Ryan Shapiro: under 10 STR listings to $322K months

Quick Summary

Jeremy's back behind the mic after about a year and a half away, and Ryan opens with the numbers. Fewer than 10 listings has become roughly 30 in Northeast Florida. June cleared $300K in gross bookings, and July landed at $322K.

Most of that growth came from what he stopped doing himself, because guest messages, maintenance calls and dealing with Airbnb all went to his team. Jeremy explains why he walked away from arbitrage, and why Casago's Steve Schwab names quality of inventory as the number one indicator of success. Check the Florida market numbers before you chase a coastal deal of your own.

Key Points

• Ryan had fewer than 10 listings the last time he was on the show. He's at roughly 30 now, with 28 or 29 live and two more going live at the end of July.
• June gross bookings cleared $300K and July came in at $322K, putting the two months together a bit above $600,000. A year earlier he was sitting around $100,000.
• Guest messages, maintenance calls and dealing with Airbnb all sit with Ryan's team, which freed him to hire a sales rep, build the sales process and refine operations.
• Jeremy applies the Pareto principle to a portfolio: out of 29 properties, about 25 run fine while four cause most of the stress. If a client needs custom operations built around them, walking away usually beats keeping them.
• Jeremy let go of every arbitrage property over the past year and a half, including three apartments, a duplex and a single family home. That duplex cash flowed about $30K a year for four years on a $25K investment, though margins compressed and a bus route change brought foot traffic into the backyard.
• Asked for the number one indicator of success in short-term rentals, Casago founder Steve Schwab named quality of inventory rather than unit count. Nice homes mean better margins, fewer team members and less burnout.
• Ryan's company, The Luxury Co-host, has only worked with beachfront homes and canal front pool houses, and he's targeting 50 properties in the area by the end of the year.

Full Transcript

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Jeremy: Wow, we are back. How have you been, man?

Ryan: Been fantastic. It's been a while since I've been on the pod, so I still have it in my LinkedIn profile.

Jeremy: It's been a while since I've done a pod. Guys, I am so sorry. I think it's been about a year, year and a half since the last episode of the Short-Term Rental Pros Podcast. And the reason for that, honestly, life got busy. I got married, just had a kid, and life happens, as many of you guys are experiencing every day, whether personally, professionally. Sometimes you got to put the mic away and be there with the people around you.

I feel very blessed that the business that I went into, short-term rentals, property management, investing, gives me the ability to... My baby was born four weeks, five weeks ago, and I've been here the whole time. She's actually on a walk with her mom and her mom's friends now, so I have a little bit of time to hang out with Ryan. But yeah, guys, life's been good, but I'm excited. We're going to get back into the swing of things here.

And with that, Ryan, man, I guess, how have you been? Tell me. I think last time you were on the pod, and Ryan's also going to be joining us to make sure that we get more consistent recordings to you guys and more helpful stuff. But I think, Ryan, last time you were probably less than 10 listings under management, and now I think you're at 31?

Ryan: Yeah, I think about 30 or 31 right now. We have two going live end of July at the current moment. But yeah, when we first hopped on the pod, it was just getting started. I mean, officially quit my job, had enough clients at that time, enough to jump into the deep end and just go all into the property management side of things, joined the coaching program, learned a lot from Jeremy himself and the rest of the people in the group, and just kind of went all in as soon as I saw the opportunity.

So yeah, about two years, I would say. I had my first listing, I think, live sometime around this podcast, July 17th. And now we have 28 or 29 live with two more along the way at the moment. So it's been...

Jeremy: Oh, I over exaggerated.

Ryan: You said 31. Oh, my bad. I'm pretty sure at 31, I got to recalculate. We've had some ups and downs. At the end of the day, you always have people coming in, people coming out. But I'm pretty sure I'm officially at 31 with two contracts. Keep me honest.

Jeremy: And I think you texted me, and I love nothing more than getting updates from folk where it's a screenshot of monthly earnings, all-time high. But what, three in terms of gross bookings, which is the amount of, not... For a co-host business, you take commissions. So there's gross commissions, which is your effective percentage management fee times the amount of bookings. But I think, what was it? 300, 350K in July?

Ryan: July. June, we did over 300. July, we're at 322. So just in two months, gross bookings were at about a bit above 600,000, where I think last year, maybe we had 100,000. So big, big jump from there.

Jeremy: Huge milestone. Yeah, you got it. You jumped me. I think I'm 200K this month in gross booking value. So nothing like surpassing your mentor. So it was good.

