Amenity Stacking, Snowstorms and Scaling STRs in New York ft. Josh Briner

February 18, 2026 00:48:38
Amenity Stacking, Snowstorms and Scaling STRs in New York ft. Josh Briner
The Short Term Show
Amenity Stacking, Snowstorms and Scaling STRs in New York ft. Josh Briner

Feb 18 2026 | 00:48:38

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Show Notes

On this week's episode, Avery is joined by Josh Briner. Josh shares how he transitioned from a background in education and flipping distressed properties into building a short term rental portfolio in upstate New York, including the Finger Lakes and Buffalo area. He dives into why he prefers value-add BRRRR deals over turnkey properties, how amenity stacking like pools and saunas can dramatically impact revenue, and what investors should realistically expect during the first year of launching a luxury rental. The conversation also covers scaling a management company to over 100 doors, navigating snow removal and winter challenges, and the mindset required to succeed long term in the hospitality-driven short term rental business.

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For more information on how to get into short term rentals, read Avery’s books:

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Episode Transcript

[00:00:05] Speaker A: Welcome to the Short Term Show. [00:00:08] Speaker B: The show about short term rentals and long term wealth with real property owners. [00:00:13] Speaker A: Hosting real properties who are crushing it in the vacation and short term rental space. [00:00:19] Speaker B: And here's your host, Avery Carle. [00:00:29] Speaker C: Hey y'. All. Welcome back to another episode of the Short Term Show. Thank you for hanging with us every week for five years Now I am feeling a little old and we have a really cool guest today. We are talking about investing in the upstate New York area, Finger Lakes and some other places. Got a really great knowledgeable guest on that, Josh Briner. How's it going, Josh? [00:00:53] Speaker A: I'm swell. I appreciate the very cool guest introduction. I have to agree. [00:00:59] Speaker C: Awesome. Well, of course you're cool. All right, so let's talk about upstate New York. So first of all, just tell us a little bit about you, how you got into real estate, why you're in, in New York, all that fun stuff. [00:01:13] Speaker A: So I'm in New York because I was born in New York. I know New York kind of gets a bad rap, so I'll try to dispel that a little bit. I actually, I really like where I live. I, I, I enjoy living in New York, especially upstate New York. I think it has a lot of great qualities in terms of my short term rental journey. I, I was like everybody else, right? Like I'm listening to bigger pockets start off with like a flip and a burr and I'm kind, I'm, I'm doing my thing and I'm like, this isn't fast enough, right? Like I need to do more, I need to make more. So then I start going into the short term rental thing and I, I buy a few cabins and I flip them and I burr out of them. And by the end of two years, I'm sitting at four cabins and I'm like, it's too slow. Everything's too slow. How do I, how do I make this faster? Right? Obviously there's a lot of different paths we can take to make something faster. But the path that I decided on with my, my co founder is why don't we do management? Like we need to build all these systems anyway for our own properties. Like I don't want to be the person to do all the things that, that's not my long term goal. I don't want to create a job for myself. Let's start a management company. We'll manage other people's short term rentals and then we can throw ours in the, in the mix and we don't have to do anything right? Like, that's the idea. And it's what we did. And Vibe, our management company, has kind of started to take off and I haven't even bought anything in the last two and a half years, so we've just kind of been focused on that. But I'm back in the game, so I'm excited to start buying soon. [00:02:37] Speaker C: Awesome. Awesome. So I want to hear about that. The beginning stuff, the flipping and the rehabbing. Tell me about that. [00:02:44] Speaker A: Yeah, I mean, my. I have a. Maybe not. So I don't know. You tell me. But my background's actually in academia. Went to school, got a master's degree. Master's in education. I've been working with at risk youth since I was 19 years old, so that the vast majority of my young adult life was spent in college being broke, working with at risk youth on the line, working in the units, which is. It's a group home, right. So they live there and then being an educator there. And eventually I realized as much as I enjoy and love that it doesn't pay any money. So that's kind of where the real estate thing came in. And I remember I was looking at houses with my dad and he's like, josh, you're approved for $80,000. Like, what do you think you are going to get your hands on? Because we kept looking at all these houses like, ah, it's not good. He's like, dude, you got to go buy a house that's like crap and fix it up. Same thing he did, right? Like, my. My dad's just like a blue collar dude. He's a machinist, and he bought an old migrant camp and fixed it up into a home. Long story short, I did the same thing. And that's when I realized I kind of liked the process of the flip. I didn't like all of it, but I enjoyed it. I actually ended up selling that house, getting a lot of my equity, well, a lot of my revenue back. And then I. I bought the house that I'm currently sitting in. That was like a monstrous flip. It was a 3, 300 square foot house that I had to flip. And then I also had to flip the. The loft above my garage. So I'll actually, I'll go into that real quick because it's kind of interesting. So I'm always about the house hack, right? Like, how do I make my house pay me money? The house I'm living in now, I was like, that was one of my main criteria. This house has to pay me money. So how do I do that and do the short term rental thing. It had a basement with an egress, and then it had a big loft that was literally exposed to nature, wasn't finished above the garage. I'm like, I'm going to flip that loft and make it a short term rental and flip that basement, make it a midterm rental. So that was what I did. So I turned my basement into an apartment that's a midterm rental. And I flipped my loft and made it a short term rental. And then, you know, you were asking about more like the flipping and origin stories. I started buying some, like, smaller cabins in the Finger Lakes region, just kind of cash offers. I knew I'd have enough cash on hand to fund it myself and do the flip and renovation myself. Did that a few times. And again, I just kind of realized