Nearly $300K in 8 Weeks and 75% Direct in Year One

Quick Summary

Kyle goes against the usual advice. Rather than chase a vacation market, he buys in towns under 1,000 people outside major metros and turns old dairy barns and vacant warehouses into places that exist nowhere else. He's at 15 locations across eight states, and he says he ran a few pro formas on BNBCalc before he bought his first one.

Rajan's route was different. He put two and a half acres under contract for $37,000 during his senior year of college, signed a $276,000 construction loan, and found that a hyper-local audience converts where a big follower count doesn't.

Key Points

• Kyle Miklasz launched an 8,000 square foot converted warehouse in Lacona, Iowa, a town of about 300 people, on June 5th. Eight weeks later it had just shy of $300,000 in gross revenue booked, his best launch to date.
• Rajan Chida's first cabin came in around $380,000 all-in: $37,000 for the land, a $276,000 construction loan, and another $50,000 on credit cards after change orders. Bids on cabin two are running $450,000 to $480,000.
• Rajan opened at about 90% direct bookings and sits near 75% seven months in. Kyle, a year after launching his direct site, is at 35% and wants 50%.
• Rajan reckons his own content has done around 200 million views, and it still didn't fill the calendar. A local wellness creator given three free nights and a giveaway drove roughly $20,000 in direct bookings instead.
• Kyle ran about ten properties with no staff, no VAs and no partners before hiring a head of operations, and says six or seven was the right moment. Guest messages had climbed from five or ten a day to 50, 80, 100.
• StayFi across every Kyle location over six months more than doubled his email list to about 20,000 subscribers, which feeds two campaigns a month.
• Jeremy figures 60% to 70% of guest issues are catchable before they happen. One skipped HVAC check on the Kentucky property cost $5,000 in refunds.

Full Transcript

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Jeremy: All right, we are live with the Short-Term Rental Pros podcast. We are here in person in Semora, North Carolina, beautiful Hyco Lake. It is 11:25 at night, but we're staying up late to bring you the action. I'm with three guys here, some crazy guys. We've been talking crazy stories, some of which we may or may not repeat on the pod.

Ryan: Can we talk about the donkey? No, I'm kidding.

Jeremy: Inside joke, inside joke. We'll leave it. It's an inside joke, guys, but I'm here. We'll go around and make some introductions, and then we'll get into things for you guys. Appreciate you guys being here today.

Speaker: Appreciate it. Happy to be here.

Jeremy: All right, Raj, you're first.

Rajan: Oh, introduction?

Jeremy: Yeah.

Rajan: I'm Rajan. I grew up in Virginia, building a luxury cabin retreat out there called Royal Oak Retreat. Documented the first build, went pretty viral. Now we're on to our next two builds, so hopefully we can do that pretty well.

Jeremy: Raj is going to be our resident Gen Z this weekend.

Rajan: I will. I'm the youngin' in the group here. Scorpio.

Ryan: Same birthday as me.

Jeremy: All right, we'll keep going. Kyle.

Kyle: My name is Kyle, founder and owner of Big Sky Barn House and Wild Wild Warehouse. We have 15 locations, Airbnb destinations across the Midwest and eight states. I specialize in turning old barns and abandoned warehouses into unique destinations.

Ryan: I'm Ryan. I'm the co-host of the Short Term Rental Pros podcast.

Jeremy: We're all co-hosts. Here's the four co-hosts of the [inaudible].

Ryan: And I also own and operate the luxury co-hosting company in Northeast Florida. We got about 30 homes right now under management. We pretty much just turn all our houses into experiential stays for all our guests.

Jeremy: And I'm Jeremy. I just wanted to convince these guys to come to the lake this weekend.

Ryan: Invite us to his dad's 60th birthday without telling us.

Jeremy: Allegedly, allegedly. All right, so for some context. Yeah, I need to give some context so it doesn't sound weird.

So we are going to be hosting a retreat next month, September 21st to 23rd, at the lake. And we hosted one in Joshua Tree in February. That was a lot of fun. Was it fun? Not fun?

Rajan: That was amazing. It was so much fun.

Jeremy: Our resident Gen Z thinks it was fun.

Rajan: I was the youngest person there, but it was so much fun.

Jeremy: So we were like, all right, we are going to host another one in September here at the lake. And thought it would be fun to come up ahead of it and just, I don't know, make some content, documents and things. Raj lives in Virginia. And hang out and maybe film some reels and collaborate.

Kyle: Mastermind.

Jeremy: So just asked these guys if they wanted to come, and then said, oh, yo, by the way, tomorrow we are going to my dad's 60th birthday party. So that was kind of a later. I didn't lead with that, but we are doing it.

Kyle: So I am super excited for his birthday too.

Jeremy: I am excited for you guys to experience that. But we are in one of the lake houses that I manage on this lake. I manage eight, and I have seven boats that I rent out. You were not here, Raj was not here yet, but took Kyle and Ryan on the boats when they got in, a little sunset cruise. It was beautiful. They got to see the beautiful real estate.

And now, yeah, really today's itinerary with this podcast is just to shoot the sh*t, maybe share some things that are on our mind or some things that we have learned recently. Raj and I, I am just picking on him first, not because he is the youngest. We did film a podcast seven months ago. At that time, guys, I am sorry, I have been away from the sticks, and now we are back. But I did not release it, and I am going to release it now. It is going to be ten months old, but that is going to come after this one.

So Raj, I guess they haven't heard your story. Probably heard Kyle's story a few times, and Ryan's. Kyle has a lot to update everybody with. We won't get into all of it. But Raj, I guess, first, let's get into, given you haven't shared it, would love to hear your story. You gave the two-second, or the 20-second, elevator pitch.

