How Ruben Kanya lands 12-month insurance placements

Quick Summary

Ruben's case for insurance placements is that one contract can book months of income at once, while a short-term calendar swings with the season. Jeremy pushes back, since he won't hand a peak month that does $20,000 or $30,000 to a 30-day guest.

Neither of them says you have to choose. Ruben keeps two listings on every property and caps the short-term calendar at 30 days out, so a long booking still has room to land. Before you commit to either model, check how seasonal your own market actually runs on BNBCalc's market data.

Key Points

• The two of them argue the tradeoff out on air. Jeremy won't give up a peak month on a lake house that can do $20,000 or $30,000, yet from January through March, when that same house does $2,000 short-term, he'd rather take $3,300 or $3,500 for a longer stay. His less seasonal houses peak nearer $17,000 or $18,000.
• The claim decides the stay. Ruben says water damage puts a family out for roughly three to five months and fire for six to eight, though the relocation company usually opens with a one month inquiry and extends from there so it doesn't overshoot its budget.
• He runs the arithmetic on why an open property is rarer than it looks. Search a market and you might see 100 properties, then 40 once you add pet friendly, then seven that are actually free for the next three months. Four of those seven are sitting empty for a reason, which leaves three real options.
• Pet friendly isn't optional in this niche. Ruben says you cut your chances by more than 50% without it, and Jeremy backs it from the management side, describing a February when his market ran 18% occupancy and every house that did get booked had pets allowed.
• Every property he runs carries two listings, one short-term and one mid-term. The mid-term one stays wide open for the next six to eight months, while PriceLabs pushes the short-term rate up sharply past 30 days so nobody locks up his May back in February. He ties that 30 days to his own market's lead time, so a market booking 60 days out would need a different number.
• A two or three week hole is worth holding, because relocation companies aren't shopping for it. Jeremy tells his own version, where he set a base rate high enough that nobody would book, sat through a week and a half of nothing, and then took a two and a half month booking.
• About 90% of his bookings come straight from the relationship rather than from a listing, and he says you have to ask for it. He tells the relocation specialist what he can supply, asks whether calling, texting or email works best, and before naming his own price he asks what the family has been approved for, on the principle that whoever states a number first loses.

Full Transcript

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Jeremy: We are live with the Short-Term Rental Pros podcast. I'm here today with my good friend, Ruben, who I just realized no longer lives in New York City. Because I was saying, oh, maybe we do this in person. But he informed me that he actually recently moved to Boston, Massachusetts. So he is now a Ma**hole. We'll get into what that means a little bit later.

But Ruben is the guy when it comes to medium-term rentals. What I mean by that is getting your property booked, not for 1 day, 2 days, 3 days, but 30 plus. So he is predominantly focused on not 2-3 year leases, but rather 2-3 months, 6 months, and has created a really, really good way. And I've heard from a bunch of people that, hey, I just got a 3-4 month booking and it's from something that Ruben recommended.

So we're going to dive into whatever Ruben recommended today and hear what are the secrets of medium-term rentals. So Ruben, first of all, give us your background, how you got into the game. And also, thank you so much for coming.

Ruben: Yeah, man. Next time, we'll have to definitely do it in the flesh. When I'm back in New York, give me an excuse to go back to my old stomping grounds. But yeah, man, it's nice. It's nice to be back here with you.

We were talking about it. We got a chance to briefly connect when we were in Nashville together, which I will say is what spearheaded a lot of the experiments. Not too many people know this, but I'll share with you today.

How I got here, I'm a big experiment guy. If you're watching this, you can see behind me, I have experiment, fail, learn, repeat. Just experimenting proof of concepts. So one of the things I had done, or what I continuously do, I was telling you, I have 260 plus episodes. I started the podcast just to educate myself on different business models.

Jeremy: Yeah, Ruben also has a podcast too beyond his medium-term rental portfolio. He talks a lot.

Ruben: I listen. I listen. That's the beauty of it. Today, I'm on the other side. Today, I'm talking the talk, but usually I'm listening and that's my hack.

I think, aside from all this, one of the best hacks that you can have is getting access. I'm a huge believer of not doing the paradox of practice, is what I call it. Paradox of practice is when you follow people who are just talking the talk but not walking the walk. So I like to surround myself and be in proximity to those who are doing what I want to do.

The podcast is a tool where everyone feels flattered. Originally, I had pushback. Many of you might have pushback. Maybe you're listening to this. I'm like, man, I didn't own a piece of real estate before I started The Real Estate Experiment. That was a long time ago. So I was like, who am I to interview someone about real estate when I didn't own real estate myself?

But at the same time, that was the very thing that literally helped me skyrocket into the arena that I'm playing in today, because I got over this limiting belief and I was like, all right, let me just interview this guy. And I asked him, are you coming to the show? And I didn't even have a show. And he's like, yeah, sure. Lock me in. I'm like, oh, shoot. I really got to get a show together. And this guy had like 300 million assets under management.

And he never asked me once. Actually, as a matter of fact, no one's ever asked me what my portfolio looks like. And I'd be proud to share it. But it doesn't even come up. So it's just this limiting belief that you have, like, I can't do this until I have this. And so essentially, I used the vehicle to...