that it's not something I can scale as quickly as I might like. So I have to make a pivot here. [00:05:10] Speaker B: From the hardest working gal in real estate, Avery Carle. We now have a new book, Smarter Short Term Rentals. Available wherever books are sold. Build a dynamic real estate business and out host the competition that's Smarter Short Term Rentals. [00:05:30] Speaker A: The book. [00:05:32] Speaker C: Okay, I. I really do enjoy the rehab and flip process. So we have bought a couple things to flip before and ended up just keeping them. But our long term rental strategy, we always just buy junky stuff with holes in the walls and, you know, looking really stuff that obviously that you can add a lot of value to and making them nice and then turning around and renting them. So that's my favorite thing to do is, is to rehab stuff and, and make it look nice. Like I'm not super into the whole design thing, like women in short term rental, but it is fun to take a junkie house and make it nice for somebody to live in. I enjoy that process. [00:06:15] Speaker A: Yeah, you don't strike me as the design type of gal. And you know what's funny, Avery? I love that too. And I'm just kind of rediscovering it. Well, I guess we'll divert from short term rentals real quick. But I've been looking for a flip for like, probably like three months and just getting back into the process. And I, I've been helping a friend look for us. I'm a realtor too. Don't typically do primary residence stuff, but it's for my, my best friend. So, like, we're gonna get you an investment, not just a house. Right. So it kind of got me back in that process of like walking through houses and hashing the numbers out. What do I got to do here? And I've really, really enjoyed that and I'm excited to get back into it. [00:06:53] Speaker C: Yeah, I, I love that process. So we started, you started off flipping. Your, your very first deal was a flip, right? [00:07:01] Speaker A: Yeah, my first five, six deals were all flips. [00:07:06] Speaker C: Okay, so you, you flipped a fair amount before you got into buying and holding then. [00:07:10] Speaker A: Yeah, when I was a teacher, I had, you know, for me, 32 hours a week isn't a work week, especially with summer's off. That, that's, that's half of a work week for me. So I'm like, what am I gonna do with all my extra time? You know? So once my. And that was always spent at school, at college, and once college was done, it's like, I gotta do something. And that's when my dad kind of got me into the idea of like flip a house. Like to make it your home was his idea. He didn't realize it was gonna make me catch the real estate bug. But yeah, after that I just kind of kept cruising and I won't even, even for short term rentals like my long term play. I always want to be able to burrow out of a deal. Like I'm really not interested in buying stuff that's turnkey ready to go. [00:07:47] Speaker C: Yeah. And I think that is the way, that's always, in my opinion, the way to do short terms, long terms, etc, well is to buy something that you can add value to. And with short terms you, you can absolutely find a turnkey something and get it to do well. But I think so many people kind of over the COVID thing there kind of became this idea that you could just go buy something turnkey and then not do anything different to it than the last person and expect to make, you know, 20% more on income than they were making just because you're managing it. And the reality is to be successful, I think in any market these days, the way the market is now is you do have to find something that you can put a little work into, add a little value to. I'm not Talking about dropping 300,000 on doing anything crazy, but just buying something a little junkie and making it a little bit nicer and, and sometimes especially with, with short terms that doesn't necessarily have to involve any construction. You can buy a grandma cabin that has grandma stuff in it and just give it a nice refresh on decor and, and amenities and you're good to go. So. But I think that a lot of people too. They listen to people like us, have these conversations. And then for their very first property, they're like, oh, cool, I'm going to go, I live in California. I'm going to buy something in the mountains in North Carolina and rehab it. And then it's going to be. And, and they've never bought a house before. They've never rehabbed a house before. And they think they're going to do all of these things from the other side of the country. And that's really tough. So I would like to hear your opinion on, you know, because you sell short term rentals in New York. And what would be your advice for people who are listening to something like this and hearing experienced investors say, yeah, you got a rehab. And knowing that they can't necessarily buy something next door to them to rehab, what would be your advice to them? [00:09:53] Speaker A: So, you know, it's, it's funny because I, I've worked with a lot of out of state investors that are now starting to come into this region because it's a beautiful region and it's a good place to invest. It's, it's really safe. We have a lot of pivots and outs. But, you know, I, I got a guy that just bought with me, he's from North Carolina, Virginia, something like that. Flew in to look at the house once. Yeah, I like it. And he was planning on handling everything, the whole process, and he had renovations in mind. I told him when I gave him my contractor, I said, listen, man, I don't know what it's like where you're from, but these guys write their own check. This is a person that I vouch for. He's not going to do drugs in your basement. He's not going to steal your money. He's going to get the job done. That's good. Like, don't start hitting them on price. Called me, like two weeks went by. He's like, I, I haven't heard from the contract. I'm freaking out, about to close. Mike, did you start hitting my price? He goes, yeah. I said, dude, don't do that. Right? Like, it's hard to find people that someone will like me, will vouch for that will show up and get the job done when you want it done. It is very difficult. So if you're going to do this, if you're gonna buy a house that needs reno, it needs work, it needs design, you better trust your, your realtor on the ground. Or like a person doesn't have to be a realtor, but somebody that is local and you better have your vendors lined up because you are really going to hurt yourself in upstate New York. Right? I can't speak for other states. [00:11:12] Speaker C: Yeah, I mean I think it's like that everywhere. We rehab in Tennessee, Alabama, Nebraska, Florida and it's, it's the same every. And sometimes honestly we will send our crew from down