But Raj, I will give him a little bit of, I am not going to gas him up too much, but Raj, in my opinion, is one of the, if not the best business short-form storytellers there is out there. His content on Instagram has probably gotten, I don't know, I am just going to say 40 million, 50 million views. There is probably a number out there.

Rajan: Yeah, it is probably like 200.

Jeremy: D*mn, my bad.

Rajan: Something around there.

Jeremy: All right, sorry, last time I checked. But also, he has done a really good job of showing other people. He has taught me a thing. He has taught an old horse some new tricks. Kyle has been getting the motion as well. Ryan is about it tomorrow, we are going to get everything going there. But with that, he has also launched a very successful ground-up construction. Virginia's number one Airbnb. The most amount of footage and storytelling per square foot of any property ever. It is a joke I make, but I think that actually might be true.

Kyle: Could be.

Jeremy: It is only, what, 926 square feet?

Rajan: On paper, it is 1,004, but it is like around 150.

Jeremy: Who is counting? Yeah, something like that.

Kyle: I could not tell you the exact square footage of any property.

Jeremy: Yeah, yeah, yeah. But I guess, so give us the numbers. I like to talk numbers on this podcast. So give us the numbers on, not just the views, 200 million, whatever, who is counting, 1,004 square feet, but in terms of the numbers of the build, and then the bookings, and then I am curious about the direct booking, like the direct marketing. And that is something we will get into with Kyle, because Kyle is really good at social media. Traditionally, I will not say traditionally, but largely on that side of things, like the booking side of things.

Ryan: It is 200,000 views per square foot, by the way. Most views per square foot.

Jeremy: Most views per square foot.

Rajan: Yeah, so I graduated college in 2025, but in the middle of my senior year, I had sold shoes forever. And I bought my first real estate property when I was 21, and I wanted to get into it more. And I reconnected with my high school friend, Renzo, and he brought me a ground-up construction. He got super inspired by someone named Isaac French. Probably most people around here know.

Jeremy: He has been on the pod. Friend of the pod.

Rajan: So Isaac built seven cabins around a lake in Waco, Texas. Sold it for $7 million after his construction was two. And we decided, our thesis was, if we bring Live Oak Lake to Virginia, we can't fail. So we bought the exact same design plan, modified it to our building code. And we decided to buy two and a half acres that were subdivided into four lots. So Renzo brought me this deal with this idea, the Isaac French model on this land. And he had just pitched me, like, yo, you are the only person I know that has money. Can you help bankroll the deal? And pretty much convinced me in five minutes, because we had a 60-day clause in there that we could back out for any reason.

So, middle of my senior year, I have this two and a half acres under contract. We bought it for $37,000, put a 1% earnest money deposit down. And in two months, I learned so much about development. Didn't know what a perc test was. Didn't know anything about anything. And after talking to engineers, contractors, I, at the time, was making social media content about shoes. And then I told the internet that I got a two and a half acre lot under contract, and the guy who built the actual number one Airbnb in Virginia, he reached out to me on Instagram. This is a property we had studied. It's called Ava Shenandoah. It's an eight bedroom, or an eight, sleeps eight cabin, and did amazing numbers. Recently sold for like $2.1 million, which is one unit, which is insane. And he went to my school. So he ended up GC-ing the project.

We closed on January 10, 2025, and then we signed a $276,000 construction loan. So $37,000 for the land, $276,000 for the construction, and then we used an extra $50,000 in credit cards because we went over budget because of change orders. So all-in build was around $380,000, including the land. And now we're about to break ground on our second cabin. The bids are coming in around $450,000 to $480,000, so when it's all said and done.

Ryan: How do you decide?

Jeremy: The first one's an A-frame. And Raj has been very good at bringing everyone along for the journey, making them feel like they're a part of it, making them feel like they're the ones making decisions. I think I voted against whatever design I saw you put up for the new one. I was like, bro, what is this? Is that what you're going with? What are you going with for the second one? You're not doing the A-frame.

Rajan: Yeah, we're not doing, like, the. So what we had bought was a pre-made Den Outdoors design, which is the same thing Isaac bought. We did a custom design with Den Outdoors, which is the architecture. The great thing about social was we were able to bring the most talented people to work on the project. So Den Outdoors is one of the biggest architect firms in the short-term rental space, and they designed our own custom Royal Oak Retreat design.

So it's actually a one-story cabin. It has a lot of natural light windows. I probably have to pop a picture up to fully explain it. But we got inspired by this property called Doha House. It had a slanted roof with a lot of windows, so we took inspiration from that. And it's going to be elevated just like the first one is. So that's going to cost around, again, $450 to $480. It's going to be a little bit more pricey, but we're doing a full two-bed, two-bath now. The first one was a two-bed, one-bath. It's technically going to be a one-bed, one-bath with a loft. But yeah, this is going to be four. We saw a lot of people doing double dates at our cabin. That was a common theme. So we were like, why don't we make an actual proper two-bed, two-bath. So it's like a double-date spot.

Ryan: Do a lot of people sleep on the floor?

Rajan: No, it's two-bed, two-bath.

Ryan: No, your cabin that you have right now, you have the upstairs bedroom.

Rajan: Yeah.

Ryan: Oh, you have a downstairs bedroom, too.

Rajan: Yeah, we have a downstairs bedroom. All the massive bedrooms.

Jeremy: It's footage per square feet. I don't even know what it is.

Rajan: Yeah, yeah, yeah. So double-date is a common thing. And then, obviously, to increase revenue.

Jeremy: Oh, yeah, now I remember the video where you and your boys are tied up.

Rajan: Yeah, oh my God.

Jeremy: That was my favorite one you ever did. That was funny.

Rajan: So yeah, in terms of the revenue numbers, to date we've done like 70,000 in revenue. We've been live for seven months. I'd say right now, off the top of my head, 75% to 80% is direct, and then 20% to 25% is through Airbnb.

