Tim Smith on Challenging the Status Quo in Vacation Rental and Why Doing the Right Thing Keeps Paying Off

Anthony Codispoti (00:00)
Welcome to another edition of the inspired stories podcast where leaders share their experiences so we can learn from their successes and be inspired by how they’ve overcome adversity. As you listen today, let one idea shape what you do next. My name is Anthony Cotaspodi and today’s guest is Tim Smitty Smith, owner and operator of CasaGo, New Smyrna Beach and Casago Daytona.

a vacation rental and property management company serving Florida’s central Atlantic coast. Part of the larger Casago network, Smitty brings a hands-on owner-first approach focused on clear pricing, spotless homes, and the five-star stay every traveler hopes for. Now, under Smitty’s leadership, the operation has grown to manage more than 200 vacation rental homes and has earned Airbnb Superhost and VRBO Premier Host recognition

year after year. Guests consistently leave glowing reviews and Smitty is frequently invited to speak at leading industry events including VRMA and VR Nation. Known for raising the standard in a rapidly evolving space, Smitty combines modern systems with a personal commitment to homeowners, guests, and long-term excellence. Now before we get into all that good stuff, today’s episode is brought to you by my company, Ad Back Benefits Agency.

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As an example, we recently helped a client increase net profits by $900 per employee per year. Gains like that can change how a business is valued. Results vary, but the consultation is free. See if you qualify today at addbackbenefits.com. All right, back to our guest today, the owner operator of Casago NSB and Casago Daytona, Tim Smith. Smitty, thanks for making the time to share your story today.

Tim Smith (02:21)
Thanks for having me.

Anthony Codispoti (02:23)
So I pronounced Cossago and Cusago multiple ways in the intro there. ⁓ What’s the correct pronunciation? How do we do this?

Tim Smith (02:32)
Either one is acceptable. The founder had decided years ago that as long as somebody’s saying it one of the two ways, they’re talking about this and he’s good with it.

Anthony Codispoti (02:33)
Okay.

I like it. let’s get kind of kind of skip over a whole bunch of your experience. We’re going to touch on it. lots of different work experiences, right? Server at Olive Garden early on, you were closing loans and boosting sales for Pinnacle companies. You help companies with their Salesforce.com consulting needs. But I want to talk about the part of your life that started back in March of 2020, when your adult kids asked you to move back

to Florida. Why was that?

Tim Smith (03:13)
Thanks. yeah, they, I lived in Manhattan for about two years at that point. I’ve been in central Florida forever. So as I get to Manhattan, I’m loving it, but kids, grandkids are coming along. They want to see more time with me. And so I came down for a long weekend, actually March 11th of 2020, and ended up purchasing what I thought was going to be a place to stay when I visited the family. And instead I’m still there.

Anthony Codispoti (03:43)
What kept you there?

Tim Smith (03:45)
March 11th of 2020, so March 13th, everything changed as we know, and that was not the best time to go back to, Manhattan down, ⁓ financial district of Manhattan was not the spot to be at that point.

Anthony Codispoti (03:59)
Yeah, COVID was running wild. ⁓ It was a hard place to live, you know, with the pandemic going on. A lot of people were moving out of Manhattan at the time. So you’re down in Florida, ⁓ states a bit more open. ⁓ You’ve got kids there, the nice weather. ⁓ And then the opportunity to purchase ⁓ Oceana Beach Club rentals came about. Tell us how that unfolds.

Tim Smith (04:26)
Yeah, I purchased in there. knew I was going to anyway. I been coming over for years to vacation there. And the onsite manager at the time said, hey, I know you’re looking to buy more property, but have you ever considered buying the company that manages the properties? ⁓ It was a great building. It’s in the perfect location for New Smyrna Beach.

And the pricing and timing was correct. It was a series of owners that just never really paid that much attention to it. And so they were, COVID really scared them. And so they wanted out, ⁓ gave me the right price and the right deal. And so I said, let’s try it.

Anthony Codispoti (05:06)
And so what exactly were you acquiring?

Tim Smith (05:09)
The short-term rental or vacation rental management company happened to have all of them in the same building. And so was Oceana Beach Club Rentals.

Anthony Codispoti (05:18)
So there’s one complex where you’ve got the management contracts for all the units. The units are owned by individual people, individual owners. And so you’re taking over the management.

Tim Smith (05:28)
Everyone’s owned by an individual.

Sorry, yes, yes. We didn’t have all of them in there. At that point, there was about 30 out of 55. But it made sense. I just sold a previous company. was, didn’t know I was looking for something to do, but I was, I guess. And so, yes, we manage it on behalf of those individual owners.

Anthony Codispoti (05:51)
Okay, what was the first big project that you undertook? Rolled up your sleeves, got in there, what did you want to do?

Tim Smith (05:59)
The first thing actually was just how to open back up with COVID because we were closed down. Fortunately, we were registered as a hotel, so we were able to open up quicker than most of the places around us. Florida was not a horrible place to share, you know, to go through COVID in. Beachside town especially, we had a lot of outdoor dining already.

So we were all still able to eat, drink, walk around, walk the beach. It was a great spot to be for that. ⁓ And so really just getting it open from there and then learning the business. I had no idea this business even really existed. So I had to start to learn the business and what was the right way to do things.

Anthony Codispoti (06:42)
So the properties that you had been buying before were these properties that you then turned over to a management company to rent out for you? Were these properties that you just used for your own personal enjoyment?

Tim Smith (06:54)
There were things I used for myself or they were long-term rentals, which is a whole different world. And so I would let someone else manage the long-term rentals or they were just mine that I would hold for a bit and get rid of. But vacation rental or short-term rental is a whole different world.

Anthony Codispoti (07:09)
And so how was it that you guys were already set up or I forget how you put it organized as a hotel?

Tim Smith (07:16)
Because at one point when it was first built, was supposed to be a hotel. And then so they had that license, they had gotten that grandfathered in. And so we use that to our advantage.

