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From Vacasa to First Chair: Lessons in Scaling Vacation Rentals

What happens when a vacation rental executive who has experienced the industry at virtually every level decides to go back to the basics? In this episode of The STR Data Lab, Jamie Lane sits down with Bob Milne, COO and President of First Chair Destinations, to unpack decades of lessons from building, scaling, and reshaping vacation rental management businesses. From running thousands of homes in Steamboat to navigating Wyndham and Vacasa, Bob shares why he believes vacation rentals are ultimately a hospitality and relationship business—not simply a technology business.

The conversation explores the tradeoffs between scale and local operations, what can—and can't—be centralized, the challenges of proprietary technology, and what Bob learned from Vacasa's rapid growth and transition to a more localized model. He also dives into why ski destinations offer opportunities beyond the traditional winter season, how events and summer demand can reshape seasonality, the role professional managers can play in local regulation, and why First Chair is pursuing moderate, deliberate growth rather than growth for growth's sake.

You don’t want to miss this episode!

Key Takeaways

  • Why vacation rental management is fundamentally a people and hospitality business, and where technology can—and can't—replace local expertise.
  • Which parts of a vacation rental business actually benefit from scale, from technology and marketing to operations and owner communications.
  • What the transition from Vacasa's national model to more localized operations reveals about the importance of boots-on-the-ground teams.
  • How ski destinations can reduce seasonality by tapping into summer travel, weddings, events, outdoor recreation, and improved air access.
  • Why sustainable growth may require a different approach than rapid expansion, particularly when balancing owner retention, local relationships, and operational quality.

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Connect with Jamie on social media

LinkedIn: https://www.linkedin.com/in/jamiehlane/

Twitter: https://twitter.com/Jamie_Lane

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Bob Milne, President/COO at First Chair Destinations

LinkedIn: https://www.linkedin.com/in/robertemilne/

Website: https://www.firstchair.com/

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Connect with AirDNA on social media:

Instagram: https://instagram.com/airdna.co

LinkedIn: https://www.linkedin.com/company/airdna/

Twitter: https://twitter.com/airdna

TikTok: https://www.tiktok.com/@airdna.co

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Episode 199

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Transcript

Welcome to the STR data lab. Welcome to the STR data lab. I'm Jamie Lane, chief economist at AirDNA. Uh, and we have today a really exciting guest. We have Bob Mil, the COO and president of First Chair Destinations on the show. Bob, welcome.

Jamie, thanks so much for having me. look forward to kind of have our conversation today. A lot to talk about.

Yeah. So, uh, if there's an a list of people that have been in this industry for a long time, sort of making big waves sort of before the OTAAS were really around and sort of seen the evolution of the industry and you were really top of the list of someone I wanted to talk to. Uh so I and whe there was I thousands of home in Steamboat which man I love Steamboat as a destination to to visit and ski at. Uh you're at Windham and the large sort of brand that Vicasa was and now and you were there through the IPO now the sale and now with first share uh I don't think anyone and sort of seen inside the industry the way at the scale that you have. So, uh, really excited to dig in with you.

Yeah. A lot of lot lot of battle scars here, Jamie, but you know, I'm I'm here. So, I I'll be able to kind of give you some of the some of the good, the bad, and the ugly.

Yeah. So, maybe just let's start with I'm in first chair and then we'll we'll sort of walk backwards. Um and you were and obviously at Vicassa now you guys have launched first share which was a subset and of the Vicasa sort of portfolio and so what have the first few months I looked like in this in this new company?

It's been really fun. And I mean it's kind of like back to back to my roots a little bit here you know I mean having gone through that kind of you know had my own company you know the entrepreneurial you know go going through you know selling selling to Windham then moving into the Vicassa world going public and then and then you know Vicassa you know deciding to sell to Casago and become private again really kind of gave us the opportunity because part of the the the way that this was able to kind of you know materialize was because Kasago was going to you know put everything into the franchise model and you know when that when that kind of started to surface as an opportunity I was able to connect with one of my good colleagues from um from Windham Richishy Nigum and we worked closely at Windham together building the Windham vacation rentals brand and we said hey you know what let's do something kind of special and fun here with the ski product and you know me being living in steamboat and and being a skier and and he's a skier as well.

We said, "Hey, this might be a a great opportunity to do something that is kind of a more than just saying that it's a niche, actually being a niche, like like really focusing in on on the ski destinations and the skiers." And we all know skiers are kind of a unique breed and there's a lot of opportunity to kind of build off of that.

