We’re four deep for this episode with Casiola and Guestor CEO and CFO!

Dennis Goedheid and Michael-Scott Lester join us to talk about Guestor, the importance of brand, and with that one’s team, and Casiola’s emergence as a property management powerhouse.

With a marketing background and a move to the States, Dennis had plans of sitting on the beach drinking cocktails and the “easy life” while running a vacation rental company with his wife.

A great conversation with a ton to digest… love this episode!

By the way, it’s magenta not pink, and investing in the vacation rental space is about to be easier than ever!

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Building Brands Organically With Featured Guests Dennis Goedheid And Michael-Scott Lester

What episode is this? I’m trying to figure it out.

This is 28.

That is awesome. It’s nice to see you. How was your weekend?

It was all right. I had a little bit of a cold, but it was okay. It wasn’t too bad.

We’re back at it. We got some amazing guests. You like the introductions, so I’m going to go ahead and let you go ahead and do the introductions. I’m excited about this episode.

It’s interesting. I’m going to start making you do all the introductions because I’m going to see how you do in that space.

I could do it, but we’ll start in the next episode.

That’s fair enough. As usual, we have an amazing lineup. We have two amazing guests. We have Dennis and Michael from Casiola and Guestor, which I am super excited to be talking about. I’ve known Dennis for a couple of years, looking back on my rental days and through the conference circuit. I have been a vendor of Casiola, but I also have been an admirer of Casiola. I was watching Dennis and what his amazing team has built in our building. It was a no-brainer to get him on here.

To jump in and sabotage this introduction here, have you been to their office?

I have not. I don’t even think I have gotten an invite.

I have been in the office. I’ve sat down at a table. I’ve seen all the Casiola vans parked outside. It was impressive. I’ll let you go back to it.

Thank you. I appreciate that.

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Michael and Dennis, we are ecstatic to have you on the show. Thank you for taking the time to come and talk to us. Let’s dig in. What we always ask is, how did you get here? How’d you get into this space? Where’d you come from? How did you get to where you are? Those are our first questions. Either one of you can dig in and start with that intro for yourself. Bring us up to speed. How’d you get here?

What an introduction. I’m almost starting to blush. You’re always welcome. Coffee is ready at the office if you’re around in Orlando.

I’m going to make some time. I’m going to get down there soon, for sure.

To answer your question, where it all started for me is far away. I’m from Belgium. I’m a long way from home. In Belgium and in Europe, I had an online printing company. It was something completely different. It was eCommerce. We sold business cards, postcards, flyers, and brochures online. We would print them and then ship them to your home or office. It is very similar to what Vistaprint does here in the US. I have been doing that for almost 12 years, since I was 18. I started my company the week after I turned eighteen. I’ve been doing that for a long time.

In 2013, I sold the company to a competitor. My plan was to slow down and come to Florida, the Sunshine State. The weather in Belgium is bad. It rains a lot. We have two summers a year if we’re lucky. I thought, “I’m going to go somewhere where the weather is a little bit nicer. I want to slow down. I’m too young to retire, so I want to keep myself busy.”

I thought property management sounded fun. I imagined seeing myself sitting at a pool all day with my laptop and a cocktail, waiting until someone came. It was a big mistake. I’ve never worked so hard in my life since I’m in property management. It was so bad that after six months, I told my wife, “This is not what I want to keep on doing. We either grow the business or sell it.” I did see a lot of opportunities in this industry. That was in 2014, so several years ago. There were fractured markets. I saw it as a growing market that would go through a lot of professionalization and evolution. I wanted to be part of that.

In seven years, almost eight years, you’ve taken your idea of sitting by the pool with a drink, which we know is an absolute joke, and how easy property management is. In that first year you had, how many units did you think you ended up with?

I started by purchasing a small existing business with 25 homes all in one resort. They were all condos, not even homes. It was supposed to be very easy. It was me doing all the office, marketing, and guest relations. My wife was the one in the properties every day checking up on housekeeping and making sure that all the supplies were there for the guests.