Ryan: But not only that, we've been helping Jeremy a little bit in terms of the sales processes for people that are coming in, learning it all. So it's been super exciting about that as well, too. So we've seen some of the people I've been through the group with surpass 100,000, which is where I was last year. So those also have been just huge wins. As much as I love having wins, I love seeing and helping people achieve their goals as well, too.

Jeremy: Some people have been hopping you, too. So you hopped me, then someone hopped you.

Ryan: I'm too competitive. One guy hopped me and I was like, that's it. I'm going to get 100 in less than a year. We're going back into it. So I hired a sales rep, built the whole process for it all. So yeah, I love the competition of it all, too. It's what keeps you going.

Jeremy: Alex, he's a top 1000 in the world tennis player. He joined us earlier this year, January, and he texted me. And Alex is a guy I might not hear from for like a month. And I'm like, yo, Alex, you okay, man? I'm checking in. I just want to make sure you're alive. And he'll say, oh yeah, things are great. Just hit 250K. Started in January. So seven months in, 250K. I'm not sleeping till a mil a month. And I'm like, all right, all right.

If someone can do it while being a full-time professional athlete and grow one of these businesses, I think I don't have an excuse. You don't have an excuse. Nobody has an excuse. I mean, there's people in our nine-to-fives, but oftentimes in your nine-to-five, you have some downtime, or at least you're not like... Look, Zoom calls can be tiring. Alex was like, yeah, dude, I literally have to sit in the shower for an hour and put it on warm water just to loosen up my body so I can practice. It's just such a physical demand. And then I'm like, well, how do you have the energy to do calls, to do sales? And he's like, I just lie on the couch, and it's, what am I supposed to do? Watch TV?

Ryan: It's definitely athletes, I would say, tech sales bros and ladies, realtors, anybody that's needed to, what I say, just kill every day to be able to eat. This is definitely a great model where you can take all that energy for just one sale and you could just get a recurring revenue business without even having to be some tech founder or come up with some SaaS product. These are real physical businesses.

Jeremy: And Alex is a beast. And I still have people in the group reach out to me being like, how did Alex do it? And I reach out to him being like, are you doing something different than what I taught you? And he's like, no, I'm just doing exactly what you taught me, and I'm just doubling and tripling down on that over and over again.

Everybody thinks there's some magic to it all. And it's just, he's just doing the work more than anybody else. And it was a good reminder for me, like I said. So I think it's a good reminder for everybody part of the group, like just stick to the basics.

Ryan: Yeah, it's not rocket science.

Jeremy: I mean, I've done other businesses. I have a software, BNBCalc, which I'm excited, I'll do our own episode that's kind of on the updates there, and everything that I've learned building that.

But a software business, there's not much of a playbook for it, in the sense where you got to make decisions and you just really have no idea what's the right or wrong decision. And it's kind of like, you make a decision, and a month later you're like, yep, that was the wrong decision. All right, I'm going to make another decision now, and then we'll see in two months if that was the right decision. That's the best way to do it. You kind of are doing five things at the same time, and you're like, two of those things worked and three of those things did not work. All right, I'm going to stop doing those three things and I'm going to keep doing those two things.

Whereas here, it's really like, pick up the damn phone, put it to your ear. All right. Maybe a guy like Alex doesn't love operations. It's not his forte. All right, find a business partner who loves operations. Kyle, I mean, I'm excited to get him in the mix here to give an update with everything. He's a creative. He loves launching new properties, finding new properties, having ideas. Crazy. I mean, he's gone crazier and crazier and crazier. He's a madman, and I say that in the best way. But he's now pretty much building almost from scratch, like 8,000 square foot properties.

Ryan: Totally.

Jeremy: He has the number one highest grossing short-term rental in the state of Iowa, that he launched like 10 weeks ago. It already is the top STR in the state. And he loves doing that. And he does not like when a guest sends him a message that's not grateful. He's like, I put all this effort into creating these crazy experiences, and you're going to come and complain to me about a towel scrape on the wall.

Ryan: Yeah, yeah.

Jeremy: A towel's in the wrong spot. After I just literally spent three months sleeping on the floor, turning this into absolute madness. Yeah, he just does not have the patience for that. So he had a team member, someone also in the program, join and is now doing the ops full time.