Anthony Codispoti (07:27)
⁓ nice. OK, so ⁓ how many units do you have in that building today? It was 30 at the time.

Tim Smith (07:36)
⁓ At the moment we’re at 49.

Anthony Codispoti (07:39)
Okay. What is casa go? How does this fit into this picture?

Tim Smith (07:46)
Yeah. So Casago is a national company. It is a franchise business. We went through some things in 2023 and realized that as much as I could learn about the business, I hadn’t been doing it 20 years. I didn’t know everything. I didn’t know all the right connections, so forth. And so I wanted to look for a way to get the support that I needed. And when you’re in a small town, that’s not always, you can’t just go grab people and bring them over to you.

And so I joined Casago specifically, I purchased the franchise area for Daytona and New Smart

Anthony Codispoti (08:21)
Okay. And what resources did this make available to you?

Tim Smith (08:27)
Yeah, it’s actually been really, really helpful from a few standpoints. The technology, there was already an existing platform that was built out the way it should be or the way that they recommend. So there was that, there was pricing power as we talked to vendors throughout the industry being part of Costco, which is now the largest property manager in North America. Then, you know, we get pricing benefits that way and they have a really great support team that has seen.

pretty much anything, they’ve been doing it 20 years. So something comes along, whether it’s a guest situation, an accounting situation, or even a technical, why is this happening this way? They’ve got a team we can call on to help fix it quickly versus trying to struggle through to figure it out.

Anthony Codispoti (09:12)
Is another one of the big ⁓ lifts or the big assists here, the fact that now your properties are listed on this national platform. And so does that help more people find you and your properties?

Tim Smith (09:25)
It does. ⁓ We, because of our history and building our own sites, we actually still get most of our bookings from our own direct websites. But Casago and now vacasa.com, which Casago purchased them last year, those are starting to really ramp up and be high volume search engines for folks.

Airbnb, Verbo, now more and more are going to Vakasa.com and KasaGo.com. So yes, it will drive business as well.

Anthony Codispoti (09:57)
So how many units do you own yourself versus how many units are you just managing for other folks?

Tim Smith (10:05)
At this moment, I only own the one I live in, which will be a rental shortly. But other than that, we manage for individual owners. Some have one, some have two, some have 10. All individual owners at this moment.

Anthony Codispoti (10:18)
Do you wanna say more about the number of units that you’re managing for folks?

Tim Smith (10:24)
So we currently manage about 230 now and growing pretty weekly, thankfully, ⁓ throughout Daytona, Nusmerda Beach, the entire area, all beachside. And they range from studio condos up to five, six, seven-bedroom homes right on the ocean. So a nice variety for folks that are looking for somewhere to stay.

Anthony Codispoti (10:49)
And how do you grow? How do you find new units to manage?

Tim Smith (10:55)
That is a fantastic question and it’s one that’s debated often in the industry. We tend to grow, to begin with, we grew just by doing a great job and that owner would tell a different owner. So then they would sign up with us and we continued to grow that way. ⁓ Over the last 12 months or so, we’ve actually taken on two other… ⁓

competitors, one competitor locally that we’ve been able to remove a lot of their owners over to us because they wanted what we are offering versus what they are offering. And then CasaGo, the corporate did buy the Casa and we had the opportunity to purchase those contracts for all of the homes in our area.

Anthony Codispoti (11:36)
Interesting. so walk us through the… Go ahead, Spani.

Tim Smith (11:37)
Thanks. Go ahead.

So that’s one way. And then there’s also just natural, organic, we’ll call it, right? Where you’re out and about and somebody says, I’m this place, will you rent it for me? They ask other owners in the building, their friends and family, and they send them to us. So we’re very grateful that we get a lot now on a regular basis from those other owners referring folks to us.

Anthony Codispoti (12:06)
Do you need a certain number of units within, call it a square mile radius in order for it to make sense for you to do?

Like if something’s 100 miles away and you’re only getting one unit, ⁓ you’re get your team there to do what they need to do doesn’t make a whole lot of sense, right?

Tim Smith (12:25)
It doesn’t and that’s something we consciously made a decision a little while ago. We had the opportunity when we purchased the Vecasa properties, we had the opportunity to take on another 70 or so in the county, the two counties below us.

And we made the decision that that’s not for us, even though it’s only an hour away. It’s just, we have plenty of opportunity here. Let’s focus on what we have and who we can serve in this area. ⁓ partly for the team’s sake, right? They’re not driving all over creation and partly because if something happens and the guests needs you, you’re not an hour or two hours away. You’re 15, 30 minutes, et cetera. So we do focus on that. We call it, ⁓ efficiency of having them close by each other.

Anthony Codispoti (13:08)
So walk us through the services that you actually provide.

Tim Smith (13:13)
Yeah, for for vacation rentals, we are actually a full service company. So that means we’re going to handle everything from the marketing to the guest services. The guests while they’re here, before they get here, ⁓ remarket to them afterwards because a lot do come back to our area. We want them to come back to the same place if they loved it. We handle pricing, not just pricing the properties, but pricing strategy, how to drive the most revenue for them, cleanings, inspections, maintenance. ⁓ We actually consider ourselves a bit more of an

asset manager for that owner, right? Making sure their property, while they rent it out, there’s going to be wear and tear. How do we take the best care of it along the way? And so we have some owners that are, all about how do you take care of the property and others are, can you give me the most money? And we blend those two together for results.

Anthony Codispoti (14:02)
curious what percentage of your clients are also using the unit themselves on occasion.

Tim Smith (14:12)
It is their property and they can use it as much or as little as they would like. ⁓ There is a 20 % of them that like to use it during the peak season. And so they’re using it as the owner. And I can’t blame them. They’re from Michigan, Wisconsin, et cetera. Why wouldn’t you rather be a new smirner or Daytona, February, March, and April? So. ⁓

about 20 % use it that way. Some use it, you know, sporadically through the year and some actually buy it, come down once a year and you know, they’re fine how you take care of it the rest of the year.

