Reality
16:44 - Building The State Terra Team And Stack
21:10 - Hands‑On Integration And Data Lake Plans
21:51 - Sponsor Spotlight: Lodgify
24:40 - Seller Transitions And OTA Mix Shift
28:10 - Introducing Cassiola’s Ambassador Franchise Push
31:10 - Redefining Luxury: Lessons From Necker Island
36:20 - Human Connection Vs Screens And Systems
40:05 - Culture Fit, Standardization, And Scale
44:20 - AI In Guest Service And Discovery
Alex Husner: 00:02
Welcome to Alex & Annie, the real women of Vacation Rentals. With more than 35 years combined industry experience, Alex Husner and Annie Holcombe have teamed up to connect the dots between inspiration and opportunity. Seeking to find the one story, idea, strategy, or decision that led to their guests' big aha moment. Join them as they highlight the real stories behind the people and brands that have built vacation rentals into the $100 billion industry it is today. And now, it's time to get real and have some fun with your hosts, Alex and Annie. Hey guys, it's Alex. If you've ever been to DARM, you know it's one of those conferences that really makes you stop and think, not just about where this industry is going, but where you are in it during that moment in time. This year especially, the conversations felt real. Less hype, more honesty, more of, okay, what are we actually going to do next? The conversations you're about to hear were recorded live at DARM, right in the middle of everything, while the energy and ideas were still unfolding. We sat down on site with Alex Sisernos of State Terra and Dennis Goadheed of Cassiola, two leaders with different backgrounds and perspectives, but a shared pulse on what's really happening right now in vacation rentals. We talk about what stood out at DARM, what people are finally starting to say out loud, and where operators need to stop waiting for perfect clarity and start making some bold decisions. If you are at DAM, this episode will help you put into words what it is you are feeling. And if you weren't, this is the conversation you'll want to catch up on. Let's jump in. Welcome to Alex and Annie, the Real Women of Vacation Rentals. I'm Alex.
Annie Holcombe: 01:36
And I'm Annie.
Alex Husner: 01:37
And we are joined today by Alex Cisneros, who is the chief commercial officer for State Terror. And we are live here at DARM. Thank you, everybody, for joining us. Alex, so good to see you. Good two Alex's news. Yeah, it's so easy. Great name. Yeah.
Annie Holcombe: 01:51
I feel like I should have put I should have put them on to the side with Alex Annie Alex. So, Alex, you and I worked together years ago when you were at Wyndham. And so I feel like this was really exciting to be able to see you kind of come back into the vacation rental. You were gone for a little bit. You went to I think the dark side. You were back at the hotel world and you came and joined us in the vacation rental world again. But tell us a little bit about State Terra. It's relatively new on the scene, but um not unheard of, and you're making a lot of moves, and it's exciting to see.
Alex Cisneros: 02:17
Yeah, well, thanks for having me. State Terra is a company that it was found about a year ago. So we are going through the process of buying great businesses. Obviously, in our industry, the definition of great means a lot of things. So we are focusing on properties that are provide a great experience to guests. It has a solid foundation. Many of the businesses that we are buying, they have amazing brands like we bought Prime Vacation Anna Maria Island. We bought Movie Mountains in Colorado, and we continue to buy businesses. We have one in Hilton Head, Cape and Coast. So we have done four acquisitions. We are actively looking for great businesses to buy. I think the joke is that we are the second oldest industry in the world, which is great to know that. But we we are going through a similar process. We recognize that the guests are looking for great experiences. There are companies also that as they get to a certain size, is very difficult to scale. So we see the opportunity, and we have the backing of GSP, Gardener Station Partners, which is a company that has been investing in other fragmented industries. And the difference here is that we are looking to invest in companies. So, like I was yesterday talking about some opportunities that we have on AI and how we can use data, they have connections to be able to do that work. We are talking about taxes and accounting and branding and all the elements of the like of our industry, and they are willing to give us assistance and really work with the companies that they have found. They have greater reputations. We just want to take it to the next level.
