5 Innovative Strategies for Cash Flow in the Airbnb Business with Brendan Thompson

Dylan Silver (00:01.058)
Hey folks, welcome back to the show. I’m your host Dylan Silver and today on the show I have Brendan Thompson, real estate investor entrepreneur out of Houston, Texas. Brendan, welcome to the show.

Brendan Thompson (00:13.858)
Thanks for welcoming me and literally before we got on I told you that there was going to be stuff in the background and one of my four kids decided to walk in.

Dylan Silver (00:21.706)
It’s okay. It’s okay. People are allowed to have allowed to have kids. I’ve had it happen on the podcast people coming into the podcast studio. So the more the merrier here. But Brendan tell us how did you get into the real estate space. Was it in your blood.

Brendan Thompson (00:36.674)
You know, I think I discovered that it was. I didn’t know this until maybe three years ago. I had never touched real estate before except for our primary home. And the way I got into this was rather interesting. I was a full-time missionary trainer. So I worked with churches and kind of worked in the nonprofit world. That was my background. And I met a guy who was really into short-term rentals and Airbnbs. And I just thought he was crazy.

And eventually he convinced me through a series of circumstances to join him in this effort to kind of create a software in that space. So my first actual foray into real estate was building software for real estate investors when I myself was not one.

Dylan Silver (01:14.444)
Okay.

Brendan Thompson (01:22.03)
As I got into the software and I started to learn more about what he was doing, I just said, man, this is life changing. If it’s changing other people’s lives, why isn’t it changing mine? And that’s when I began to take the steps to get my first rental properties and begin the short-term rental. Really the short-term rental side is where I focus, but we kind of open and do all of it at this point.

Dylan Silver (01:22.413)
Wow.

Dylan Silver (01:34.338)
mine.

Dylan Silver (01:47.032)
So at that point in time, when you’re getting into the idea of being a real estate entrepreneur, what was your day-to-day like? You mentioned software. Was that your background, where you came from?

Brendan Thompson (02:00.67)
No, it was kind of a just.

roundabout story how I got here. You know, I was always, when you work with missionaries and you work in that context, you’re working with people that go overseas and they do crazy things in crazy places. And you have to have a little bit of an appetite for risk to do that. And I think I discovered something in the midst of COVID, like many people were shifting jobs and kind of exploring different things is I began to do different little side businesses really just as an opportunity to.

Sorry, telling the kids to be quiet there. I think what I learned about myself was that I really loved new things and I really loved starting. I really loved kind of investing in a new idea and kind of getting it off the ground. And so I kind of found a niche doing that on a few different things. So I had some little businesses that we started that we had a Christmas light company that we ran and kind of got to sell that, which was really great.

Dylan Silver (02:34.456)
You

Brendan Thompson (03:00.574)
And he approached me because he kind of saw some of that experience and he said, hey, I want to start this. Can you help? And, I had not had any software experience, but I did work on a small kind of digital startup. So I had some, I guess, some understanding about how to run something like that. And we ended up going for starting the software together and he brought me in as an equity partner. And then the rest was history. I started working on that with him. And so kind of a roundabout way to get into the real estate world.

Dylan Silver (03:09.272)
Hmm.

Brendan Thompson (03:30.448)
But here we are.

Dylan Silver (03:31.65)
That’s how it happens. And I think that people who are risk adverse many times find real estate highly risky but also highly attractive. And so you look at it, you’re like, well, I don’t necessarily want to have all my money in Wall Street. So what else can I do? Let me try this real estate thing. And then you have other people who are just literally I’ve had someone who was a skydiving instructor and he took that and he said, I’m going to use kind of this.

thrill-seeking, you know, and let me do this in real estate in a way. And so, you know, it’s amazing that you can have those two types of avatars in the same space, but you do see it, you know?

Brendan Thompson (04:05.698)
That’s funny.