Anthony Codispoti (14:45)
And I would assume that your pricing is some sort of a fixed monthly or annual fee plus a success fee for whatever percentage of the times that you’re able to sell it or fill it.

Tim Smith (15:00)
So we actually take the commission on the bookings themselves. So our job is to get them booked at the right price, the right amount to the right guest. And then we get a commission on that rent.

Anthony Codispoti (15:13)
no flat fee.

Tim Smith (15:15)
We don’t, there are

some that do that and we’ve just decided we’re okay paying on, you being paid based on results. And so we don’t have a monthly fee. We don’t have a annual fee, nothing like that. We expect them to invest in their property if we point out things that need to be fixed or upgraded, but there’s no set fee to us every month now.

Anthony Codispoti (15:36)
wow. So that client that comes down and stays for a month during peak season, it’s taken it’s taken out of your pocket.

Tim Smith (15:45)
It is taken out of our pocket. Yes, it’s taken way more out of their pocket, but yes, it is a, it does. And of course we still take care of them while they’re here too. If they need something taken care of in their property, we’re going to do it for them. If they, you know, somehow destroyed linens and we need to bring them new linens, we’re going to still take care of them. We appreciate the fact that they let us use their asset the rest of the year. So it’s part of the business.

Anthony Codispoti (16:11)
What is gunsmith holding, Smitty? Is this something relevant here?

Tim Smith (16:16)
⁓ Not so much. It’s our umbrella company. My wife and I, her maiden name is Gunn. ⁓ We decided that about five years ago, as we started to buy things or invest, that it would be under the holding company. That’s all.

Anthony Codispoti (16:20)
Hmm.

got it. Okay. So not a separate business. Just Yeah, the holding company for what you guys are doing what we’re already talking about. Yeah.

Tim Smith (16:35)
No. Yeah, this business is

enough to keep anybody busy.

Anthony Codispoti (16:41)
Yeah, and you’re very much a hands on operator, right? I mean, you’re often the one that’s picking up the phone when somebody calls.

Tim Smith (16:48)
It could be that it could be even as last night I happen to be the closest one when somebody’s heat wasn’t working and yes, we still need heat sometimes in Florida. And so I was the one that went by, made sure it got taken care of. Heater was put in, the electric was working, everything was good to go. So I am involved that way. I do have an amazing team though. So most of the day to day now I don’t know anything about or, you know, I trust them.

Anthony Codispoti (17:15)
Tell me more about your team. How big is it? How do you train them? How do you find good folks? How do you hold on to them?

Tim Smith (17:23)
That is the crux of any good business, I think. one thing I like to brag about is our team, if we were in a different industry, we’d still be a success, I believe, because they are that good. Most of them haven’t had any experience in the hospitality space. They were really good at X, Y, and Z, be it leadership. My COO ran real estate investment firms and stuff. And so she has come over.

She’s the glue that makes sure everybody is taken care of and happy and operations aspect of things. And so she’s also my translator. say, as an entrepreneur, sometimes we throw out crazy, wonderful, wild ideas. And while they might be great, it scares the everyday staff. And so she translates that for them. ⁓ We find them through referrals have been the biggest way we’ve done it. It’s really the only way in a small town that you can do that. And so referrals.

We spend an enormous amount of time on training hand in hand. We do inspections. The biggest business, the biggest number of employees we have is cleaners and maintenance. They’re also the whole critical part of the business. We can sell all day, price all day and everything else. If it’s not clean and not taken care of, it’s just not a good experience for the guest and we’re going to lose them and lose the owner over time.

And so the cleaners and the maintenance have all been 100 % referral based. They get training constantly, they get inspected constantly, and we could not do it without them. We are now at 40 people on the team.

Anthony Codispoti (19:03)
Yeah, I know what you’re saying in terms of ⁓ cleaners and maintenance being such a critical part of all this. I’ve not been on your side of the business. I’ve been on the customer side where my family goes to the same place in North Carolina for beach vacation every year. And the thing that we want, right, we want to check in as early as we can. Right. So when those cleaners are there and they do a great job and they turn the units around so fast, you know, they’ve got

hundreds of units in the area to do on that same day. And then, right, if something’s broken when we check in, how soon is somebody gonna get here?

Tim Smith (19:40)
That is the one area they do not let me help. It is cleaning or maintenance. I’m like, I used to be in the military, I can clean. Nope, not allowed. that’s okay. Their standards, yes, yes, their standards are better than mine even. So.

Anthony Codispoti (19:44)
Ha

Know your limits. Stay in your lane, Smitty.

You know, the other part that I can really relate to though, is, you know, being an entrepreneur, you come up with all these great ideas, right? You want to get so excited about something you want to tell your team, you want to get them started on that. And, man, if you if you don’t have a filter, ⁓ you can give your team whiplash going from one great idea to the next.

Tim Smith (20:16)
You can, and I’ve even had to learn, I’m a big guy and now a big bald guy and you’re the owner, you’re the CEO. So you say something, even if it’s just a question, trying to be curious about how they did something or did they notice this or did they take care of that? They get worried, you know, and even though

They’ve never seen me angry. We’re always laughing. We poke great fun with each other. You’re still the CEO. And so sometimes they take that too personal. And so I have to be careful that feed that to Brittany. She’ll take care of them and make sure that what I still want to achieve happens, but without, without freaking them out.

Anthony Codispoti (20:52)
Yeah. What sets you apart from other companies? When somebody chooses you guys, Smitty, why are they choosing you over another option?

Tim Smith (21:05)
Yeah, that’s pretty much something that we’ve tried to determine so that we can then continue to do that. We’ve been who we are and we’ve made the decisions we’ve made over the last few years because we thought it was the right thing to do. And as people are attracted to that, then any business owner should want to go, all right, if that’s working, how do we make sure that we do it going forward? How do we market that? How do we let people know that? And so we are owner-centric.