Alex Husner: 04:21
Okay, gotcha. Yeah. So I think there's a lot of different ways people are doing this type of kind of consolidation these days. You've got franchise, you've got this type of model, and within each, there's there's you know different players. But at the end of the day, it's about trying to you know make the resources all work best for as a larger group. Maybe tell us a little bit about how you approach that and like what are what are some of the things the economies of scale that you're able to push down to the companies that you purchase?
Alex Cisneros: 04:46
Yeah, so it it this comes from some of the the previous franchise models that the hotel industries did. You've you look for functions and areas of the business that are difficult to to navigate and properly uh support. So take finance, for example. I think that's a function that it can be centralized and we can provide support to the local teams. Revenue management is another interesting area, and we are here at the conference. So that's that's that's something that we we are looking to implement more advanced tools to the existing revenue managers. Like we have really good people in many of these businesses. They know the product, they know the distribution. So it it allows us to think about okay, if we want to bring, for example, a large AI model to train on tax analytics, we can do that from a centralized place and make their lives easier. Same with picking and choosing the right revenue management system tool or the right BI solution. So we we are picking and choosing what are the right technologies and functions that can make everyone's life easier. Like by no means we want to go and centralize everything. I think that's something that we over the years we have learned that not everything can be centralized, but just picking like anything that creates friction is a headache. We want to be able to really have that in a central place.
Annie Holcombe: 06:11
Well, and I think there's a lot of friction in this business. So I think anybody's you know looking for ways to remove remove the friction that they do have. But in terms of identifying the property management groups, what is your ideal uh group look like? Is there a specific location you're trying to get? Are you trying to make sure that you have a good balance between beach and ski? You know, what is it that you're looking for in an operator?
Alex Cisneros: 06:33
We want to buy uh good businesses that have been operating long enough that they have a reputation. They need to have a good reputation with guests. They have to have be part of a community where they have connections that allows us to operate effectively. That's something that we have seen with movie man, for example, and Steamboat. Some of the work that that Robin and the team have done allows us to find a really good foundation that allows us to enter other markets. Similar situation with Prime and other acquisitions is really the when I think about our business, it's a lot about people, right? So if you have a very strong uh team, uh foundation, you have a reputation with guests, with owners, with your communities. I think those are good businesses to buy. We are not necessarily focused on, okay, we need to balance beach and ski. We are really looking for the experiences that people are looking for. Like mountains is another great example that during my time at Wyndham, um the smoky mountains in areas like that. I remember the joke I started the industry in Tamshare. So Branson, Missouri. I didn't know much about Branson. But as I started working with different sets of inventory products and destinations, you recognize that customers are looking to go to these places to have a good time. So I think it has to be the combination of where guests want to go and good product, good business that we can take on and being able to add more resources, more support, and grow those businesses.
Alex Husner: 08:08
From a marketing standpoint, what is the plan to try and leverage the areas against, or not against each other, but to work together, right? So that people that go to the beach, they next year want to try the mountain destinations. Is there a plan to converge those?
Alex Cisneros: 08:21
That's actually a hot topic. And it was always a hot topic for a larger organization, whether uh you operate in 10 markets, is like how do you cross, yeah cross-sell different markets? The way I view it is that we have the ability to continue to build on the existing foundation. People want to go and ski and have a great time. Similarly, they want to go to Florida, enjoy the beach. We want to continue to focus on those markets and with those customers. But at the same time, I think this is another area of you know buying businesses that you can bring expertise. If you start looking at the customer profiles, there's some overlapping.
Speaker 3: 08:60
Yeah.
Alex Cisneros: 09:00
And you recognize that, like just take somebody that is spending $20,000 in a home to go and ski in Steamboat, it may be equally interested, especially in markets that you have, like Texas is the ideal market because they go north and they and they come to Florida. So there's some overlapping. So we are we are already in the process of centralizing all of the data, bringing good understanding of who are the customers, how we can leverage that information in one place, so we can start eventually playing with that. The question then becomes is what is the right message for those customers? Because they know movie mounts, they know uh you know Anna Maria Island, but they don't know the each other.
Speaker 3: 09:45
Yeah.
Alex Cisneros: 09:45
So we're gonna go through the process of it's like dating. We need to first introduce them and then eventually build on that those relationships.