Brendan Thompson (04:09.942)
Yeah. I’ve done a, I’ve gone skydiving twice. You know, I, I didn’t like it the first time. And then I realized that, you know, I’ll try anything twice and try it a second time. And the fear that I had skydiving the first time was only amplified the second time. So it was not a great experience. I thought maybe, you know, you take a swig of something, you’re like, that’s new and interesting. Maybe I’ll try it again to see if I like it. Not the case for me. Skydiving is…

Dylan Silver (04:37.004)
You’re saying jumping out of a plane is not for everybody?

Brendan Thompson (04:40.652)
you know, and not for everybody. He can keep that, you know, he can keep that domain.

Dylan Silver (04:45.624)
Okay, so missionary, you have the software company, break that down for us here, because of course, now 2025, we have so much AI, it sounds like this was in the latter part of the 2010, 2020, that time period there. AI was maybe a thing, but not as mainstream as it is today. So this sounds like a lot of intensive work integrating with software developers, so on and so forth in the short term rental space.

Brendan Thompson (04:50.029)
Right.

Brendan Thompson (04:55.991)
Yeah.

Brendan Thompson (05:01.858)
Right.

Brendan Thompson (05:06.808)
Right.

Brendan Thompson (05:14.988)
Yeah, so it focused primarily on underwriting. so when our CEO of this company, it’s called STRIQ, like short-term rental intelligence. And when he came to me about it, he said, hey, look, people that are investing in short-term rentals and rates are changing, it’s getting harder and harder to find profitable properties. So how do we underwrite these in a way to know if they’re profitable and give it as a tool to short-term rental investors? And it was a lot of work. We had to gather information. There’s some data sources people generally

trust to underwrite and say it’s going to make X amount of dollars for me, then you got to put in your expenses and then there’s some of the negotiating on your deal terms. Are you buying it outright? Do you have leverage? Those kinds of things. And putting all that together in one spot so that people can actually shop cash on cash rather than going to Zillow, finding something and then running it into your spreadsheets and then having to do that over and over and over again. What if you could just see a map that showed you

green bubbles that said, here’s a high performing potential property for you, and it already has your buy box. So that I actually learned to underwrite before I learned to operate short-term rentals. So I went in, I think that was the right order because getting our first rental, I didn’t know what I was doing, but thankfully making this software alongside my buddy taught me how to get good properties from the outset.

Dylan Silver (06:41.25)
this is interesting and i’ve actually maybe with the first guest that i’ve had that take a similar path in a way to to the path that i have because i went from selling cars is that this another podcast no idea about anything related to real estate like it wasn’t even on my radar to then thinking okay well i’m twelve hours a day since fourteen hours a day here six days a week and i i really don’t have anything

Brendan Thompson (06:55.736)
Yeah.

Brendan Thompson (07:05.87)
All

Dylan Silver (07:07.032)
to show for other than money in the bank, and I don’t even know what to do with this. Where do I go from here? And then seeing people buying real estate. And I remember thinking like, this is too much of a risk for me. I have no idea how this would even work. I’m gonna lose the money. I’m gonna end up in debt. So I ended up switching careers to learn about real estate. I was like, I’ll make less money, but I need to learn about real estate. And so that’s what I did. And I’m still…

this I’m now a year and half into the journey here. It’s taken me a little bit longer than I would like to, but I’m still waiting to get some deeds in my name or an LLC that I own. But having done, you know, 20 wholesale, wholesale deals there about I have this podcast that I co-host, and then I have my real estate license. So I see like, it’s building. And in a sense, you had a similar, of course, not not the same, but a similar path, because it wasn’t like you went in thinking like, I’m just gonna buy a bunch of properties at the gate, you actually learned the

Brendan Thompson (07:41.676)
Right.

Brendan Thompson (07:55.469)
Right.

Dylan Silver (08:06.058)
analytics before you learned, before you had that experience of being a landlord.

Brendan Thompson (08:12.47)
Yeah, I think it really set us up for success, because something I’ve observed just now that I’ve been in it for a few years is that a lot of people get in, they have rose-colored glasses and they get into least short-term rentals and they think, this property’s gonna make me a lot of money. Airbnb’s hot right now. And so they go and buy something and they don’t do their homework. And so they end up upside down on a mortgage. And we have friends that, that’s their story right now, is they’re kind of upside down on a mortgage and they don’t know what to do about it.