A lot of folks love to talk about guest experience and getting repeat guests and so forth. And yes, guests, of course, they’re the ones that pay our bills. But for us, it’s all about the owner. These owners are trusting us, especially in our market. They’re trusting us with their second home most of the time. They want you to take great care of it. It’s a big investment, especially beachside now it’s going up. And so we are focused on them. What makes sense for them?

That could be anything from not just putting any guest in there at any price, like some companies will do. It could be ⁓ constantly inspecting their property, going the extra mile to say, hey, you got to do this. We’re going to take care of it. Well, you can pay us back later on it, that kind of thing. Really partnering with them. So I think from an owner perspective and from an overall who we are perspective, why they would give us our property is

The fact that we take care of them, we treat it as a partnership. We over communicate with them. I just did an owner webinar a couple of days ago, sharing and telling them, you know, here’s what we messed up in January. Here’s what we’re doing to change that. And so it never happens again. Just being transparent and moving forward.

Anthony Codispoti (22:48)
Mm-hmm. know one of the things that you put a big emphasis on is transparent pricing, Smitty. Can you explain how maybe some others in the industry are using pricing that is less than transparent?

Tim Smith (23:04)
Yeah, so it’s changed a little bit because of course during the last administration they decided and they

started to enforce ⁓ no more teaser pricing as it were, right? And that went across a lot of industries. From day one, we wanted all in pricing. It’s so annoying on any website, and this is true whether it’s a flight or hotel, tickets, whatever it might be, where you go, ⁓ that’s a great price. And then you click and it’s 40 % higher because of fees and taxes and so forth. I think most travelers today, they just want to know what the number is. What’s it going to cost me to

And if I’m okay with that, I don’t care what’s rent, what’s taxes, what’s fees. They just want to know what it’s going to cost them. So from day one, especially when we rolled out our new site, it was all about transparent pricing. This is what you’re going to get. Yes, it does put a bit of a challenge, honestly, because there’s others that don’t do that.

So if you’re comparing my two bedroom, two bath condo for a week in July, on their initial page, it’s going to show you the full price. The other sites are going to show you what the nightly is and you won’t realize that we’re actually better until you get to their checkout page. So that’s a big part of it is we just wanted to, you get what you see, you get, well, you get what you see, but you’re also paying, you know, know, from the moment you’re looking what your total costs are going to be.

Anthony Codispoti (24:25)
Do you ever feel like a pull to go back on that strategy? Do you feel like you’re disadvantaged at all? Because maybe you weren’t getting the initial clicks that you would.

Tim Smith (24:35)
of course. Especially at the beginning, especially being at least half direct bookings, people coming to our site. We’ve done a great job of building the SEO. So they see Newsware to be, so let’s go stay there. Daytona, let’s go stay there. And where do we stay? And if they do compare against a different site, it is. And so while there is a pull to go back to that, I still think maybe it sounds cliche or easy, but

I still think doing the right thing is the right thing. And it’s our job to let them know why it’s different and why it’s that way. And hopefully enough will realize that and appreciate it.

Anthony Codispoti (25:13)
Let’s

talk a little bit more about doing the right thing. How do you do that for your team? How do you do the right thing and take care of them?

Tim Smith (25:23)
there’s many ways to do that. Of course, setting expectations from day one, right? What we expect from them, what we don’t expect. ⁓ Constantly guiding them, coaching them, giving them the second chance if there’s a mess up. One of the big things I’ve always done in business and I still do today. We just had this last week. ⁓

Let’s say a front desk person, you know, a guest services person messes up on the pricing. They gave a ridiculous discount and they promised this something XYZ to the guest. And it turns out that’s actually going to cost us money. We’re not going to take it from the owner. That wouldn’t be right. So it’s going to cost us money on that particular vacation for that guest. Do not call them out on it. We have a one-on-one. We explain what happened, how to change it. And you know, it’s a training opportunity.

never ever in fact they reached out and said why don’t you just take the difference out of my pay over the next few weeks no that is not going to happen and so doing the right thing by them is doing the right thing by them same time we do not allow guest owners to treat them horribly cursing is never allowed treating them you know like they’re just a peon in a

and work for you is not acceptable. We will and we have removed owners from our program for not being partners with us and treating our team badly.

Anthony Codispoti (26:51)
Wow. Can you, ⁓ you feel comfortable sharing one of those stories?

Tim Smith (26:57)
Yeah, it’s just one particular one and they’re in the building that we have a large number of properties in and just a horrible attitude and treating people, ⁓ cursing at them.

even on things that weren’t really problems, but you know, if, if you purchase a property at the wrong price and you think you’re going to make money on it, that’s suddenly becomes our problem. And she just kept going on and on and mistreating them, undercutting them, trying to go behind them, blame them for things, et cetera. And it just became like, no, that you’re, it’s not okay for you to treat our people that way. She’s like, you’re, she wasn’t happy about it, but

I care more about the team and that long-term success of the team and the person, our people, than I do any one particular owner. We actually have a saying, no one owner, no one guest, no one team member is going to prevent the success of all the rest of us.

Anthony Codispoti (27:57)
is all about the team. You mean that wholeheartedly.

Tim Smith (28:02)
I do.

Anthony Codispoti (28:03)
What are some things that you guys are doing differently behind the scenes to ensure that guests are getting that five star experience every time?

Tim Smith (28:18)
There’s things, and sometimes it’s hard to say because I know what we believe is just a standard. This is just the way it’s supposed to be. And it’s not always that way. So when we go above and beyond, we just figure that’s the way you’re supposed to do it. I think the easiest way to make the case is to show you. So we took on, like I said, a local competitor here locally. ⁓ They…

They weren’t really taking care of the owners. They weren’t taking care of the properties. They were marketing on one channel alone. And the one of their employees just decided, you know what? They’re not taking care of my owners. How can we do it better? She joined us. We’ve been able to one by one, those owners found out about it, came over. They were shocked at how their properties were taken care of by us versus previously. And

We don’t need to go into details as how gross some of those things were because guests were staying in them. But the moment we got a hold of them, they were taken care of. They were brought up to standards. And yes, sometimes my team will go overboard with trips to fix stuff, trips to clean things, extra chemicals, extra doing it the right way, et cetera. And that’s okay. With the properties that we just took on, 150 plus all at one time, there’s been quite the revelation that other companies are okay with, you know,

maybe ⁓ not quite fixing a door, the microwave doesn’t have to work correctly, or a shower curtain doesn’t have to be replaced every week or every month, and they just let it go. That’s just not okay.