Yeah. So maybe taking that back to Steamboat like and you guys had thousands of homes uh back then and and it was sort of operating during the 1990s 2000s. Uh what and has the industry and sort of needed or what have you sort of brought back into and first share that you first learned back in those uh uh steamboat days? Yeah. I mean, look, I think the one thing that we all as an industry got kind of we we we we kind of drank the Kool-Aid, if you will, and kind of started to believe our own stuff that technology would solve everything, right? And so, I mean, you go back to even to just the the whole Vicassa IPO. I mean, we we went we went public on the NASDAQ, right? So, you think about that, you know, that's pretty interesting. a vacation rental company, a hospitality company, you know, um doing their their IPO on the NASDAQ. And I I think it's it's oh, we're a tech company. But I think what's brought me full circle is that, you know, when I was building um my company, Steamboat Resorts and the resort company, yeah, you need technology, of course, you know, you need tech technology, but um at the same time, it's really still a hospitality, a relationship, a people, business.

And I think that's what's got me the most excited, Jamie, is kind of coming full circle because look, when you're when you're, you know, doing the Wall Street game, which is which is fine, it's fun, it's interesting, and and and a lot of good things happen from it, but you're playing that, you know, live and die by the quarter. And I think this business, it's much more of a, you know, live and die by your relationship and the people and the partnerships that you have that are kind of supporting you every single day.

No, that that makes sense. and and I I imagine and the sort of ups and downs of vacation rental management and the and nuances of the business and you guys were the first vacation rental management company to go public. Um hopefully not the last and though um and I I I I sense that it's it's going to take a lot now to get an a company to that scale again. Um wondering and and you were at Windham obviously and another large and public and hotel chain. Um and how do you feel about and that I business model like how it worked with vacation rentals, how it didn't work with vacation rentals? Like do do you think I a hotel brand is ever going to get into our industry in any meaningful way again?

I mean I it's a great question. And I mean I look I I obviously had a really good experience at Windham and wi and and with that team and um we were able to do something. I mean Wendham was in the vacation rental space and you know for a long time and people didn't realize it. I mean they they had built a portfolio of I think almost a 100,000 homes in Europe and across and and so no one really kind of understood that. So when they bought Resort Quest in my company, they already had a pretty good team of people that had a good background in in the vacation rental space and then we were able to build the brand Windom Vacation Rentals North America. I mean, look, there's a lot of things that there's there's parallels between the between the businesses.

Again, particularly come back to that hospitality and the guest experience, right? I think where where where it starts to bifurcate a little bit and where you really kind is when you bring in that extra component of yeah at at Vicassa for example we had 34,000 homes we had 34 you know not not one for one but let's just say we had 32,000 owners right so so it it becomes a little bit more of a dynamic when you know when the hotel world you're dealing with the owner of a hotel or owner of a franchise and here you've got you know you've got all the owners that are your clients as well. So, it makes it the dynamic a little bit different. And I think it also then means that your philosophy has to be a little bit different because you have to make sure that you know when you're dealing with guests and with owners and with your your your team, your employees, their needs are all different at any given time and you need to be able to balance that.

And that's something Jamie I haven't found technology be able to do yet. I think that uh it requires good people skills and good communication and that kind of spirit of hospitality that that you need to be successful in this business. So, I I definitely want to get into those learnings, but I I still am really interested of like what is or what are some examples of things that scale really help with in our business because I I can't imagine like everyone that was sort of searching for this scale like was was totally off in terms of the benefits that it it gave a business.

No, look, I mean, good another great question. Yeah, some things are scale and and that was kind of like the this the this the search the journey like okay let's figure out what's scalable and what isn't right like so obviously you can scale you can scale technology you can scale your product team you can do that you can scale marketing to a certain degree you can you can scale some of the um operational things with respect to your um your platform that you're on right it becomes really difficult to try to scale things like um owner owner communications, owner experience, it really comes really difficult to be able to scale parts of the the the guest journey as well. I mean, sure, you can have a central, you know, reservations function or a central uh CX function, but with respect to actually servicing the guests, that's that's really not that's really not scalable. Provide actually delivering the services becomes where it's really hard.