Annie Holcombe: 09:53
And on that, are you gonna be do you think that you're gonna evolve into marketing state terra, or is it gonna be moving mountains by state terra? Like how what does that look like in terms of the messaging going forward? Still in the world.
Alex Cisneros: 10:07
I think State Terra is a brand that we we want to be able to present to man property managers that wanna they want to move to the next level and we want to be part of a good relationship. I think from a guest perspective, we learned that this at Wyndham that even with a hotel brand, it's very difficult to promote a different experience in the vacation rental space. So I think we want to continue to focus on what the current brands are, continue to build on that. I think the State Terra decision will come later. Uh, it also is very expensive to build a brand. I think when you look at the work that Airbnb has done, I remember that my first trip to Airbnb in 2013. Airbnb was not a brand. And it has taken them about 15 years to get to where they are. So it's a process, it's expensive. You need to be able to tell a story. And I think we we have some good local brands that it allows us to continue to build that relationship with what we have.
Alex Husner: 11:07
Maybe a loyalty program in the future could tie it together from your experience on the hotel and loyalty.
Alex Cisneros: 11:14
That is a you know, I don't know. Lock them in. So I left in 2019. I came back. I'm fascinated by the number of vendors that we see upstairs, a lot of good technology. Uh, but uh loyalty is not upstairs, yeah, which is is interesting to see that yeah, that is an area that we haven't solved for it and whether there's a place for it. I think loyalty is one of those terms that we lose loosely use it. I think loyalty is uh to me, it's more in the current hotel space, is more about you're just part of a club, but you're not loyal to it. Yeah, I think loyalty. There's no connection. I think that's what is missing. Uh at Window, we spent, I spent three years analyzing that uh with the Window Rewards program, and we never found a way to make it work financially because you need to replenish the cost of points for with the incremental demand. And the math didn't work out. And you really need to you need to almost lift demand by uh bookings by about 20% in order to pay for your loyalty program. But there's still a place. I think there's somebody somebody's gonna figure that out.
Annie Holcombe: 12:26
Yeah, maybe you guys will.
Alex Cisneros: 12:27
Yeah, maybe. That's we'll be talking about that uh quite a bit, I'm sure.
Speaker 3: 12:31
Yeah.
Annie Holcombe: 12:32
So why don't you tell us about the team that you put together? I noticed that Wendy Glover just joined you recently. She's been, well, she worked with you at Wyndham, she's been around for the industry for a long time. But tell us a little bit about the people, the key players that are in State Terra right now.
Alex Cisneros: 12:44
Yeah, so we have a uh a corporate team that we are supporting the businesses that we are acquiring, is led by ML Clark. She's the president of State Terra. She came from Wyndham. I I worked with for ML for five years. Uh before that, she was with Rich Scalton. I so what's good about ML is that she has an emphasis on hospitality. And I think a lot of the businesses, when you see what the businesses that we're buying, is that we want to work with people that love hospitality, the complexities of it, the ability to provide great experiences. So we have a strong foundation with somebody like that and the experience that ML has. We have put uh different team members in the finance world. Like we have Mike Toscano, our CFO. He has led organizations on the and more on the timeshare hotels, and he's bringing up a lot of that experience as well. So we are putting the pieces together. You mentioned part of what we're gonna be facing, and and I already see it, is that the our industry has evolved a lot from when I when I left to now, but it technology is fragmented. So you have you are solving for different components of the journey, the customer journey by implementing new technologies and more technologies and so on and so forth. So having somebody like Wendy is going to allow us to look at the customer journey, pick the right technology. We need a platform. Uh, and we need to be able to have the right the right PMS. That's what we what was great at Wyndham. We manage 110,000 units in 32 countries with a core platform. And we want to be able to bring technology, enhance the experience, help the businesses. I don't know what that is going to look like. You know, uh we have almost, I want to say more than 60 technology pieces right now in all of our businesses. Now, what is gonna be what what we need is gonna Wendy is gonna play a key role. We just hire somebody that is going to be leading our development team. We also are investing on other areas that on on that are going to be centralized, providing support to the different businesses from you know the corporate level.
Alex Husner: 15:02
So on a daily basis, how hands-on are you with the companies?