Anthony Codispoti (29:55)
He said he didn’t want to get into the details about how filthy some of these places were, but maybe give us one story if you don’t mind.

What are we talking like cockroaches? What’s going on?

Tim Smith (30:04)
So with the company,

no, no, no, not roaches, but mold. We had one building that had mold throughout, and yet they’ve been, the previous company was still renting those out. We immediately put a stop to it, moved the guests to other places so they’re not losing out on their vacation. But the owners are fixing it, they’ve had to fix it, or we move on. We’re not gonna allow guests to have that experience. That’s part of it. The shower curtain thing was not a side note.

The local company, I don’t think, had changed the shark curtain in years. I I change mine twice a year anyway, much less a guess. So we change those constantly. We change the comforters. I didn’t realize this. A lot of companies don’t wash the comforters ever on a bed.

Hotels even don’t do it that often. I found out we actually do it after every stay which increases my cost increases the headaches increases the Transition time and everything else but the teams decided that’s the best way to make sure the guest has the five-star experience and they put it in place without Getting my input. Okay, I’m not gonna go back on that. That’s perfect

Anthony Codispoti (31:08)
I want to understand that from a logistical standpoint. Does that mean you’ve got two sets of comforters? So one that you’re bringing in and then you’re taking the ones off and taking it to a cleaner?

Tim Smith (31:18)
Ideally in this industry you have three you have one on backup one on the bed and one Being cleaned we happen to own our own laundry. So that does help with that But no there are times where you know, it may not be able to get cleaned in time So you got to go grab one from somewhere else and it could be a logistically challenging But again the team it’s the right thing to do

Anthony Codispoti (31:42)
Have you ever heard of that before in the hospitality space?

Tim Smith (31:46)
No. I…

Anthony Codispoti (31:47)
Yeah, I’m

gonna say I have not even close. What else you is there another story like that something like because that one’s like wild to me you change the comforter after every stay.

Tim Smith (32:01)
Yeah, like I said, I wasn’t aware of that, but they insist on it. I’m like, okay. That’s Jeff.

Anthony Codispoti (32:05)
That’s how great your team is. They’re just making those decisions.

Yeah. You built the, you built the, ⁓ the culture there and now they’re all on board. They’re, they’ve fed into it and they’re just, they’re the ones pushing it forward now.

Tim Smith (32:20)
They take it to the next level and that’s fantastic. And I didn’t counteract them, even though yes, from an entrepreneur or from a business owner standpoint, you think about the costs, the mileage, the extra cleans, the extra cost of having them on hand, et cetera. But A, it makes the guests feel even more special and more importantly, the team doesn’t feel betrayed or that it comes down to every dollar.

their task is to make that guest get a five-star experience. And that’s true whether it’s a studio on the beach or it’s a seven-bedroom home, that they decided that’s what was needed to make sure they felt like they were providing that value to them. So, okay, I can’t counteract that.

Anthony Codispoti (33:02)
That’s wow. Okay. What’s on the horizon? What does future growth look like?

Tim Smith (33:11)
In our area, we have a huge opportunity to take on additional properties by letting folks know that we are different. The word’s getting out from the owners that have come over to us. So we’ll be growing, we’ll be growing steadily. I say steadily and then all of sudden something comes along and we have the opportunity to grab 20, 25, 30. But after we just did 150, 25, 30 sounds pretty light.

⁓ So we’ll be growing. We’ll be growing with the right properties. We’ll be growing with the right owners. That’s still going to be a key. Nobody wants to partner with somebody that’s not a fit. So just continue to grow as long as we can still do the job at the level that we expect as a company, then I’m okay with growing.

Anthony Codispoti (34:03)
Any fun or interesting internal initiatives, maybe things that aren’t directly tied to bringing in new clients, but I don’t know, things you’re doing for efficiencies or something on the operational side.

Tim Smith (34:22)
We have done a few things lately because what we thought was really working well at 70 in November 1st and now we’re at 230. You know, you can plan and strategize and study and map it all out and everything else, but until, where they say until you’re in the ring, the plan goes out the window. The team, the team has really evolved some of them into, oh,

They might have been doing this for us for two or three years, but now that there’s an opportunity to do something else and they’re better at it and enjoy it more. So we’re doing a lot of team transition to get them more in the spots where they should be for their sake and for the results. ⁓ Another big area that we are rolling out is

⁓ We will have to roll out benefits this year. We’re hitting numbers that will make us do benefits and we’re okay with that. I’m looking forward to having that opportunity for them. know, so many of them, especially cleaners, are living, you know, week to week and it shouldn’t be that way. We pay higher than everybody else around here already, but there’s other ways you can… There’s other ways you can reward them and just thank them for being around. ⁓ Internally, we also have rolled out…

New marketing campaigns that we had never done before. We’re out policies and procedures for guests that we had never done before and nobody else is doing yet. ⁓

Anthony Codispoti (35:49)
Like what?

Tim Smith (35:51)
So we have gone to the most flexible cancellation policy you can have. That means even Airbnb the day before, right? You can cancel and still get a full refund. For our direct sites and every other channel, you can cancel seven days before. I want to point out though that that is not only unique, it’s, I don’t say, I don’t necessarily say put a flag on, but it’s something that makes us so different. For the good of the guest,

especially in today’s world where everybody’s unsure about, you know, be it tariffs or whether or whatever it might be, you know, how do I book something this far ahead? So many of our guests are coming back and back every year, but now their grandkids are playing baseball and they don’t know if can come back next year. Why prevent them from booking? Let’s not give them the peace of mind. Let’s provide them the peace of mind that they can book knowing that they can cancel up to seven days before, still get a full refund and our owner still gets paid.