Jeremy: That's what you did. Fake it till you make it. And I think I want to parlay this. Well, first, I want to get into your background. For those listening, who are you? Who is Ruben? What is your real estate portfolio today?

But then also, it was funny when we were in Nashville. So we had scheduled this time to talk probably two previous times. And one of the times, I think we had it scheduled for 9am and 9am hits and Ruben's virtual assistant messages me that Ruben can't make it today. And then Nashville was the next week. So I saw him there and we were kind of joking about it. And you essentially said that the reason you couldn't make it because you had an emergency, because essentially, you had gotten like a six-month insurance rental contract.

Ruben: 12 months. 12 months, man.

Jeremy: 12 months. Sorry, I don't want to misquote. I'll give the short details and then you can fill it in. But you got like a year-long rental contract. And then you had found an apartment or a house after you had got this contract. And you literally had it scheduled. So the day you're supposed to start the lease at this house, the insurance renters were supposed to move in.

And then you got hit with a little bit of a dilemma or an issue where the person who represented the property to you was kind of flaky and had some BS behind it. So in that case, you kind of faked it till you make it. But you were dealing with someone else who maybe faked it till they make it too. And everybody was faking it a little too much. And then what happened?

Okay, first of all, let's step back for a second. What do you do? And then tell us about that story.

Ruben: Okay, cool. Yeah, I'll definitely stop. So I'll take some notes here because there's a few things that I definitely want to clarify on the whole thing where you said about faking it till you're making it.

So who am I? My background is, I guess, growing up, I was a student athlete. I think one of the biggest blessings that I had was I truly believe being a student athlete gave me a lot of that discipline and grit.

And at the same time, I was blessed because when I went to college, I'll start there, I was the only basketball player, I played basketball, that was not roomed with another basketball player by mistake. And my best friends, they're both twins, were not basketball players, where I had like a four-striple as well. And my coach was like, you want me to change it and fix the error? I'm like, no. It was the best decision or best mistake or by laws that say that would have happened, because they ended up being entrepreneurs.

So for me, I had the drive, I had the work ethic, and they had the vehicle. They showed me very early, I was like, hey, we're doing digital marketing, we're doing ads, we're doing this. They actually ended up exiting their business before we graduated, their first business.

So that introduced to me a side of curiosity, because when people say what I do, I don't really associate myself with what... I think people typically go to careers. I like to go based on how I identify myself, and I identify myself as a curious person who always wants to learn more.

And so that ended up opening up a door of entrepreneurship for me, because the only thing that I had... I wish I was the guy who sold lemonades then when he was young, etc. I don't have that story. And I think it sounds nice, I don't have it. I never sold candy, I never had that hustle. I was a good student, I was getting grades, I was a student athlete, that's it. And I worked hard for it.

I wasn't naturally smart, I had to work, bust my tail off every time to get the same results that some people get. I'd be like, well, I only studied for an hour. So I was always curious. I'm like, how can I get more?

That opened up when I was in college, started doing personal training, got a taste of that. Then when I started personal training, I ended up training a lot of athletes, a lot of professors, etc. I was like the go-to guy on campus. I was like, I kind of like that. I can control my own schedule around my academics. And then I started to create programs from it. You can still go on YouTube, check it out. It's called RubenFit Kanya. That's when I got my reps. You talk about 260 plus episodes. For me, it's like flexing on muscle reps.

Then fast forward, I went down the route of I was going to become a chiropractor, create my own practice, own a bunch of different, etc. And I ended up going a different route. Consulting opened up. I was always a great listener. So I ended up asking people questions for a living as to how, why they're doing things, the way they're doing it, etc.

A lot of my background comes from learning how to leverage VAs because I did that on the digital marketing side, because I ended up partnering with my partners from college. We had an e-commerce business. So then I took all those experiments from consulting and listening to creating systems. And then I created a few different businesses. One was e-commerce business. We didn't exit the way we wanted to, but I learned very quickly what the difference is between gross revenue and profit. But I learned a lot, Facebook ads, etc.

And then fast forward today, while I still consult clients, I ended up falling into the short-term rental space. But the reason why I started off the interview by talking about how I got there is because the podcast is what actually ended up getting me closer to real estate.

I listen to Bigger Pockets all the time. But one of the things of how I got here is on episode 91, I had a gentleman that came on the show by the name of Mike Sjogren who ended up being... If I actually take a step back, I had received a referral from him because I had a gentleman who came on my podcast. He loved what I was doing with my content. He said, hey, can you do this for us? And I immediately said, yes. And that's how my agency was actually born. I was not ready. I just had VAs and I knew how to build systems.

And that gentleman was an M1, shout out to Jamie. And he had a bunch of people in his mastermind that loved our work. And that's how I landed Michael Sjogren as a client, where we launched Short-Term Rental Secrets as an agency. So we were launching that podcast until he took an in-house. That's the real story.

And then on episode 91, when he came on my podcast, I'm like, this is a client of mine. Let me have him on because I interview a bunch of different real estate people. And he said, I retired my mother, I retired my wife, and I retired myself in 18 months. And I was like, what? The whole time I'm interviewing people with syndication, multifamily, storage, all that. I didn't really have the Airbnb guy until I met the Airbnb guy. So fast forward.