And I think when you start to fall in the trap and you think and start to run everything like a model like oh you have this many homes that means you have this many you know guest experienced people and this many you know managers and this it becomes where all of a sudden you lose the spirit of hospitality. I mean if you look at some of the most you know successful hotel chains they're not sit they're not sitting there counting the number of people that are kind of servicing their guests. they're making sure that they've got enough people to make sure that that guest experience is topnotch and top top drawer. And I think that's where it sometimes gets lost a little bit is that trying to think that everything can sit in one little central place, whether

that's in, you know, um, Precipity, New Jersey or Portland, Oregon. Right? The reality of it is it makes the most sense to have it, you know, the the the operations be localized. And yes, you can scale some things. Like I say, for example, you know, you can scale some of your marketing. That's definitely scalable. Absolutely. No question about it. But I think you have to be really wise about what you determine you're going to put your wood behind in terms of scalability and what you're going to put your investment behind in terms of actual local people and boots on the ground. It feels like that's in a lot of the reason why Kasigo wanted to try to make the infranchise model work, right? Of like let us

take a lot of the tech, let us take a lot of the marketing aspects off and that each one of these destinations is more an operations company as opposed to the a tech company that's trying to figure it all out on their their all the and sort of broader uh stuff on their own.

100%. Like look, Steve Schwab saw an opportunity. He he built he built Kasa Go he built that franchise. He saw an opportunity and and took advantage of it. And I think it was the right thing that was needed at the time, right? I mean, Vicasa needed that kind of, you know, pivot in that kind of redirection, if you will. And that's what that's what Kasiggo and Steve brought to the table. And I'm obviously grateful because it gave you know us the opportunity to kind of branch out and kind of do something that that was um you know I thought was that the industry needed and gets me excited you know like it's it's fun to talk about skiing. It's fun to talk about the ski product. It's fun to kind of you know build a company again with uh with Richish Nigum who's kind of you know my my co-founder. We brought a lot of the key people from you know from Vicassa. So a lot of my colleagues at Vicassa are with us.

He brought a lot of the colleagues from Windom. So, we got a really cool team of people that are all of the same mindset, Jamie. And that's the other thing like when you're building a business, you know, like like when you're building a business, you want to have people of the same mindset. It's good to have, of course, diversity of ideas, but at the same time, when you're building a business, you it's nice to have us all kind of having that same shared vision. And so, it's been it's been really fun so far. Yeah.

Yeah. I'm interested in your your take on proprietary tech versus using sort of offtheshelf from the industry. Uh I interviewed Eric Bion obvious the the CEO former founder of Vicasa

uh about his new venture and he was are told walked me through like why he's building proprietary again and I'm I'm interested in your take on and sort of the benefits of proprietary. obviously you had you were able to see see the benefits of proprietary tech uh and also seen I non-proprietary tech in the industry. So what's your view on that?

Yeah. Um, yeah, look, Eric, Eric had a had a great vision with Vicasa and I think you said, I don't think it's going to be anybody that can accumulate 34,000, you know, homes um in in the near future and and a lot of that was was predicated on having your own proprietary tech stack, right? And so, um, lot of wins that happen with that for sure. A lot of things that can expedite the whole process. I think it's probably been the one of the bigger adjustments that I've had to have because you know although at Windham we had more than one tech stack we were primarily at using using one one one tech stack and of course with Vicasa we were in the we were all in the same tech stack you know top to bottom and so one of the biggest adjustments that I've had to make along with the team is okay how do you adapt to that because we now we have basically you know you we've got you know three different you know um systems that we operate really four when you think about our accounting system and that again they all have really good systems that you can operate in but the challenge is always the connectivity right that that that is the 100% you know challenge like you can you can all say hey the APIs are going to connect and everything but it takes a little bit more than that to get everything to work seamlessly so I think that's been one of the challenges that we've had but on the flip side on the flip flip side as we're kind of getting through this because it's been I mean we went live on June 1.

the flip side, we're already starting to see some of the benefits of that like in terms of being able to say, okay, and because because when you're in one tech stack, when you're in one tech stack, you've got to think of all the things that that might happen in one particular, you know, to so that you weren't stepping on each other. Here, I can say, hey, look, we want to have this change made in here. And yes, you need to know how it's going to impact the others, but it happens really quickly, like really quickly. So, there's been some tradeoffs. Um, I don't I think it's early days for me to be able to say I can say one is better than the other, but it's certainly been a learning experience.

Yeah. No, I I'm interested to sort of check back in and like get a sense of like long term whether you think it's I mean it's doable to sort of get the efficiencies off of sort of an industry sort of standard stuff and be able to connect them all together and get what you need or if there really is I a layer or or something missing in the industry that I and you saw and and running Vicasa that and people are are missing.

Hey, look, we should definitely connect it in another three months because I mean I think one thing that happened with with Vicas when we when we bought Turnkey, so John Banzac's business and and and and TJ's business,

we there was a lot of learnings from what he had built with with with his uh with turnkey as well. And we were able to incorporate those fairly quickly into the Vicasa tech stack and there was some good wins that came out of that. But it was because he was also operating in his own, you know, proprietary tech stack as well. So, look, it it they they were kind of emerging things. And so, right now, we're using, as I say, some some different systems. And and we're on we're on we're on streamline is our is kind of our, you know, our our main software. We've got we've got Breezeway that that we're using as well. So, those two systems are kind of our key where our day-to-day operations work and live.

