“When you’re doing something hard, it’s supposed to feel hard… but know that you’re on the right path.”
Skyler knows firsthand: building a direct‑booking short‑term rental business from the ground up is not easy, but it can be extraordinary. In this week’s episode of the Booked Solid Show, Skyler shares how he and his wife, Maddie, went from furnishing arbitrage properties in San Diego to launching investor-backed, luxury wellness retreats in Upstate New York—complete with custom saunas, cold plunges, and bridal‑ready properties. You’ll learn their scrappy strategies, brand‑building secrets, and how they’re leaning into a book club community to fuel expansion—without losing balance.
Summary and Highlights
Skyler and Maddi Vaughn’s Journey
Skyler Vaughn and Madi Johnson are the founders of The Short Term Rental Book Club and For the Love of Upstate, a boutique real estate brand that renovates historic homes into high-end short-term rentals across Upstate New York. Their specialty lies in blending timeless architecture with modern comforts—turning late 1800s houses into memorable wellness retreats.
Episode Highlights & Key Takeaways
➤ From Rental Arbitrage to Real Estate Equity
Skyler and Maddie started with rental arbitrage in San Diego, scaling from 2 to 4 units before using profits to buy their first vacation home in Big Bear—where a savvy exit funded their move to Upstate NY.
➤ Wellness Retreats as Destination Properties
Their portfolio emphasizes immersive, wellness‑focused stays with on‑site saunas, cold plunges, hot tubs, and outdoor showers—transforming properties into unforgettable experiences.
➤ Strategic Branding & Consistency
Every toilet, wallpaper, and postcard is consistent across properties. From website to in‑property signage and photography, they bolster their direct‑booking funnel.
➤ Tech‑Enabled Guest Conversion
Integration with HostAway, Google Maps, email funnels, and partnerships (like Fede’s property management) is powering both direct bookings and event rentals.
➤ Investor Structures & Sweat Equity
Holding individual property LLCs and funneling renovations through a master company gives them flexibility for investor partnerships and future client‑based design work.
➤ Community Through STR Book Club
The monthly $30 subscription includes books, Zoom discussions, breakout sessions, and real networking—fostering property partnerships and ongoing growth.
➤ Mindset & Identity
Skyler’s mental health insight: stress and anxiety often signal progress. His mindset tip—embrace the difficulty and stay grounded—aligns directly with how they built a thriving business.
Rapid‑Fire Round Questions 📚
- Book recommendation: Rocket Fuel – Helps founders understand whether they’re Visionaries or Integrators, and why both roles are equally vital.
- Mindset tip: Lean into anxiety and stress—they’re often indicators you’re on the right path.
- Tactical advice: “Focus on your product. Direct bookings follow when the property speaks for itself.”
Connect with Skyler here
- Email: skyler@fortheloveofupstate.com | madi@fortheloveofupstate.com
- Instagram: @skylerandmadi
- TikTok: @madiandskyler
- STR Book Club IG: @thestrbookclub
Finally, 🎧 listen to the full episode to discover how material details—from wallpaper to saunas—build a seamless guest experience, and why they believe “Focus on your product. Direct bookings follow.” Then explore CraftedStays.co for more expert strategies.
Transcription
Skyler: When you’re doing something hard, it’s supposed to feel hard, you know, and it’s gonna give you that stress and it’s gonna give you that anxiety. But at the end of the day, you really have to kind of take a step back and I, I have to do this daily and I have techniques that I have learned to make sure that I’m not going crazy daily.
Skyler: But in terms of just like, you know, it’s gonna be okay, at the end of the day, it is just work. At the end of the day, it is just money and investing in things and you know, making sure you’re doing right by other people. But this doesn’t define who I am as a person, and so. Allowing yourself to like understand your stress and understand your anxiety, and kind of just be able to live with it, but know that you’re on the right path is a good thing, even though it may not feel like it in the moment that you’re feeling those feelings.
Good.
Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring on top operators to discuss marketing, revenue management, and the guest experiences to drive towards being booked solid.
Gil: On today’s show, I have Skyler from For the Love of Upstate. He’s a short term rental investor from originally California. He’s doing a whole bunch of things in the space. He has a phenomenal story of kind of how he started investing in California, in the Northern Cal Southern California market and how he’s now investing in upstate New York.
Gil: He’s also the founder or one of the founders of the STR Book Club. We get to talk a lot about really how he has grown throughout his career, all the different phases in his vesting career, how he approaches really designing out his space, the building a brand, and really how he attracts people to come back to his days.
Gil: We talk a bit about how he is approaching direct bookings, how he approaches partnerships, and then we cap it off with really something pretty unique where he talks about one of the other. Ventures that he has, which is the STR book club. So definitely this is a show that’s worth listening to, and I just love his story.
So without further ado, let’s bring him in.
Gil: Hey Skyler, welcome to the show.
Skyler: Thank you so much, Gil. I appreciate it.
Gil: Yeah, it’s, uh, it’s great to have you on. Uh, I knew when we first met at, uh, level Up that I wanted to have you and or Maddie on the
Gil: show, so definitely I’m excited to have you here. I,
Skyler: Awesome. Yeah, thank you so much. I know Level Up is always such a good time. One of our favorite conferences. Shout out to Natalie Palmer and Tatiana as well. They do a great job there.
Gil: they do. It’s a
Gil: very different type of conference, like our
Gil: listeners here, if you’ve never been to a Level Up before, it’s not
Gil: like any other STR conference, um, that you get to experience out there.
Skyler: Absolutely. I think everyone is like the most welcoming you’re ever gonna find at a conference setting. At that conference. Yeah.
Gil: Yeah. Did you, um, did you go to the previous years as well?
Skyler: So we only did the one year prior. Um, and so I think they had maybe, I think that was the second year. I think this was the third Level Up conference from this past year. Yeah, so we, we did the year prior, which, uh, that was our first ever, that was actually when we launched, which we’ll get into in a little bit.
Skyler: That was when we launched our short term rental book club at the first level Up your listing.
Gil: Yeah, I remember last year, uh, I was trying to figure out which conferences I should go to and people were like, hinting like, you check out, level up.
Gil: Um, and I went onto the website and it was like pops of pink everywhere. I was like, I don’t know if this is
Gil: like for me. And I, I remember mentioning to to Natalie, I, I, I dmd her and I was like, can males go to
Gil: this?
Skyler: yeah.
Gil: Am I gonna be turned away at the door? She’s like, no, totally. You can have it. You
Gil: can go there. A lot of, um, a lot of the ladies bring their husbands. I was like, well, I don’t wanna be a plus one type of type of thing. So I opted not to go last
Gil: year and this year, um, folks were like, dude, Gil, you have to go.
Gil: And
Gil: I was like, okay, fine. I’ll suck it up. Even if I may feel like a plus one there.
Gil: I’ll, I’ll try it out. And I’m actually very happy that I went.
Skyler: Oh, absolutely. And you can’t beat Scottsdale in the springtime either, so
Gil: It was beautiful that
Skyler: Incredible. Yeah, it was so good. We ma uh, Maddie, my wife and her brother that we’re all big baseball fans too, so we always try and squeeze in a couple spring training games when we’re there as well. So that’s always fine. Yeah.
Gil: Yeah, it was beautiful that day. And I think like, was it raining like before and after? I think the right when everybody was packing up and
Gil: like bringing their stuff to the cars.
Gil: It was like it was raining.
Skyler: Starting to drizzle on the last day, last minute. So it
Gil: know. It was like, yeah. I was
Gil: like, the sun just came out just for the, the conference and, and,
Gil: and came back out.
Skyler: I know. I know. But yeah, it was really fun. I’m glad they did this one in downtown Phoenix too. I thought it was a lot more just like fun and people could walk around after things like that, see, which was cool.