So we’re protecting the owners. We’re protecting, you know, we’re providing great value to the guests. Most folks in this area, you have to pay 60 days in advance before arrival. You have to be paid in full and you don’t get a refund if you cancel. There’s some folks in this area that charge a $600 deposit, for example, and the moment you’ve paid it, it’s gone. It doesn’t matter what happens in life for you.

You lose that money. We don’t think that’s right.

Anthony Codispoti (37:26)
So part of me is like, okay, this is a fantastic policy, ⁓ protects the guests, protects the owners, but then as the business owner, you’re highly exposed. I mean, if you let folks cancel seven days in advance and get their money back and you are still paying the owners, I mean, what’s the likelihood that you’re gonna fill that spot with somebody else?

Tim Smith (37:51)
So there are financial mechanisms behind the scenes that are allowing us to do that. ⁓ Yes, there’s a cost. Of course there is. And there’s extra cost and headache for my accounting team. ⁓ But what we would do in that case, what we’ve always done in that case, is if somebody cancels that close, social media burst, some AI tools that we use, ⁓ email marketing.

calls, et cetera, things that you can try to do. There’s a couple of channels that focus on last minute bookings. So yeah, you’re pretty much being very aggressive with the pricing, but you can still try to fill it. ⁓ we still, we’ll still be okay financially as a company. And the main thing is the owner will still be okay. We still have their asset to keep trying to get new people in there and keep them happy.

Anthony Codispoti (38:40)
That’s wild. You guys are like Southwest Airlines up until recently anyways.

Tim Smith (38:48)
Right. That’s a great comparison. like that, it honestly, I’ll be honest, I fought that idea for probably six to eight months until I realized that it is the right thing to do. I was able to do the math. Yes, it could cost us money in the short term, but over the long term, it’s the right thing for the guest. It still protects the owner. And so let’s go do that. And by the way, the results speak volume.

Bookings, the first 45 days we rolled it out, Bookings year over year went up 89%.

Anthony Codispoti (39:25)
Wow.

Tim Smith (39:26)
Yes, cancellations went up 10 to 14 percent. I will take that change any day.

Anthony Codispoti (39:33)
Okay, the proof is in the pudding. You had no idea it was gonna play out that way.

Tim Smith (39:37)
We’ll see you as the day.

No, I thought it will increase bookings of course, because it gets people and I knew cancellations would go up. And of course my mind’s like, boy, does it go up too much, then with this and that. no, the proof is in the pudding and maybe it’s cheesy, but it’s also kind of cool to be rewarded for doing the right thing, if that makes sense. mean, it’s like, ⁓ we did the right thing because it’s the right thing. ⁓ and it’s working out great for our owners and us. Okay.

Anthony Codispoti (40:09)
Isn’t it funny how that happens? So tell us a little bit about the way that you guys are using AI.

Tim Smith (40:13)
Yeah.

We use AI in a couple of different manners. We use it in our communications, of course. Oftentimes, if it’s an upset guest or an upset owner or a questioning owner, they’re not really upset. They’re you know, they want hand-holding. They want to know what you’re doing for them. We’re to use AI to help us structure that, that answers or all those answers. It is trained to be our voice and also my team can use our AI to make sure that they’re still sounding like us.

⁓ That’s part of it. But then behind the scenes on the website, for example, we have AI in place where if you go look at a two-bedroom, two-bath condo in ⁓ Daytona Beach shores and there’s

probably 5,000 of them, but if you’re looking for one of those and you click on that, you’re like, this might be work, this might not. Down below, have lot of a CD, so they say, ⁓ you might also like or also recommend it. Those three are created, or excuse me, those three are put there by AI. Based on your online persona, it knows a lot about you, so it’s gonna put the three properties in front of you ⁓ that you might click on first. It actually now has started rolling out where even the picture.

in those also recommended are going to be the picture you’re most likely to click on based on previous behavior. ⁓ That’s true on our websites. That’s also true in our email marketing. We no longer have to go, okay, I want these four to be focused on.

in this email campaign. It’s going to be the four or three or four that that recipient is most likely to click on and AI makes that possible so that every email actually has different properties in it based on that who’s receiving it.

Anthony Codispoti (42:07)
That’s really cool. Are there some ways that you intend to roll AI out? Maybe some projects you’re thinking of or started working on?

Tim Smith (42:15)
No, there’s definitely ⁓ a lot of opportunity in the space to use AI. I’m sure this is true in every industry, but you go to a conference, it’s supposed to be about revenue management also, and it’s about AI through and through. And so it needs to take hold a little bit better. And also right now, everybody’s just tending to go, all right, well, I’m just going to turn it over to AI.

I’ve been in Salesforce world, I’ve been in software world forever. I believe in processes, I love technology, I love AI, I use it constantly. But it doesn’t replace us, especially in the hospitality business, it needs to handle the minutia, the instant answers, the common sense things in the background, while our team actually focused in on that guest. If my team’s not having to worry about responding to where…

the coffee baker is or when the pool opens and all that, because AI can handle that, that’s great. We can spend more time with that true relationship. ⁓ We also use AI to build all of our listings. So that’s taken hold just in the last few months. And so AI is constantly looking at them and even tweaking them some based on results and where people click and all that.

⁓ And then pricing of course has AI and algorithm and algorithms in place. ⁓ So we’re that out more and more as well.

Anthony Codispoti (43:38)
most of your AI tools or utilizations in-house or are using third-party platforms that are using AI to help deliver these results.

Tim Smith (43:51)
For communications and listings, that’s all in-house. It’s things that we’ve built or took other people’s and built upon. ⁓ For the websites, for pricing, ⁓ for other things like that, that’s all, that’s third-party providers.