Yeah. So uh maybe going back to and and a few few more questions on Vicasa just why I have you and then we'll we'll talk about and sort of um uh first share a bit more. Uh but and clearly the sort of roller coaster ride that the industry saw sort of postcoid of occupancies going crazy. everyone wanted to travel, fewer and less inventory competition, great rate growth, and that was and made everyone's business look incredible. Uh, and it was probably a great thing to sort of IPO into given the sort of tailwinds. Uh but sort of in the sort of post IPO um time like do you think it was a question of like the Vicasso business model? Do you think it was I just industry framework that I revs were going down no matter what there's and there was just some macro sort of headwind that you guys are dealing with or is it just that vacation rental management companies shouldn't be public companies and that it probably would have been fine if it was private and just the public nature of and the company sort of led to its downfalls.

What how do you how do you see like the I and how it would have maybe played out in in different scenarios?

Yeah, I mean I look I think we all know that the the the pressures and expectations of a publicly traded company are far different than when you're privately held. I think the whole kind of you know how you have to manage your cash flow your expectations what you know what as I said earlier kind of what what the street is expectations for earnings are and again in a business that's the as much as you know we had homes across the entire US and and international there's still a bit of seasonality to this business that I think is hard for you know for a publicly traded organization to kind of they you know they like things smoothed out and make sure that everything is that there's not a lot of peaks and valleys and it's just the nature of our business, right? There's a lot of peaks and valleys and and especially as you point out coming you go public then there's these expectations. Oh my gosh, every year's and that's that's the nature of of of of Wall Street, right?

Grow growth and so you come out of you come out of COVID, you go public, you have this unbelievable meteoric rise in ADRs and occupancy and repan and then all of a sudden whoa, it's maybe not quite like that. And so then you're starting to kind of, you know, do a little bit of backpedaling and a little side shuffling here. So I think it could have been different, but at the same time being public allowed us to raise a lot of money and to do a lot of things and to keep that proprietary, you know, growth uh product going, allowed us to keep our growth going. So there was some there was some really good things that came out of it. I think your your point is probably a good one. the sustainability of that growth expectation probably could have been managed better as a private company than as a public company.

Do do you think there was a sort of level of scale that Vicasso worked like that you guys needed to get to or was it just and sort of right sizing where the company was?

I I think it was both. I think there was some definitely some some some we we' gotten to that point where scalability was starting to was starting to kind of yield yield some good results but at the same time it's the sustainability of that growth in order to be able to keep that level. So you had to make sure that again one of the biggest things we all know is retaining your customers, right? And so if you're trying to grow at such a rapid pace and and and that's what's your expectations are as a public company, that means taking on a lot of homes every single year in order to offset that that that churn, right? And that was a challenge.

Yeah. No, it was it was definitely and and from my observation like I and it looked like a challenge and I sort of see it and on the host investor side all the time and they're like oh they the easiest management company to pick off is Vicasa. Um and and you saw it in the turn data and but you guys had a system of owner acquisition that was probably unmatched in terms of the industry of being able to find new owners, get them into the system, onboard them, operate them. Um and can you talk a bit about like what that system looked like? Like what was what is the trick of owner acquisition that we couldn't see from the outside? I mean I mean what you couldn't see from the outside is that you know a we had we had a lot of really dedicated good people that that were really kind of um professional and wanted to see the business succeed and and we so we did we had a really awesome sales team had a good we had a good owner marketing team as well.

So we generated a lot of leads um and and I think look we had a good marketing we we you know Vicassa we generated our our website the Vicasa website was really strong. We generated a lot of business internally for owners and and they like to see that. So, and we were a competitive like Bicassa was a very competitive company at the time in terms of our management fee and everything else. From the out from the outside, of course, it was easy to throw the target the lobs in of oh, publicly traded company, not local. That's that that was about as far from the truth as possible because everybody again local the the company's headquarters wasn't local. We had a lot of people that were in Portland, Oregon, and a lot of people scattered around the world. But as far as those delivering the services, it was local. So again, from a sales standpoint, I think that that resonated with with owners, right?