You took it from 25 properties in year one back in 2014. What’s the approximate number? I know you probably know exactly what it is, but how many units do you have?

It’s around 450.

When I think of Orlando property manager, I think of Casiola. I know we’re going to talk about this a lot, but let’s talk about the brand. When I see you at a conference, I see any of your team, anywhere you are, that you guys are pink. It is so smart.

Can I correct you, John?

Is it magenta?

It’s not pink. It’s magenta. You remember that from your office visit, right?

Yes. I apologize. It’s magenta, not pink. You and your team have made some conscious efforts early on with your logo and branding with the magenta color. Can you talk a little bit about that? I go online and you’re everywhere. It’s amazing. If they would observe you, many other property managers would up their game so much. Let’s dive into that a little bit.

I get that question a lot, like, “Why magenta? Why did you go for that color?” That’s my marketing background. Before I started here, I did some market research. What I did was I took every single company and logo that I could find in Central Florida. I put them all together on one big sheet. There were all these different colors. I picked the exact opposite color no one else had. That’s how we ended up with magenta. That was the farthest away from all the blues, yellows, greens, and browns that other people had.

In the beginning, when you start out as a small business, you don’t think much about branding or becoming a big brand, but it hit me. One time, I met someone. She said, “I remember you. I met you two years ago at an event.” She did not know my name anymore. She didn’t know the company name. She didn’t know Casiola, but she did remember the color.

From that day on, I have sworn never to wear suits at conferences or events anymore. We always wear our pink uniforms, everybody in the company. You see us walking because it’s such a different color. All the vans have the same thing. We have around 12 or 13 vans, but they’re all over Orlando because the color stands out so much. It worked out great.

You said something earlier I want to tap into. You were talking about whether you were going to scale or quit the business. We were talking before the show. I was talking about my vision, knowing you for a while as a vendor, and watching you grow. For as long as I’ve known you, it seems like you started out with this idea of building out a brand. There’s so much talk in the short-term rental space about who’s going to be the brand. What’s the brand going to be? Is it going to be for Vacasa? Is it going to be whoever? Is it going to be VTrips? Who’s building your brand?

I don’t want to say you’ve been under the radar, but you’ve been consistently building a brand solidly for as long as I’ve been around. It seems to be becoming more successful. From the outside looking in, it seems like you know how to do this perfectly. I want to get to your mindset. At that point, when you decided to grow this business and you decided to grow Casiola, was that in your mind? What was your strategy? Were you out to build a brand? Did it come naturally? Talk to me a bit about your headspace, then.

I did not know anything about property management when I got into the industry, which shows what my vision was of doing. For the last couple of years before that, the only thing we have been doing was online marketing and branding. As an eCommerce business, that’s the thing you have. You have to sell yourself through the website, social media, and AdWords.

We did not have any salespeople on the road visiting customers. Everything was done online. That was all I knew. That’s what you apply in your new business. For me, it wasn’t so much of having a vision, like, “We’re going build this and it’s going to be big.” It was doing what I had been doing for the last couple of years. It happened naturally. It’s not that there’s a big master plan behind it. It’s what I do.

I love that. There’s so much that can be taken from that. You did it organically. This is what you had done. You wanted to build a brand and you wanted to build a logo. You wanted to be remembered, and it happened organically. You didn’t realize you were putting the horse first, but you did when everyone else seemed to be putting the cart in front of the horse. Retrospectively, they’re like, “We don’t have a brand here. We have a decent product, but how do we differentiate?”

In turn, what happened organically for you and Casiola were your other brands, which we’re excited to be talking about here in a minute. We got Michael here sitting here, like, “I want to say something.” We’ll get to Michael here in a second. To me, it’s a lesson not for a tips and tricks show, but this is what happened organically to you. Others have to struggle and think about it and put it in the forefront. Those that do that early on in the process are going to be more successful.