Anthony Codispoti (44:09)
Gotcha. Let’s shift gears here, Smitty. In my experience, every success story, is something behind that story that almost broke somebody. I would be curious to hear about a big challenge that you’ve overcome in your life, whether it’s personal or professional, how you got through that, what you learned.

Tim Smith (44:31)
Yeah, so most recent, 2023, we were doing this business. I was trying to figure it all out on my own. This was before we went with Casago. We brought in an outside operations person and there was a misappropriation of funds, we’ll say. And so much so that it meant we weren’t going to be able to pay owners. And

you know, those owners, those funds sit in trust with us that we gather money now, once the guest stays, then the owner gets paid, that money’s in trust. We shouldn’t have be using that anyway. So we went through that and it was, of course it was personally painful because you trust this person, you’re building a business together, et cetera. And then it was financially painful.

in that we had to go raise money to make sure that we came out of that with the owners intact and our business intact. We did that. It was also a little, ⁓ humbling, rewarding maybe. I’m not sure. We did not lose a single owner through the process and

I know that we all talk about gaining trust and earning trust from the folks we work with and so forth. And I think that proved to me that doing things the right way the previous three years met when something like this happens and being transparent, which we always are, being transparent, being open, being honest what happened and what we’re going to do to fix it. We didn’t lose a single owner from that experience. They were all made whole, of course. And we were stronger and tighter controls because of it.

Anthony Codispoti (46:17)
So a couple of follow ups there. How did you guys go out and raise money? Like who wants to get who wants to throw into the pot for you know, an environment where money was just stolen internally?

Tim Smith (46:30)
Yeah, it was worked with local attorney. put together a, you know, a raised document and I went out to folks I know. So it was friends and family. And actually it was two of our owners as well turned around and made the biggest investment believing in myself, what we were doing different and where we were going to take the business.

Anthony Codispoti (46:52)
Was it just ⁓ a debt note? Is it ⁓ convertible into equity? Like, how’d you structure it? Just no. Okay. And then what did the communications with the owners look like during this time?

Tim Smith (46:58)
Just that note.

The moment we realized it, we immediately sent an email out and told them what we were going to do and we’re going get back to you the next day with a plan. And we kept every commitment that we put in place at that moment when we were going to answer them, how they were going to get paid, ⁓ the structure to get them paid. And there were phone calls, but there weren’t as many as I expected, partly because here’s what we’re going to do. And this should happen anytime there’s a…

bigger than a hiccup, but anytime there’s a setback or hiccup is here’s what happened, here’s what we’re going to do to fix it and then meet those obligations or those commitments that you said. And we did that and there’s a lot of, a lot of communication going on.

Anthony Codispoti (47:52)
What was the timeline from when you discovered the problem to when you had a plan in place?

Tim Smith (48:00)
We discovered the problem and the plan in place was maybe two weeks. It wasn’t something that you could wait on, right? We needed to pay out owners the following month. And so we needed to have a plan in place really, really quickly. ⁓ and that was 2023. I wasn’t quite there. didn’t know how much I could use it to take care of things with me or to help me. And so it was all me and attorney and accountant and so forth, trying to work all that out.

From there it was about four months of raising funds and then we were okay from that point forward.

Anthony Codispoti (48:38)
Do you feel comfortable saying more about how you discovered the problem?

Tim Smith (48:47)
⁓ The person suddenly disappeared from communications and he was somebody that always talked to us constantly and he wasn’t local. That’s another catch there. ⁓

And so we started diving into, where is he? What’s going on? We heard that he was picked up and arrested for something else. And that caused us to go, on. And immediately started looking into every account, every connection, every conversation, so forth.

Anthony Codispoti (49:20)
so painful. But I go ahead, you got more you want to say there, Smitty.

Tim Smith (49:26)
No, painful is that’s a, that’s a fair way to put it both. Like I said, professionally and I get it. It’s business. could just say, Oh, it happens. Move on owners to get over it, et cetera. But I took it personal. took a personal to betrayal, but I also took personal. These folks trust me to take care of their property to also pay them when they’re supposed to be paid. My staff requires, you know, payroll and um,

It was a tough time period,

Anthony Codispoti (49:57)
What are some controls that you’ve put in place from this painful experience?

Tim Smith (50:03)
My accounting team can see bank balances. They can’t make internal transfers even. Nobody can move money around on the bank accounts. ⁓ Nobody can sign checks. ⁓ I, maybe a bad habit, but I look at the bank account every single morning. know, and I know that’s, folks have said, yeah, that’s gonna be the hardest thing is trusting people again. I said, yeah, okay, so be it. ⁓

That’s from a personal standpoint what we’ve done, but then also with the business, when we went to Casago, the software that we gained as part of that, we don’t have any owner’s details. As far as their bank account information, not at all. We don’t write checks anymore to them. It’s all through a software that automatically, it holds their private information. I don’t want anybody on my team to be able to see it. It’s just, we removed all risk as possible.

Anthony Codispoti (51:00)
Smitty, what’s your superpower?

Tim Smith (51:06)
Yeah, we can, you know, you can be glib about it and say one word or think it’s more.

I’m not comfortable with things, things have always been done this way. I’m just wired to ask, you know, can we do this better? Can we do it different? If I had to do one word, I would say like challenger, just challenge the status quo, particularly in this industry, in this area.

It’s always been done this way for 30, 40, 60 years. And I wasn’t okay with that. And so I knew that coming in, if I challenged those assumptions and some of them they’ve been doing that way because it’s the right way to do it. And that’s great. But if you don’t just fall back on those things and you see about how you could do better, how you could challenge the status quo, then you, that’s when opportunity happens. That’s when fun happens. That’s when opportunity happens as well.

Anthony Codispoti (52:05)
What does your process look like? Is it just continuing to ask the question why?

Tim Smith (52:11)
It is. Somebody asked me one time, what’s the skill set that is required? And I think kind of like a journalist, just why, right? And I know I’ve read different articles and books and stuff about the five whys or this or that, but to me it’s always, okay, and my mom would tell you I’ve been this way my whole life. Don’t just because that’s the way it’s done is never going to work for me.