here up to Tennessee even where we're super connected. Just because it's so hard to find somebody that you can trust that you know is going to do a good job, that's not going to do stupid things. Like, like Luke is really, really anal about the direction that wood floors point. They, they need to go front to back on the house. Not, not left to right. [00:11:46] Speaker A: I'm in alignment. It makes the house bigger. Like if you're walking it makes sense. [00:11:50] Speaker C: Yeah, yeah. And they have to be, he doesn't like when they, I don't really know how to, how to explain this. So people that are listening can understand when it's, if they look too uniform, like if they just do okay, one. [00:12:05] Speaker A: Here typically, boom, boom, boom. I don't like that either. Yeah, I agree. [00:12:09] Speaker C: So find somebody who's going to do good work. They're not going to make stupid decisions. They're gonna show up, which is the main thing. And work isn't good. Quick work is not cheap either. So yes, I agree. [00:12:22] Speaker A: 100 and I, I do the same thing. Like if I find a place that's like two hours away, like I would send my crew that I know and I trust. And it's, it's not to say that you just have to accept whatever, like 50 grand to do a bathroom. Like you can say no, right. And like, but if it's a price that you're agreeing on, just be real careful. Be careful in how you deal with people and work with people. Obviously when it comes to a short term rental, there's a lot that takes place after the renovation process. Like, who's your cleaner? Treat them like gold, man. Like, if you, you're not going to hire a manager on the ground like me, then your cleaner better be getting a gift basket every Christmas. You better be throwing them an extra 50 bucks. Every time they do. You change a smoke detector because that is going to be like your person and then obviously having that handyman, you know, it's. I, I, I think the biggest thing just, I hate to harp on it, but I go back to is like when people start to nickel and dime, they're not going to answer your phone call. Like your fifteen hundred Dollars a year of inconvenient projects is cost a certain premium to, to make somebody go, yeah, sure, I'll go over and do that, you know, so just be ready for that. [00:13:32] Speaker C: I would say, yeah, yeah. And if it's a small thing where it's not something that is a big job for them, which is going to be a lot of income for them, a lot of times they're. They don't want to do that. You have to make it worth their while. And I'm somebody. I do this with babysitters too. I shouldn't even say this. I pay them extra. I pay them more than what they're asking for. Because when it comes down to a situation when you're in the high season and there's multiple people that need them, I want to be chosen. Pick me. [00:14:00] Speaker A: I do it with every. Everything almost. I always overpay. I overpay my transaction coordinators, I overpay my referrals. I don't know, it just feels normal to me. [00:14:09] Speaker C: Yeah, I agree. I agree. All right, so we covered rehabbing, which is a fun topic. We don't talk about that much on here. So let's talk about what you look for in a short term rental deal. So you've done how many, how many, like buy and holds. [00:14:25] Speaker A: So I only did five before I started vibe and then when I started Vibe, it took up all my time. So. But like outside of short, I don't know, probably like nine, maybe ten. [00:14:37] Speaker C: All right, so let's talk about what it is you look for in a short term rental deal that you're going to buy and hold yourself. [00:14:44] Speaker A: Yeah. So like number one again, I like to burr. I've never bought a house that's even close to turnkey. If you can choose between crap and crappier, always go with crappier because you have to replace both. And, and crap here is just a discount. It's just gonna, it's gonna save you more money. Right. So I'm looking for a house that's like in rough shape, but hopefully has a roof that I don't need to touch for 10 years. Hopefully has a 200amp panel box. Hopefully has no knob and tube wiring. Hopefully has no lath and plaster. Hopefully has a block foundation. Like we get a lot of like field stone foundations out where I live. A lot of old farmhouses and anything that's kind of like before that 1920s. I just, I don't personally love it. It's not my, it's not my thing. So there's a Lot that goes into what I'm looking for in the house. And then for the house itself, I want to go smaller, I want to go big. I hate that in between phase. I hate that 4 to 8, it's just an even like 4 to 10. I would say it's just an awkward number. Like you and seven of your best friends are getting together to go somewhere. It's like this is kind of weird. Like you and one other family, you know, like, okay, I don't know, like I like that small, intimate family couple experience and. Or that 12 plus, 16 plus super property, big experience. You know, obviously I'm looking for location. Like I want either. I have a couple different ways I categorize this. But like I have like my fixed attraction slash urban is what I call it. Right. So I'm selling a house right now, about to close on it next week, hopefully. Cooperstown, New York. Right. You have the Field of Dreams park. You have the Baseball hall of Fame. That's going to account for 50 plus of the guests that are coming to stay at your place. Right? I have a house. I have multiple houses that border the Buffalo Bills Stadium. 50 plus of my revenue at those houses come as a direct result the stadium. Right. So I'm looking for like something like that and. Or the actual experience short term rental stay. What about this location is special, Right? How can I add to create an amenity stack and create a design where it's what I would call the Field of Dreams house. Like you build it and they come like I'm coming because this is the house. It's got the inground pool barrels on a hot tub, professional design. And I can fit 16 people in here. Right. So especially in the Finger Lakes region, like think of it, we have 11 lakes. We have like the little lakes over here. Then you kind of have the bigger ones. There's five big ones and you got some smaller ones over here. And the five big ones. Everything kind of coalesces around them because we have breweries and wineries. It's a really nice wine country. And when we talk about that fixed attraction, that's kind of more of a supplementary fixed attraction I would call it, where people come and they go on the wine tours. That's a really big thing. There's a lot of like event venues. So I'm looking for all of that stuff obviously. And then, you know, I, I cannot overstate the importance of the amenity stack. And