The proof is in the pudding with what you’ve built here at Casiola. Congrats. Let’s talk about this new thing which I saw at VRMA. I was like, “What the heck is Guestor?” I’ve done my research. I’ll be very transparent with you. I looked at it. Let’s have Michael introduce himself here. Let’s jump in and talk about this Guestor and what this is. I’m super intrigued.

This is Michael Lester. I joined the Casiola team this summer of 2021. Previously, I had worked with Dennis as a consultant through a prior company. Part of Dennis’s strength is his ability to see things a little bit differently than other people who have approached things in the past. It’s not necessarily coming from that property management background and coming from the eCommerce background. He’s approached things a different way. He’s very innovative. That’s what attracted me to Casiola and what’s shown them to be an industry leader, especially here in Florida.

Let me go back to my background a little bit. I took traditional accounting. It’s what a lot of people do in accounting. I grew up in a firm called PricewaterhouseCoopers, which is the largest global accounting firm in the world. I spent thirteen years with PwC. I worked here in the US and I also worked in Europe. I was based in Ireland for over two years.

I was working in the UK, France, and Switzerland. I had a great global accounting experience there and then relocated back to the US. After about thirteen years, I ended up leaving PwC and joined an accounting firm specializing in vacation rentals called Ximplifi. That’s how I met John in the past when he was with a different company at that time as well.

When I was with Ximplifi, that’s where I met Dennis. I worked as a consultant for Casiola for about a year and a half. Around the COVID time, I split with Ximplifi and did something else for a little bit. The opportunity came to rejoin Casiola. I was very excited to join Dennis, help the company grow, and work on Guestor. I’m super excited to be a part of the team. It’s been an exciting few months since I joined this summer of 2021. I’m excited to see how the next year or so and more is going to go with Guestor and Casiola.

We knew it was going to work because you also look good in magenta. You can’t join the team if you don’t look good in magenta.

That’s part of the interview process. They’re like, “Can you take some pictures and show me magenta?”

Cultural fit is everything. I get it.

Everybody looks good in magenta. It’s a simple color.

It does look good. Mateo mentioned cultural fit. Not to bring this to me, but I’m building out a team at Hopper. That’s the hardest thing. It is trying to get these foundational hires with a couple of other key players that are on our team and finding that cultural fit that is willing to go ahead, push their sleeves up, get dirty, and build something amazing. That’s hard as heck. I’ve never been knee-deep in the hiring process before. I’m super excited about what I’m doing, but this is hard. You’re like, “They’ll be great six months from now once we’ve built the core foundational hires,” but it’s difficult. I’m glad that you guys came together and you joined the team.

The hardest part as a CEO, but also the most important part, is building your team. It’s a little bit of what we discussed earlier with the branding. The harder you try, the harder it is probably because that has to click. It’s something completely different than what you envisioned. In the beginning, you have the weirdest people with completely different backgrounds that make up a great team. You would imagine that when you first met them. It’s hard, but if it works out, it’s great.

When building a team, the harder you try, the harder it is.

It’s interesting. I’m going to bring this up, too. There are two points I want to make around this and, and I want to highlight. The other is it’s a deliberate effort to do it. Even within building, what is the culture of Casiola going to be? I’m into verbs. If you know me, I say that all the time. I’m into verbs. I’m into action.

John, when we were putting together the DEI stuff, Casiola stepped right up. Dennis was the only CEO and the only leader of a company that attended our session. We had a lot of support, but he was in there. He was in there with his team. They were present and gave feedback. That is, to me, the essence of how you build that culture. It is through your leadership and your leadership’s actions.

Number one, kudos to you and Casiola for that. Thank you for your support. As you grow and as you continue to build out your business with that deliberate strategy in mind, I also think you’re 100% the beneficiary of that because it’s going to provide a better guest experience. You’re going to provide a better experience for your employees and those who are in your ecosystem. Please talk about that. A lot of people talk about it. Maybe they don’t know how to do it, or they’re uncomfortable with how to do it, or whatever. I don’t want to make excuses for anybody, but it’s good to see you do that in action. We would love to hear how that became a part of your philosophy for the culture at the company.