Gil: Yeah. That’s true. That’s
Gil: true. Um, I forgot what was near there Was verma there before?
Skyler: I
Gil: I think Verma was like near right nearby there too.
Skyler: Yeah. Yeah, I know. It’s close to like the, I know the Diamondbacks have their stadium there. There’s the basketball arena there as well, so yeah, there’s just like so many restaurants and things to do there.
Gil: Yeah.
Gil: Yeah,
Gil: Well, Skyler, we kind of went deep into it, or already, or we started to, to kind of dive, dive deep. But,
Gil: uh, let’s back up a little bit. Who’s, uh, who’s Skyler?
Gil: Give us, give us a little, uh, intro.
Skyler: Absolutely. So I am a California boy. Grew up in California. Uh, lived there for, gosh, about 26, yeah, 26 years or so. So lived all over California, Southern California, Northern California. I met my wife Maddie in college at the University of San Francisco. Um, and
Gil: did not know that. Wait, did I know that?
Skyler: I think we briefly talked about living in San Francisco with you, but yeah, that’s where, that’s where we met.
Skyler: So she, she’s originally from Redding, which is a small town close to Oregon, and I’m from Long Beach, Southern California. But yeah, we met in San Francisco, lived there for about six years or so. Um, and that’s kind of where we. Started our investment journey, if you will. We, um, I was working, actually, I, I always think, this is a funny story.
Skyler: I was working at a cannabis company working in marketing, uh, in San Francisco and right after it became legal and then, uh, Maddie has always wanted to be an entrepre. She actually majored in entrepreneurship and innovation in college and then had worked at a bunch of startups, was doing marketing as well.
Skyler: Um, and really, it’s a funny story. The way we got into short-term rentals was Maddie was getting into an Uber and her Uber driver, as they do especially in San Francisco, started chatting her ear off about all things. And so he got onto a topic called rental arbitrage. And so he had mentioned this topic, mentioned a guy that was doing it that he knew down in San Diego.
Skyler: And at that point, a light bulb went off in Maddy’s head and thinking, okay, this may be a good. Way for Skyler and I to get into real estate at a very low cost level. So that’s what we did. We were living in San Francisco, I was from Southern California. Um, and so over like a Christmas break period, we decided to fly down to San Diego, check out a couple listings that were for rent, just that we found on Zillow.
Skyler: Um, literally the first landlord that we talked to at a rental unit said, yeah, that sounds fine to me. Like we’ll get the sublease agreement going. You can take over this unit. And it happened to be a Quadplex property. And so he had a second unit within that quadplex that was available as well. So we ended up taking two units that first day.
Skyler: Um, and then over the course of the next year or so, the other two units became available. So we kind of scaled that rental arbitrage from two to four within that first year. Um, and this was pre COVI and we’re in down downtown San Diego for the most part. So. Very high occupancy rate. We knew nothing. We didn’t know what an occupancy rate was.
Skyler: We didn’t know what ADRs were. We knew nothing. We just kind of knew how to furnish an apartment because we had lived in apartments before and decided it was maybe a, a fun opportunity to get ourselves into. Um, and it ended up being life changing. Um, so we made quite a bit of money with those arbitrage units over the course of a few years.
Skyler: Um. We ended up using those profits from those arbitrage units to purchase our first property in Big Bear, California. Um, and that was kind of our fir that was, that was our first ever like real estate purchase. Um, ended up becoming like a live-in flip situation. So we, uh, actually purchased a single family home and there was a very long hallway in this single family home that led to the back of the property.
Skyler: And so we decided to put a door in that hallway, close it up with like these makeshift IKEA cabinets, um, so that the guest that was going to eventually stay in the back unit would be separate from us in the front of the house. And, uh, we started running that back unit as a short term rental as well. So, um, we kept running the San Diego units for a few more years.