Jeremy: That is his thing, his username.

Ruben: That's it. And so that's how we got here by asking questions. And then fast forward, we got into Airbnb. And then when we got into Airbnb, the same relationships I made from the podcast, Planned and More Seasoned, and we get into mid-term rentals. And we haven't looked back. We're just growing our portfolio using the two models combined.

Jeremy: So, okay. So you started a podcast. So, okay. Let me just get this.

Ruben: Oh, you didn't know that?

Jeremy: Yeah. Your way into short-term rentals was starting a podcast agency, having a client who did short-term rentals, having the client on your podcast being like, whoa, this is interesting. Then you got into short-term rentals. And then from there, you got into mid-term rentals. So let's look at the dots here.

Ruben: Yeah. It's built. So I want to take a... Because this is actually going to help someone who's listening, right? Because you said something about faking it until you make it. And I actually want to correct you on that.

When I had the podcast, I wasn't faking anything. I was actually just interviewing people and getting close to the data. I was getting a masterclass, right? I wasn't going on podcasts. A lot of people go on podcasts and maybe tell their story. I'm actually trying to get the story. So I get to ask, how did you raise the capital? How did you close your first deal? How were you able to...

So basically, I'm using the podcast as a way to build a relationship, get information straight from the source, not from third party. I get to talk to the person. And then as you can see in my life, it's turning into these amazing relationships that I couldn't have fathomed, right? Landing a client. That came not from starting the agency. That came from starting a podcast, which was a limiting belief of mine. And then someone saying, can you do what you're doing for yourself for me? And then getting a bunch of referrals.

So at the end of the day, the lesson of the story is start when you're not ready because I, for the longest time, was recording episodes by myself, documenting my journey. But until I had the courage to say, you know what? Let me just interview someone I want to be like. And it doesn't matter what they think about me, because now I'm making it about myself. I'm going to make it about me. It's about them. It's about me getting the information from them and then serving community that can also benefit from that information. That was the catalyst to where I am today.

And to connect the dots, if you want to get into the mid-term rental space, you already are at an advantage if you understand the short-term rental industry, because that's the foundation that we're built on. And as a matter of fact, we run a hybrid. If I don't have a three-month contract, guess what I'm doing? I'm not sitting empty. I'm renting it as a short-term rental.

Now, I do have ways that we manipulate the listing. So I'm not exposing an open too far out so that I'm able to make sure that I'm still capitalizing on being with Atlanta contract long-term. And one of the things we specialize in is not any type of mid-term rentals. We specialize in mid-term rental insurance contracts because they're the most lucrative.

Jeremy: Got it. Okay. And actually, I'm going to just parlay that with... So I initially started with boat rentals and I did not have a master plan. And actually, initially, I didn't even have boats. So I put a website out there and I started running ads to it, just a basic landing page with a Typeform. And I ran ads to it. So when people would look up that lake and boat rentals, I'd be the first thing that popped up. And they would fill out the form saying they would want a boat.

And that gave me the constant. And essentially, people were saying, hey, we'd pay you $1,500 for five days of a boat rental. I said, okay, well, here's my Square. Can you send the money or I send an invoice? And then they'd pay for it. And I was like, okay, now I need to get a boat. So that was...

Ruben: But isn't that fascinating though? Because I think people want to plan things to be perfect instead of just what is the next step. Because when this gentleman asked me, can I do this for his agency? I'm like, yeah. I just commit.

First, if you think about it, and this is where I really resonate with what you just said, is if you think about it, it starts with a decision. That's why my mindset coach always tells me, don't try to figure out the how. Just make the decision. If you want to be an investor, make the decision right now. You don't have to have money. You don't have to have it figured out because the decision will then start to open up opportunities that you weren't even on your reticular activating system.

Or if you're a person of integrity, like I believe you and I are, you're going to have to figure it out. Because as soon as you get the $1,500 that hits your account, it's real now. You got to figure it out.

Jeremy: It wasn't like, hey, I'm going to rent you a Ferrari boat and the boat's sitting here. It was like, hey, give me this money and I promise you'll have a boat. But you have to have integrity.

Ruben: But you have to have integrity because if you have integrity, it'll force you to figure it out. I think that's the key takeaway. If you're someone with integrity, put it on yourself because you figure stuff out when your back's against the wall.

Jeremy: Exactly. So for you, what is your... I know people are interested and there's a lot of the buzz today about medium-term rentals. I hear about it all the time. I feel like it became like a scapegoat sentence to a lot of people like, oh, well, if it doesn't work as a short, you can just do medium-term rentals. Medium-term rentals, you make almost as much money and they're a lot easier. I feel like that.

And for me, I do a hybrid strategy. So in peak season, when I can make $20,000, $30,000 a month on a single property, I do not want a medium-term renter in there for 30 days. But in January, February, March, when I can make $2,000 as a short-term rental, I'd rather make $3,300, $3,500 as a medium-term rental.

Ruben: That's a big swing. It's not an elite.