Jeremy: Brought to you by Hospitable Direct Bookings.

Rajan: Yes, Hospitable Direct Bookings. Shout out, Hospitable. And yeah, we did a really good job launching it. I would say, obviously, it was very uphill, and now it's like, okay, now we have to keep marketing, retargeting. So that's been a challenge. I'm really good at making videos, but the actual systems behind retargeting and reach out and funnels, I still have a lot to learn.

Ryan: Can you talk a bit about that beginning? Did you pre-launch it? How did you get that direct bookings?

Rajan: Yeah, so originally I gained a huge personal brand following, and I thought that would lead to a lot of, obviously, direct bookings, and we launched our bookings.

Jeremy: I told you that wasn't going to happen.

Rajan: Yeah, yeah, yeah.

Jeremy: I was like, bro, the people, I see the people playing basketball with Raj at the gym in Dumbo, and the people coming up to Raj saying, what's up? I don't need to give too much color as to who it is, but I just say, yeah, these aren't the people booking your property.

Rajan: Yeah, so I learned that the hard way. We were two months out from finishing construction, and we launched the bookings, and one person booked, so I was like, oh my God, what's going to happen? And we got really lucky.

Jeremy: And you got that wellness girl in there.

Rajan: Yeah.

Jeremy: She helped, right?

Rajan: Yeah, there was a girl that I went to school with who was a grade above me. She did me such a solid. She started blowing up on social media, and her boyfriend is actually a basketball YouTuber that I'd watched since I was a kid, so it was a full circle moment.

Jeremy: Nice.

Rajan: And she stayed at the cabin. We did a giveaway, and she crushed. She brought in like 15,000 to 20,000, I think it was 20,000 of direct bookings off the rip, and she stayed right after we got our CO. We just gave her three free nights, and it completely crushed. And then we did it again with another health influencer, and she started crushing, too.

Ryan: So what kind of lesson is, like, your target market of who you were doing versus who's actually staying? The avatar. I feel like I could talk on this, too, a bit about how you actually use your social media and who you partner with, where it doesn't matter if they have a million views or a million followers. It's who's your actual target market for those social media influencers. And where are they coming from?

Jeremy: Yeah. She's a girl from D.C., right?

Rajan: Exactly, yeah. It's got to be a hyper-localized audience. And then I also wanted to get, for the future now, when we're going to do it in the fall, wanted to get a girl that's worked with a property that's near us as well that's converted. So there's another girl that's going to be there in the pipeline for fall bookings. But yeah, that's what I realized.

It's also probably a question everyone here has. The influencer marketing definitely works, but it's uptick for three months, and then it's down. It doesn't seem like the most sustainable model over two, three years. I'm not sure.

Jeremy: Well, also, and then what Kyle can touch on, this is something Kyle and I were talking about, like year-over-year pacing. So that's why, when you're the first year, you don't have any track record or history.

Kyle: And your calendar is open, too.

Jeremy: So it's all from scratch. But then after year two, year three, you can look and be like, oh, last year I got this many bookings this month. And then, wait, this year I'm not getting those bookings. What's going on? And, well, yeah, when you have influencer marketing, how do you, because let's say you go viral or a barn goes viral, but the calendar is already booked for the next year. Well, okay, people can't book it then, you know? So it's like, how do you time things?

And I guess maybe we'll, as Raj is launching number two, Kyle is launching, or in the process of, number what, 15?

Kyle: Just launched 15.

Jeremy: Okay, 16.

Kyle: 16 soon, yeah.

Jeremy: So yeah, since you've been on the pod last, give your update. And then maybe that's something to kind of dive in today, is like, how do you.

Ryan: Social media push, yeah.

Jeremy: Yeah, or like, is there, and I feel like it's something that there is no, there's no, you can't look online right now and there's no exact answer on how to do it and when to do it. And it's something that I think we're all trying to figure out, or kind of in the front of that wave.

Ryan: Yeah, especially in the world of fees nowadays, too, where every Facebook group is like, f*ck Airbnb, they charge 50.5%. I sometimes go into those, too. It's like, well, you're still getting booked, and if you are managing it correctly and you do upcharge on your fees, you're not really in a bad position. They still do a lot of work for us as well, too, and help out.

Jeremy: But I think it's somewhat consistent. Like, the number of people looking on Airbnb, the houses that I have that are just pure Airbnb traffic, the trends between the years are very similar. I mean, yes, maybe a specific market has more supply and demand, but the number of views the listings are getting, whereas when it's based off viral social media, it's just like the tsunami comes, and it comes, and you're ready or you're not ready. It's hard to know when that earthquake's going to hit.

Ryan: Yeah. In terms of context of where those houses are as well, too, obviously all mine are in a vacation market. Like, people are coming down for you guys.

Jeremy: Well, I mean, I guess we'll pass this off to Kyle, like how important it is for you considering the fact that a lot of your houses are not in high traffic areas.

Kyle: Yeah. The most recent one that we did is in a 300-person town in Lacona, Iowa.

Jeremy: Any donkeys?

Kyle: No donkeys. No donkeys in Iowa.

Ryan: No more donkeys.

Kyle: No. No more donkeys in Iowa. There was a few.

Our strategy is a little bit different. We don't go to major vacation destination markets, but we go against the grain a bit and go to towns less than 1,000 people outside of major metros, and set up unique destinations that don't exist not only in that town but anywhere. And social media has had a huge impact on our business and our success today. For Big Sky Barn House largely, we have 14 of them, and we just launched our new brand, Wild Wild Warehouse, our sister brand of Big Sky Barn House. And I think we did over 15 million views on the warehouse that we just launched in Lacona, Iowa.

Jeremy: Wow. So many views per square feet.