The challenge, I think, came with again just coming out of COVID expectations um expectations of being public. And so it was trying to match those up where I think we got a little bit sideways. But as far as the growth engine goes, I mean there was a lot of good things that you could say about uh if you were a sales executive that you could say was a national exposure, great website we could point to, could point to good revenue generation, could point to good connectivity with all the channels, um had a local team. So I think those were the things that that allowed us to kind of, you know, and not to mention, Jame, we had a good we had a good balance sheet, so our M&A was pretty good, too, right? So, we were able to do a lot of acquisitions that also kind of helped that growth machine, if you will.

Yeah.

Yeah.

So, and it I think it was about a year ago now. I was talking to Steve Schwab uh and he was sort of talking me through like the next year and what was going to need to happen like the sort of relocization of the 32,000 listings under management uh of how it was going to and sort of split out into owner and franchises that finally finished. Um, I think you've called it a soft landing. Uh, which I think and that's that's a great sort of description of what they were trying to succeed. Uh, so interested in your view of like your sort of grade on how well it worked and um, anything that you think might get sort of lost in in the handoff that was working well.

Look, I no, I think that I think it it was it was a it was a soft landing. It was a pivot that needed to happen. And again, the reason why I I I'm I'm being completely um I think objective in this. The reason why it landed so well was because a lot of these uh markets and these teams were doing all the heavy they were they were doing the job, Jamie. Right. So So it it wasn't like a big stretch to say, "Hey, in Gulf Shores, Alabama, the team was rocking the house. Hey, in Myrtle Beach, the team was rocking the house. Hey, in Aspen, Colorado, the team was crushing it. In Steamboat Springs, they were delivering unbelievable like um guest and owner experience. Like, so those markets and teams all pretty much remained intact. It was just that that what kind of got taken apart was everything at the top, if that makes sense. Right. So, it it doesn't surprise me. It might to an outsider how successful this has been in terms of the transition.

Sure, there's been some lumps. Of course, there always is. But as far as the delivery of service to owners, guests, and the teams that are in place, I think it's been pretty remarkable. And and and whether it's with, you know, I I can see it with first share, like with our with our owners and our guests and our our um owner NPS, our guest review scores in the connectivity with the channels has all been pretty seamless. you know, not not to say it's been perfect, but as far as delivering the service, the rooms are getting cleaned. You know, the owners are being taken care of, everything's happening out in the field. And yes, behind the scenes, if we've had a little bit of trouble with our connectivity with our internal tech stack, yeah, that's there, but it hasn't really impacted the quality of the guest or the owner experience, which I think is pretty cool. It's a it's a testament to the people in the field, quite honestly, you know.

Yeah. So, and a skeptic could say that yes, a lot of the sort of new franchises that have come out of AASA are are local because it's in a very distinct local market. But that first chair is still sort of a national brand. You guys are across what, nine states, multiple markets. Would you argue that that's still local? I mean, is it a national company with different branding? like what makes what you guys have now structurally different than the old o old company?

I mean to a couple things like I I think that there's some terminology that can just kind of maybe kind of make things seem more muddled than they are. I mean, you know, a national company can be a national company, but you still need the local people there that live there. So, so I would say that we're national in the sense of yeah, we we we're in we're in nine different states, but at the same time, we're really focused on something that's pretty unique, which is this which is primarily the ski markets, right? So, when you think about it, if you're trying to, you know, capitalize on on on something, I don't think that's been done before. Like, like with with with with Vicasa, we were in every, you know, every market. We wanted to be in every country for crying out loud. Um, and I think what we're trying to say is look, let's maybe try to, you know, do something that's a little more unique and go after a targeted demographic, a targeted, you know, kind of activity, if you will.

And whether that's in eight different states, nine different states, 10 different states, 11 different states, you're still saying, okay, we're going to make sure that what we're targeting is the ski is the skier. and what they they um find important in Vermont is probably similar to what they would find important in Jackson Hole and try to deliver that consistency of service. But you cannot even think about doing that if you if you're if you're not local, right? You just can't, right? So, I mean, I I I couldn't have first chair shuttle buses driving around in Steamboat Springs or Breen Ridge or Veil from from from the central office, right? It just so happens our central office happens to be in Steamboat Springs, but you know, it's just a coincidence, I guess.

So, and can you explain to me now and just a little bit about the relationship with Costco uh sort of franchisee and what and sort of first years operating as now?

Yes. So, so ours is a little bit different. We're not we're not technically a franchisee. We have a license agreement with Casago to to use their brand, to use their website, to do some co-arketing with them. So, it's it's a little bit different more so from a marketing and and brand positioning standpoint. Behind the scenes, it's probably very it would seem very similar um in terms of the economics, but it gives us a little bit more flexibility. We thought that was important because we really are trying to build a brand that's primarily around skiers and ski destinations, right? It doesn't mean that's the only place we are. We have a a nice portfolio on the on the New England coast, which is pretty cool, but it's primarily going for that ski brand and that ski market. And with the Kasago um being able to have a little bit more flexibility with our branding with Kasago and how we do it, we thought that was important and it works for them too.