Jeremy: Yeah. Lake houses are extremely seasonal. I have some houses that are less seasonal, but then you don't have the upswings of $30,000 months. You have the upswings of $17,000, $18,000 months. So seasonality, pros and cons of it.

But that being said, correct me if I'm wrong, at this point, I know you're doing a lot, but you're focused on, from a real estate perspective, medium-term rentals. How did that come to be? And then what's your portfolio today look like?

Ruben: Yeah. So I just did the math and what it was, it came from a place of... I was surrounded with guys like you who are just always crushing and I'm like, all right, how can I get really good numbers with what I have today? Because...

Jeremy: And not every property is a $20,000, $30,000 a month property. There are properties that make $10,000 a month.

Ruben: I know, but I'm hanging around these sharks, man. I'm like, d*mn, I'm trying to be like Jeremy, man. What's going on? And so that's what it was. I was part of a mastermind. I'm like, people are bringing 20K a month here. They get these properties with these infinity pools and this and that. And I'm like, dude, I don't got that. I don't own one vacation rental. So I don't even know what you're talking about, about 30,000 a month. I don't have that. So that's where I start from.

I'm like, how do I solve my problem to make more with what I have? Because the grass is always greener. Okay, I got to go to this market and make more. Let's go. And we'll get to a point, as a matter of fact, we're currently exploring some properties in some vacation rental markets, but we had short-term rentals, which are different than vacation rentals. And the short-term rentals that we had in Atlanta, they weren't getting the kind of numbers that these guys were getting in the Florida as in our mastermind. I'm like, okay, so what can we do?

So what ended up happening was we had a... Shout out to Dr. Rachel Gainsbrew, because again, someone else that was part of my agency is also a partner now. And I had her on the podcast. We would exchange information. She's like, look at what I just got in bookings, et cetera. And I'm like, how are you getting these numbers in my backyard? We're both from Georgia. And she's like, oh, these insurance deals. I'm like, well, tell me more.

And so just that curiosity of what I find fascinating, to give you a little bit of context of how I look at things. When you change the way you look at things, the things you look at change. So if you look at a single family home and you run an LTR model, that exact same home is going to make X amount of money. You take that exact same home and you take a different model, like short-term rental, you're going to extract more of that property. You take that exact same model and you put mid-term rental insurance, which is what we do, and we are literally 4X'ing what we would make.

So I'm like, okay, let me try a strategy that allows me to get more with what I have now, because I'm not in a position where I can buy these half a million dollar homes, et cetera, or maybe $600,000, $500. Our sweet spot around was like 350K. So we're getting four or five threes in here in Georgia. We're making a decent amount. But we're not getting those $10,000 a month numbers or $30,000 compared to that. So that's how we got into the space. And as...

Jeremy: So you got into it because you just followed the numbers and you surrounded yourselves with a good community, a mastermind, and you saw folks were crushing it, and you wanted in. So that being said, I guess my question mark is, how do you find these 12-month high revenue, high dollar amount contracts with insurance companies? Where are they? I mean, they're out there, but how do you get in front of them?

Ruben: Yeah, first, I think you got to ask yourself, what kind of asset did I have? Because when people hear mid-term rentals, they're like, oh, my two-bedroom home or my one-bedroom home. I think that's a very different asset class, right? When you think of the mid-term rental insurance space, I always like to start with insurance because you can always reverse engineer mid-term rental insurance into other types of mid-term rentals. I just like to start with the most lucrative. So if you're optimized for mid-term rental insurance, you're going to be optimized for that traveling nurse or et cetera.

It's a very different avatar, by the way, so I should take a step back. When I say traveling nurse, I mean, it could be construction workers, it could be, et cetera, but they're very different avatar.

The mid-term rental insurance comes from having the right asset type. Now, the number one thing you want to do is live in their database. People are like, what do you mean, live in their database? Well, that's where these insurance companies are going.

Just if you want to get technical, the way it works, when you're a policyholder and something happens to your home, like water damage, it could be a fire, pipe burst, et cetera, when you file a claim, you file a claim with your insurance company, right? So it could be State Farm, Allstate, et cetera. Allstate, State Farm is not calling you, Jeremy, like, hey, you got anything available? They're not doing that. Allstate, State Farm, they're working with temporary relocation agencies that specialize in that.

You can think of them like a staffing agency. You need a job, you go to a staffing agency, they have connections with the IBMs, connections with Apple, Microsoft, et cetera, they find you a job, okay? That's what these temporary relocation agencies do.

So when we say insurance, I don't want to mistake, it's an easy way to kind of put them in both buckets because one is representing the other, but really, you're not talking to Allstate, you're not talking to State Farm, you're really talking to the temporary relocation companies of the world, like the ALE Solutions, the THDs, the CRS, there are so many, the MyKeys, there's a lot of these.

And if you would just do, spare me, and just do a ChatGPT search at this point. I mean, what a time to be alive. And you say, find me companies like ALE Solutions in my market, and hit enter, and keep hitting enter, and keep hitting enter, you'll have an exhaustive list of databases that you should at least, if you want to have a chance, right, have your property submitted in those databases. Because one of the things they do when they find themselves in a situation to relocate a family on a specific zip code, they don't just look in their database, but that is one of the places that they go, right? So that's number one, if you want to at least be a player in the space.

