Chillin' with Dylan: How to Build a People-First Culture in a Competitive Vacation Rental Market
In this episode, Alex & Annie head to Florida’s scenic 30A to sit down with Dylan Bozarth, General Manager of 30A Escapes, for a real conversation about leadership, culture, and what it takes to build a team that truly lasts in the fast-paced vacation rental world.
Dylan shares how his decade-long journey at 30A Escapes has shaped a people-first approach to property management. One that values work-life balance, communication, and genuine hospitality as the keys to long-term success.
We discuss:
1️⃣ The challenges of managing vacation rentals along the 30A corridor
2️⃣ How leadership and team structure can prevent burnout
3️⃣ Creative ways to engage and communicate with homeowners
4️⃣ Why defining core values transforms company culture
5️⃣ The importance of collaboration among local property managers
6️⃣ Insights on market shifts post-2021 and preparing for sustainable growth
This episode is a reminder that growth starts with your people and that sustainable success in hospitality is built from the inside out.
Connect with Dylan:
LinkedIn: https://www.linkedin.com/in/dylan-bozarth-6225b8338/
Website: https://www.30aescapes.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?
Discover how Nocturne Luxury Villas helps vacation rental founders protect their legacy while unlocking new opportunities.
👉 Contact anthonybarrera@nocturneluxuryvillas.com
#vacationrentals #shorttermrentals #culture
Alex Husner
Welcome to Alex & Annie: The real women of vacation rentals. I'm Alex and I'm Annie, and we are joined today, live in 30 a with Dylan Bozarth, who is the GM of 30 a escapes Dylan. So good to
Dylan Bozarth
see you. Yeah, thanks for having me feel very honored. Well,
Annie Holcombe
we've been trying to do this for, it feels like a year now, trying to make it happen. And we finally did, and we noticed that you even got shirts to prove that it's happening. We're chilling with Dylan. Chilling with Dylan. We're excited about that, but before we get started, when we give us, like people, a recap of who you are and what 30 a escapes is, sure.
Dylan Bozarth
So I am the general manager at 30A escapes. I have been there for just a little bit over 10 years. Have seen a lot of things change on this beach in that amount of time. And yeah, yeah, anything else,
Speaker 1
yeah, no. I mean, you guys have done an incredible job in this area. This is not an easy area to rent properties. There's a lot of companies that do it, but it's probably one of the more complex areas, I would say, just because the density, it's a short amount of space with a ton of properties, and it gets super busy here in the summertime, maybe for anybody that's not familiar with 38 kind of talk about what those challenges and nuances are.
Dylan Bozarth
One of the biggest challenges is the amount of of quality property managers on 38 and in and around the area, just a ton of talent in property management on 38 and so that really increases the bar and makes it very difficult to break into a market such as as 30 a there are maybe the infrastructure was not always build, or we did not have in mind that the growth that we have seen over the past five years would result in such a demand for our beach, which is which is very cool. I grew up on this beach and always love the quaintness of 30 A, and really hope to be able to keep it that way. But the growth is one of the challenges, the roads, some of the Wi Fi. If you've ever been to 30 a, you know, Wi Fi and Mediacom can be a little bit of a challenge, but, yeah, just, just some of the maybe challenges that other people face as their beaches have grown, or as their destination have grown, cell phone service can be a bit of a challenge sometimes. And being able to communicate with our teams and and to utilize our softwares, and just communicating with our field staff in general, also our logistics to get parts and to get like, a replacement TV on a turn day, sometimes we have to go 1015, miles one direction to have that. So in turn, we have a lot of back stock in appliances or TVs or just things that we might need on a day to day basis.
Annie Holcombe
Yeah, I think one of the things that, because I live here, not too far from 38 but one of the things that's always been unique about the 38 core, about the 38 corridor is that there are, and I can't remember what the stat was, but there's like 20 some different beaches, like beach town names, like every little every 150 yards is a new beach town. So from a marketing standpoint, it makes it very difficult to your point about the volume of managers. There are some incredible managers here, but you know, the vast majority of them have 30 a or something in in their name. So it does become very jumbled, and it's hard for a management company to stand out, but you guys have done a great job doing that. What do you attribute that to? You attribute to the service, to the whole package of offerings that you have, or any one specific thing that you made you stand out. You think our
Dylan Bozarth
commitment, our commitment to excellence, and our team's commitment to excellence and the belief that we can offer the best vacation experience to travelers on 30 day and that being our goal and our vision, is what ends up setting us apart from someone else who may be in this for the money or not as driven by the Genuine Hospitality as our team is.