Alex Cisneros: 15:06
Right now we are very hands-on. So I can, you know, with in the commercial side, my role is revenue management, marketing, sales, technology, data. And we've been working on bringing the information into one central place. That was that was crucial that to to be able to operate and and navigate quickly. So now I every day we have reports and we have the ability to look at performance. On the marketing front, same conversations Monday. We start working with each of the teams, understanding what are the plans. You know, from the get-go, you see opportunities to enhance the the this businesses by bringing maybe some of your knowledge that has worked on the you know, multifamily business, hotels and whatnot. So very closely involved on a daily basis. I I think it's as we build the team, it's going to allow the different team members to dedicate more time. I think that's something that we finished the day and we we we regret that we didn't spend enough time on what on the business today, but tomorrow, as we continue to make it more efficient, I think we will be doing more of that.
Annie Holcombe: 16:19
I wanted to ask, um, just going back to when you when you purchase a company, are you purchasing them with this the understanding that maybe the owner stays in for a certain amount of time or they do they exit immediately at that point? Like, or are they just hybrids based on the companies that you are purchasing?
Alex Cisneros: 16:34
You know, one thing that I've learned over the years is that for many people that many property owners that are selling the business, this is their baby. Yeah, right. So none of us are going to walk away from our baby day one. So we want to be able to have them close to us and as as long as they want to as well. Because in some cases, they need a break. The ones that want to stay with us, we want to keep them, and sometimes it may be as an advisor, sometimes it may be running the company for the next six months, and then until we have a solid transition plan. But we definitely want them to, you know, pick their brain and know what the secret sauce has been in order to continue to grow these businesses.
Alex Husner: 17:18
So, what's one thing that you're really excited about to try in 2026 that you haven't tried yet in your many years' career?
Alex Cisneros: 17:24
I think this year for us is continue to build a platform. And I think by the beginning of next year, we will be in a better place that we have the ability to anticipate demand, uh, I think more consistently, being able to bring new customers. I'm looking forward to finding the right balance of what the mix needs to be in the in our business. I think the the other observation coming back from being outside of vacation rentals for five years is that they're reliance on some of the OTAs. I think there's an opportunity to continue to leverage these great brands that many of our businesses have and really find ways that we can connect with customers. We are already working on AI. So I think everybody now is an AI company, which is good and bad. But I think the opportunity to bring some automation into our daily lives and being able to take advantage of what AI is doing across different organizations. I think I'll be spending a lot of time on that. That's part of my background. You know, I started in this in this industry as a data scientist. Uh so that was my first job for Sendon back then. So seeing how the industry, all the industries are now using data and algorithms and math. I'm also a math major, so it's very exciting for me to eventually use that next year.
Alex Husner: 18:47
And did you build your own technology on top of the different PMSs that the companies are on to be able to see that type of reporting? That's one thing that's very hard for companies, especially if they're multi-market.
Alex Cisneros: 18:56
Yeah, so right now we are in the process of bringing the data into a data lake. Uh we are using Microsoft Fabric is going to be the foundation of everything that we have. Uh there's there are opportunities to bring in the right set of data. So right now we are focusing on PMS information, transactional. There's also Google data that I think is an opportunity. Uh, I think maintenance and operations and and reviews, kind of everybody lives in their own world. I want to be able to bring that and create dashboards so we can anticipate what some of those challenges are. But we started with let's bring what we have. I think we have also good partners that help us build good reports. And I think that's something that we are we are in early stages of navigating through what is you know, managing an enterprise of multiple brands, multiple systems.
Annie Holcombe: 19:51
Yeah. So we're live streaming these um throughout the day on um the YouTube channel, correct? Um so it's the if there's anybody in the audience, anybody watching, anybody that goes back and watching. if they're interested in maybe perhaps pursuing a possibility of exiting and getting you know selling their company, what would you c what would you tell them to consider and would they should they reach out to you to to have a conversation about that?