Number two, if you understand the biggest opportunity in this space is you're going to be properly optimized on, love it or hate it, the number one OTA in the world, right? It's Airbnb. I don't know if Expedia is giving them a run for their money, et cetera, but we know Airbnb, right? VRBO, we know those guys. So those OTAs, you want to live on there.

But the biggest thing that people do on those OTAs is they're not properly optimized to be able to receive leads. Why? Because they have scattered calendars. And what that means is when you have a scattered calendar, it means you're not ready to receive the business. Because these companies are not coming in for these two weeks that you have open on your STR listing, or the three weeks that you may have open.

Ruben: Because if your calendar is anything like most people, it's either 100%, great, nothing to change there, or it's scattered. You got a booking for next weekend, and then you got a couple days open, and then you're booked out for April. Or maybe some of you guys are even taking bookings in June already. Maybe that's your market, maybe that's your business model. Oh, cool.

But keep in mind, if I'm relocating a family for the next three months and I filter on Airbnb, guess who I'm not going to find? The person that has scattered bookings. So that right there cuts the inventory in half.

And then another thing, if you want to be found, you best be pet-friendly. Because a lot of these families that are moving are not just moving by themselves, they're moving with pets. And so as soon as you toggle that on...

Jeremy: You tangible tip, number one of the day, you best be pet-friendly.

Ruben: You best be pet-friendly. If you're not ready to be pet-friendly, don't even join the space, because you're cutting your chances by more than 50%, I would say.

Jeremy: That's what I tell for the properties I manage for homeowners. And they're like, oh, it's February and we're not getting bookings. So in the market, there's 18% occupancy this month. And wow, you look at the houses who are getting rented, and what do you see on every single one of them? Pets, check. Pets, check. Pets, check. That's just a given.

Why is someone going to go to somewhere freezing, like a lake or a beach versus a hotel? Well, they probably have a pet, and that's why they want to go there in January, February.

Ruben: So you're right on. So yeah, you best be pet-friendly. That's tangible tip number one.

Jeremy: You've already given some goals. So the other one is get on the list.

Ruben: Get on the list.

Jeremy: So the databases, and people ask me, they're like, oh, what databases should I get on? I'm like, well, there's a couple of ones that are national, but honestly, and correct me if I'm wrong, in a lot of specific areas, there's bigger players in other places.

Ruben: Yeah, you can even go local.

Jeremy: Yeah.

Ruben: Yeah. So the insurance companies that are specific to Atlanta, they might not be specific to Spokane, Washington, but there's going to be ones there. You best find the ones in Spokane, Washington that are...

Jeremy: So yeah, we're on the list. We're optimized for Airbnb. That means do not let your calendar get sabotaged by two, three, four-day bookings three months in advance. How do you go about that?

Ruben: Yeah, sure. So one way you can start, there's two things that if I were to look back that I would do differently, is you can set up a whole new profile. Just make it super MTR-friendly, and just have your exact same listings you have on your STR, you have on your MTR, that are open for business. Doesn't mean they're open and guaranteeing that someone's going to instantly book, don't do that to yourself, but make it open so the conversation can start. Because you can always be open for negotiation if someone comes in for a six-month booking or like a 12-month booking, you can move some things around.

Now, you can get granular of how to go about it. There's an entire strategy of how you do it, but you want to make sure you either have a duplicate listing or you have a separate account that can at least open yourself up for business.

Another thing that you should not sleep on is, I talk about OTAs, but one of the things you should not sleep on is, I guess, the Zillows of the world, the Furnished Finders of the world. Those are not OTAs, but those are listing platforms. List on there furnished, but you want to be listed as a premium.

The reason I say that is because I don't want to deal with a day-to-day, or at least my assistant, whoever's dealing with it, to deal with inquiries from a bunch of people who are just looking for regular homes. I'm specifically priced at a premium to speak to my avatar. My avatar, the relocation company, they don't have any skin in the game. When you name a premium price, they're ready to pay for it because they understand that you're solving a premium problem.

Jeremy: So, they're at a premium price and they're solving a premium property, but I know a lot of times I preach on this podcast. So, I mean, again, we all have our niches. Yeah. In my opinion, the way that I'm doing it, the folk I work with, the way that we're crushing it in 2024 is we are buying houses while we're also managing other people's properties where it doesn't really matter what you do there. The margins are good. But also when we're buying, the way we're crushing it is we are pimping these houses out with amenities galore.

Like right now, and I'm sorry if I'm texting a little bit, but I have a movie theater specialist at my newest property because this is my first time doing a movie theater and I didn't realize how complicated it was with the projector, the screen, the audio system, having them all speaking to each other. I thought I got a smart projector, but apparently I didn't get a smart projector. So, I had to get a Roku stick and plug the Roku stick into the projector and then have to connect the audio from the Roku to this. It's complicated, but we pimp them out with amenities galore.

For you, you're not really looking at like, hey, this first five pictures need to be a hot tub and a movie theater and a fire pit. What is a premium product in the mid-term rental game?