Alex Husner
It's a good point. Yeah, and just talking to your team. This week, we were here doing a video shoot, and if anybody's not watching, please go over to YouTube, because we've got absolutely gorgeous, gorgeous view behind us, and this amazing home that we're just we're in today. But one of the things I noticed talking to your team, and I've known many of you for a long time, but everybody really loves their job that works there, and it's very clear that they really care and take pride in what they do. And talking today to Andy, your director of operations a little bit more today, he said, You know, we've we've structured our team so that they have a great work like balance, that every department head has a like a liaison or a second in command, so that it's not okay if one person is out, then, you know, the whole business is going to go down. And that's how a lot of companies run. But I mean, you guys have taken a
Dylan Bozarth
different approach. We lived that way from inception, right? And it was because we had some people that were, you know, workaholics, and that was what helped us thrive. And it does get to be burnout, and you can lose good people that way, and it has happened, right? And so my goal, after having that happen and seeing that happen, was to create a work environment that isn't sustainable, but that. You get some time off. Everybody needs some time off, yeah, and to reset, recharge your batteries, and then come back ready to give it your all again. And so that's where the creation of these departments I had, I had it kind of in my head of how we would structure the team. It just takes a little while to get there and to fit all the right people on all the right seats on the bus, but, but we have achieved that, and it's really cool to see that exactly what you said. People are excited and it's a fun place to be, and there's not this burnout or this exhaustion and and then that just carries over to guests, our homeowner interactions, our vendors, really every aspect of the business then increases. And just one of the most probably wonderful things that I've seen happen in this business is just the growth in the sustainability that we built in the team.
Annie Holcombe
That's really good. And a lot of people can't say that, especially after covid. I think so many people were just burnt out. They just wanted to, really wanted to get, get away from it all. But one of the things I actually introduced a session at vrma this year where one of your girls actually spoke up after it was kind of like the Q and A session, but she shared how you communicate with homeowners. And I thought it was people were sharing ideas. And I loved what she was telling about. They go to the homes and they take selfies and they do fun things with the owners to communicate. And it was just, and it was, I thought it was a great takeaway. I was just like writing notes to add it to, like, you know, talking with owner or, you know, groups in other areas. Because I think that, you know, with social media, people get to see all this stuff, but it's like they're not really getting to see their home, like, intimately in that, in that perspective and having fun with it. But I also think it's given your team the leeway to just express themselves and be themselves, kind of in their authentic way every day. And I thought that was really great. And it just kind of speaks to what you were just saying about giving everybody a place that they can come to work and not feel completely burned out, be excited about it, take their time away, and they come back with all these creative ideas to be creative for the owners, creative for the guests. So I loved that. And I don't know if you, like, have any other, like, really cool gems that you have for dealing with owners, because that's a challenge for everybody.
Alex Husner
How do you keep it chill?
Annie Holcombe
Chilling with owners is
Dylan Bozarth
not high on the list. Sometimes we have to pull the shirt out and remind ourselves, like we put the safety shirt
on. You know, that's
Annie Holcombe
why it's safety orange. Exactly.