Skyler: As everyone knows, rental arbitrage has its pros and cons and eventually. They got a little bit too run down and some of the stuff had to do with the landlord not wanting to pay for things. At one point he didn’t even wanna pay for heat in the apartments either. So, um, we ended up having to walk away from those units unfortunately.
Skyler: But, um, being able to purchase our first home in Big Bear, uh, right before, uh, or actually kind of in the middle of the pandemic, but I think as people kind of are getting or way more familiar with that big bear market during the pandemic, the real estate prices just skyrocketed in Big Bear, California.
Skyler: Um, and so we took plenty of advantage of that. We ran the, the Airbnb for quite a while. We actually moved out of the front unit as well and ran it as two separate units. Uh, we moved down to like a little Airbnb in Los Angeles for a little bit of time. Um, and so we were running those and they were doing really well.
Skyler: And, uh, one day we started looking at the equity and the value appreciation in the home and decided like. Oh wow. We can actually make a couple hundred thousand dollars if we sold, decided to sell this house today. And so that actually was roughly, we kind of, we did a little bit of simple math and we’re like, okay, that’s, we’re we, if we sell now, we could probably get like four to five years of profit on our short-term rental here right now and use that for, you know, future endeavors.
Skyler: So we pulled the trigger on that. Thankfully we sold that property at a, in our opinion, just a ridiculous price at the time. And, um, that actually funded our journey from living in California and moving out to upstate New York where we’ve been living for the last three years. And, um, we can get into kind of our endeavor here, but this is kind of where our true professional real estate journey really began.
Skyler: Um, here in upstate New York.
Gil: Wow. So you, you, you deployed a couple of T tactics. You did,
Gil: I heard a little house hacking in there.
Gil: I heard a little, uh, fix and flip,
Gil: uh, live and flip. Actually, you probably called it, uh, a bit of arbitrage.
Gil: Well, you, you, you deployed a bunch of different tactics to, to get to where you are now.
Skyler: Absolutely. And you have to be scrappy, you know, early on, especially, I mean, we were, you know, broke college students had graduated like a year before we started our rental arbitrage. So live in paycheck to paycheck on a hefty San Francisco rent. Um, so didn’t have a ton of money to deploy. But, you know, rental arbitrage like for so many other people is such a great first step into, you know, full on real estate investing.
Gil: Yeah. And that, that’s what I find with a lot of folks that, that
Gil: they may start off with rental arbitrage because the, the cash flows are just insane. Like the upfront capital to, to get into it is,
Gil: it’s much lower. Um, but I think a lot of, a lot of the smart folks, they, they realize like they actual, the actual wealth making is not in the cash flow.
Gil: It’s on the
Gil: equity play there. And you see the shift of people mo migrating from the arbitrage over to their own assets.
Skyler: Absolutely, absolutely a hundred percent. I mean, the, the rental arbitrage situation was great just to get, get, you know, wind in our sails and kind of learn the ropes on a, on a low risk environment, if you will. And so that really gave us the confidence to go ahead and purchase our first property. And that’s kind of led the way to where we are today as well.
Gil: What, um, what led you to upstate New York?
Skyler: So while we were living in Big Bear, um, we were approached from, it was a company, it’s called Tech Vester. They’re a short-term rental fund. Um, they’re probably the biggest short-term rental fund in the United States. Um, I. Maybe not even, probably they probably are. So I know that they’ve done about 200 properties over the course of the last three years or so.
Skyler: And so, um, thankfully when Maddie and I started our rental arbitrage, uh, units down in San Diego, we also decided to start our social media. And so we got relatively popular on TikTok and Instagram as we were doing rental arbitrage, talking about, um, sort of what rental arbitrage is, how we’re running the units.
Skyler: And then, um, this company, tech Vester reached out to us looking for, um, you know, looking to hire employees in any capacity at that point. So, um, Maddie and I were two of the first sort of employees with Tech Vester a few years ago. Um, Maddie was doing. Sort of like acquisitions, looking at different markets where tech vests should be purchasing properties and then doing really specific deal analysis for them.