Alex Cisneros: 20:12
Yeah, we we are definitely interested in in talking and we have our Citera team here. So we are more we're it's not just me and definitely we we have the right people here to have those conversations. We are a company that wanna be able to to continue to integrate businesses that are at the point that they're already delivering great experiences. They they they have a reputation. That we need to find the right balance because the experience is happening at the local level. So we need to continue to empower them. So by no means this is uh the the there's also this stigma of being backed by private equity. What I can what I personally can say is that not all private equities are the same. And I think in our case the banking that we have is with resources, knowledge, financial support to be able to grow grow this business is you know don't I think I've done about maybe 30 acquisitions throughout my career. And I always fascinated find find it fascinating that one business gets to a certain point and they cannot move to the next level I think we can take that that help that those companies go to the next level by really being good partners with them.
Alex Husner: 21:39
Well thank you for joining us today everybody this is our first ever live stream so that was pretty good we'll be back in just a minute but first a word from our premier brand sponsor.
Speaker 6: 21:51
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Speaker 5: 23:51
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Alex Husner: 24:15
We are here live with Dennis from Cassiola a many time repeat visitor on our real show great to see you.
Annie Holcombe: 24:22
Yeah thank you for having me well there's no mistaking where the Casciola team is always in the magenta so I love to we I can always find you in a crowd so it's always it's good. But we wanted to talk to you about a couple of things you've got going on one of them is this really uh kind of a huge program that you just put out after VRMA the ambassador program for your franchise. Why don't you tell us a little bit about that and I love the fact that you were able to incorporate the experience that you had at Sir Richard Branson's island as kind of a carrot for people to participate which I'm super excited about.
Dennis Goedheid: 24:51
I want to go so no it was really a life changing experience and and when we were when we were coming up with an ambassador program yes we need some kind of a financial stick to motivate people but what can we offer them that is something that the most people never get to experience in their life what is so unique that you think like hey let me join the ambassador program because it's it's not something that that most people can just do on their own. So um that was really a great uh tie-in with with my experience and and to make the program really unique.
Alex Husner: 25:26
Yeah yeah I remember when you did that experience yourself last year you posted pictures and everybody was saying that's AI there's no way that you were really with uh Richard Branson at his private house and we had you come on the show to tell us about it.
Dennis Goedheid: 25:40
And it sounded like it was an incredible experience that you got to eat with him you went scuba diving with him or you swam with him all sorts of things I I spent the whole week with him and and now with his wife who unfortunately just uh passed away uh uh last week so I was literally sitting with with her at the table uh last year around this time so but it was a unique experience it it really redefined what what hospitality means uh for me it's it's not always about the the luxury but really I I know it's a cliche we've we've heard that so many times but how do you make people feel yeah like like Necker Island you've got celebrities presidents billionaires vacationing there and and when I first arrived I was like hmm is this it's I've stayed at nicer vacation rentals even in other hotels but that feeling changed pretty quickly uh once you you got to interact with their staff uh there are a bunch of of young people and they're really trained the exact opposite of of what most luxury hotels and resorts train their staff on they really uh push to to interact with with guests to hang out with guests um even after their shifts uh drinking with guests is is completely allowed partying with guests is allowed so they they really almost become like like your your friends um during the week that you're there and and um it's it's like they show you when you arrive like oh yeah we've got 50 bars all over the island but no one's gonna be there just go in open the fridge and take whatever you want and we've got a few kitchens set up so if you're hungry just go in open the fridge and take whatever you want and in the beginning it's like hmm it it's it's I was expecting like a butler following me the whole entire day but it it's it's so relieving you don't have yeah it's it's it's not so formal it's it's really like you're visiting a friend's a billionaire friend's island and and you're at his home uh um another thing thing that really stood out uh to me is there were no locks on any of the the guest uh rooms which is weird right usually you have to walk around with like a key card or or a key and and most people that go there they I assume have jewelry and and diamonds uh with them i i don't but most other people love your jewels and diamonds at home so which is right but it's it it it makes you feel like like yeah you're not yeah like like home exactly and I've got one more question too because yesterday there was a panel here that I missed unfortunately but it sounded like it was a great panel it was about what is luxury and it was a pretty heated debate there. I think uh Nir was on it and Rachel and Steve Schwab and just hearing what you're talking about did it redefine in your mind what luxury is because it it doesn't sound like it's luxurious but the level of service exactly they really want to take all your worries away so so you go there they ask you when do you arrive and from the moment that you um set foot on on the ground you don't have to think about anything you don't need your credit card to pay for anything you don't need a room key um they pick you up at the airport there's a a boat bringing you to the island um and and from there on then you don't even have to pick what you're gonna have for dinner there's like one main menu it's it's all big communal uh tables so you you just take what you want uh um to together with like I said the staff the staff is eating with the guest which is also something weird can you imagine that the the hotel staff is eating at the buffet like oh um but that that's really what's going on the the DJ is sitting there and then at night he's uh yeah throwing a party and and yeah it it was it it was really really uh special uh yeah something I've never experienced but but I took a lot away and and try to implement that in our business too.