Dylan Bozarth
Safety orange shirt comes out like, just make sure you stay far away. No, that's exactly it. And that was an idea we had to number one, we didn't want to call the owners. And each time we're calling them, it's the air conditioner is broken, or the pool is down, or this guest had a problem, or, you know, that gets to be not great news. After a long time, and then the owner is looking at their phone like, Yeah, great. Another problem, right? So we wanted to communicate with them, saying, Hey, we come to your property every week, yeah, and we say that. And then sometimes, maybe that's hard to believe, because of the day after we left, something happened. Who knows? So we just wanted to show the owners, but also just encourage that communication back and forth. Hey, we're going to communicate to you and say, Hello. Hope you're having a Happy Friday. The beach is gorgeous today. Or, hey, we saw this little lizard running across the sidewalk, anything, all kind of fun things. Sometimes it's rainy day pictures, I love the the ones where we're sending drenched pictures of us in our jackets and hey, we're still out there, right? We're still we're still doing it, so just trying to build that trust with our homeowners, because ultimately, that's the relationship that we're looking
Alex Husner
for. Yeah, yeah, that's huge. And one other thing that you were talking about this week too, you guys have just rolled out a very robust mission statement, I guess you could call for the company and like the core values and how you're really putting some extra thought and time into teaching all your team members. Can you tell us a little
Dylan Bozarth
bit about that? Yeah, so we have eight core values, and in turn, they spell it, star, life. And so we started with a star life employee of the month. And we're looking for above and beyond. And employees get to nominate other employees that they might see throughout the course of the month doing something above and beyond. Some examples of that are we had a property manager turn in a Rolex. One of our core values is integrity, yeah, and that's huge integrity. We've had a maintenance man turn in $200 in cash, and then other things where a team member may jump in and help on something that was totally not their department saw someone needing help and just jumped in without asking. And then the really cool thing is, when the team nominates their, you know, our own team, yep, their peers, to receive that award for the month. And then at the end of the year, all of the winners are in the running for the star life Employee of the Year, so all the monthly winners. And then as a team, Max in the $200 Well, it's very similar, very similar, because it's very appreciated. But I. Not, not exactly the Rolex. We did return the Rolex. We tried to find the owner of the cash. Yeah, exactly, exactly. Now we then have the team vote on who the Employee of the Year is
Annie Holcombe
exciting. And so that's first this year, the first year where,
Dylan Bozarth
well, we started that last year. And so this year we're also going to be doing some different awards based around the star life. We're doing some training like you mentioned, with our team. So we have about 16 leaders on our team, between directors and assistant directors. We've paired them up to teach one of the eight core values to the team, just to build, you know, they have to hear me and Andy, yeah, all the time, yeah. So instead of us saying it, we want to build that, that camaraderie with a team and and also build our leaders up as leaders, and let the team see them as leaders. Well, it's
Annie Holcombe
interesting, because conversations that I've been having in my consulting side is with managers, and I try to guide them for their business development is that your entire team needs to be part of that business development the process, because everybody has a stake in it. And I think being able to train everybody from the lowest employee all the way up on your core values, and being able to talk about the mission of the company makes them more tied to what everybody's doing every day, and the fact that you're doing this, I think that that that's it's key, and a lot of companies miss that. They just think that some of these employees that are hourly or contract are not necessarily part of the whole big picture. And so it sounds like you've taken everybody and just put them all together and said, like you're all one puzzle piece of this puzzle, and we have to work together to make
Dylan Bozarth
it That's right. But you make a great point that everyone on the team is a salesperson, so no matter if they're at the grocery store or the gas station or when they're at their property, checking their property, doing it the way that we intend, and what we've set out, we've actually signed a couple of homeowners that were neighbors to our home, because they've watched our property manager go in, do a thorough inspection, complete their checklist in breezeway, and then leave, and the homeowner actually stopped them and say, Hey, I noticed that you really did that. And like no one is watching you do this, but you did it anyway, and I appreciate that. And so we don't feel like we maybe are getting that service. We want to switch and come to you
Annie Holcombe
guys, sir, and in a dense market like 38 where you've got homes that are literally like you could almost touch one from the other porch, like you want to be making sure that your staff is visible and that they can see that, but also that their work is not, you know, is not going unnoticed. I mean, there are people watching them, whether they realize it or not, and if they understand that, goes back to the integrity, you know, the integrity of them doing their job, and the pride for doing their job. And so I think that that's that's really important, and it just everything that you're saying is like, just like an ideal way to set up your team for success all the way around. And we
Dylan Bozarth