Skyler: Um, and I actually started doing investor relations where I was on the phone with investors all day long trying to pitch them the investment opportunity that tech investor was offering at the time. Um, but very quickly, and I knew that going into it, I’m not a sales person by any means. And so I quickly found my way over to the operations team with Tech Ster, where um, I ended up being a project manager, um, for them.
Skyler: So I, over the course of about a two year period, I worked on about 45 different home renovations across the United States, and it was all from my laptop, so I would never go to the properties. I would coordinate the entire renovation from the day that we closed on the property to the day that we listed on Airbnb.
Skyler: And so that was a. Crash course, if you will, and how to get property stood up as quickly as possible within a very specific allotted front end budget. So, um, between Maddie’s experience with Tech Ster and my experience, it was kind of the perfect combination to be out, to be able to go out and do what we wanted with our own property, you know, investing and, you know, getting our own investors on board with, with, with some of the properties that we were working on.
Skyler: But while we were working at Techster, one of the markets that we went out to, um, was upstate New York. Uh, Maddie actually helped developed a specific product called Airbnb in a Box, which was a service-based, uh, kind of business where, uh, an investor could come and say they didn’t want to invest in like a fund environment like Tech Ster was offering.
Skyler: They wanted to 100% own a short-term rental, specifically for most of the time the tax benefits that that would allot to them. Um, but it was a service base. So we were pretty much doing what we were doing for tech ster in the fund environment. But we were working with like a one-off investor that owned a property, uh, or, or was looking to buy a property.
Skyler: So we would help them identify the home and once they closed on the property, we would do full service project management and then actually manage the property for them once they went live on Airbnb. So that’s what originally brought us out to upstate New York. Um, and then now that Maddie and I have sort of branched off away from Techster, um, we raise our own capital for our own deals here in upstate New York.
Skyler: Um, with the help of our, uh, we have very specific capital raising partners that we utilize, and Maddie and I use everything from our acquisitions to project management. And now Maddie gets to do what she really loves the most, which is design these beautiful homes here in upstate New York for us.
Gil: Yeah, yeah, yeah. Um, the Airbnb in a box,
Gil: um, project that Maddie was doing, was that independent of TechFest or, or was that kind of within
Skyler: So that one was with Tech Fester. She did about, I think they took maybe four or five clients through the tech ster, Airbnb in a box. But, um, tech Fester as a company decided like that wasn’t the best bang for their buck and also just too much time spent on a property that wasn’t within their fund, which I can totally understand.
Skyler: And so, um, that was actually when Maddie and Tech Vester decided to sort of part ways. She wanted to continue that business model and also start potentially raising capital for our own deals. So, um, very graceful exit from Tech Fester with Maddie and I. But, um, it was very, uh, helpful to get those under our belts before we started to do them ourselves,
Gil: Yeah. Yeah.
Gil: Um, as you mentioned, like tech vester, like it gives me like a lot of like, I don’t know if you know the term be or Man Off, I
Gil: think it’s how you say it. Um, but earlier this week I was talking to Taylor,
Gil: um,
Skyler: Taylor Jones. Yep.
Gil: yeah, yeah, yeah. And, and he was mentioning, and I, I met SFA a little while ago as well too.
Gil: It’s just like, it’s a small world that like,
Gil: it’s actually, there’s not, I mean, yes, there’s a lot of people in it, but like once you kind of get in there, it’s, it’s actually the same people that keep on coming up.
Skyler: Oh, a hundred percent. It’s a small world in the short term rental space. And, you know, if I, if take any advice from this podcast specifically, I would say, you know, don’t, don’t burn any bridges. You know, things are gonna come up, people are gonna go different paths in lives and different paths in their businesses, but, um, you end up seeing the same faces and having the same conversations with people.
Skyler: So don’t, don’t ever burn any of those bridges in this space specifically.
Gil: Yeah. I
Gil: actually find like the, the culture in this industry, and I’ve mentioned this many times on the podcast, is very different than a lot of other industries.