We never wanted to be in that situation. coming out of, don’t know what you think about the nonprofit world, but you don’t usually make a ton of money. So it was all the more important for us to make sure that we could cover our bases and not get a bad egg. You can do all your homework and things can still go sideways. And so we just felt like the most important thing was to do everything diligently and the things we could control, let’s factor those in.

Dylan Silver (09:11.832)
So let’s talk about scaling within the STR company. you’re in that space. Did the company end up selling at a certain point in time?

Brendan Thompson (09:14.839)
Yeah.

Brendan Thompson (09:21.974)
No, they’re still operating right now. It’s still going strong. People can still use it. I’m not as actively involved, but people can still do that.

Dylan Silver (09:29.4)
Okay, and so your role with them, I’m imagining expanded with time as did the company. so growing with time, what were some of the activities that changed for you day to day and how did your role change with them?

Brendan Thompson (09:47.074)
Yeah, so, you know that I kind of isolate that software as like one thing in the short-term rental industry that I’ve been able to do.

What it actually led to for me though was the purchase of our first property and we did that kind of outside of the software. The software, you know, gave me some of the learning and the knowledge and got to really understand the industry there. But we bought our first rental about six months into that project and somehow we found a partner, capital partner, that was willing to put all the money down. And I don’t know why he said yes to a bozo like me, but he did. And we still have that property

Dylan Silver (10:01.634)
Got it.

Brendan Thompson (10:24.984)
and it’s going pretty good and that was our first taste into like operations and so scaling in the industry that was really you know maybe a pivotal step for us is getting that first one and there’s a lot of people that don’t people go to long term because they really don’t like to do some of the operations you know they don’t like to be a landlord they don’t want to have to deal with the issues I don’t know why but I just really like solving the problems and

you get a lot of them in the short-term rental space because it’s a lot of turnover, a lot of guests, a lot of wear and tear on the property.

So we learned when we got that first rental how much we actually like to operate and actually like to kind of deal with guests and some of the things that other people, it’s a nightmare for them. For us, we get some kind of weird pleasure out of solving their problems and giving them a good guest experience. you do have your occasional nightmare guest and unavoidable, but we really like it.

Dylan Silver (11:24.972)
You know, the thing that I’ve found about Airbnb, I’ve said this before, is one of the hallmark traits of being an Airbnb host is loving to host people. And people, I’ve only heard this said once before, and I don’t remember which guest who gave me this advice, but one of the guests said, you know, if you want to be good at Airbnb, you need to be good at hosting people, and you need to like to host people.

Brendan Thompson (11:49.015)
Yeah.

Dylan Silver (11:49.952)
And so it sounds like in a way that this was within your wheelhouse and it was something that you enjoyed thoroughly.

Brendan Thompson (11:57.196)
Yeah, I’d agree with that. You definitely need to not hate hosting people. If dealing with people is something that you don’t enjoy, Airbnb may not be for you. There are ways to scale and to hire VAs and you can do some of those automations and I actually, it’s almost necessary as you grow. But to start, you really kind of have to have a knack or a…

desire to because that is what it is. It’s hosting so you have to have the ability to Get through that and deal with some of the problems. I think a thick skin helps Separating it and keeping it thinking of it is like a business is really helpful to me I can deal with a messy guest or Because to that to me they are they may be presenting problems and maybe a problem for me But in any industry you’re gonna have some of those things happen

Dylan Silver (12:49.813)
No doubt.

Brendan Thompson (12:50.222)
So that’s helpful, I think, in the process as well.

Dylan Silver (12:53.58)
Now, let’s do a little bit of a dive here, Brendan, into Airbnb strategy, right? So going from inception to how you acquire these deals to how you get them ready for the Airbnb themselves to maintenance, to pricing, let’s do a little bit of a dive here. current day, bring us up to speed, you’re still active in the Airbnb space. When you’re looking for these deals, how are you finding?

Brendan Thompson (12:58.83)
Sure.

Thank

Brendan Thompson (13:15.447)
Yes.