want, we want our team to be proud of the work that we're doing and the properties that we have. And so we're very discerning of the properties that we bring on to our program. It's not every single home. We don't want to have the most homes in the area. We want to have the best portfolio, and we want to work with owners that are good partners, that are committed to keeping their home clean, well, maintained and updated. That is our three that's, that's our well throughout our team, and they're going to laugh, because I think we'll call that an Andy ism, yeah, that's that's our goal, right? Clean, well maintained and updated. And if you can hit those three things, then you've, you've satisfied the guest experience for the most
Alex Husner
part. Now you can do those things, but you can also be difficult to work with. We all know that there are homeowners that sometimes like, just personalities and yeah, what they are thinking coming into the relationship, maybe just it's it's not matching. Does that ever happen in 38 or is it just perfect? Do
Dylan Bozarth
you ever always perfect? Always perfect? No issues. Everything is good. That's how we keep it Sure. No, there's, yeah. No complaining. That's number number one on the contract. No complaining. If it was
Annie Holcombe
only that easy, right? How
Alex Husner
have you learned over the years to set those expectations so that you don't get into a relationship that you're like, we gotta, we have to let them go, even though they have a nice home. We can't do this. It's
Dylan Bozarth
exactly that it is trying or really executing on what the expectation is going to be, and setting the expectation up front and letting the owners know that while this is a partnership, and you are the homeowner and it is your home, we completely understand that, however, this is our brand, and you want to come to us for our brand, because we have brand trust with travelers, and we do book 70% of our reservations direct through our website. So these are good metrics, and people do want to be part of our program. The flip side of that is we have to be able to control some parts of the of the property and its rentals. You
Annie Holcombe
also want to make sure that your your your team, is respected too, for sure. And I think that that's where, that's where a lot of times that you know, one thing we talk about this business is, is related. Relationships. And the homeowners have relationships with their investments. And a lot of times, those investments are their long range strategy for retirement and and they may have, you know, personal memories tied to it. So there's a lot of emotion, a lot of emotion that's tied to it. So trying to level set that up front is so I definitely would encourage in
Dylan Bozarth
identifying that we try to identify what, what is your goal for the property? Is your goal to own this for 10 years? Or is this strictly an investment and you're hoping to sell it in two years? Let's just be on the same page about that. It's there's a strategy for each and we can, we can help with that. Yeah, we've talked
Alex Husner
about this on the show before, but the different personality types, like the Enneagram and all the different ones that we've done, but it would be interesting. We haven't met a company yet that does this, but if you gave your home potential homeowners, or once they've signed, give them that, yeah, that personality test. So not trying to find anything wrong with them, but just understand, I know, just you know, I mean doing it with people you work with, like you can understand the things that make you you tick positive and negative, right? And like how you want to be responded to, and like what things are important to you and what things aren't important to you. Maybe we roll that out.
Dylan Bozarth
I'll talk to the owner relations team when I get back, and we'll see. I'll just, I'm sure they're going to be super happy about this.
Annie Holcombe
Well, that would, that would actually be, I mean, it would be super helpful for your team to know what they're
Dylan Bozarth
walking into. So we pair all of our owners up with a owner relations manager. So sometimes the original pairing doesn't work, didn't didn't mesh. And so we have the ability to adjust sometimes, and you realign the personality. And so, yeah, to your point, it would be awesome. But achieving that, and all you know,
Annie Holcombe
without it feeling intrusive, and
Alex Husner
having everyone of the new onboarding process,
Annie Holcombe
kind of looking back over this year, I think that conversations that we've been having with other managers around the country, it's, it's not been the best year. It hasn't been a bad year. I mean, relatively to, you know, last 10 years, but I think we're, we're on the downward slope from 21 when it was just gangbusters crazy, hitting 2019 and I think everybody was like, Well, no, we'll never get back down to 2019 but people forget that 2019 was actually a really good year, yeah, and so but, but looking at that, like, how did, how did this year turn out for you guys? And what are you thinking 2026 is gonna
Dylan Bozarth
look like? Yeah, definitely down from 2021 unprecedented. Even while it was happening, we were all kind of sitting around going, okay, when does this end? It's too good to be true. But we're almost at a plateau of this is where it's going to be. We're starting to see maybe a small shift in booking window headed back the other direction. Still a lot of supply on 30 a and demand not necessarily matching that, especially in shoulder season, offseason type. But I do believe that we are at about the plateau of the this is where we should be. We did have some homes this year that did slightly better than they did last year, so that's a positive thing to see, and some numbers headed back in the correct direction. It's not the steep downs or UPS that's very hard to manage and plan for when, when it's happening, and especially unplanned. Yeah,
Alex Husner
yeah, yeah, it's a, I don't know. It's been an interesting year. I don't think we've heard anybody that's come on and said, like, this was great, you know, this was an awesome year, unless they've either bought a company, grown their inventory, you know? And those, those things obviously make it different. So recently, you shared that you have just taken on a new role, leadership wise, locally here as the chair of the Northwest chapter of favor. So tell us a little bit about that.