Rajan: Not 200,000 per square foot.

Ryan: That's crazy. That's like one view per square feet for that house.

Kyle: We have 8,000 square feet there, so I'm still catching up on the views. Still catching up on the views per square foot in Lacona.

But yeah, we took this 8,000 square foot abandoned warehouse and turned it into a really unique destination in the middle of nowhere Iowa cornfields. And we don't rely on social media, but we use it as a tool. Every launch that we've had, when I'm under contracting a property and I'm there with the realtor, we're envisioning, like, how can we not just go viral, but how can we position this on social, because we use social media as an OTA. So we're using Instagram, TikTok, and Facebook as one of our OTA channels. So when we're sitting there and we're looking at these abandoned commercial spaces, like old dairy barns and vacant warehouses, and there's just massive square footage that are completely vacant, how can we turn this into a viral destination in the middle of nowhere? It's a really big challenge, but that's what makes it exciting, and that's what turns it into the success that it is today.

Lacona, for example, we launched it eight weeks ago to the date on June 5th, and we're just shy of $300,000 in gross revenue booked since we launched, which is the most successful launch we've had to date. And a lot of that is because of the social media that we've done on it. And Raj has done an awesome job. He came out, hung out with us in Lacona for a few days, helped us capture the story and really just show how unique the property is.

I mean, we have a three-bedroom, two-bathroom house component of it that's kind of like your traditional house, and that's about 1,000 square feet. And then we have about 7,000 square feet of a warehouse that was gravel floors, not insulated, no ceilings, just joists in the ceilings. And we turned it into an indoor party pool room with a volleyball net, full court sports stadium that has indoor soccer field, basketball, toss and touchdown. Next to that, in the other quadrant, we have a commercial playground with an infinity mini-golf loop around it, and then next to that in the same warehouse space we have a karaoke bar and stage. Just completely immersed in artwork and murals, and really tying it into the cowboy versus alien theme. And you don't find that anywhere. I always say our strategy is like, if you build it they will come.

Ryan: I remember you were saying another strategy too was, when I was speaking to you when you're first making it, was you're building the virality where these influencers also want to work with you, because it's a win-win situation as well too, versus a lot of people I feel like have that conversation of, like, how much you pay these influencers, how does that go?

Kyle: But we get a lot of inbound influencer reach because we're creating these content factories, content playgrounds, where they can come in and they know they're gonna go viral because of the way we set them up. Steve Swope, Courtney Swope, you guys are the best. Some of the best in the industry, Swope Family Adventures. They do an awesome job. They're one of the first travel influencers we've worked with.

But yeah, the warehouse is a really unique place, and I feel like it's been set up to be a place for, if you think about Disney, right? I always say this to people when they ask about the company. Disney wasn't Disney before Disney became Disney, and then now they're Disney, you know. And Orlando was nothing before Disney came in and they made Disney. Orlando was a no-name town. And look at them today, how many tens of millions of people come to visit Disney every year. So next thing you guys know, Lacona might be Disney one day.

Jeremy: We got to get our views per square foot up first. Who had more fun in Iowa, Raj or Dylan?

Kyle: That's a close call.

Rajan: I think Dylan. If you're listening, I think you had more fun.

Kyle: Yeah, we have a good time. We have a good time setting them up. We love hosting families that also have good times at our places.

Jeremy: No one has a better time than Dylan though.

Kyle: Yeah, for sure. Dylan's our operations manager. He does a phenomenal job running the business.

Jeremy: If you guys listened last episode, we had Kyle on. I think I remember, I think we were live and talking about how Kyle had manually linked multiple PriceLabs to three different booking channels, VRBO, Airbnb, and. And I was like, bro, what?

Kyle: Yeah, you turned white in the face when I told you that I was.

Jeremy: How are you doing this? Like, no PMS. So since then, Kyle's been a madman and doubled or tripled or whatever. So yeah, tell, I guess, what was the conversation, or I guess how have the ops been built out as you're doing these 14, 15 properties in different places with different amenities? Talk us through the ops.

Kyle: Yeah, I've focused very heavily from the beginning, from one through ten, on just the experience, the acquisition, the location, the design, and just the build-outs and the marketing and revenue generation. That's what I've focused on heavily. So then we got to about ten locations and I was doing everything myself. Had no other staff, no VAs, no partners. I was doing everything myself. I remember I called you one day.

Jeremy: We did, yeah, we did, on the two properties I'm a partner on. I tried to give some assistance. The other eight were struggling though.

Kyle: And I remember calling you and I was like, I'm breaking down. I need help. I need help.

Jeremy: Cracks in the armor showing.

Kyle: And yeah, we ended up working with a referral of Jeremy's, and brought on a head of operations and brought in some VAs, and really streamlined our operational excellence. And allowed me to kind of free up my time and focus on what I'm good at and what I like doing and what I'm best at doing, and brought in someone who is really good at operational excellence and built some systems out. It's been the biggest unlock for the business though.

Ryan: For, like, I guess big question would be, [inaudible]. But so I guess my question was to you, like, do you feel like you would have benefited from doing it earlier? Or was it the right timing for it all? Like, what?

Kyle: Absolutely. Yeah. Yeah, it was the right time. It was the exact right time. I mean, I would say it was the right time, I would say we were probably past the right time. I would say probably at, what, six, seven properties was probably the right time, and then we scaled past that and started to see some growing pains. And when we got to ten, it was like, if we want to keep growing and get to 15, 20 plus, there were changes that needed to be made to make sure that we were growing the right way, and we couldn't fix some of the things internally.

Ryan: I guess for, like, the viewers, deep diving into it a little bit, what were those pains that people should be looking for before they hit?

Kyle: I mean, the sheer amount of just messaging.