sometimes amenity stacks can be really expensive to add retroactively. And I'll give You a great example like pools and in New York and being someone that doesn't give a crap about pools, I don't like pools. I don't really go on them. They move the needle big time. You have a house with an in ground pool and it just really gets the numbers up. Like I have houses that are off lake out by the little lakes that outperform my houses on the lake, on the main lakes because of that in ground pool because it's got the hot tub and the barrel sauna and that amenity stack. If it's already in place before I buy at least a good portion of it, that's great because putting in hardscaping and in ground pool retroactively is going to get really costly. So I don't want to keep bloving on. Hopefully I got to the question. I'm not sure. [00:18:32] Speaker C: No, yeah, yeah. And I agree pools really do make a difference in a lot of markets. But. And as somebody who I'm building a house now and also the house that I live in before we sell it, we'll probably add a pool and it's just for a decent pool around here. I don't know about how it is up in New York, Florida. There's a ton of pools everywhere and it's like a hundred thousand just to get a decent rectangular, nothing crazy, not even a hot tub in there next to it pool. So yeah, it can get super expensive. [00:19:04] Speaker A: And then that's dead money. Right. Like the bank's not coming in like oh, you spend 150 grand on hardscaping in a pool, your house is not worth this. Like it's not gonna. [00:19:12] Speaker C: Yeah, yeah. For dollar value add either. [00:19:17] Speaker A: It's all short term rental value add and that is huge. It's great, but it's tough. [00:19:23] Speaker C: Sure. If you're going to do that. If you're going to buy something, it's cheap. Basically it's cheaper to buy something that already has a pool than buying something that doesn't and adding a pool. So for me, if you're going to buy something and then add a pool, you kind of do have to plan to be holding that for quite a while because if like you said, if you spend 150,000 on a pool, it doesn't make your house worth 150,000 more. So as long as you know that going in. Yes, this is absolutely going to make me a lot more money in cash flow every year. But I do need to plan to hold this, I would say a minimum of 10 years. Maybe that's A little too much. But I just, I've been kind of. I've gotten sensitive over the years of people expecting. Because of COVID expecting their houses to be worth double, like two years after they bought it. [00:20:08] Speaker A: And so you appreciate the choir. [00:20:10] Speaker C: Yeah. [00:20:10] Speaker A: So I'm like, Avery, I got. I got to tell you, at the short term rental wealth conference, your. I think you only did like an hour. Is that right? [00:20:20] Speaker C: Yeah, I. I have. [00:20:21] Speaker A: Yes. [00:20:22] Speaker C: I'm pretty sure it was an hour. Yeah. [00:20:23] Speaker A: Of a value packed weekend. That was the most value. I mean, it was so good. I mean, I took notes on like everything I did the entire time. And your section was like a whole page just in that hour. And like, that's one of the things that you mentioned during your. Your seminar was. And this gave me a lot of confidence where you showed a graph and it showed like the COVID spike. And anybody that was paying close attention, we knew that the COVID spike was a covet spike. Right. [00:20:50] Speaker C: Like, right. [00:20:51] Speaker A: None of us were surprised, but you showed it coming down and you're like, this isn't down. This is a return to the norm. And we're still seeing the top 10% of the market, the traditional Pareto distribution, outperforming and increasing the revenue. So this isn't like the sky is falling down. This is just a settling back in of what has always been. And that made me feel really good. I think, I think I said that right, I hope. [00:21:16] Speaker C: Yeah, yeah, absolutely. Where everybody who bought at the peak were like, oh my God, everything crashed. I'm like, actually, no, it didn't. If you zoom out and look at what the last 10 years have done, everything was like a nice gentle upward slope trend and then a big spike and then kind of back. It didn't even come all the way back down to the level that things were before the big spike. It stayed. I would say it came down like maybe halfway. Not even. But everybody freaked out because they didn't own their property for long enough to really see a full cycle. So all they saw was the town. So, guys, real estate is a long term investment. Long term gains. I mean, you might could get away with five years of. With saying, okay, I'm going to own this thing at least five years. But I would say if you're planning to buy a short term rental, that's a 10 year commitment. And it's going to take, in my opinion, several years. Maybe not 5. 3. 3 to 5 to really even know if you're so good. [00:22:21] Speaker B: This episode is brought to you by Short Term Shop Plus. Are you looking for someone to help you analyze a deal? Do you want instant access to lectures on management and short term rental success? Join Short Term Shop plus for all of your vacation rental needs. STS plus is open to the public and offered for the first time at a tremendous value. Also included is World Famous Management Monday, a weekly live session with everything you need to know about setting up up your property and learning how to manage from a distance. Join [email protected] that's stsplus.com. [00:23:07] Speaker C: This episode of the Short Term show is brought to you by the short term shop. 30 year fixed mortgages, tax benefits and long distance management training made easy are just a few of the perks of owning a short term rental. The Short Term Shop can help you buy and learn how to manage your property from anywhere in the world. Just go to the shorttermshop.com and click get connected again. That's the shorttermshop.com and we are brokered by exp. See y' all over there. [00:23:34] Speaker A: Do you mind if I ask you a question? I know I'm. It's not often I get to talk to an expert of your caliber and this is another thing you touched on at the seminar. And it's a serious struggle that I've been having with my business is the launch of specifically luxury vacation rentals has been a nightmare. And I try really hard to set expectations my clients and be like, guys, you, you are going to hate this for a little bit. Like if you're not with a traditional vacation rental management company that has a back Rolodex of 50,000 people, you're not going to command the ADR that you want for at least six months at a property that's going to eventually be a 1500-2000 dollars a night ADR. And just convincing them