Brendan Thompson (13:19.628)
You know, this might be a cop-out, but it feels a little bit like God brings them to us because we have had a fortunate experience, and it’s certainly not a replicable experience, but we have had referrals from nearly all of our clients, bringing other clients.

And we started, you know, my background working in the missions world with churches is I just have a large network. And if you don’t know this, missionaries generally leave the country. So they have homes that they don’t want to get rid of because they want to keep equity and keep building wealth, but they also don’t know what to do with that house. And because of my ties into that industry, we’ve had people just reach out just because they know about what we’re doing. And so we haven’t worked too hard or been too proactive.

as we’re scaling up over the last 14 months as we started our management side, we haven’t had to work too hard to get our first initial clients. So I know that’s not a replicable thing for others. It’s just how it happened for us, and I would be lying if I were to tell you otherwise. we do have processes for how we’re trying to assess the kinds of properties and clients that we want to take on and really what we’re looking for.

marketing, we haven’t had to do a ton. So we’ve gone from, you know, my one property that I had, my business partner has one as well, so two between us, to now over 27 units in the span of about 14 months.

Dylan Silver (14:51.572)
I don’t pretend to know the inner workings of the Almighty, I will say that networking and having focused intent and strategic relationships tends to be utilized and

Brendan Thompson (14:59.0)
Yes. Yeah.

Yeah.

Dylan Silver (15:08.162)
helpful over the long term in ways that you cannot foresee at the time. in acquiring these 27, walk us through one for instance, just any anyone maybe recently, was it one of the sellers said, Hey, I know this person and they’re looking to sell their home quickly. Was it a situation like that? How do one of these deals come about?

Brendan Thompson (15:10.275)
Yeah.

Brendan Thompson (15:16.716)
Yeah.

Brendan Thompson (15:27.81)
Yeah, so for some of our clients, we manage the property for them. They keep the home. And then for others, we’ve been able to kind of find a deal to acquire it ourselves. just as an example, we had one property that I was just looking on Zillow. This is when we first started working together, my business partner. And one of the things I noticed was that the seller was somebody that I actually knew.

Dylan Silver (15:46.391)
Yeah.

Brendan Thompson (15:55.694)
That was a crazy, crazy thing because I was just looking and I was obviously using the mobile app that we helped create to undo the underwriting. And I said, oh, I know this person. And so I still had their number in my cell. And so I texted him and said, hey, the crazy thing, I’ve been looking at properties in this area and I saw your property. Are you still selling it? And she’s like, yeah, it’s still listed. That’s crazy. We should meet up. So my wife and I drove out. This is in the Hill Country in Texas. And we went and visited the property and a much draw on the floor.

beautiful three and a half acre property with a house right there. Two sheds on the property that I knew instantly I’d be converting those into some ADUs that we would run a short-term rentals as well and ample room to kind of grow and do some other things as well. And that’s how we got the first one is and she owned it outright and so we were we ended up because of the personal relationship and she owned it outright we were able to work out some seller finance terms that were very favorable for us but also helped her.

there were some things that she was trying to do in her own life. so, you know, it’s just, when two people come together in good faith, I love that, like, those are the best kind of deals because you’re trying to kind of outdo one another and like kind of showing honor to them. And that’s a glorious thing, I think. And it’s really enjoyable to do a real estate transaction like that. They’re not always like that. Sometimes they’re cutthroat and you’re just trying to get down to the wire. But this one in particular, that’s how we found it.

We founded, I think it was November 17th, we closed December 17th after a few visits and we had it listed for short-term rental rent on January 1. So pretty wild turnaround, yeah, pretty quick.

Dylan Silver (17:38.262)
Wow, three month turnaround. Okay, so from, would you say that’s typical or a lot of them a heavy rehab or some of them a heavy rehab?

Brendan Thompson (17:49.078)
Not a lot of rehabs. We obviously have to go and furnish. This is a big thing in the short-term rental world, is people don’t know how much amenities and your furniture impacts your ROI. So that’s part of the analysis that we’ll do. So there was one property, this is a little nontraditional, but the homeowner, he wanted us to manage for him, and we said, okay, well what kind of investment are you making in the furniture and the amenities? And he said, well don’t have that much money. And we said, well, why don’t we do this instead? You want to sell it to us? And he was not ready to sell.