Jeremy: Yeah, I mean, inquiries.

Kyle: Inquiries about, you know, people that are looking to stay, after they've booked and they have an upcoming stay, people that are at the property and they're staying with you, post checkout and they left something. Just sheer amount of messages in any given day. It wasn't five or ten messages a day anymore. It was 50, 80, 100 messages a day, which is, it becomes a lot.

Jeremy: It's a lot of them.

Kyle: And that's just one component of it.

Jeremy: I would say, well, the point where I knew you definitely needed some reinforcement, because I, well, that was before. I don't know exactly where that was on the sphere of things. But yeah, the properties I was a partner on, I could see the messages. I knew what was going on, and my VAs would help with those. I think I had visibility, in other words.

And he goes and sets up these places and he lives in a trailer, sleeps on the floor, and puts his heart and soul into the property, and it shows. They're very creative. And shout out Eric Harrold, he's amazing as well. And then you really, you put your heart, I mean, I'll say you put your heart and soul into this place, and then a guest is gonna come at you and send you a two paragraph message complaining about this little of this and that. And you're just like, you don't even know how much effort I put into this and you're gonna complain about all this crap.

Well, I don't want you, I don't want you at our product, like, you know. [inaudible] Your reaction, your responses to them. A few times I saw the messages where it wasn't quite the, you know, oh, I'm so sorry. The people that are in the audience are like, you know, I'm so sorry, oh I'm so sorry that the bed wasn't tucked the perfect way and you found one hair on it. You know, it's a little bit. I don't need to say what he said.

Kyle: Everyone had their strong suits, you know. Yeah, I mean, I think you have to focus on the things that you're good at and you like, and hire out the things that.

Jeremy: I think that was burning out though.

Kyle: It was long messages, and you could just, like, everything. I'm just finding seven little things that were like that.

Jeremy: Those were like, I could tell, like talking to you, you're like, yeah, I'm just getting those messages. I just can't, dude.

Ryan: I feel you. For me, it was like when you start seeing the messages of people that are trying to get a refund for nothing. You could tell that they're starting to nitpick things left, right, and center for it. And they don't see the grand picture of what I actually did. You're like, why are you focusing? That's when I knew too. I was like, I need to, that was like at five properties. No, I was already like, I don't want to do this. I'm good.

So shout out to anybody's trying to do this business, like it is not just set it and forget it. I mean, Raj, I feel like you probably figured that out fast too, now even with one property. Like, where are you at with partnerships and everything as well too, since we're on that topic?

Rajan: Yeah, I mean, so on the operation side, I still manage it. We're too small for it to make sense for me to pay someone. Our top line isn't big enough for me to pay out 20%. And I think property is freaking easy.

Jeremy: Why are we saying property is not great? I do one property with your eyes closed.

Rajan: Yeah, it's not hard at all. I guess on the operation side, partnerships, we have a massage therapist that comes up. So that's an upsell, which is sick. We basically copied Isaac, so we have like a romance and like a birthday package, and streamlined those. Just ordered petals and cakes off of Amazon and wine bottles.

Jeremy: You're selling love.

Rajan: We're selling love, essentially. Yeah. Yeah, I think that's pretty much it on the partnerships.

I guess, hitting back on what Kyle, like our original question about social media and knowing when to time it. I think actually a good answer to why social media is so important is because creating a brand, I feel like, gives you such a premium to sell eventually.

Jeremy: It's kind of a quick, quick, don't mean to cut you off, and I was actually thinking about this earlier. I mean, we all met on social media, right?

Ryan: Yeah, all of us.

Jeremy: That's a huge part too. Like, we all listen to this pod. Yeah, I guess Kyle actually did listen to the pod and hit me up through the pod, right?

Kyle: Yeah, I listened to like every single one of your podcast episodes like two or three times over, and I formed my buy box and strategy off of Jeremy's knowledge of the industry, just from the free knowledge you were dropping on your podcast and just everywhere that you were posting. And I set up the first one without talking to you, and after it blew up.

Jeremy: Right before you watched it. It was right before or like during, I remember. And I remember I thought, cool. Yes, the lender though. Some lender hit me up, and he'd be like, yo, someone [inaudible]. Because, you know, whatever, he's listed on BNBCalc. I'm talking to Brian. Yeah, he hit, someone is buying this place, and I just want it. He just wanted to send it to me. Yeah, he just wanted to send it to me, and I saw it and I was like, holy sh*t. Like this is it. This is like a check. You could probably see the BNBCalc pro forma.

Kyle: Oh yeah, I may have looked at that. At that time, go in and look at that. But I definitely ran a few pro formas on BNBCalc before I bought it.

Jeremy: Yeah, I think Kyle messaged me about it. I was like, yo, I know this, we got to get on the phone, I've seen this house before. And then he told me his plan, and I was like, yeah, this, I mean, yeah.

Kyle: I remember sending you a Facebook message and I was like, I know we don't know each other, but I feel like I know you really well already. Like I feel like we're buddies already. And I was like, I've created my entire buy box and strategy off of all the free knowledge you've dropped.

Jeremy: You took it to like another, it's like I'm speaking in like hypotheticals, if you do this, if you do this.

Kyle: And I'll sleep on it for one night. I woke up and I was like, all right, I'm doing it.

Jeremy: Did you ever listen to the pod?

Rajan: No. Maybe a little bit.

Jeremy: But you guys will be on the couch next week.

Ryan: We're on a couch right now.

Rajan: It was mostly your social media. I was actually looking at, like, Robuilt for a while. That was who first brought me into the short-term industry, and then I almost went with his coaching program, and I have no idea how I ended up on yours, and then met up with Blake and you guys, and I was like, guys my age. And for me, it was more like I just wanted somebody that was gonna give me kind of like just a stamp of approval, and I also was just looking for a community. And there's so many of them, there are like five hundred to a thousand people, and you guys were just like, we're just a small knit group of dudes.