that the right move is to take these bookings that you hate. But we need to get these algorithms working in our favor. We need to get the review history, we need to establish this product has been a serious challenge for me. And I remember at the seminar you kind of, you touched on this a little bit and you said, you said, look man, data's not data until you hit three years. And even then it's suspect. Right. So I just wanted to get your thoughts on that and see if that's still like holding true for you and you still think that's the case. [00:24:51] Speaker C: Yeah, yeah. I mean you can't with one year or even two years of short term rental experience on a property that's really not enough because your first year is whatever you probably did not buy in J like in January. So you haven't seen a full year. And even then you may not have been open at the and available for bookings at the time that people start booking for your high season. So for example, down here in Florida our high season doesn't start until March. But if you're not available, if you're, if your listing is not up January 1st, you may not get those good spring break bookings. You'll get some last minute spring break bookings. But just because you open March 1st doesn't mean you, I would not say you optimized your spring break high season so that first year you really can't. You will probably cash flow like you will make more money than what your expenses are but it's not going to be your full potential of what the property can do. Year two you'll, it will be better but I would say it will take at least to year three to get up to, you know what your expectations might have been. And you are going to hate it at first because so many people think especially now I've noticed over time, you know we used to have before COVID everybody was a cash flow buyer and over time now we have I would say more people who just who, who maybe heard about the short term rental tax loophole in October and they like consumed all this content really really fast to try and close something by January 1st. [00:26:29] Speaker A: Yeah. [00:26:30] Speaker C: And they do it and it gets done. But then they're like oh my gosh, I, I hate this. I didn't realize it was going to be work. They're like I'm just going to buy this really pre property and it'll be great. I'm going to self manage it. But you are dealing with other people. And I can't remember what famous author said it but hell is other people. And so you have to learn that yes, in your brain you're exhausted because you've just put all this work into this property and it's beautiful and you love it and you're presenting it to the public and somebody's like there was dust under the refrigerator when I moved it. And you take it so personally and you just really do have to get through that first six months of okay, this was really tough. And then it will things, things will settle in. You'll get used to things. You'll stop taking things personally. You get in a routine and then it becomes like okay, yeah, I can absolutely do this. Yeah, you are gonna hate it. For, for a little while. [00:27:24] Speaker A: And you, you know, you said it, you, you are in hospitality, you're not in real estate. Right? Like you're in real estate when you make the transaction and you find the investment and then you enter the hospitality business, which is very different business, you know, just to kind of go back on that too. See if this is your experience in that first year, especially that first six months, it's like, man, even if I can get the revenue comparable to what it's going to be in year two, the path to getting that revenue is going to be exponentially more work than it's going to be in year two. And your quality of guests is going to be exponentially worse than it is in year two. Like I'm at a two day booking minimum instead of like the five to seven that I want, right? Like I'm getting a one week book out in the book today window instead of like a two month. And it's just like the amalgamation of all those things in the first six months. It's just been really tough and I don't know, I'm just kind, I guess I'm wondering if you have any advice or tips or tricks of how you've dealt with that. [00:28:24] Speaker C: So I don't. Okay. Nobody's gonna like my tips because I, the way I was raised and the way I grew up in an era of serious athletics, of where what coaches did was they just screamed at you all the time and that was the way they coached. There was no gentle coaching, There was no like, oh, let's, you know, think about how this 12 year old girl's brain works and what can motivate her. It was like, no, I'm going to make you cry, I'm going to scream at you until you get this thing right. So, so for me it's just like, stop being so damn soft all the time. Like sometimes people are going to be annoying and you have to deal with that and you're going to do hard things and if you want to make money, you have to do hard things. So stop being so soft. [00:29:03] Speaker A: I agree 100%. And like this is the hard part too. As a manager, I'm like, please, for one, if this sucks for you, imagine what it's like for me. It's me and my team doing all the work, right? I'm the one, I'm the one making 50 bucks on this 250 booking. You think that's worth it to me? Like I'm doing it for you, number one. And number two, just grit your Teeth and get through it. Your house ain't going to burn down a dog. The Rufus isn't going to chew all your beds apart. Just get through this first six months, get the listing established, and we're going to be good. You just got to get through it, you know? [00:29:38] Speaker C: Yeah, I agree. First six months, you're going to, you know, you're pricing lower than what you normally would because you got to build up your review base six. So you might get. I found the lower the price, not necessarily the worst quality of guests, like, they're not going to mess your house up, but the more nitpicky they are for some reason. Like the. The people who are spending a ton of money, they don't say a word. They leave it perfect. [00:30:02] Speaker A: I know, it's crazy, right? [00:30:03] Speaker C: But the people who are not spending a lot, they're like, the hot tub is 103 degrees and I need it to be 104. [00:30:11] Speaker A: That's a nightmare. [00:30:12] Speaker C: Yeah. [00:30:12] Speaker A: So you get PTSD right now. [00:30:15] Speaker C: So you get your first six months nitpicky people. But then the. The quality of guests does improve over time. And when I say quality of guests, I don't mean they're going to rip your house down. I just mean they're going to be a little annoying until you get established that's just part of it. [00:30:32] Speaker A: 100% agreed? [00:30:34] Speaker