Ruben: Yeah. So, let me preface by saying, yeah, you're solving a premium problem, but you don't have to have a premium product, right? The problem is this, right? There's a family of five, there's two dogs, and they need to relocate for the next three months.

So, I go on Airbnb, if I'm the family myself trying to relocate, or you go on Airbnb as my relocation specialist, and I do a filter. There might be a hundred properties available. I do pet friendly. I see that filter go to 40 properties available. Now, I look at, okay, what's available for the next three months? And guess what I have? Seven properties available. Not a lot. Because guess what everybody else is doing? STRs. They got someone booked in April, right? There's something about an eclipse, something coming up, right? There's this event happening.

So now, out of the seven, I see four that I would never really book because there's a reason why they're sitting empty, right? They're sloppy and no one wants to stay there. That's why they're free. And then three that I would actually book, right?

Jeremy: And but the issue with those three is they don't know how to price, optimize pricing for medium-term rent. Correct me if I'm wrong, but when I look for medium-term, the ones that are available because they price so stupidly, then nobody's going to book. Whereas I'm assuming you know how to make it competitive for these three, six, nine month rentals.

Ruben: Well, there's a few things I think you're adding onto my list, but this is why it makes me smile because there's a huge opportunity, bro. It's like those three remaining, I might reach out to one as you might reach out because you're the relocation specialist and say, hey, I'm Jeremy Werden. I'm calling on behalf of...

Jeremy: I'm from ALE Solutions.

Ruben: Yeah, I'm from JW Solutions, right?

Jeremy: I like that better. I own everything, right?

Ruben: Yeah.

Jeremy: So I own nothing, control everything.

Ruben: I'm from JW Solutions. You see, I'm trying to place you right in the position. So JW Solutions here, I'm a relocation specialist. I got a family looking to relocate, et cetera. There's two things that happen. You'd be surprised. We were like, is this a scam? Who are these guys? I've never heard of them before. Some of their profiles don't even look legit, right? So then they don't respond.

Let's say now you're left with two options. Now let's say you're left with one option and you've done the same on Zillow Rental Manager. As a relocation specialist, you go on Zillow Rental Manager, you reach out to a homeowner and says, oh, no, I only do 12 month leases. My place is furnished, but I only do 12 months. I don't do two months.

The reason you don't do two months, or even one month, is you don't understand most of these companies will start with a one month inquiry and then continue to extend and extend because they don't want to overshoot their budget. So we've done that multiple times. We'll start with one month and you tell me if it's water, I know it's about to be three or five months. If it's fire, it's about to be six to eight months. I just know. But if you don't know, you might be like, oh, sorry. Guess who they're left with? The person who understands how to cater to them.

So pricing is one thing. Availability is another. Pet friendly is another. So now because of those reasons, now keep this in mind. The person that's available for a month who is available is not going to finish like you and I who have a foundation of taking professional photos, of having a foundation, of having a listing that actually looks appealing.

So let's say you present those two options to a family. They're going to be like, oh, I want to check out that listing. It looks like they know what they're doing. Can we go visit that property? Because it just looks better. It has better quality. We've optimized it. There's smart locks. There's everything that you would learn in the short-term rental industry, but you don't have to have a luxury listing. It just needs to look clean. It needs to be presentable.

And another thing, dare I add, is functionality. You're optimizing for dedicated workspace. Do you have a fenced in backyard? These are the things I'm looking at.

Jeremy: Grill, maybe.

Ruben: Yeah, sure. I mean, if you have a grill where you came from, do you have a grill? You don't have to have a pool or anything like that. You don't have to think about fire pits, but is it going to be functional for my family and I to move in temporarily?

And one of the big things that I love is staying away from carpets, having a fenced in backyard, master on main if I can, walk-in showers, et cetera. Those are the things that I'm looking at for functionality. And of course, most importantly also, do you have a garage? Some of these homes don't have garages. It is a plus. So those are the things.

You see how quickly we started looking on 100 properties and all of a sudden you become available because you understand. So that's what serves you to be optimized to serve this big problem that they're willing to pay a premium, because the question is always, Jeremy, what is the alternative? You're not taking a family of five with two dogs into a hotel. You're going to have to put the two dogs at the kennel and kennel fees, they'll add up real quick. So soon you'll realize why it's actually a discount for the family to stay with you rather than to have them in a hotel and pay kennel fees and, by the way, not be with their pets in one place on their roof, right?

Jeremy: Yeah. No, I think that's actually so. I talked to my buddy, Bailey, who has been on this show before. So he does A, co-hosting, but then B, he buys like 100 grand properties in the Midwest and turns them into medium-term rentals that he can rent out for $3,500 a month. That's his model there. So that's mortgage payment of $8,000, $9,000 a month, medium-term rentals for $3,500.

And he kept posting about his bookings and I hit him up and I was like, I mean, I've seen his properties. I'm like, yo, your properties, they look pretty. I'm not going to lie. They don't look very, very fun or very nice. What's the secret? How are you getting these?