And so, I’m just constantly asking why can we do it different? Again, it may be better, may not be better, but can we do it better? Can we do it differently?

Anthony Codispoti (52:46)
Any daily practices, Smitty, that, you know, something to help you start your day, maybe something to help you end the day or just keep you on track in between?

Tim Smith (52:58)
The biggest thing for me from a personal standpoint is meditation. I took on Transcendental Meditation in the fall of 2023. I knew I had to do something different. so I tell people all the time, I don’t know if it necessarily helps, but I sure know if I don’t do it, it matters.

And so every morning that’s one of the first things done. Depends if the dog’s ready to go out or not. Other than that, it’s usually the first thing and then we go out for walks. It’s usually done twice a day. And I’ll be honest, there’s times when stress happens again and you go, know what? Let me take that 20 minutes to meditate, free the mind. I think we come back stronger after something like that. And people’s meditation could be running or ⁓ weights or whatever it might be. ⁓

But that’s been the biggest thing to change my success.

Anthony Codispoti (53:52)
what does that meditation look like for you? You’re seated, cross legged, you’re ⁓ focusing on your breath.

Tim Smith (54:01)
No, I said I’m a big guy. So there’s no cross seated. There’s no crisscross on the floor. ⁓ There’s not even really the yoga that you’re supposed to start with. A little bit of stretching, but then I’m sitting on the couch. Nothing’s crossed. ⁓ Quiet. It’s amazing how quiet it can be in the morning here. ⁓ just there’s a mantra that I use ⁓ and it goes and…

Then you’re done and you slowly come out of it and you go, all right, I got this.

Anthony Codispoti (54:32)
So for you the mantra is a sound or a single word that you’re either vocalizing or just focusing on.

Tim Smith (54:39)
It’s a word that I focus on. mean, the idea is that there’s no thoughts, but that doesn’t happen in my head. And so as those other thoughts come in, then you go back to the mantra to replace them. Um, and then there’s times where you really do transcend and all of sudden there, it is silence and you don’t hear a thing. So even in your own.

Anthony Codispoti (55:00)
And what

does that moment feel like?

Tim Smith (55:04)
Peace. It’s the first word that comes to mind. No one’s asked me that yet. So that’s the first word that comes to mind though. Yeah, it’s peace. It’s the rest of it is gonna be okay.

Anthony Codispoti (55:17)
We talked a little bit about what the future looks like specifically for you and your product, Kasego. What do you think the future of the overall industry looks like? What are some changes that are coming?

Tim Smith (55:31)
Wow, that is a great question. I do think there’s gonna be some consolidation. Again, I hope that it’s not the consolidation that happened with the Vecasa world where suddenly they had 40,000 and they were doing it from all, you know, all from one spot or a couple of call centers. It just, doesn’t work that way. So I think there’s gonna be some consolidation as long as they keep the local mindset behind it, it’s gonna be good. Technology.

is still going to be there. It’s still a long way to go. A lot of folks do not use it. Flexible pricing. A lot of people don’t market at all except maybe on Airbnb. So I think there’s going to be the industry is going to step up to do more and better for the owners.

and not just focus 100 % on the guest experience, which yes, we have to, like I said, but it’s about the owners. Without them, we don’t have anything to market, to rent.

Anthony Codispoti (56:34)
What’s your favorite thing to do outside of work, Smitty?

Tim Smith (56:39)
Grandkids on the beach. There’s ⁓ I have five they range from seven to twenty

Anthony Codispoti (56:42)
How old are your grandkids?

Tim Smith (56:49)
So just getting out there, the phones put away and you’re on the beach and you know, I haven’t been in the water in a year or two, but sitting there right on the beach with them having a blast, that works.

Anthony Codispoti (57:02)
Nice. I’ve just got one more question for you today, Smitty. But before I ask it, I want to do three quick things. Anybody who wants to get in touch with Smitty, Tim Smith, a couple of options. We’ve got his email address, smitty, S-M-I-T-T-Y at casaGo.com, smitty at casaGo.com. Also, you can find him on LinkedIn. He’s Tim Smith 19. That’s pretty easy, right? Tim Smith 19 on LinkedIn. So if you’re enjoying the show today,

please take a moment to subscribe wherever you’re listening. It sends a signal that helps others discover our show. So thank you for taking a quick moment to do that right now. And as a reminder, if you want to get more hospitality employees access to therapists, doctors, and prescription meds that is paradoxical as it seems, actually increases companies net profits, reach out to us at addbackbenefits.com. So last question for you, Smitty, a year from now, what is one very specific thing that you hope to be selling?

Tim Smith (58:03)
I hope to be celebrating that we’ve actually got through this latest transition and the additional ones that I know are going to come. And we do it a little bit better, less stress on the guest, or sorry, less stress on the team. And, you know, the guests still think everything’s fantastic. That’s the key thing. And that we continue to grow the right way, doing the right thing, but without it driving anybody bonkers or burning them out.

including myself.

Anthony Codispoti (58:33)
Yeah.

What’s something that you learned from this recent growth? You know, back in November, you guys took on a whole bunch of additional units at one time that you can apply to that next burst that’s likely to come.

Tim Smith (58:50)
The planning is as planning as you can do, as much planning as you can do, it’s not enough. You can plan and plan, but you have to be flexible enough that when that moment hits, and because things are gonna come your way, it just always does, that you’ve gotta be ready for that. And all that happens because you’ve told the team.

You built the environment for them that they can go be who they’re supposed to be. so plans can fall apart, but the team doesn’t. It works out.

Anthony Codispoti (59:23)
Tim Smith, Smitty from Costco. I wanna be the first to thank you for sharing both your time and your story with us today. I really appreciate you being here.

Tim Smith (59:32)
Thank you for the time, I enjoyed it.

Anthony Codispoti (59:34)
Folks, that’s a wrap on another episode of the Inspired Stories podcast. Thanks for learning with us. And if one thing stood out, put that into action today.