C: Yep. What else? So we've got about five more minutes before we get to the last three questions of the show that we ask everyone. So let's see. So I want to hear about snow removal. So that's not something that I have to deal with in a lot of my markets. And I want to make sure we're covering things that people in other markets have to deal with. So when you're buying in a market like upstate New York and you got to deal with snow, how do you do that? Like, what's the process? [00:31:08] Speaker A: Yeah, it's. It's a nightmare. I mean, there's just so many things about this business that are so difficult. Right. Like where I'm at in particular, like I said, I have houses up by Buffalo Bill Stadium and Orchard Park, Buffalo area. So you got Lake Erie, and then the Finger Lakes is not far from Lake Ontario, and we're already in upstate New York, so we're getting hammered with snow. And at the end of the day, we have great relationships. Right. I have over 100 doors now in the area. So we have relationships with people that will pick up the phone when I call because they know that they're going to Get a lot of work, right? But I cannot set up a system to have one of my staff stare out the window until it snows and sit out there with a measure and be like, there's three inches. Call like, no, it's a contract, right? Like, either you're going to get contractually signed up to somebody that's going to come remove your snow every year. It's a set price. Sometimes they win, sometimes you win. That's that. Or you're going to have to facilitate that service yourself. And then to add to that nightmare, you don't really know, like, when your. Your bookings are so, like, you could be paying for this snow removal service all year, and then you. You had an entire month that was unbooked, right? And I have not found a system or a team that is willing to only remove snow when there's incoming guests and watch a calendar enough with fidelity to pull that off, right? So it's a process. And then you have your sidewalks, your steps, like a lot of our houses. Again, like, think about it this way, Avery. I have a house that I'm doing 45, 50k a year on. I have 8 staff. Is it feasible for me to send somebody out to shovel the. The steps every time it snows? I don't even charge for maintenance right now. I can't do that. Like, it's just the numbers don't add up. I'm going to. I'm going to be in the red. So we leave the guests salt and a shovel. Say, look, man, you're coming to upstate New York. You know the deal. Here's a shovel. If it snows, like, the driveway is going to be plowed, but we, we can't do that. We try if we can, if we have our cleaners there or whatever, but it's. It's tough. The snow really complicates things. Everything's mad. Pipes burst. I've had a lot of houses that have like burst pipes because the heat went out or something. People get stuck. They go off the driveway, they blame you. Like, the driveway was wild. You drove off it. I'm not. I can't pay the toe bill, man. Like, I had a guy left me a one star review last year for that. And he sent me a picture of the driveway. It was perfectly plowed. It literally just been plowed an hour before. He's like, I want you to pay for this. I said, dog, I'm not behind the steering wheel. And he left me a one star review and said it was because I didn't pay for the tow truck, and Airbnb didn't remove it, so make sure that. But. Sorry, I'm ranting. It complicates things. Avery, it's very tough, but there's a lot of people in these areas that will remove the snow for you, and they'll even get out of the truck and shovel the. The sidewalk and stuff for you sometimes, but you gotta pay them, and it's contractual. It's very rare that you find somebody that's just gonna go show up when it snows. [00:34:08] Speaker C: Yeah, I agree with that. Okay. So, Josh, you said you have a hundred doors that you manage in upstate New York? [00:34:16] Speaker A: Yeah, we're actually probably over that now. We. We got a backlog that we're onboarding, so. Yeah, we. Quite a few. [00:34:23] Speaker C: So what would be your advice for somebody who, you know, maybe they manage a few, a handful? What would be your advice for scaling up to something of that size? Because at that point, you're getting, you know, that's a lot of. A lot of properties. [00:34:38] Speaker A: Yeah. Especially when they're, like, high earners. Like, we're pretty selective now about what we take on. So it's a. It's a. It's turning into a good portfolio. My advice would be do something that costs you nothing but your time, which would be management, co hosting, something like that. To. To be honest, I want to get on a whole tangent. I'm not really big on the co hosting thing. I don't love the idea of attaching yourself to somebody else's profile. It's not really sticky. Doesn't really give you that ownership. The contracts aren't sticky. A lot of people make a lot more money than me doing it, so kudos to you. But I would focus more on, like, a regional management expertise, like Boots on the Ground. I'll knock on your door, I'm here. I think that's where the real value lies. And put the word out, man. Like, Avery, you started. What is your Facebook. Facebook group called? The Short Term Rental Shop. I. [00:35:25] Speaker C: Forget it. So it was. It was called Short Term Rental, Long Term wealth, and then we changed it to when the new book came out to Smarter Short Term Rentals. And we have a client only one that is the Short Term Shop Client club, where we talk about, you know, where we share vendors and things like that, too. So have a number of. [00:35:42] Speaker A: And that's great. And like, I saw that early on. I saw. You know, I used to listen to your podcast all the time and other podcasts that have since been on, which has Been a really cool experience. And I saw the success you guys were having on Facebook, and I started my own Facebook groups, you know, upstate New York, Airbnb investors. And you start getting people in these Facebook groups and presenting yourself as the person that knows how to do this. And you say, all you got to do is just say yes. You don't got to pay me any money and I'll take over your house and I can do a better job than you. That's an appealing offer for a lot of people. So I would say that, like, get on social media, tell everybody what you're up to. Tell everybody what you're doing, and then do the management. And then once you do that, you start getting that additional revenue that you can then invest into your own properties. Ideally. [00:36:25] Speaker C: Yeah. Yeah. I think that's really great advice. And I had another question related to that volume of doors, and it just. [00:36:37] Speaker A: Yeah, it's funny. I kind of got there so quick and