Gil: I find that specifically in short term rentals, that’s a very collaborative space here.
Gil: Like people, even if you’re in the same market, you’re talking to other investors, you’re having meetups, you’re sharing ideas, we’re sharing what our tech stack looks like, what we’re doing, which is very different than like, maybe, maybe before, like in, in the long-term rental days
Gil: there like is very different than long-term rental investing, uh, long-term rental investing like. You try to keep, like, which markets would, neighborhoods to your vest,
Gil: you don’t share contractors. It’s a very different culture there between,
Gil: between the investing types.
Skyler: Yeah, a hundred percent. I think short term rentals, it’s, it’s such a, a niche, but it’s also very general, right? Like what Tech Vester does versus what Natalie does versus what we do. Like, they’re all similar, but they’re all very different, and we’re all catering to a different guest avatar. Um, we’re all somewhat in different markets, but, you know, I think it’s, it’s definitely more collaborative than other, you know, industries that I’ve been in as well, that’s for
Gil: for sure.
Gil: For sure. Um, what’s, uh, help, help me understand, help me conceptualize
Gil: some of the properties that you, that you’ve been building and, and working on. What, what are those like?
Skyler: Yeah, a hundred percent. So, um, right now we are, so we have three, let me, let me make sure I get this right. We have three active short term rental properties. We also just closed on a boutique hotel, which I know you said you talked to feta yesterday. I don’t know if you mentioned that. So, F Fe a helps us manage that hotel as well.
Skyler: But, so we have three short-term rentals, one boutique hotel, and then we’re working on another two properties here as well. Um, and under contract on another one. So very busy. But typically the properties that we identify here are old, old properties, like that’s number one. We typically find houses that are, I mean, literally this one that I’m sitting in, it may not look like it ’cause one of the previous owners renovated it, but this house was built in 1807, so.
Skyler: Houses here in upstate New York can be very, very old. And that comes with its own renovation plan in itself. So that’s one, one facet that we always look at is we always try and find properties that need work. We’re not afraid. We have, you know, we actually have our own renovation crew and construction crew now as well.
Skyler: So being able to work on houses that need work is actually a positive for us. We know we can immediately add the value to those homes, um, as well while we do some crazy things to the properties. And so we’ve really been leaning into, um, sort of the wellness spa of properties as well. So, um, just this last year we kind of did one of those first three that we have live.
Skyler: Um. It’s in a town that you would never have known of. It’s in a town that even upstate New Yorkers have no clue where that is or what it’s about. And, um, it is pulling some of the highest revenue that we’ve seen on a property up to date. And the reason for that is because we did more than enough to the property to make guests want to get to that house and never leave their entire stay.
Skyler: So, um, what we do typically is add a whole wellness theme to typically the backyard. So we will do things like build out a custom sauna to fit the deck in the backyard. We will put in cold plunge bathtubs in the backyard. We’ll add outdoor showers. We’ll wrap our hot tub with wood so it’s integrated to the deck.
Skyler: And then oftentimes these properties have some sort of waterfront feature. So whether it be on a river, a creek, or if we get lucky enough to even find a property at the right purchase price to be on a lake, that is amazing. And so those are the ones that we prioritize when we are looking for potential deals here in New York.
Gil: Wow, that sounds, that sounds amazing. So it sounds like the properties here, your property is the destination. It’s
Gil: not like they’re actually traveling there to go to all the attractions.
Gil: Your place is the place that they’re trying to go to.
Skyler: Yeah. And you know, one of, one of the big reasons as to why we picked Upstate New York also is because, um, there’s just not a lot of data here. Like your average investor looking on air, DNA is gonna look at New York and be like, Hmm, all right, that’s just a state that I’m gonna stay away from.