Annie Holcombe: 29:34
Yeah I remember you talking about um just being in his presence or Richard Brant's presence and that he was never on his phone that he was just that so he made you you were seen and you were heard and you were felt and I think one of the things that the industry is struggling with a lot is you know with AI there's just so much robotics that it's that's happening behind the scenes that we we feel like we might be losing that personal touch. And I think that was a good reminder of like how much that human connection is so desperately needed in the business that we're in. I mean we can we can automate as much behind the scenes but people are still going to crave that interaction with people.
Dennis Goedheid: 30:06
Yeah absolutely so there were no screens whatsoever on almost the entire island I would say so you arrive but they already know you by name so they don't need to check you in and and look you up on a computer um there's no TVs in any of the guest rooms that now they do have Wi-Fi and and and a lot of people have to work obviously also when they're there when they're running companies but for Richard Branson yeah I I don't know how many companies he runs probably around uh 400 different companies under the Virgin uh brand I saw him on his phone once during the whole entire week and I was probably his wife calling to tell him that the lunch was ready um but yeah when you talk to him he's he's really present he's all there um he focuses a hundred percent on on you no distractions and um yeah he listens he's he's not what I expected the guy that would walk in and and sucks all the uh attention out of the room it's it's if if you didn't know him um you would never guess that he that he's a billionaire and that he has done everything that he has done uh he's so down to to earth and and he's always even at this level when you talk with him he's always thinking like how can I help that person who do I know yeah that could benefit from from a connection how can I bring them uh together even if I have nothing to to benefit uh from it and and that is really nice people connector yeah that's really yeah that's really special and so with the ambassador program is just one person per year that will win that trip or no so what we're um trying to do so uh Cassiola has a very ambitious uh goal so we wanna uh be in a hundred destinations have 10,000 homes under management and and generate half a billion dollars in in rental revenue each uh year so we have very ambitious uh growth goals but we also know we're we're not gonna be able to to get there alone we we need our industry on the ground uh yeah we we also want to do that through partnerships um not just by by us going all over the world because that's gonna be very hard to to run an operation from from Orlando uh on the other side of the world so we're really looking for for industry experts people that are talking with property managers every single day that are on the software side or on the service uh side and know which property managers may maybe need some help um or all are asking uh for help uh uh where we could help them scale grow their business and and that's why we launched the ambassador uh program to to extend basically our network and and and our sales uh team to to reach other people that we may never reach uh on our own yeah that's super exciting and I was reading through it and it was just so well thought out and I thought the execution of the program was tremendous I haven't seen anybody do that so congratulations on that but I wanted to ask you so how did you how are you able to leverage Necker Island like did you call Richard Branson's office and say like hey I want to bring some people back and they were like sure like how does that work out so he he is he's a billionaire for a reason right so he he lives there but he rents out the island uh um so probably he lives there for free and you let other people for all the the services there so um you can rent out the the islands um and there's a few weeks a year that they um that you can rent individual uh rooms uh so we uh um yeah we reached out with uh to my contacts uh there and we have a few uh weeks in in September that we can uh uh bring in some people so uh um obviously we're gonna have to pay for it but uh um yeah it's it's it's such a unique experience so I hope I I can share it with people so exciting yeah I think that I think that was an absolutely like just cherry on the top of what you're trying to do for this program.
Annie Holcombe: 34:01
I think it's really enticing.
Alex Husner: 34:02
So very cool yeah very cool. So and the franchise model and how you grow this I mean heart and love has always been at the center of your brand.