And he just goes, you got to be comfortable. A lot of short-term rental or just hosts in general get scared if their calendar is available the next six months and they don't get a booking for a week, they freak out. He's like, they freak out. They think the world is coming to an end. He's like, my calendar is open for two weeks. I have no bookings and bang, someone comes in for four months. So he's like, you just really have to hold tight. You got to believe.

Ruben: Yeah. You got to believe.

Jeremy: That's a good point. He's like, someone's going to come in and say, hey, I'd love to book for graduation weekend. I'll pay top dollar. Please let me book your place. There's nothing else available. And you got to just, no way. I'm sorry. So that's kind of what it is. It's just like, you got to know that.

And I tried that on one of my properties. I literally was like, all right, we're going to come in here. I'm going to make the base rate so high. I know no one's going to book it. And it didn't get booked for a week and a half. And my partner, Blake, who's also had Blake on the podcast as well. He was kind of like, yo, we're not getting a booking here. What's wrong? And I'm like, let's hold tight for a week or two and just see what happens. And then bang, we got a two and a half month booking. So is there some truth to that?

Ruben: Yeah, yeah. There's a deeper strategy. So I talked about the duplicate listing. The way you do it, and the way we do it, at least, I'm not here to tell you how to do anything. Just suggest what has worked. We're taking that with Skimmel now. So every property that we have has an STR and an MTR listing.

Now, the thing is with the STR listing, I don't make it available too far out. Strategically, I actually use a dynamic pricing tool. We use PriceLabs. There's multiple out there. Where after 30 days, it goes up dramatically in price to decentralize the person from wanting to book out your May when it's in February.

And the idea with that is if you understand your lead time in your marketplace, what you'll do is you'll set it up outside of that lead time that it gets super aggressive. Because look, at the end of the day, can I secure something in May, June, July, August, September? Absolutely. I know I can. But I don't want to get thirsty too early and get those secured on the earlier side if it means that I could potentially have a family come in and stay for a three-month minimum with an opportunity to extend over and over again.

So I want to give myself a chance, and that's why I have my MTR listing wide open. But at the same time, like I said, I'm still able to have my cake and eat it too by having an STR listing where I'm still capitalizing on still getting bookings within the next couple of weeks within my lead time. So I don't want to over...

Jeremy: So you're okay with getting short. So you wouldn't have your STR calendar open five months in advance, but you have it open two weeks in advance? What are the rules you set there?

Ruben: 30 days. I do 30 days with respect to my marketplace and lead time. Now it might be different, obviously, if you're in a different market. When people are booking 60 days out, that's a whole different story, right? You just have to look at your lead time.

But what I'm trying to do, Jeremy, is it's like the airline industry. You don't ever want the plane to take off with empty seats, right? You'd rather just give them away or have somebody on a... What is it called? Walk-on... Not walk-on, standby. Same thing. If I know I got this Friday, Saturday, Sunday open, I know that I can host a family for the weekend the exact same way the STR market would do. So that's exactly what I'm going to do.

But guess what? I'm not tripping because I have an MTR listing that's completely wide open for those exact same days for the next six to eight months. So I'm not losing on anything. So someone who has FOMO, you don't have to worry about it.

Because the only time you have to worry about it, and there's a strategy on how to do this, is if someone reaches out and says, hey, I'd like to book for the next four months, and then you have three other bookings that are existing in your calendar. Well, guess what? The reality is when someone needs to book for four months, do they have flexibility to maybe start next... but I'm saying you can assess the situation, especially if they really like your property.

Or you can move booking strategically by reaching out to the guest on your STR listing, but that's also why I don't have it past 30 days, because I can easily do that for one or two listings. Because that's easy, we've done it before. But it's hard to do that when people are booked out until June and you're going to have to do like eight, nine listings. You might compromise your STR business or host situation overall, so you have to be strategic.

I like having the best of both worlds, make money while I'm waiting, and still leave it open, because then I'll truly know. I'll know, someone inquires, I'll be like, oh shoot, perfect. Well guess what, you inquired for March 5th, I have someone until February 3rd, how about you walk February 4th, oh February 4th, March 4th, right? In the next couple days, does that work? Because that's what we're going to need to do anyways, and as a matter of fact, you're going to need to get that property approved by the adjuster, which takes about a week or two, or less, depending on who you're working with. Sometimes it takes longer.

I got proposals right now that I'm still waiting to respond for. Imagine if I'm just sitting empty, not making money. That's not the move. We always burn in the hand, but you can also have your cake and eat it too, and that's what we teach in our mastermind. How do you kind of structure that, the whole science of manipulating listings, but once you get that, you can have your cake and eat it too, as you should.

Jeremy: Got it. So, and then I hear in this game, and I've seen this firsthand, a lot of times when you connect with these relocation specialists, and you do a good job, they go four issues, their clients don't have problems, because think about it from their end, because they're kind of the middleman.

So, whereas a guest who just books on Airbnb is going to reach out to you and complain about every little thing, you the host. In this situation, they reach out to the insurance specialist. So, if the water pressure is terrible, if something's broken, they reach out to them first.

So, my point being is, if you do a good job, and their clients don't have issues, they're going to love you. And they're going to go directly to you next time and just say, hey, what do you got for me? And do you build a relationship with them directly?