Jeremy: Just kind of. All right, so for our operations round circle. Raj, it's pretty easy. Kyle, it's, I feel like it's cool when you've, sure, I've done things like myself, but also seen other people go through their progression from, you know, Ryan from zero to 31 properties, Kyle from zero to 27 million square feet, Raj, well, one, but you know you're doing other things as well.

And one thing with operations, it's like I kind of have foresight. I guess that's what happens when you do things. Like with Kyle, I'm like, yeah, I know you're gonna hit a certain point where you're not gonna want to do more. You're gonna be like, all right, I actually don't want another property, because if I do another property it's gonna be more headaches. And then you brought in Dylan. Dylan's not on this couch. I did live in the same room as Dylan. I don't know why I had to bring that up there, but he was my roommate, so shout out Dylan. We tried to build the wall, it fell down.

But you brought Dylan in and it's like, all right, that problem goes away. But now it's like, all right, you're free to do whatever. No, it's like, Dylan, this is your problem. You might hit a point where it becomes a little troublesome, or, you know, a lot of different houses in different places.

Kyle: It is difficult, because at least for my portfolio there's 15 properties across eight states, and there's only, like, what, there's two cleaners that have, like one cleaner has three properties, and one in Wisconsin, they have four properties. But all the other ones are satellite locations, and it's difficult when you don't have streamlined operations where you have a lot of cleaning crews in the same areas. It's also rural.

Jeremy: So there's just like not, it's like for me, I have urban and rural markets, and my urban markets I can fire my cleaning crew that day and I'll have somebody there the next day. I might not know that they're like perfect, but I will be able to get someone over the next day. Whereas I'm a property, well, I don't want to say, because then these cleaners might like hold me ransom.

Like for some of my, or I have a property, you know what, I have a property in Western North Carolina where I did have a cleaner before who was pretty bad. But [inaudible] just say, we do have new cleaners now and we've been with them for years and they're great, and husband and wife crew, and they make it so we can keep the house. But in rural areas, it's definitely like that. I feel like that component, one, like not having scale.

But that being said, I do think there are ways, and I've talked to Dylan about things you can do proactively. And I think maybe I'll pull this into like Ryan and to Florida, but like proactive maintenance. I mean, 90% of the issues you deal with with guests is when a guest shows up and the toilet's broken and the HVAC is not working. And obviously you're not going to catch everything, and guests are gonna do stupid stuff and they're gonna break things. But I would say like 60 to 70 percent of the issues you can actually catch before they happen.

So, you know, I'm telling Dylan, for example, all right, yeah, there's gonna be times 11 p.m. on a Friday where there's gonna be some specialized issue that comes where you're not going to be able to get that specific vendor there that night. However, what can you do? Well, you can block the houses twice a year, and you do have centralized crews and you can have them come for three, four days and tighten all the furniture and touch up paint all the walls. You can change out all the carpets for LVP. You can have an HVAC vendor come twice a year and check out all the HVACs. Like, we're having issues at our partner property in Kentucky with HVAC.

Kyle: Struck by lightning.

Jeremy: Yeah, it got split, but it had an issue where it didn't have, what's it called, ground fault thing? So, okay, if we had an HVAC person come in March and they said, oh, by the way, it doesn't have a ground fault thing, we wouldn't have had to do $5,000 of refunds and get window units and make Dylan's life a little bit, well, we like to make Dylan's life a little hard. But the point is, we could have caught that before it happened. So it's like, try it, you know, when you're.

Ryan: Yeah, just preventative maintenance.

Kyle: I don't like, add on that, but I was actually talking to this guy, I met him on Facebook too. He was asking me questions about like, how do you find good cleaners? What questions do you have for them? And I told him, I've been through like eight cleaning crews now, and one of the main things I said to him was, just because they clean well, but if they're not also your eyes and ears and maintenance people, they still have to go. They can't just be good cleaners if things are broken and they miss those too. They have to be able to also communicate and follow the process that you have in place.

And then the second thing that I told him was, you can find cleaners that are what I call hotel grade cleaners that are coming to you with the process. When you're first getting started, maybe you have the time to actually teach somebody, but by the time I got to like 20 locations, I didn't have time to sit down with cleaning crews and teach them how to do the level of clean. I didn't have time to tell them like, you need four f*cking pillows on the bed for every single bed. Like if you don't know that, I just can't work with you. And then I found, thankfully, for rural areas there are people that actually do understand it, and this industry's been around long enough that you just have to go find those professionals that get it.

Ryan: So it's like finding that crew. Obviously we do bi-monthly maintenance for all our houses, where we have a handyman that walks through and does the home inspections, like does the fridge work? Does the dishwasher work? Let's switch out the HVAC ventilations and all that kind of stuff. But then the other end is, if the cleaners aren't letting us know that there's damages at the houses after people go, our owners are gonna give a sht and they're gonna be pssed. So they also have to go if they can't do that.

Kyle: Okay, you are in a market where, I guess, Virginia. Is there, obviously not the state of Virginia, but in your market, is there depth? Is there a roster of cleaners, so to speak?

Rajan: No, we don't have like a big roster of cleaners. We had an issue with our cleaner, put out bids on Turno, but we only have one cleaner right now.

Ryan: [inaudible] around that, you know, you might just have to maneuver where your maintenance guy does come by every month to go check on it instead of like a bi-monthly, to make sure that the cleaners are doing their stuff, but. Or you have someone do an inspection check who's like not a cleaner. You just have, you know, the neighbor. Which you could find on like TaskRabbit too even, and stuff like that as well, where they come by $20, $25 and just follow a checklist to just walk in after them. You just add it into your cleaning fee, which is possible as well too.