Dennis Goedheid: 34:11
Yeah what does that look like from a culture perspective of you get an existing property management company that they want to join Casciola how do you get them there from a culture point yeah so that's something very very important for us much more than than the money is the the culture fit and and are the people that we um gonna work with are they aligned do they share the same values the the same uh mindset um so we we do a lot of of of uh research uh there and we we talk to to people uh that have worked with them uh we do personality uh tests so uh we spend a lot of we spend a lot of time on that because it's it's like getting married right it's it's easy to get into an agreement but um unraveling all that later on is is a lot uh harder so we we want to be sure that we're teaming up with the right people that we share the the the right uh uh vision and and and the same values uh yeah yeah so what does it look like in terms of someone who does decide to join Cassiola with your technology stack I think that's that's been a conversation with uh the the various groups as to way the way that they handle some of them are everybody goes to the same PMS some of them are allowing people to stay like how what is your thought on that is it you know streamline everybody or let them do with their eventually where we want to differentiate ourselves is is really building a brand uh in invocation rentals which is something I I think is still missing a little bit um you have a bigger of the the franchise um brands out there but to me they don't feel like a um cohesive like entity it it if if you go from one um destination to another you may have a completely different uh experience so we want to standardize things a little bit more so um we'll be similar tech stack uh too i i I don't think you you can get around that um if if you want to try to scale it's also very important that you simplify your your business models so we we try to to keep our tech tech stack very limited um make it uh simple and easy uh to use but we also offer a lot of of support so that uh um our our partners don't have to worry about a lot of things that they have to worry uh today in in their own uh business so we we try to to take a lot of the things that they're usually not not um that they don't like doing or that is very hard away and we try to have them focus on their their owners their their growth and and their properties so I guess yeah yeah and you've built a lot of tech for the company over the years too so I mean you guys have your uh secret sauce and industry knowledge which is is huge to help these property managers with that but I would be remiss if I didn't ask about AI and how you're infusing that within the business I know that you're working with with Boom also and maybe just share a little bit about that. Yeah um AI I think on on the guest side has been uh for me mind blowing what we have uh seen uh there um I think we're right now at around 80% uh fully automation on on the guest uh uh service side um and and a lot of people look at it from from a cost savings uh perspective and and that was initially also our thought like hey what what can we do here to make it more efficient but then I started working with it and and it just blew my mind entirely like AI is it's not just cheaper but it's so much better also than our our team um just to give you an example um I I set up our first destination myself I I love technology and trying things out so I always always want to be very involved in in the beginning. So I had a guest in in a building was staying in in Miami in a big high rise and and they asked um the team like on what floor is the pool located and our team answered like hey thank you for reaching out pool is located on the 12th floor uh let me know if there's anything else I can help you with have a great day something a perfectly fine acceptable answer I would probably answer the same if if I was uh um was doing uh the job there but then I saw the um AI proposed answer and and it was like hey thank you for reaching out pool is located on the 12th floor so same thing uh but then they also added like the pool is open from sunrise to sunset and if you go to um the pool area don't forget your your amenity card because you need that to open uh the door to the pool area and by the way don't worry about pool towels because they're available at the the bar and and I was thinking like oh my god I would have never yeah it would have taken forever exactly I wouldn't even think about like the pool table because guests didn't ask about it and um to top it all off that guest was actually from France so her question was in in French our team answered in English and I know Airbnb also does a translation but the AI did it in like perfect uh French uh so that was for me like a pivotal moment like hey this is not just a nice gimmick or nice tool to have this I mean if you're not using this uh on today or in the next year you're gonna be irrelevant as a manager you you're just gonna have to do what guest expectations are gonna change they're gonna expect instant answers in their language on on their platform whether that's Airbnb or WhatsApp or text uh whatever it is um and and if if you're not doing it you you're gonna miss out uh you're not gonna be in business very very long I think yeah so it's it's not a matter of oh I would like to do it you just have to have you seen a difference in your review scores too um yeah absolutely uh we've we've seen uh um now sometimes we also get uh um feedback from guests like hey it feels like ai so it's it's very important to to keep that balance because sometimes it keeps going in a loop Like, oh, I will notify the team and get back to you. And then uh, hey, did you already have an update? Oh, I will check with the team and get back to you. So they we need to get out of that uh harm, that loop. But uh overall, I I think even if you call it, it's just insane. Most people don't realize that they're talking to an AI uh system. And if the AI doesn't know the answer, it's just gonna tell the guest, hey, can I please uh uh place you on a brief hold? It sends a text or WhatsApp message to whoever is in charge of operation, you you answer, and then the AI just uh continues the conversation. Hey, thank you for holding. This is what you were asking uh about. So it's it's it's uh really mind-blowing. Yeah, the the biggest disruption uh for sure in our industry uh um in as long as uh I I always say since the introduction of um dynamic pricing and revenue management, what is it, seven, eight uh years ago?