They they were very um agreeable to that kind of setup as well.

Yeah. So, and ski markets feel like it has its own sort of risk uh associated being and so

yeah, great time great time to start it. Great time to start a ski a ski a ski business short-term rental ski business right after last ski season which was the worst ski season worst I think I think I read in Colorado it was our worst gear or ski ski snowfall in 30 years right so um yeah great great time to start certainly uh have uh have have some uh some opportunities in front of us based off of last but but look I've been in the ski business and living in steamboat for 30 years and you the the the the snow comes and Yeah. But certainly it's never fun when you have a a bad snow year right when you're starting out of the gate, right?

Yeah. But but even so, and like there's and just the short season like I I feel like a lot of your a lot of the ski markets have been able to expand more this summer. Like I I'm interested in your sort of opinion here just like the summer season and Seabboat now versus what it was 30 years ago. like how how has it evolved?

It's been look it it's it's been a a good journey. I I actually chair the local marketing district and we um in Steamboat Springs and we partner with this gear and we bring in all the uh the non-stop flights from the different markets and we've been expanding those so that you know we're moving into a year round type of resort. I mean Jackson Hole I mean Jackson Hole is as busy in the summer as it is in the winter. Mammoth same thing. Mammoth is extremely busy in in the summer now and and of course in the winter. You know, the Colorado markets aren't quite there, but you know, you look at Aspen, Bale, Steamboat, Breck, all have really strong summers. So, absolutely. I mean, you're not going to fill those shoulder seasons, of course, like April, May, and and kind of the the tail end, but you you look at June through September, June through October, it's really sweet. And in Vermont, I mean, I was surprised at just how busy um the the markets are in in New England, primarily Vermont, New Hampshire for that fall season.

Everyone wants to see the leaves change and we have some unbelievable high occupancies in those in those ski towns, right?

Yeah. Yeah. I mean, and do you see in additional ways to sort of change the seasonality of the market? like I the ability for you guys to and create demand or and whether it's event venues, whether it's and working with the local and and um and CVBS to and and get more events, get more things like and what do you what do you is it or is it just that and mountain biking and remote weddings have gotten popular and it's like that's stuff outside of the control?

I mean, no. Look, there's some things like I I mentioned like the if you look around the states and and the markets that we're in that have, you know, air airports, right? So, you think about, okay, you can fly into Aspen, you know, you can fly into Aspen year round, you can fly into Jackson, you can fly in Jackson and fly into Eagle County Veil, you can fly into Steamboat, you can fly. So, so I think being able to expand the the your business around the markets that have goods good good, you know, air air um access is really important. You mentioned another thing that really um events is something that also having event space is huge. Like you know, we were just talking about Lion Square Lodge, a property we manage in Veil and the number of weddings that happen there in the summertime and the tents and the venue that's right there. So, I think sometimes a lot of people don't think outside the box when they think about short-term rentals and how they so it's not maybe maybe you have your you go and you ski there Jamie and Vale or Steamboat or Breck or Jackson or Mammoth or or Killington, but you think, "Oh my gosh, this would be a great place to have a wedding and you don't really think about that." And then all of a sudden that opens up a whole another avenue of short-term rental business during that kind of that off season.

Yeah. No, I I love that. And coming from my hotel industry days of like the ability for a large hotel to just create their own demand, bid on citywides, sort of fill the market, not just waiting for and the market to fill, I think, and brings you into another realm of

and putting things with and in your control that many others just see as entirely outside their control.

100%. Yep. and and that's why some of the the HOAs and and the properties that we manage that have event space and meeting space we really try to capitalize on. Um and the the other sort of regularly regular and risk I see in VA in ski markets is regulation. Um obviously I bre veil steamboat I have all gone through their and ups and downs in terms of regulation. So and as you were looking at this business underwriting the business and how much did you see that as a a sort of existential risk versus something that's largely been figured out and that you can operate under?