From my experience, culture is everything. It determines how your company’s going to be and how it’s going to be moving forward. As a CEO, you have some influence, but it’s impossible to do it all myself. I need people to do all the daily operations and daily stuff. Those are preferably people that are better at it than I am. I’m going to be honest. It has been a big challenge here to find people. Even before COVID, it was hard. This has always put a break in our growth. If it was easier to find good people for me, we would probably be even further than where we are. It has been hard.

Culture is everything. It determines how your company is going to be moving forward.

For me also, there’s a big difference in culture. Being from Europe, if you join a company and you want to part ways, you have to give three months’ notice. Here, I’ve seen people walking out. If I hire John and I’m not happy and want to fire him, we still have to work together for three months. If you want to quit, John, you only have to give me two months’ notice. It’s a big difference.

In the US, it’s an employer’s dream. You can fire anyone wherever you want and they’re gone. I also start to see the backside of it. People are not as loyal to their jobs. They hop from one to another if they can make a few bucks more. You have to offer them something more than money because there’s always going to be someone that wants to pay more. It’s as simple as that. You cannot compete with every single company around here.

We are in Orlando. We have Disney. We have Universal. We have all the big hotel chains. They have benefits. They have free parking tickets and so on. You need to come up with other ways to keep people. The culture there is very important. We’re an open company. For example, I don’t have an office. I sit in the main office like everybody else. I want to hear what’s going on. I want to hear people talking. They can talk to Nate or me. They can ask their questions. That’s the first step. Everybody’s at the same level. If a good idea is good, it doesn’t matter if it comes from a housekeeper, me, or another manager. We want to hear all those ideas and be quick to change.

There are a whole bunch of other things. For example, we also have monthly events. It’s called the CCC or the Casiola Crew Celebrations. Each month, it’s organized by two different people from different departments. They’re selected at random. Michael, our CFO, has to organize our Thanksgiving event together with one of Casiola’s managers. I don’t think they’ve met before in person. They have to organize an event together. It’s those kinds of things that open up the culture. It makes you work with people that you usually don’t work with and get to know them. It works out great.

I know we’re going to be talking here about Guestor, but I want to pause on this. Another thing that I’ve noticed in the few years that I’ve known you, Dennis, and been following Casiola and what you’ve been doing there is on top of the brand, you’ve always had a high focus on tech. You want to go ahead and stay ahead of the game. A lot of what you’ve done is proprietary. You have a really amazing proprietary homeowner platform, for example. Those are owner logins and that kind of thing.

I know you’re doing some transitions. You’re staying focused and building out some amazing things on the tech side. Additionally, what I noticed on the social side and what you’re doing in the marketing is your team is always staying up-to-date with Disney and all the major theme parks. You’re going and doing your 75th anniversary. Your team is getting an education, so you can, in turn allow to relay that same information and give a better guest experience to your guests. I love that. It’s brand. It brings it all together. It’s that experience. You’ve been doing some amazing stuff. Kudos to you and your team for staying ahead of that curve there.

For most markets, you have the beach, forest, or whatever landmark. It doesn’t change that much. It’s the same every year. Here in Orlando, all those team parks are competing for everyone’s business. There are new rides, theme parks, newly-opened water parks, and attractions. Every single month, there’s something new opening. This 2021, we have the 50th anniversary of Disney. It’s a big celebration. There are new shows.

Also, how to go to the parks has changed a lot. You need theme park reservations. You don’t have fast passes anymore, but you have something new, like Disney Genie. It’s not as easy anymore as it was in the past going to Disney. Don’t show up there, buy a ticket at door, and go in. That’s impossible. We do need to educate our guests because that’s, in most cases, why they visit Orlando.

I remember last spring break in 2020 when we had people staying with us. They called us up crying because they wanted to go to Disney, but they didn’t make theme park reservations. They spent all that money to bring their whole family to Orlando. They booked flights. They had a home with us, and then it turned out that they couldn’t go to Disney anymore because they didn’t have a reservation. All the theme parks were completely full. To avoid this kind of experience, we need to educate our guests about how it works.