So the point is, like, connect. Yeah, people who know themselves, and they keep the foot on the pedal on whatever gives them energy. And that is super key to success. And I think also taking two steps forward and one step back. I feel like that's what I, you know, people like Alex or Thomas, for example, he was kind of putting pedal on the metal for a while, and I would always tell him, yo, this is a game of two steps forward, one step back.

And what I mean by that, you know, the Pareto principle, 80% of your issues are caused by 20% of your activities. And I think in life, that's true. I mean, if you think about everything you do in a day, there's probably a couple things that give you the most stress, I would imagine, whether it's personally or professionally. But with co-hosting, property management, I think it rings truer than anywhere else, where it's like, you have 29 properties, you're going to have like four that are just the bane of your life. Like 25 are good.

Ryan: Yeah, 25 are going to be good.

Jeremy: And like four are going to stress the living crap out of you. Or maybe you have to do things differently with those four where it doesn't fit into your operations. I've had clients where they just have such unique rules on who they'll rent to and what their restrictions are and what pricing they'll do. And they want to do everything a certain way. And it's just like, yeah, this just doesn't fit the way I do operations. If I have to create a custom way of doing things for you, then it's probably not worth it.

Ryan: Well, at least at scale, if you're doing that for every single... I mean, mind you, when you first get started, you'll do anything. So it definitely gets...

Jeremy: Totally, beggars can't be choosers at first.

Ryan: So I've definitely bent the rules of what I said when I first got started. But the biggest thing is to get to that point where you can make those choices, and the things you don't like doing, like what Kyle, like you mentioned, me, you, and pretty much mostly everybody in the group at this point now are not answering guest messages, are not calling maintenance people, are not the people that need to hop on when there's a minor issue, aren't the ones talking to Airbnb, and are pretty much doing 90% of the business, where I get to focus on doing the sales, building pipelines, and refining operations while the day-to-day stuff is being taken care of. Kyle, like you said, partnership. You taught the whole way for it all. So I think that's the best part.

You know, I did go golfing, I'll be honest with you, yesterday at two o'clock in the afternoon. I was able to.

Jeremy: I don't do that. I don't do that.

Ryan: It was a nice day of the week, so.

Jeremy: I'm on the Upper West Side of Manhattan now. Yeah, you can't do that stuff.

Ryan: I'm in Canada, so when you only have three months of summer, it really hits you hard when there's a nice day. And New York's not that far off, I'm going to be honest.

Jeremy: But we have like you Canadians with your wildfires. You guys are sending smoke our way. It's so messed up.

Ryan: Oh my god, I know.

Jeremy: Be a little bit mindful of your partners on the southern side.

Ryan: Yeah, I tried to play basketball, I think like two days ago, and I almost passed out.

Jeremy: Send your wildfires to Antarctica. Kind of not funny. I know there's a lot going on with that whole thing, so I hope everybody's okay. But I didn't even know yet. I thought it was a cloud. I was like, oh, it looks super depressing outside yesterday. I was like, yeah, I don't know if I really want to go for a run. And then my wife was like, oh, the air condition, people are wearing masks outside. And I'm like, oh, I wouldn't even know. If you didn't tell me, I just wasn't going to go outside. I didn't know it was from a wildfire. I had no idea.

Ryan: Yeah, I looked up and the sun was like red. And I was like, this is strange. Kind of felt like zombie apocalypse vibes.

Jeremy: But yeah, I digress. Anyways, all that. I think with that, it's a good time to reintroduce ourselves. So Ryan manages his portfolio, co-hosted properties. He is a resident of Montreal. That was, sorry, I haven't done the French in a second. But he's Quebecois. However, the properties are in the good old state of Florida. Canadians love their Florida.

Ryan: We do love Florida. Yeah, I'm in Northeast Florida, pretty much strictly at this current moment, trying to grow over there. But we do love Florida. I picked it just because I love surfing, and it's one of the only places on the East Coast. So yeah, it was cool.

Jeremy: It's funny that the Canadians always go with Florida. I talk to a Canadian, where should I go? And I'm like, I know.

Ryan: I don't think we know anywhere other than Florida in the US. That's the problem. Montana, never heard of it. Florida, the only place.

Jeremy: It's probably to do with how cold it is in Canada in the winter. It's the closest to happiness. And it's an escape.

Ryan: Oh my god, yeah. If you go to certain areas in Florida during Christmas time, you'll pretty much only meet Montrealers there. I don't go to those areas, just because when I travel, I do like to meet new people. But you could basically see your whole neighborhood in like Hallandale, if you go down in a certain area.