Dylan Bozarth
I'm excited to be in that role. Have been involved with favor for the past three or four years now, and they have some excellent local events, and have known Louisa Baldock, who has really been heading up the favor Northwest chapter for the past two or three years, along with Beth from Blue swell, yeah, and so excited to be involved and to see what we can offer and and do to help increase the visibility of favor and also to help local vacation rental companies. That's something that I've been committed to over the past probably almost two years. So we've also started a rental operator Alliance professional property managers on 30 a that was a little bit in response to the short term rental ordinance that happened in Walnut County. And again, just trying to be a good neighbor. We we want to blend, and we don't want to be the people who are bringing problem loops or, you know, angst to neighborhoods that we totally understand that people live here full time as do we, and we would not want to be disturbed either. And so we're looking to bring respectful guests. And if that's not what's happening. Then we'll have to intervene. Yeah. But back to the back to the favor and the rental operator Alliance. There was a there was a time on 38 when we as property managers, especially for the excellence and professionalism of a lot of the property managers, on 38 we didn't talk to each other, yeah, very true, yeah. And we were very siloed out. And so when regulations happened, or when things were happening around the county or on the beaches and things like that, we didn't, we didn't communicate, although we had a little bit of a driving force, having 7000 of the maybe 10,000 runners on 38 so we have since started to communicate, and it's been very helpful. We meet with the sheriff, actually, a lieutenant on the Walton County Sheriff's Office every month, and we talk about things that have happened, what we are going to do for spring break, what we can do together as the county and property managers to be able to kind of eliminate some of those, those issues that are being brought up in these neighborhoods by rental
Annie Holcombe
and I think it's important, and it's a reminder that, you know, it's not a matter of if, but when a regulation is going to pop up. And if you're taking a more proactive approach, yes, things have started to happen on either side, but you're taking a proactive approach to be kind of mobilized. So when you do need people to be actionary and get let their voices heard, you have a collective voice. And yeah, that that's really important, because having lived and worked in this market for 30 years, like there was, there was a time when everybody was just man, by themselves. Yeah, no one talked. No, we you didn't share how you were running your business. You didn't share anything because you were afraid somebody was going to steal you all providers, absolutely, absolutely, but it just, it created a it created a lack of trust, not only between the companies, but a lack of trust with the community, and therefore a lack of trust with people that were coming into the market. So it's really important, and I think that it's it's good, and again, a good reminder for managers that are out there like, get your voice heard, be part of your
Dylan Bozarth
local alliances and talk to each other guys. It's not, yeah, there's nothing to hide, especially at this point with all the data and and abilities and technology and yeah, there's, there's, yeah, there's no real secret sauce. Yeah, I've heard that before where you can tell people what your strategy is. They're not going to do it
the same way, right? Exactly that same passion, Yeah, same team. Then it does end up the same way. Yeah, 100%
Alex Husner
Well, thank you for having us here. Dylan, it's been a great, great, great week down in the area too for me, and getting to work with your team has just been lost. Yeah, here so yeah, until next time, keep it chill and let us know if something happens that you don't keep your chill, because we really want
Dylan Bozarth
to know. Yeah, I'm sure that after this episode, if ever not chill your team.
Annie Holcombe
Hashtag around the Yeah, we'll probably get some anonymous notes to say
Alex Husner
that he's not chill. He's hot. Okay, if anybody wants to get in touch with you, what's best way to reach out?
Dylan Bozarth
Um, LinkedIn, I'm on LinkedIn, Dylan Bozarth, and also email me at Dylan, my first name, Dylan, Dylan at 30 days tapes.com Great.
Alex Husner
All right. If you anyone wants to get in touch with Annie and I, you can go to Alex and Annie podcast.com till next time. Thanks, everybody.
Transcribed by https://otter.ai
Dylan Bozarth
General Manager | 30A Escapes
As loyal FSU fan and Northwest Florida Native, I`m passionate about helping people have the best possible experience when they vacation with us on 30A. I`ve been part of the 30A Escapes team since 2014 when I started as a property manager.