It’s awesome. You get to go ahead and test out this stuff, too, like a new ride. I have to go check that out.

I can’t wait to get down there. There’s so much Star Wars stuff I need to go to. My son is excited, too, so I’m dreading it. I will be down there sooner than later. Can we get into Guestor? I’ve been excited. I want to talk about this for a while.

Let’s do it.

Are we ready for that?

We are.

Let’s dig right into this.

Guestor happened because of a couple of things. First of all, dealing with owners is the hardest part, at least for us, of the whole property management business. It’s not dealing with guests, but it’s dealing with owners. You have to explain everything over and over again. You have to, in our case, convince or try to convince 450 people about the same thing that you know 100% that it’s going to work. They all have different opinions about something.

The hardest part of having a property management business is not dealing with guests. It’s dealing with owners.

On the other hand, what we were seeing is that a lot of our owners that did invest in vacation rentals were not doing it the right way. We also do a lot of business development. We try to attract more owners to join our program. What we did see there is that 90% of the people contacting us under brand online did not have a vacation home yet. They were interested in management but did not have a vacation home yet. They were looking to see if we could assist them and point them in the right direction.

We have a whole CRM system, so we follow up on all those leads. Even after 1 year or 2 years, we saw that 90% of those people still did not buy a vacation home after two years of being interested. What we noticed is it’s still a very long and complicated process buying real estate. You have two groups. You have, on one side, people with a lot of money. They don’t want to spend time looking at homes and picking out furniture. They want to invest and see a return on their money.

You then have on the other side people who want to buy a vacation home but may not have all the funds they need. They think that they can buy a good home with $50,000 and that they’re going to have business each year, but that’s not happening. If you want to buy a home in a good location, you have to spend much more than that.

We saw those two disconnects there. We thought, “What if we could just buy those homes? We know the market. We know the business. We can create some kind of fund. Instead of people having to buy individual homes and making all those different decisions, we can make those decisions for them. We know exactly what works. We know what amenities the guests are looking for, what type of bedding, and what type of furniture works in the areas that have a great return. Let’s do it for them. People can buy in and buy a share in those homes.”

We started with a project pre-COVID. It was me and our marketing guy, Cedric. COVID happened, so everything got back on the back burner. We started it and got stuck in all the legal mumbo jumbo. It’s so hard and complicated. That’s when Michael came in. We needed someone with experience that had been doing similar things before. For us, or at least for me, that’s a whole new world. I know property management, but I don’t know anything about the financial part. Michael has been great in helping us get to that step. You need SEC approval from the Securities and Exchange Commission. It’s hundreds of pages with legal language. I’m glad Michael was able to help us and get this going.

It’s amazing. Dumb it down for the 90% who are interested and like, “I want to buy a vacation rental home. I have $50,000.” You’re like, “That’s never happening.” For that person, if you were to reconnect with them and say, “This is what Guestor is now,” what would that conversation be?

Guestor is making vacation rental home investment accessible for everyone. That’s our mission. That’s our goal. We want everyone to be able to invest in vacation homes, from our housekeepers to our maintenance techs to me, to you, and to everyone. We wanted to become an investment class. It’s like how you buy stocks on Robinhood. That’s how easy we want to make it. You can also invest in vacation rentals.

Guestor’s mission is to make vacation rental home investment accessible to everyone.

What we do is do all the work. We want to build a portfolio of worldwide vacation rentals. Some are in Orlando, Miami, and Paris. You name it. We are in every big tourist destination. We are going to source the homes. We are going to renovate them. We’re going to look for the best-in-class local property managers. The goal is not for Casiola to manage all of them. We know how hard it is to scale operations. We want to work with the best-in-class property managers.

As an investor, let’s say you want to put in $100. You own a little part of all the homes in that portfolio and you get a return on rental income and proper appreciation on all those homes. It’s a way even for existing homeowners to diversify their investments and not put all their money in one basket. It’s to be able to have a worldwide portfolio of homes.