Jeremy: Operations are what keep you in the game.

Ryan: It comes from you going insane, that's for sure, so.

Jeremy: Yeah, so with that, well, I guess topic. I guess this is top of mind for me right now. But yeah, two things. One, when you've been, it's kind of weird to be like, oh, I've been at this game like a long time, but I guess in the grand scheme of things, you know, somewhat of an infant industry. But I've been, you know, six, seven years. So you can see like year over year trends, things happening in your portfolio, other portfolios. And that boils down into like, how do you improve assets over time? Like, you know, you buy something in 2020, what are you doing with it in 2025?

I'm not gonna go through the story of this house, but this is actually a house that we bought, we've sold, but I'm still managing it. But I really think the owner should improve it. Like I'm staying at the house and I'm looking around, I'm like, oh, there's so many ways to improve it. Like not just make it a more valuable house, market it, but then it's also like, how do you price product? I think a lot of people just set prices on Airbnb or set prices on PriceLabs, and then they just come back five years later.

And right now I'm working with Kyle, is figuring out how do you price these things? How do you price them if these things get like a big jump off the bat from virality? How do you price them on day one? And then do you price them the same on day one that you do on day 400? Like for example, Lacona came off the bat, got $300,000 of bookings. If it was priced differently, would that be 360? Or maybe it would be 200, but it'd be 200 at higher rates.

I'm really speaking gibberish and nonsense right now, it is midnight, but pull this all in, three things you gotta think about. Setting up the properties well is obviously important on the front end. Second, operating them well is what keeps you in the game. But I would say operating them and pricing them is what keeps you in the game for a long time, not just a good time.

Rajan: I think a fourth thing for like me and Kyle specifically is creating a brand. So like, I want to exit eventually. The goal is to, not exactly sure yet, but to have Royal Oak Retreats outside of major metropolitan cities outside of America. And Isaac French talks about this extensively, but the reason he sold Live Oak Lake was because he had a brand and he got a premium for that brand. And obviously Kyle has Big Sky Barn House and Wild Wild Warehouse, and he's creating a brand through social media. And obviously we love Airbnb and Airbnb is great, but eventually.

Ryan: That sounds like you love it too much.

Rajan: Well, if you want to sell the portfolio at a premium, I feel like the fourth thing you have to do, especially if you own the asset, is create a brand.

Jeremy: And what percentage direct are you on bookings right now?

Rajan: Right now it's like 75%. Originally it was like 90, but it's gone down, I will say. That's why I will say the viral thing is like a swing for us personally. Like even when I first came out to Iowa, even four weeks ago, we've only gotten Airbnb bookings since then. None have been direct. So that number's going down. The direct bookings are going down, and the Airbnb stuff is kind of consistent.

Ryan: I mean, I speak to some owners about that. I was talking with like the VRBO versus Airbnb bookings themselves. And it's like, I try and hope that our listings do get Airbnb. Obviously I'm not really doing much direct until we do like remarketing campaigns. The past guest is our big thing. But you're hoping Airbnb takes off before VRBO does, because if the calendar gets blocked from VRBO, then Airbnb's just going to deem you as a sh*tty listing. And then you're kind of fighting your way back up.

Jeremy: I want to talk about that for a second, because you played that down. Like, we're only at 75% direct. And you launched Live Oak, or Live Oak Lake, you launched Royal Oak, [inaudible], you launched Royal Oak Retreat how many months ago?

Rajan: We launched in end of December.

Jeremy: And you started at 90% direct, and you're about 75%. That is crazy.

Ryan: Yeah, it's amazing.

Jeremy: Even 75% direct in a year of infancy is insane. Like that is insanity.

Kyle: It's crazy. Like three out of every four bookings are through your website. That's like, we launched our direct booking website one year ago, a little over a year ago, and we're at.

Jeremy: I'm pushing the reels to Airbnb. I was like, Airbnb must love you.

Kyle: We're at 35% direct bookings. And we do a little bit of, we direct some of the social media to Airbnb so that we can rank on page number one.

Jeremy: Yeah.

Kyle: And then we direct it back to our website. It's kind of a game you gotta play. We want to get to just 50% direct. That's our goal right now, and we're at 35. But like 75%, 75 to 90% where you're fluctuating between, is a crazy thing to be at, like in year one. That's insane.

Rajan: I'm wondering, like, yeah, my point is, I'm wondering like in year two if that number drops to like 35%. Because now we're starting to take off on Airbnb finally, which I guess I didn't even know about when we had first started. We had all these direct bookings, and we were not cooking on Airbnb at all.

Jeremy: Well, it's because your calendar. If your calendar is blocked on Airbnb, they're not going to show you.

Rajan: Exactly, yeah, yeah, yeah.

Jeremy: Like Airbnb wants you, like I'm part of some program. Are you part of the program where they're literally like, open up your calendar more, and we'll give you a bonus?

Ryan: Yeah, yeah, I get like an account manager sometimes that hits you up, and you're like, your prices are off here and there, so.

Jeremy: I got a $1,000 bonus in July just because I essentially, quote unquote, opened up my calendar, like to the point they wanted my calendar open to, which I didn't even, I didn't do anything. But that's what they, like, because they don't see that you got a VRBO booking. They just see a block. They don't see a direct booking. They see a block. So to them, you might just be staying there, which, if you're living in this house, they don't want to show it to a guest, you know? They want a big, fat, empty calendar to show to people.

Ryan: So it is, I mean, it probably wasn't even a bad idea that you were directing it at the beginning too, because it just is longevity to keep it going.

Jeremy: It's also convert, I mean, it's focus, I think. And Kyle and I talked about this. Airbnb converts very well. They are focused on having a highly converting website. So if you're focused on the creative and finding and launching new properties, let them focus on, again, over time you should fill in the gaps, but it makes sense to let them focus on converting. Let Dylan focus on operations.