Jeremy: I think it's so funny with like Matt and Lori. They got clients because Matt would take his shirt off and just mow the lawn and start talking to people. And I'm just imagining like a Canadian. Oh, hey, hi. Oh yeah, this is a property I manage for a client. And he's like, dude, I take my shirt off and it just feels so good. I get the sun. Life is great. And I'm like, all right, us Americans, we take things for granted. I'm not going to be excited about flying somewhere to go mow a lawn. But I guess when you're stuck in the cold for nine months out of the year, that sounds like a very appealing thing to do.

Ryan: Yeah, I mean, hey, the last few times I've driven down, a lot of people won't even drive 20 or so hours. I'm excited the whole time. And as I was driving, I went from having a jacket to then a shirt, to a t-shirt, to then a tank top, slowly as I made my way through.

Yeah, no, we love Florida, and it's been a great market as well. Tons of vacationers at all times coming in and out. It's a great vacation rental market as well too. But yeah, very happy with how it's been growing. Looking to try to get to 50 properties in this area by the end of the year, and then as well buy a house down there to rent out. So all that thanks to just doing property management.

Jeremy: Ryan's got buying fever. Big time. I can tell.

Ryan: Yeah, yeah. I just, you know, it's always been a dream. I think like a lot of people had, just owned something. And I definitely at this point would spend $5,000 on a plot of land just to say I own something, but try to keep it all together to not make dumb decisions.

Jeremy: So yeah, I feel like the last year for me has been very much living the two steps forward, one step back. Maybe the podcast was an example of that. I did start YouTube. So I was posting on YouTube pretty consistently and enjoyed making, that was just a new test for me creatively, as well as learning how to produce that type of content. So it was kind of like, all right, I'm making two forms of long form content, I might have to take one step back. It's just a lot of stuff there.

And then also in terms of my portfolio, I let go of all my arbitrage properties over the last year and a half. I may have let go of a few before then, but had three apartments right next to each other that I let go of, had a duplex that I let go of, had another, a single family home. And the reason being is just that wasn't the growth factor for me anymore. The margins definitely compressed too. I think I've learned that the commoditized game is dead. I only want to do something if it's a unique defensible asset, like if it's three apartments, five apartments, 10 apartments.

The issue was that our landlord literally renovated a building, said, hey, you guys, we're going to launch 18 units down the street. Do you guys want them? And I was like, well, no. I mean, no. And then he's like, all right, well, I'm going to rent them to another person who's going to rent all 18 of them. And what am I going to say? I mean, I did tell him, I was like, who is this person? If they do 18 more, they're not going to make money. That's going to kill it for everybody. Ironically, I did talk to him actually a couple of months ago and that did happen. They ended their lease very early. It didn't work out. Yeah.

That's been a lesson for me. My revenue actually, even with letting them go, my revenue is still going up. I'm still adding. I'm helping a client right now build out an awesome, awesome property. It was bought as a four bed, two and a half bath. We're going to turn it into a six bed, three and a half bath. We're converting the attic into like 700 additional finished square feet with a bathroom, and it'll be like a movie theater room. And then we're going to turn the bonus room into a bed. It's going to be great. But that's the type of property I want in my portfolio. That property by itself is going to do as much as eight apartments would together. So anything I add...

Ryan: You don't love arbitrage is basically what you're trying to say.

Jeremy: I mean, the issue is that you don't own the property. Look, I made my money, don't get me wrong. This should be an episode where I just do all the pros and cons of arbitrage. I'm going to do that as its own episode. I mean, there's a lot of specific topics over the last year and a half that I feel like I'm pretty keen to speak to.

But the issue when you don't own a property is you can't do anything to it to make it do better. The duplex I had, the owner up front, I made him do a fenced in backyard. He was happy to do it. And yeah, cash flowed 30 grand a year for like four years. Probably made in total about a hundred K profit on a hundred K, and initial investment 25K. So great return on...

But the issue is that this particular house was in an area that was kind of borderline between sketchy and nice. My thought was the area was just going to gentrify, gentrify, gentrify. But for whatever reason, I actually was talking to him and he said that they changed the bus routes a little bit. So the bus started dropping people off a block away from the house. And yeah, people were just... I mean, I hear it.

The last straw was when our cleaner was like, hey, there's poop on the house. And I was thinking it's a dog. I'm like, okay, must have been a dog. That's obviously poop. So I'm just like, well, I don't know. Pour some cat litter on it and deal with it. This isn't the first time a dog has... This is common. Dogs do that. And then she's like, no, it's like a human. I don't want to touch it. And I was kind of like, yeah, this is probably time.