If the market is up, for example, in Europe and down in the US, you still get a much more stable return on investment. We’re targeting returns between 17% and 25% on a yearly basis. Vacation rentals are outperforming most other classes of real estate. You almost have to be a millionaire to invest in a vacation rental. You only have 1 or maybe 2, depending on the location, which is still very risky. We want to make it safe and accessible for everyone.

It’s a no-brainer. To me, if you have some money, the return is 17%. Even looking at the short end of it’s a pretty phenomenal return. The obvious risk, like anything, is if vacation rentals stopped performing altogether, there’s no yield. You’re not going to make anything. You, I, and everyone reading this will notice that from now and until the unforeseen future, that’s not the case.

There are other ways around it. You can reach long-term rentals in the worst case. That’s the great thing about vacation rentals. You’re flexible. You can do multiple things, like midterm rentals or long-term rentals. If the real estate market crashes completely, you’re going to feel that in your returns, too. It doesn’t matter what you invest in. If something like 2008 happens, you’re probably going to lose money or have a lower return than you are anticipating.

The other thing, too, is, and I’m sure all the disclaimers come out, there’s always risk in investment regardless of what that investment is. You’re bringing something to the table that allows everyone to participate in this. The little guys and I say little guys loosely, are people who do not have the ability to even get into this ecosystem at any point.

How many people do you know that can drop the cash or are in a financial position to take advantage of a segment of hospitality and travel that is continuing to boom and is going to continue to grow? We know that’s going to happen. I’m not saying it’s going to be perfect or up and down. That’s with any investment. This is a way to do it without having to have the capital and also being able to weather the storms.

One of the things I love about this is that it’s so dynamic in so many ways that it can be converted. When people know what convertible notes are and things of that nature, they can convert them to the midterm or to the long-term. One of the things I love, and I want you to talk about it, is you’ll be able to pick projects, too. Please correct me if I’m wrong, but I believe you can pick. If something fits your fancy in a market or space, you can pick which investments you want to put your money into. That is phenomenal, too.

What we want to do is also build a community around it. The big difference between stores and, for example, buying stocks on Robinhood is that you can boost the performance of your investments. Let’s say that you invest in a house destination where you have to travel a lot for work or for leisure. You can stay at home. You can book it.

I do get the question a lot, like, “Do we have 3 days or 3 weeks in the home?” We are not a timeshare concept. It’s a pure investment vehicle. We don’t get free stays. We do offer Guestor perks for investors. Those are things like early check-in, late checkout, or maybe an extra night if the night is unbooked. You can send all your friends and family. You can stay yourself in Guestor homes and more. If those homes are booked, the higher your return on investment is going to be.

What we want to create is a combination of Marriot Bonvoy Travel Club. You had those people when we joined Homes and Villas by Marriot. Initially, we were getting calls from guests booked on our website. They were asking us, “Can we still cancel our reservation? I saw the same home on Homes and Villas by Marriot.”

We were like, “Sure, you can, but why would you want to book on Marriot? It’s 20% to 30% more expensive than if you book directly on the website.” They’re like, “That’s okay. I want to use my points,” or, “I want to earn points. I’m okay with the price.” That opened my eyes to how strong their brand is. If we can accomplish that, then you not can only invest in Guestor worldwide, but you can also travel with them and stay in Guestor homes wherever you travel. You almost have an Airbnb where everybody owns the homes that they’re staying in. That’s our long-term goal of it.

I love the trajectory. I love where you’re going with it. Michael, you’re a part of this. My question for you is, what has the adoption been? The first I saw you was VRMa International. I’m not sure exactly when that was and if you were before that, but how’s the adoption been? Where do you see the trajectory and where is this going to take you in 2022 and into the future?

That was the first launch. It was at VRMA International. We have two funds or two investment vehicles that we’re launching concurrently. Our second fund is launching. We’re starting to acquire our properties. We’re targeting about 10 to 20 properties a quarter. Depending on how capital flows in, that may be increasing. That’s our target. It’s exciting looking at some of the different markets we’re going into and the different opportunities we see on the horizon. We’re hoping for big things.