Annie Holcombe: 40:56
Yeah, yeah. Well, speaking of um, you know, revenue management, it's obviously a revenue management conference, but with the AI, I mean I think there's been a lot of talk about like there's is does AI put the the revenue management like team sideline, put them in another, you know, in another part of the company. What do you what do you think about data or the revenue management component with AI?
Dennis Goedheid: 41:16
So um I know Amy just walked in, but I I don't think we're gonna have a revenue manager conference anymore in in five years. That's that's my real honest opinion. Um, if you see what AI can do um just on on image and music and and and like things that we never thought that that a machine could do, I would be really surprised if AI cannot build the best revenue manager ever. Now you're always gonna need someone that is in control and that keeps an eye out, but that that could be anyone. You don't have to be uh um a data scientist anymore. But I I think AI is gonna completely take over revenue management and and do a better job than than the very best revenue manager than maybe at this conference uh today. So it's not what most people want to hear, but um at least as a business owner, I I I I think that's that's what's gonna happen. Now, the bigger challenge is gonna be how are we gonna be discovered, right? Like if if you ask uh AI, like, hey, I'm looking for a beach home with with uh um with three rooms uh on those dates. I I don't people I don't I don't think people are gonna use OTAs anymore the way they've been using them in the past. So you may get one or two or three options, and that's gonna be it. So it's really gonna be key like to be in those three options. Uh um, so uh that is uh uh that is a new area that we're all gonna have to to learn and and study on. Um but it's excited. It's gonna be.
Alex Husner: 42:49
So this might be the AI conference in a few years, is what you're saying.
Annie Holcombe: 42:53
But will AI, Alex, and Amy be sitting here.
Alex Husner: 42:60
Yeah, exactly. We can just clone our voices and don't say that.
Dennis Goedheid: 43:05
Yeah, hopefully you're in your island. Right. Yeah, exactly. There you go.
Alex Husner: 43:09
Yeah, yeah. Well, that's great. Well, super excited for what you've grown and just to see you, you know, personally, professionally over the years. I mean, it's just it's incredible what you've built. And your team, too. Yeah, just an incredible team.
Dennis Goedheid: 43:22
It it is all about the team, too, to be honest, because it's it's no longer about me. It hasn't been for a few uh years. It's it's it's also a cliche, but it's about finding the right people, like the A players that can bring your business to the next uh stage. It's it's uh much, much bigger now than one uh person. So uh yeah, we've got an amazing team, and and we keep adding more and more uh amazing team members.
Annie Holcombe: 43:48
Very cool. Well Dennis, we always appreciate you coming by. I know you actually you're a busy man, you're in demand, and you have a session that you have to go to. So hopefully you're gonna impart some of your wonderful wisdom about AI. And I don't know if it's about the revenue management component.
Dennis Goedheid: 44:03
EOS. Okay, well that's great. That's great.
Annie Holcombe: 44:05
Well, we appreciate you coming by. We appreciate you supporting the industry. Yeah, so thank you so much.
Alex Husner: 44:10
Yeah, thanks to everybody who came and also who's watching from home.
Founder & CEO at Casiola vacation homes
Experienced entrepreneur specialized in technology, marketing, real estate & company culture.
Started my first company at the age of 18 (Xedron)
2 successful exits: Xedron (2005 - event management ) and PrintConcept (2013 - online printing)
Born and raised in Belgium (Europe). Relocated to Orlando (USA) to revolutionize vacation rental investing and management.