Ryan: But at the same time, you'll never get your 100% occupancy, 90% occupancy and having it direct from Airbnb. It's always a work your way up, where when you're doing it pre-launch is like nonetheless still fantastic. Like to me, honestly, I'd pre-launch it, just try to get direct, wait six months and then launch it on Airbnb after that. Kind of for the next model. So it's like, if you don't need Airbnb, if you already know you're pulling in those bookings because of your pre-launch, then it's like, just don't even launch.

Like, so for example, I signed a contract with a guy for a condo, but then I got a direct booking for six months right away. My listing is not live on Airbnb. So I'm waiting until like a month before.

Jeremy: Airbnb is gonna be like, well, what's going on here? Like, why would you be like, this isn't real? Because it's like, they promote you as soon as you're live.

Ryan: So it could be a nice like trial and error model for the next one. It's like, hey, maybe we just try direct for the first like four months, see how that calendar goes. Only go live there and then, you know, open it up to Airbnb if the continuation kind of drops.

Rajan: Yeah, that makes sense. I'd say like most, like all of our, pretty much all of our August bookings are Airbnb and September are Airbnb.

Jeremy: And you both capture like all the info. Like, are you guys using, I guess we'll plug, what's it called? The one, like the Wi-Fi connector?

Kyle: StayFi.

Jeremy: Yeah, are you guys? Shout out Arthur, friend of the pod. Yeah, and like doing the remarketing stuff?

Rajan: Yeah, I haven't done that. We haven't done a ton of, there's tons of gaps we still have to fill.

Jeremy: Yeah.

Kyle: Yeah, we've implemented StayFi at all of our locations over the last six months. And we've more than doubled our email list. We're at about 20,000 email subscribers now since implementing StayFi at all of our locations.

Jeremy: Which, if you're not familiar with StayFi, it's a great device where if someone, it's like Marriott, right? You go to a hotel, you wanna get on Wi-Fi, you gotta give your phone number, your email, you get free Wi-Fi. It's the same thing for like an Airbnb. Which, if you don't have that and you have an Airbnb booking, you maybe can get the phone number and email address of the one booker. But what about the other 29 people? Who are they? And how can you remarket and target them on an ongoing basis?

Kyle: That has substantially grown our remarketing efforts and our email list from like the last six months.

Jeremy: Do you use their, what do they have, like a white label, go high level or something?

Kyle: I mean, they have a lot of options you can do. They have splash pages, you can sell services.

Jeremy: But they have some CRM that's like you can use with them.

Kyle: Yeah, it's a native CRM.

Jeremy: Are you sending like automated emails out?

Kyle: Automated, no. We have an email campaign manager that does twice a month emails, yeah.

Jeremy: But yeah, you said, well, I'm curious to see what those emails are. Like, is it?

Kyle: You don't subscribe?

Jeremy: I haven't got, I mean, maybe I do. Maybe it's hitting my spam, I don't know. [inaudible] this email manager. Well, I don't know, I guess I haven't stayed. I haven't put my email in and I haven't gotten the wifi.

Kyle: Hey, you guys. Yeah, we gotta get Jeremy subscribed to the email subscription. We gotta get you on it.

Jeremy: Next retreat we're gonna do in either Wisconsin or Kentucky. This time we're doing North Carolina, but then everyone's getting on the wifi.

Kyle: Beware.

Jeremy: Next thing and then you're getting two emails a month. What are these emails? What are they? Is it like 20% off discounts? What are we talking?

Kyle: We do some winter and fall and like shoulder season discounts and like new property launches. We're always pushing those. And then just properties that have vacancies, we usually push those as well.

Jeremy: Yeah, need some love, yep.

Kyle: Not gonna call any names. There's a few.

Jeremy: There's always a few though. You're always gonna have a ranking. Yeah, well, it's on you to figure out why. What's going on here? Why is one doing well?

And also I think it's cool with Kyle's portfolio is you can see like, all right, these five are doing extremely well. Oh, all five of them share something in common. Like, oh, maybe that's it. I'm not gonna tell you guys all the secrets right now, but I'm just kidding. We have some ideas. But like when you have like 15 amenities per property and they share three of them, you're like, are these amenities what are drawing traffic?

All right, any guys, well, anything? I think we've got a few yawns here. We're past the midnight. Raj, where can they find you?

Rajan: chida.rajan, C-H-I-D-A dot R-A-J-A-N on all socials. Royal Oak Retreat, also on all socials.

Jeremy: Kyle?

Kyle: Yep, Big Sky Barn House and Wild Wild Warehouse all over social, and personal page, Kyle Miklasz, M-I-K-L-A-S-Z, like zebra.

Jeremy: And then guys, make sure we have, I think like 15 people, I mean, we're a couple months out right now, who are coming already. I think we want, I don't know, I'm trying to think what the perfect amount of people would be for this Lake Retreat. Maybe 30 people.

Ryan: Depending on how many houses you could open up.

Jeremy: Yeah, I have four of our houses booked, so I think I have 22 bedrooms. But yeah, we can probably get up to like 30 bedrooms. And I was saying bedroom because people are staying at the lake. But if you guys wanna come hang with us, make sure to, maybe I'm gonna put a link to that in the show notes, or DM me at jeremywerden on Instagram. If you're listening to this after September 21st, 23rd, we'll do something fun in the future. So stay tuned, the show will go on. And join our co-hosting program. DM Ryan for a good time.

Ryan: Yeah, and reach out to us if you have any questions about starting property management or social media, anything, short-term rentals, what we're here for.

Jeremy: Beautiful, and with that, stay tuned to the next episode of the Short-Term Rental Pros Podcast.