One thing that I wanted to go back to also is the benefits of diversification. Dennis hit on this pretty well. Let’s say you have $500,000 to invest and you’re looking to invest in a vacation home in the Orlando market. That might get you perhaps one home. If you were to invest in that one home and the roof goes out or the AC goes out, depending on how serious the issue is, you could lose months of revenue.

If you take even a smaller fraction of the $50,000 and put that into a fund of diversified homes and you have 1 or 2 homes that have some type of issues, you get the benefits of that diversification spread out amongst all the homes. That hit to your financials is quite a bit less when you’re able to diversify like that. The other big benefit of this investment versus putting the money in the stock market is that it is backed by real estate, which helps when it comes to even that diversification piece compared to the stock market.

What is the average? You’ve mentioned $100 as someone that could come in and this is available to anybody. This has been live for a month or so. Where do you see the average investment for the average person wanting to come ahead and throw some money at it? Is it $10,000? Is it $500,000? If you can’t say that, where do you expect it to be?

It’s hard based on the size of the individual investors that are approaching you. Some hedge funds have given us a call on the spot with a fifteen-minute phone call wanting to wire over $1 million pretty quickly. This is something that we want as part of our fund are everyday investors, too. We don’t want all hedge funds. That’s nice to have some capital infusions like that, but we wanted to make it attractive for every investor.

All our housekeeping team, maintenance team, and everybody that wants to have exposure to vacation rentals that didn’t have that opportunity in the past will not be $1 million investments. It’s going to be less than that. We want to be able to make that accessible for everybody. Our first two funds are available for our credit investors. Those are the ones that are launching. Depending on the fund, those funds have either a $10,000 minimum or a $1,000 minimum. We are working on what’s called a Reg A+ filing, which should be around the end of the first quarter. That’s where our minimum drops to a $100 minimum investment. That’s available for everybody, accredited and non-accredited investors.

This is super exciting. Is there anyone else that is doing anything like this at all? I don’t think it’s this, but I know that there are some different pivots in this space where it’s to help buy more properties personally, but more of homeowner acquisition. It’s not necessarily investing. Are you the first? I think you are. Have you heard any rumblings of anyone else trying to do the same thing?

This has been done many times, but mostly behind closed doors. A couple of people and friends that are pulling money together to invest in real estate is not something that’s new at all. The big difference is that these are industry-driven things. I’ve heard of a couple of other hedge funds that are doing similar things on their own. They’re trying to build operations nationwide. They’re buying up homes, but I don’t think they realize yet how hard it’s to run a property management business. They’re going to have to find that out the hard way, I’m afraid.

There are a couple of other funds that are working on similar things. What gives us the edge is that we know the industry and the business. We have been doing it for many years. We already have the funds. We want to build that community around not just investing. We want to have that whole club around it with realtors, managers, and guests all together building and then boosting those sub-performances.

Were you going to say something, Mateo?

No, you got it.

What do you see as your biggest challenge in 2022, getting this off the ground? I’m not going to say this is going to send us sideways, but what are the things that you’re going to have to overcome in 2022 or the next two years?

Getting the right properties is going to be a challenge. We all know that the market is high, so we have to be careful. We have to look at markets and what their appreciation is going to be over the next few years. It’s like investing in the stock market. It’s hard to market and buy at the low and sell at the high. What we want to do is buy several homes every quarter so that we also spread our investment.

We may buy some homes at the top of the market and buy more homes at the bottom of the market. It’s going to average out. That’s the benefit of depreciation. If you only buy one home and buy it at the top of the market for maybe ten years, you may still not get the return, but the amount should give you a much more stable income.

That was the beauty of the model, too. It’s that concept of dollar-cost averaging. As long as you’re buying consistently, some will be higher and lower. The interest in compounding over time, as far as we can see, will leave even the positive of that concept.