So he said, well, we still think this one will cash flow. So how about this? What if we rent it from you with a longterm lease, you let us furnish it and we’ll be your tenants and we’ll put it on Airbnb.

And he said, well, I can accept. So for him, he saw this as a monthly paycheck to keep their home. We saw it as an opportunity to build cash flow. And he is one of those guys that he’s really interested to get into the short-term rental world. And so our expectation is that in about a year, we’ll be able to talk with him about potentially buying a property alongside him and continuing to grow our property management alongside him with him as our financial partner.

Dylan Silver (19:04.779)
Brendan, that strategy is utterly genius. You said that so nonchalantly, but I’m over here taking notes. You know, I, of course, I have my show notes over here, but I, for some reason, wrote your name down again and triple underlined it because you came up with a real estate strategy for us. So people who are, you’re approaching them, we’ll get into how you met that gentleman, but approaching him, talking about putting the home onto

Brendan Thompson (19:07.148)
Yeah.

Yeah.

Brendan Thompson (19:19.053)
Ha

Dylan Silver (19:32.62)
Airbnb directly, maybe some type of service fee that you would charge or something along these lines. He wasn’t interested in that. Instead, you rented out the home and then had in the agreement that you could effectively, you know, sublet it out short, short term, which in many cases you can’t do. But if you specifically say the hey, I’m to do this, you can do it. So it’s almost like a way easier way to acquire something subject to without any of the risk because you’re renting so you can

Brendan Thompson (19:38.904)
Yeah.

Brendan Thompson (19:47.288)
That’s right. Yeah.

Brendan Thompson (19:52.589)
Right.

Brendan Thompson (20:01.634)
That’s right.

Dylan Silver (20:01.944)
You know.

Brendan Thompson (20:02.604)
Yeah, in the short-term rental world, they call it arbitrage. So you get a long-term lease and then you arbitrage the difference between what you make short-term, what you make long-term, or what you’re paying in your long-term lease. there’s a lot of people that do rental arbitrage, but this asset itself, the house, was so good we couldn’t pass it up. We typically would prefer to earn the equity, but we couldn’t pass it up because the cash flow was so good. I think we’re projecting to see

all of our capital we put in the furniture, which you know, it’s depreciable assets. Those aren’t, those don’t make us anything. So we’re projecting though to make all that money back by the end of the year and we started this one January 1 as well. with things, yeah, yeah. there, yeah.

Dylan Silver (20:45.814)
rental arbitrage. We could dive into that. God bless. is awesome.

Brendan Thompson (20:51.694)
It’s a great way to build cash flow. when we coach people, some of the things we tell them is like, look, if you don’t have cash flow, one of the best things you can do to get started is start co-hosting or property managing for people. Because you can be a co-host on their property, do all the things they don’t want to do, deal with the guests, schedule the maintenance, and get paid and it’s risk free. You’re not building equity,

Dylan Silver (21:12.631)
Yeah.

Brendan Thompson (21:14.696)
And the next step is, you know, potentially to do something like a rental arbitrage because now you remove the owner, you don’t have like a lot of red tape there. Once you get the lease signed, you can pretty much do what you want and you can increase your cash flow. But the ultimate goal is to, as you’re building that cash flow, reinvest that into assets that you own so that you can build equity over time. And then you’re going to learn a lot along the way. So you’ll probably be a really good operator by the time you start investing in your own.

So if I was meeting with somebody that had no money to invest, that’d be one potential strategy I would talk with them about.

Dylan Silver (21:51.798)
Wow, gold nuggets here, gold nuggets. So catching us up, we hit on this a little bit before talking about where you’re at today, but day to day today, it sounds like you have these 27 rental properties scattered. Are they all in Texas?

Brendan Thompson (21:54.254)
You

Brendan Thompson (22:06.35)
That’s right.