Ruben: That's exactly what we do. So, like, 90% of our bookings are just straight from the relationship.

Jeremy: They just email you, call you, hey, what do you got?

Ruben: But we tell them to though. Don't expect someone to, you have to understand, people are busy, they have multiple accounts, there's a lot of things going on. It's in your best interest to educate them of how you can actually serve them. And then hear it out from them.

By the way, Jeremy, is it okay if I periodically follow up JW Solutions with you? Because I have actually a lot of properties. And by the way, if there's anything you're looking for in my area, just let me know, because I can be very resourceful. I'm also a licensed realtor, so if there's anything you can't find on your end, I can help you out. Does that sound okay? Oh, by the way, is calling or texting better? What's, or emailing? What's the best way for me to keep you up to date with what I have going on?

Like, you're fostering a relationship, right? And then they say, oh, honestly, Ruben, like, Mondays, my Mondays are shot. And honestly, Tuesday, we have our town hall, where we do a roundup of our KPIs. Well, tell me more about the KPIs. Oh, yeah, we got to meet our quota. What's the quota?

Like, I'm doing the exact same thing I'm doing on my podcast with these relocation specialists. And that's why I think I wanted to highlight before, like, being curious, asking questions, listening, serving, it's all the same stuff that I did, whether it was at the podcast agency, in my consulting, in this business.

Jeremy: I really want to echo that, like, the exact same skillsets that you can take in one place does transfer well, especially people's skills in communication and listening in all areas.

Ruben: How could it not? Businesses do business with people for people. So if you're in the business of serving, which we are, hello, you're in hospitality now, it's in your best interest to be a great listener, right? And we do that even for the guests. We don't put in our relocation company, it's still on us. We want to give them a five-star experience, because it echoes back to the head office, and they'll keep coming back.

As a matter of fact, the reason why I'm really excited is because if you continue to foster these relationships, now it'll be like having a good contractor, right? It's like, yeah, I can shop around. Yeah, I can look on TurnoverBnB for a new cleaner, but if I already have a really good relationship with Jeremy, based out of New York, why am I going to call somebody else? So it's in our best interest.

Jeremy: You don't need anybody else. You can call me anytime, man.

Ruben: I'll call you anytime.

Jeremy: I don't have KPI meetings on Tuesday. I've got a Ruben. Okay, all right, I'd say Ruby Tuesdays.

Ruben: Oh, I get that. I like that, Ruby Tuesdays.

Jeremy: Ruben Tuesdays, that's a thing, right? Ruby Tuesdays, I didn't just make that up, right?

Ruben: No, dude, bro, you know my name gets all the nicknames. I've got them all, Ruby Rube, Ruby Tuesdays. I get it.

Jeremy: All right, well, Ruby Tuesdays, we're reaching the top of the hour here, but what is your pro tip for those listening to succeed in the game in 2024?

Ruben: Just becoming a good listener. I think you said it earlier. If you can listen, even when someone walks a property and they say, oh, it's too bad, I usually have an office, or I usually have a stand-up desk at home. No problem, we'll get you one. Right, like you got to listen.

Stop selling and start listening, because that's the best form of communication, whether it's a relocation specialist, whether it's new data that you're trying to get, and the best thing is if you get on the phone with these people, they'll tell you a lot more than you even need to know if you ask the right questions.

I've asked for budget approvals. I'm like, by the way, what's this family approved for? Before you even state your number, because you know he who states their number first loses. But like, oh, I got them anywhere around 9,000. I'm like, oh, well, good thing, because I was about to say 7,000. You just made yourself $2,000 by asking the right question. Oh, perfect, because we're 89.97. He's like, we're going to save you $3.

Dude, listening is the best skill, man. That's all I could say. Listen and get in proximity to the people who are where you want to be, because that's my hack. That's why I'm on here with Jeremy, man.

Jeremy: Nah, I got to get on yours.

Ruben: Yeah, and I'm trying to, likewise, likewise.

Jeremy: Well, Ruben, man, I appreciate you. I really appreciate you coming on, and for those listening, how could they follow your journey?

Ruben: Yeah, I mean, I've been documenting my journey on Instagram since time now, so I could always use some like-minded individuals to connect with at The Real Estate Experiment. I think you'll see all my links there, my episodes on my podcast, what I'm up to, deals we're doing, and even snippets of hot insights from students. We do this Empty Your Hot Seat, Coaching Hot Seats, if you ever want to get on a call for free. I know, right? Just book. We have like one slot for the people, just to serve as many people as possible.

Jeremy: Well, that is awesome. Let's bring it in for the people, Ruben. Thank you so much for coming today, and everybody, stay tuned until the next episode of the Short-Term Rental Pros Podcast.

Ruben: Yes, yes, ooh, and by the way, for those of you guys who got some game today, you can go on, yes, you can follow me on Instagram, but I'll give you guys a little gift. You can go on experimentrealestate.com and grab my Mid-Term Rental Insurance Blueprint. So it'll be right on the website there. Just put your name and email, and you can grab that, and you'll have the goods. You'll have some goods, right?

Jeremy: Awesome, awesome, well, I appreciate that as well. Ruben, thanks so much again.