The other challenge is regulations, which is something we all deal with. If we buy homes and regulations will change, those homes may lose some value. That’s why it’s important to spread our portfolio and not buy everything in one destination or one location. Have some homes everywhere, all around the country or the world.

If you buy homes and regulations change, those homes may lose some value. That’s why it’s important to spread your portfolio and not buy everything in one location.

On our website, we’re for sure going to link with this episode, both Guestor and Casiola. If someone wants to go ahead and is interested in reaching out to you, is it to go to your website, follow instructions, and join the waiting list? I’m looking at it. It says How it Works for Property Managers and Join the Waiting List. If someone’s interested in investing with you, would it be best to do some research on the website and then join that waiting list?

Yeah. Everything is going to be done online. You’re going to be able to sign up. As Michael explained, we need to do some checks to see if you’re an accredited investor, and then you can get going. Everything can be done through the website.

For example, someone like me that is not an accredited investor but I had $10,000 I wanted to go ahead and invest. Is that something I can do after you go ahead and do that?

Yeah. Once we have the Reg A+ certification, you can do that. That would be the first quarter of 2022.

You all read it here. There are a lot of non-accredited investors that have some money that they want to go ahead and throw. I’m excited for you all. Other than this, and I know this is a huge thing, what’s next? With Casiola and the magenta, your brand is growing. What’s next for you all?

We are expanding into different destinations. At the beginning of 2021, we expanded into Aruba. In 2022, we were adding Miami to our list. The goal is to add more destinations. We have a very strong brand. We have a lot of technology. We want to license that brand to other local property managers. We are good at the marketing and technology part. If we can partner up with good local operators, we will have a golden combination. We’ll be able to grow the Casiola brand.

Is a franchise model what you’re looking for with the right managers?

Exactly. That is very similar.

We’ve had past conversations forecasting the future. We have good friends in the space here that are finding the most success with that franchise model and what that looks like. That aligns right with that brand. I’m excited to see your growth. I’m super excited for you all. Thank you so much for joining us. This has been a great conversation. I’m super geeked up about Guestor. I may or may not have some money I want to go ahead and throw your way. I’m pretty excited about it. Is there anything else you’d like to leave the audience with?

Any golden quotes?

It doesn’t have to be a golden quote. I wasn’t sure if you had anything that wasn’t able to be said, either you or Michael, that you’d like to go ahead and share with the audience.

Something that puts us on the map is don’t do the same thing as everybody else is doing. They’re different as well in branding, technology, and the choices that you make. That’s what sets us apart. Don’t follow the herd. Be a little bit different. You’re going to have great success.

Let it come organically. If I took anything away from this episode, that’s about it.

The harder you try, the less the thing is going to happen. It’s like dating. If you’re looking for the love of your life, it’s going to happen when you least expect it.

Dennis and Michael, thank you so much for coming on. We will have you back on the show. We want to continue. Clearly, John and I are going to be watching Guestor and Casiola moving forward. You’re friends with the show. We’re happy to have you back on. I’m coming down there, Dennis. I’ll call you and let you know. I want to see this office. Will’s been there. John’s been there. I haven’t been there.

You’re the only one.

That’s sad. I have to talk to Seth about that, too. We got to talk about it.

I want to put a disclaimer out there, too. Will, if you’re reading, truly, we’re not watching your show going, “He had Dennis on. We should have Dennis on. He had Michael on. We should have Michael on.”

I got a call from Will. I got pictures of these guys together.

I know. I saw.

They’re sending them. I’m getting these text messages. They’re like, “They’re together.” I was like, “I didn’t get an invite. Is phone intact?” It’s all good.

He went to see your Halloween event. He probably did not expect that, but it was fun.

We’re good friends with Will. We go back and forth. We’re talking with him soon. We love Will. We love what he is doing over there. I like giving him crap. Thank you so much. It’s been a great conversation. Anytime you want to come back and give us an update, please, we’d love to have you back on the show.

Thank you for having us.

Important Links

• Casiola
• Guestor