Brendan Thompson (22:10.294)
Not all of them, we’ve got some in Tennessee. One in Punta Cana in the Dominican. That one was an outlier.

Dylan Silver (22:12.631)
Okay.

Dylan Silver (22:16.375)
so you speak a little Spanish or not?

Dylan Silver (22:22.832)
you’re a Spanish teacher?

Brendan Thompson (22:26.094)
Sí, pero hace como dice años, 15, no 20 años. So it’s been a while. But I was a Spanish teacher for quite a long time.

Dylan Silver (22:32.339)
Okay, okay.

Where did you teach Spanish?

Brendan Thompson (22:37.834)
right here in Houston, Texas. So I did some traveling when I was in college and I came back thinking, man, I don’t know what I was thinking, but I said, I’m gonna become a Spanish major because all the countries I visited too were Spanish speaking. And got out of school and I spent a year teaching Spanish to kids like I was, like I was in high school. And not my cup of tea, it’s for some people, was not for me.

Dylan Silver (22:39.819)
No kidding.

Dylan Silver (22:52.022)
Yeah.

Dylan Silver (23:04.44)
Yeah, I could never be a teacher. It’s very, very difficult, I think. And I have the utmost respect, utmost respect for everybody who does any type of teaching, you know, specifically in the public schools. God bless all those people. But Punta Cana. OK, so I actually love the Dominican Republic. We could talk a whole podcast about this, but I’ve I’ve been to Santo Domingo and Santo Domingo Este five times in the last like 14 months.

Brendan Thompson (23:09.73)
Yeah.

Brendan Thompson (23:20.056)
Right.

Brendan Thompson (23:27.132)
wow.

Brendan Thompson (23:32.706)
Alright.

Dylan Silver (23:34.296)
I intend to move there actually. Yeah, so that’s how I learned Spanish. went there, I of course have heard Spanish. I’m in the United States, so you hear Spanish. Grew up on the East Coast. Had never been to a place where they do. Punta Cana’s a little different. You got Americans over there, people. Santo Domingo, when I touch down there, Brendan, when I tell you there was no English happening, there was no English happening. Like it was amazing. So I get over there, phone doesn’t work, know, no, the internet’s right.

Brendan Thompson (23:36.351)
That’s awesome.

Brendan Thompson (23:46.061)
Yeah.

Brendan Thompson (23:58.574)
Yeah.

Dylan Silver (24:03.478)
And so I go to the rental car place. I’m realizing they don’t speak any English at all. Like I call my bank. Banks like you didn’t tell us. I was so unprepared. So unprepared. But guess what? I had to learn Spanish at that point. Like your brain, your brain, I feel like this is so true. Your brain is tricking you into thinking that it can’t learn it. Because when you’re forced to, Brendan, that week I learned, I learned so much Spanish in that couple of days that I was there was unbelievable.

Brendan Thompson (24:12.174)
Those are the best memories though.

Yes.

Brendan Thompson (24:33.058)
Yeah, it kind of forces you to do it, you know? And it is wild what your brain can do whenever you have to.

Dylan Silver (24:39.448)
Yeah. I would love to have you back on to just talk about some of those properties that you got. mentioned Tennessee, Punta Cana. But we are coming up on time here as much as I would love to chew your ear off about all those topics. Where can folks go to get a hold of you?

Brendan Thompson (24:48.951)
Yeah.

Brendan Thompson (24:55.598)
Ha

Yeah, they need to find me, we do have a website. It’s oikospropertyventures.com. And I know it’s a weird name, oikos, like the yogurt, O-I-K-O-S. It’s the Greek word for home. And what we try to do is manage our properties in a way that they feel like home for folks. so we’re not just a management company. We do some coaching and consulting a lot of times on the underwriting side. And we, of course, do investing as well.

kind of all over the place. But if it’s short-term rentals, we’re doing it. This is pretty much what I’m trying to tell you.

Dylan Silver (25:34.7)
Brendan, thank you so, so much for coming on the show. I really enjoyed this podcast. Thank you so much for coming on.

Brendan Thompson (25:41.656)
Thanks for having me, Dylan.