I just kind of dropped that number. But apparently it is not like a common amount, is my understanding. There's not. Most portfolios are somewhere between, like, the 15 to 30 range. So we've been very fortunate and blessed. It's been. It's been really great. [00:36:54] Speaker C: Yeah. So I think my next question is so it. In the markets that I'm in, where I've watched, there's either. There's a few different types of true managers. I'm going to not talk about co host for a minute, but there's the big dinosaurs that have been around for decades already that have thousands of properties. Their properties are always the junky and dirty, and their rent is never good because they're just trying to get 20% of a high amount of volume. They're not optimizing each property to make as much as it can. Then there's. I've seen a few start from the startup phase and they'll be great. And I'm like, oh, yes. Anybody that we have that, that needs a property manager, we're going to send them to them. They're doing such a great job. And then they kind of have this, like, bell curve of like, they're great, they're great, they're great, they're great. And then all of a sudden, they fall off a cliff and suck. [00:37:43] Speaker A: Yes. [00:37:43] Speaker C: Then my clients are like, why did you send us these people? They suck. I'm like, I'm so sorry. They've always been great. I don't know. And then all of a sudden, everybody says they suck. I'm like, well, I mean, how do we. If you're going to do this and you're going to get to that scale of doors, how do you not suck after a while? [00:37:58] Speaker A: You know, Avery, that is so funny and it's so true. And I'm very cognizant of that. And I don't want to be the person that someone's having that conversation about. Like, yo vibe used to be amazing. What happened? And I'll give you the answer. When I see people like walk away from their W2s over like co hosting or met, I'm like, don't, don't do that. Like, wait a little bit. Like, my fix was like, I hire people that are a lot better than me at the jobs that I once did, and they're smarter than me. I have an operations manager, I have a maintenance manager, I have a hospitality manager. I have great vendors. I stick to my radius. I cast a pretty wide net. But still, like, it's a, it's a within. Everything's within a two hour drive, hour and a half drive, rather. So I don't look at my business right now as like this profit machine. I. I'm trying to get out of my W2. I'm in the rat race. Good, I'm done. It's like, no, no, I need to make this the best. And to be the best, I have to have in house staff. Like, it blows my mind how many management companies, like, just have like, vendors they use. I. I don't know how that works. Like, I need people that are responsible to me and my standards. And I think that's the number one answer is people are just taking money from these things too quick. They're taking money and I, I want to make my money off the verticals, you know, Like, I'm not a martyr. Eventually I'll make money off the management business, but it's not a huge wealth generator. Like, it's. I think it eventually can be. But right now I'm just trying to do a really good job. And then if I couple that with my real estate brokerage and some type of other rental business I'm working on and these other vertical things, eventually start charging for maintenance, you know, show everybody what a great job you did with your maintenance program for three years and say, look, man, we're gonna keep it up, but it's 50 bucks a month. Not a lot of my clients are going to complain about that, right? They're not going to be stoked about it, but they're gonna be like, yeah, it's worth it, right? So, yeah, I think that's the answer. [00:39:46] Speaker C: Yeah, I agree with that. And what is. I mean, what even would be 50 bucks a month times 100 properties? What? That's 5,000 bucks a month. Extra 60 grand a year for you. [00:39:56] Speaker A: I just got to cover. And again, like, I'm not. Look, my business partner and I, when we started this, we weren't in a position where we needed this to. To get through the day. Right. Like, I don't need this money. I'd like it. And again, I'm not a martyr, but I want to build something that's good. And I think that if I have a maintenance program that just pays for itself, I'll be stoked. Like, I don't need it to make. [00:40:15] Speaker C: Me a bunch of money, just not lose money. [00:40:18] Speaker A: Exactly. [00:40:18] Speaker C: Yeah. Yeah, I agree with that. So, Josh, you've been such a great guest, and now we're to the end of the show and we have. So sad. We'll have you back on sometime, though, because you've been great. [00:40:33] Speaker A: I want to get back on with Luke because when I did Luke's, I didn't have like, the setup I have now, and the quote quality is terrible. So I'm dying to get back on with Luke one day. [00:40:41] Speaker C: Well, I mean, right now, his background, I'm like, can you please clean up your background? But anyway, he's getting a new office shortly that it will be much cooler. So I'm sure he would love to have you back on. And y' all can both have good backgrounds. [00:40:54] Speaker A: Yeah. [00:40:55] Speaker C: All right, last three questions. First question, what would. If you. What advice would you give? Sorry, I tried to do it out order. What advice would you give 20 year old Josh if you knew then what you know now? [00:41:08] Speaker A: All right, I. I have a proclivity toward being a little long winded, so I'll try to not do that here. I would say trust your gut and your instinct. I think that I'm a person of many faults, but I'm also a person of many skills. I don't believe in false modesty. I'm gonna call out the things I am good at, and I think I have pretty good vision and good insights. And I always thought there was something intrinsically wrong about me spending the amount of money that I spent on college. And not just that, more importantly the time. And that's the thing people don't talk about, man. Like, the money. I'll always make money, whatever. The time that I spent sitting in classrooms and learning things to get these three pieces of paper that I have now that really don't do that much for me. That. That's pretty tough. So I would have said, like, josh, stick with your gut. You know, my parents, great people. I don't have a sob story. They're middle class people, right. They always told me I could do anything I wanted, but anytime I brought up anything, having to with generating wealth, they're like, oh, no, no, no, no, not that. Right? You go to college, you get a job, right? You put into your 401k, that's what you can do. You can't do all these other. The rich people. You can't do that. So just trusting