Ryan: It's time.

Jeremy: And I had some guests being like, hey, yeah. I mean, it just became a headache.

Ryan: For the margins too, right?

Jeremy: Yeah. And you'd have every four guests, they would say, hey, there's someone in the backyard. What's going on here? And it's in a city. So when I say backyard, it's not like someone's jumping in the pool and swimming around. It's someone's in the driveway out back. And yeah, it just became a headache.

And yeah, at this point, the portfolio, last year, bought a house with Kyle, a business partner, a private lake in Kentucky, a literal private lake. We have not had a guest ever say, hey, we have someone going to the bathroom on the side of the house. It's a 14 acre property. I mean, I don't think there's people walking around there causing issues. I mean, don't get me wrong, there's been issues, but that's not something.

I bought another property last year, turned a four bed, two and a half bath into a seven bed, three and a half bath, pool, pickleball court. It's doing very well. It's defensible. In that area, there's not a lot of properties with big yards and pools and pickleball courts. I mean, I'm trying to find another one and it's been a year and it hasn't really happened.

So the point being is that I've focused the portfolio, the client property I just mentioned, launched another lakefront client property, beautiful house, flat backyard, just adding inventory that's just good, high quality inventory. My reviews have gone up. Usually over time, your reviews go down. Everybody's reviews go down over time. My average rating has actually gone up. The operational ease has gone a lot higher.

To the point where, actually I think this is something I heard that I want to pass along to you guys. What's his name? The founder of, they just bought Vacasa, Casago, Steve Schwab. Steve got asked, I think Patrick told me this, what's the number one indicator for success, margins, happiness, everything in the short-term rental game? And he said, quality of inventory. It's not unit count. It's you have nice homes. If you have nice homes, you last longer, you don't burn out, your margins are better. You don't need as many team members. Good properties are what creates longevity.

So I've taken that to heart the last year and a half, and bad properties, bye-bye, and only being selective about properties adding to the portfolio. And that has freed up time for some stuff we've done at BNBCalc, which I'm excited to talk about. Freed up time for us hopping back on this podcast.

Ryan: Yeah, I'm excited.

Jeremy: I'm excited. I'm excited to share with everybody. So Ryan, appreciate you. He's also going to take the sticks. He is a sales maestro. He can talk on that front much better than I can. He has a tech sales background. He's an ops champion at this time. He has 31 units, 350K this last month. A big operation has had to really, really roll the sleeves and build out an ops system. So yeah, there's going to be things that Ryan just hops on either by himself, either has interviews, anybody he wants to interview. I'll be doing the same.

And yeah, appreciate you guys. I'm going to be honest, I was shocked. I went into the system to see if people have been listening to the pod. I looked, I said, oh, we actually got a really nice review recently. The guy actually said that I said the word folk wrong. That was his only negative comment. It's supposed to be folks, but I say folk. I'm like, all right, if that's your criticism, I'll take it. I'll take it.

Ryan: Yeah, no, it's super exciting. Excited for this next journey as well too, and just talking more about co-hosting specifically. Jeremy is the maestro at this point, and like you said, buying these super properties and getting to that point. And that's where I'm trying to go. But the journey from where I'm at now to get to Jeremy, I think a lot of people resonate with. So I'm excited to kind of talk about that, going after quality homes, to not exhaust yourself as well too.

It's such a huge point for me. Our company is called The Luxury Co-host. Right now, we've only worked with beachfront homes, canal front pool houses, location specific, that has something unique about them. Because at the same time too, we're selling vacations and experiences for everybody. So if the house isn't an experience or you can't turn it into something, well, again, this is specific to Florida. Everybody's coming down for vacation specifically most of the time. So if we're not selling something that's a vacation or experience, you're going to get bad reviews. You're going to get disappointed clients, and it happens all the time. So having that mindset that you're always offering something that people can create memories with has been a big driver as well too for our company and for me as well.

So yeah, excited to talk more about that. We're still open for helping people out. And if there's anybody interested in learning more about it as well too, I'm sure Jeremy will link our calendars to just hop on a call with either one of us to talk about either purchasing or co-hosting.

Jeremy: Beautiful. Well, I appreciate you, man. Everybody, thank you guys for staying patient with us. And as always, stay tuned for the next episode of the Short-Term Rental Pros Podcast.