I mean you you look you've been in the business and watching the business for a long time as well. I think we went through that kind of period and and it was where everything was all the communities were starting to panic a little bit. Oh, we're going to put in all these regulations and quite honestly, you're starting to see them even dial it back just a little bit because now all of a sudden they're starting to realize that, you know, some of the economic engine that that they rely upon is is being impacted. I mean, so I don't think you're going to see the them swing the pendulum back the other way, but at the same time, I think it's maybe kind of reached its kind of peak in terms of where you're going to see I don't I don't think you're going to see a lot more kind of really invasive regulations or or or whatever. I think you're going to see if anything maybe a little bit more of a I won't say relaxing, but maybe just a toning back a little bit.

and and and in the ski markets like um I mean I I think that you know the good news is with some of our markets we've also seen the expansion of the communities kind of move outwards you know whether it's in you know veil and you see down Eagle Edwards Avon and you start to see those communities say hey guess what this is a good economic engine for us so there's some there's some opportunity in terms of improving your your your CAM as well as maybe seeing where it's been reduced So, I'm not It was a It was a discussion point, but but not something that we spent an over a lot of time on.

Yeah. and being one of the larger managers in probably every every market that you're in. And what do you see as the vacation rental and management companies sort of their their role in helping um and uh lead uh in terms of and and working with city councils, working with and different constituencies in in those markets. I mean, look, I I think that professional managers have a great opportunity in all the communities that are that they're in. I mean, city councils, I mean, typically when they make decisions that you're that are not ones that are popular, it's because they made the decision out of a void of knowledge and and and information, right? And and maybe even fear to a certain degree, like, oh my gosh, we better do this. and and and I believe that, you know, being actively engaged, that's why I I still chair the local marketing district. I'm actively engaged with the city council and the local lodging community in Steamboat Springs.

And I think that what our position is is that an educated city council or whatever government you is is a much better partner to have. And that whether that's working with them on noise ordinances, on trash ordinances, on transportation, things that you can kind of collaborate with them, all of a sudden they start to realize that, hey, short-term rentals maybe um get some bad PR, but they really are a good partner, especially on the professionally managed side, and we do bring a lot to the table. But if you don't do it, Jamie, then you don't really have a whole lot of people to blame because you really need to be out there and and actively. And that's why being local is it does count. It does, man. It really does.

Yeah.

Yeah. So interested now in and in and a little bit of like what you and see is the future of first share. I mean obviously you guys you've been in so many different companies where growth has been I a key part of the business model or are you looking to grow this to be a large company? are you guys looking to and maintain like what what is what is the vision over the next few years? I mean, look, we want we want to have moderate growth and the right growth. Like, I think that's one thing with with Vicasa is that we wanted to grow so quickly and that was our kind of what what what our our vision was that sometimes you don't always have it be the right growth. And I think what we want to do is we want to make sure that we're going after the right homes and the right HOAs and the and the right resorts that that fit with the demographic that we're trying to build the business around. So I think no growth is you know not not something anybody wants to be a part of but you know growth that's out of control also is kind of a a tough environment to be in.

So I think look between Rishi and myself and and the team that we brought with us we all kind of believe that you need to have a good steady growth and a good a good um process and and that'll include some M&A too don't get me wrong for sure. I mean, I I've always got my eyes open on a on a really good company that's well-managed and is in some of the ski markets that we're in or even some that we're not, but I want to make sure it's it's it's moderated with a with a a a a good responsible outlook and not just growth for the sake of growth. So, we say, "Hey, guess what, Wall Street, we get a we hit our number, you know?" So, yeah.

Yeah. Well, what what does an ideal properties look like for you guys? What do what do you want the first year portfolio to look like?

I mean I mean great question. I mean the thing about skiers and being a skier is that is that skiers go through different transitions like we all do in life like so when you're getting out of college or you're having that college ski vacation, it's a different kind of product that you want, right? And then as you kind of move up through and you and you have a a a ski vacation with your family, maybe a little bit different than as you maybe say, "Hey, you know what? We can afford to be at a ski in, ski out and a little bit more luxury." So, I'm not saying that we want to be every single place, but at the same time, I've been through all those. Like, I remember my first ski trip in college, right? And I remember that, you know, we had probably the best time, you know, and we rented a place and we all jammed in. wasn't ski in, ski out, you know, we we we had to get to the slopes, but but then I also remember some of my first trips with my family and teaching my kids to ski.

So, I think having that mix of of things is really important. Like, you can't just say, "Oh, we're just going to be luxury, high-end, ski in, ski out. That's it." Because what's going to happen is you'll I mean, is it, you know, like the the the number of skiers in the US is um growing at a very slow slow rate. So you want to you don't want to you know weed yourself out either. So I think we want to be smart about it and really to me it's more about the resorts trying to be in some of the resorts that where people want to go and then building your product around that.

Yeah. No, that that makes sense. Um and we're we're just about to kick off ski season and we're get it's coming up close. How's it looking? Are are people sort of cautious uh coming into the year? Are they ready to get back? uh just hoping that it's going to be good. What are you seeing?