my gut, trusting my instinct, and just really jumping both feet in and buy bitcoin. Yeah. [00:42:22] Speaker C: I remember in like 200, I don't know, 10, one of my super, like, punk rock crowd friends was posting about bitcoin all the time. I'm like, he's crazy. What is he talking about? And like the Austin airport start, one of the bars there started accepting bitcoin as payment. And I was like, that sounds stupid. [00:42:47] Speaker A: I did it, man. I had xrp, litecoin, I had bitcoin. I mean, I. I'd have probably close to a million dollars in crypto if I didn't sell when I did. But, I mean, I made a little money and I bought some real estate investments et ce fine. But yeah, it's. It is what it is. What are you gonna do? [00:43:04] Speaker C: Yeah. Yeah. All right, so what advice would you give a new investor investing in short term rentals who's looking to get started today? [00:43:12] Speaker A: That. And that's. That's the easiest one, I think, Avery. And really the advice I would give is like, just get your mindset. Don't reach for the low hanging fruit. Get your mindset out of, like, I want to leave my job. Like, I need to replace my W2. Like, don't reach for that low hanging fruit because then you're never going to get to the nice ripe fruit sitting at the top of the tree. You're monetizing things too quickly, Right? Like, don't try to monetize everything I've heard. This is my Facebook group. Like, Josh, why don't you do this? Why don't you? I'm like, it's not cool. I don't want to do that. I don't. I get plenty of value from just getting everybody. I have other managers all the time that live 20 minutes away from me, that advertise in my Facebook group, right? Like, it's my cooperation. There's enough food on the table for everybody to eat and just having that mindset and having that abundance mindset and ensuring that you're not after the profit. You're trying to learn, right? Like co. If this is the only time I like co hosting, like co host to learn. I hate. Don't like arbitrage. Arbitrage to learn. That's okay. That's a paid internship, right? Figure it out and decide if it's something you really want to do because it is a detail oriented business and it's a bear, as we both know. So make sure you're not picturing like the hallmark version of owning a bed and breakfast in your head where some hunky guy shows up and you fall in love. And like the real life version where it's some fat lady complaining about a Cheeto she found on your couch. You know, like, this is a tough business. So. Yes. [00:44:41] Speaker C: And I like that you said there's enough food on the table for everybody to eat. Because I feel like for some reason the short term rental industry, all the little businesses and the people, they're so mean to each other and like. [00:44:56] Speaker A: Like. [00:44:56] Speaker C: There'S like, they have to talk about other people's businesses to. In order to build theirs up. And like that's not. You don't have to do that. There's. We can all exist without doing that. And so I just, I've noticed that about the short term rental industry versus like the larger real estate investing, general industry. And I don't know why. Short terms, everybody, there's so many, There's a lot of wonderful people. I, I don't want to say that but like, there's a lot of cattiness going on between the businesses and it's like everybody can just chill and run their businesses and be fine. There's no reason for all of these other things. [00:45:32] Speaker A: So yeah, I'm starting to get my fingers in the pulse of the drama a little bit. Like the guy that was at the, the wealth conference. Who was the guy? He does cash. Or like he had a unique name. He does like owner financing stuff. Really, really interesting guy. But he kept commenting. He's like, you guys are weird. He's like, something's wrong with you. Like, this is a weird community. And he like, wasn't kidding. He's like, what's up with the short term rental investor community? He's like, I don't know about you guys. And I was like, fair enough, man. Like, there's something a little weird about this community. [00:46:00] Speaker C: Yeah, I mean, yeah, it's. And it really is just like there is enough food on the table for everyone to eat and everybody to get along and live their lives and raise their kids and just live. But anyway, I could do a whole podcast on that. Last question, what's your favorite book that's impacted your mindset? [00:46:18] Speaker A: Oh, man, that's a tough one. I would say. Man, I hate. I. I always give like the basic answers, but I truly love 4048 laws of power. And it's not so I can decide what I want to do and how I want to move forward through life because I think it's a little psychopathic. It's very Machiavellian. But it helps me understand the mindsets of other people that don't want what's best for me. That's something I've always struggled with. Going back to like the mentality in the short term rental community. There's people that don't want you to succeed, they don't want you to do well. And you have to understand how they think because they're shocks and they'll get you. I've also enjoyed Machiavelli's the Prince. I've enjoyed Atomic Habits by James Clear. I believe it was James Clear. Trying to think of what I listened to recently. I've been listening to the Founders Podcast a lot recently. [00:47:17] Speaker C: Oh. [00:47:17] Speaker A: So I know you asked about a book, but I think the phrase of being well read is kind of changing to fit the modern zeitgeist of our time to being well listened as well. Right. And I feel like I'm pretty well listened and the Founders podcast is very cool. So that would be my big. [00:47:34] Speaker C: All right, well, Josh, we'll definitely have you back on and so will Luke because you've been a delightful guest. You get it, you're easy to talk to. So we always need people to talk talk to us to off these podcasts that come out every week. So. [00:47:49] Speaker A: Good. Yeah, I know because I don't want to have my own podcast. I prefer to be a guest. So please, I'll come back anytime. [00:47:54] Speaker C: Yeah. All right, well, we would love to have you if our listeners want to follow you on social media. How do they do that? [00:48:00] Speaker A: Kind of a geezer, a bit of a boomer. But Facebook is. Is where my business is. You know, I'm not with the kids on Instagram. Joshua, Max, Bryan are on Facebook. You can check out my Facebook groups. Upstate New York Airbnb investors and upstate New York real estate investors. That's the best places to find me. [00:48:16] Speaker C: All right, well, thank you so much and, guys, thanks for listening. We'll see you next week. [00:48:26] Speaker A: Ram.

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