Well, look, I I'll I'll tell you. I was reading an article last night and it and it basically said that, you know,

Colorado skiers are uh approaching the season with a little bit of trepidation, right?

And isn't that so typical of skiers? You know, we have, you know, we we we our memory is only like as soon as it snows immediately, everyone will forget. So, we haven't had that first snowfall yet. But look, I mean, Advanced Reservations, I I'll share this with you. This is part of some pretty interesting stat. So, last year, you know, we're pacing like every like the whole industry is, the ski industry behind last year, right? Not not by a ton, but but but we're pacing behind last year. Last year got out to a really good start because guess what? The year before was a really good ski season, right? So, typical skiers. But if you go back two years, we're almost on that same curve, that same demand and advanced reservation curve as we were two years ago.

So to me, that gives me some good confidence that that people are. It's not that they're not they're not out there. I think we just we're we're pacing ourselves against last year, which was a really kind of out out in front year. But the first snow happens, Jamie, I'm just like all skiers, man. I think already I'm I'm thinking I'm looking at my my skis going, "Okay, it it's it's getting time. The leaves are changing. It's going to happen, you know."

Yeah.

So, if anything, it's going to be one of those years that people don't book early and then they wait too long and then then they can't ski when they want to because every I mean, first snow that happens, everyone's going to book uh and a lot of people are going to be left out uh in the cold.

Exactly. you you you you just you just summed it up like that you're you're you're the weather prognosticator, right? Like look at open snow. I mean those guys are forecasted a killer year. I mean this the super El Nino I mean I think a lot of people are going to they're gonna they're waiting right now as soon as it snows they're going to okay this is going to be a killer year. So

yeah. So, and maybe maybe closing up now and we we've gone through and and I feel like a ton in terms of and your sort of journey and um and the the changing business models that you've seen. So, and now that and you've sort of and seen sort of the scale at on almost every level. If you looked out over the next few years, like do you think and local is here to stay? It feels like very much we're in this like local is the business model now and maybe PE owned local is the business model, but it and it's still a locally sort of and local first. And do you think we're going to go through another sort of scale cycle? Do you think there can ever be sort of a big national brand that sort of takes on the industry like Vicasa did? Like uh yeah, how do you how do you see the the next cycle playing out? I think that you could swim in both worlds. And what I mean by that is that you I could see a a national brand being successful provided that they did not lose sight of the importance of what we talked about in the very beginning, what's scalable and what isn't, right?

And so if you start to believe in yourself that technology will solve everything and that everything can be done and saved by technology, I think you'll fall into that trap where all of a sudden everything's scalable. If you can balance it and find the balance, I think there's probably um that opportunity. But the thing is honestly is it's going to be be capital intensive to get to that you know and so the question is do you have is is there some company or companies that are willing to invest that amount of capital to really build a portfolio of 34,000 I mean if you think about Vicassa we were actually over 40,000 homes before we you know when we were international so before we sold off the internet. So to try to get to that scale again Jamie is going to take some serious capital. I'm not sure if there's anybody that has that willing to take on that risk and that has that appetite, you know.

Yeah. So maybe maybe final question um and open up being presumptuous and saying but you probably could have require retired after Vicasa but instead you decided to take on this new adventure. Um which it it sounds like you're having a lot of fun. Uh so like wh what why like what what are you looking to get out of this sort of next uh ne next phase?

I mean it's it kind of goes back to in the beginning it's going back to kind of that entrepreneurial spirit that that yeah you just can't get out of yourself like like I'm sure you have it you just can't get it out of your system and you want to do it right. you want to say okay let's learn let's say take the learnings from the last experience and the last journey and and try to you know you know put it into into a new kind of adventure here and I think also like having like I said having a good team and working with people that you really like is so important and so I think we have an opportunity to take all the learnings from you know going all the way back to Windham Vicasa Kaso and even when I you know started my own company long time ago and and really build something special here for skiers and and that's kind of what gets me excited. So, yeah, I'm I'm ready to kind of keep this journey going here.

Awesome. Well, Bob, uh thank you so much for joining. Uh I've really enjoyed this conversation with you. Uh if people want to find more about you, want to more find more about First Share, where should they go look?

firsthestinations.com, you know, check out our website. We have a really fun website, like a lot of good content for skiers. And I'll trick you, there's even if you're good, there's even a little um a skier challenge there that you can that you can do and you can ski down a slope. So, I'll let you find that yourself, but um it's a really cool website.

Awesome, Bob. Thank you.

Thanks, Jamie. Great talking to you.

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