Skyler: ’cause there’s not a lot of comms here. So when we were first raising for our first couple deals, that was, uh, you know, a huge sticking point to get through with potential investors and making sure that they knew, like, you know, we come with the experience. This is a little bit of, you know, a hypothetical situation of sort of these revenue numbers that we’re trying to hit.
Skyler: But we believe in the product that we’re selling and we know that we’re close to some of these. I mean, some of the most wealthiest places in the United States, like, you know, New York City and even some of these smaller markets like Connecticut, you have some very, very wealthy people here in upstate New York and around the northeast region in general.
Skyler: So we’ve always abided by, you know, if we build it, they will come. And so far so good.
Gil: Yeah,
Gil: I don’t know if you have any plans to come back to California and do something similar. I’ve been, I’ve been wanting
Gil: to invest back into my backyard.
Gil: Um, but I think it’s similar kind of to kinda the makeup where you have such a high concentration of like high net worth people. There
Gil: an area that doesn’t get a lot of, at least vacation rental investing because it’s not typically a market that people invest into.
Gil: Like when you think about New York, people are like, I do not wanna build a short-term rental
Gil: in New York. Same thing goes for California. No, one wants to build a short-term rental in California.
Gil: But, but at the same time, I, I, I completely understand like. Because of that, no one’s investing into it. You have these high net worth people. There’s actually a big opportunity from a market demand standpoint where people are looking for these types of attractions or stays and just not available. And same thing for,
Gil: for California, like if I wanted to escape somewhere, there’s not like one destination that I would like want to, to, to escape to.
Skyler: No, a hundred percent. And I think upstate New York has its unique features to it. Like, I mean, the most well-known thing upstate New York is known for is that fall season of like the fall foliage and all of that. So you’ll have a lot of travelers come up in October. But, um, I think what people don’t know about upstate New York is that there’s so much water here.
Skyler: Like anytime you’re driving from place to place, you’re gonna pass a river, you’re gonna pass a creek, you’re gonna pass massive lakes. And so, um, even me, like when I moved to upstate New York, we moved to, uh, it’s in the Hudson Valley. We were about two hours north of New York City. The Hudson Valley is pretty well known, even from people that don’t live in New York.
Skyler: A lot of people know what that is, but the farther you go west, kind of towards Buffalo in New York, the less and less people know about these small little towns. But, um, like I said, so far so good. And I think one of the major, you know, sticking points. In addition to just the numbers and, you know, things not working out on the investment front is sort of that construction business that we’ve been able to kind of, um, wrap our heads around here in upstate New York.
Skyler: So it’s really difficult to find contractors and when you do, they always seem to be overpriced and things like that. So, coming into this market, I won’t say is the easiest thing in the world, but if you have some systems or you have a, another close by market where, you know, maybe you can pull a contractor from out of state or something along those lines, um, it’s very viable option for those types of people.
Gil: Yeah, I bet you those, uh, 45 projects that you did at the, at Techster really helped out in making sure that you know, you know how to, uh, do your own deals.
Skyler: Yeah, a hundred percent. I think like one of the first things I said right, is like, just don’t burn, don’t burn bridges and Right. Like we always, especially with contractors and our labor force like. Anytime I ever have even a guy come over and, you know, measure for like a glass panel or you know, a landscaper like as small, small things or large things like a bathroom renovation, like don’t burn those bridges ’cause you’ll never know when you’re gonna be doing that specific thing again and when you’re gonna have to pull someone.
Skyler: And what I’ve learned is contractors are also very willing to travel, like, you know, for the right price, for the right opportunity. Um, especially, I mean, at least what we’ve seen in the Northeast, like all the states are so close by that, you know, they can really get to and from places relatively easy within a few hours drive.
Skyler: And so again, don’t burn those bridges. If you had a really good experience with a contractor, always, always, always, you know, keep in touch with them ’cause you never know when they’re gonna come back in your life.
Gil: Yeah,
Gil: Yeah.
Gil: absolutely. So, given that your places are, I don’t know if remote’s the right word, but they’re a little bit outside of the typical attraction areas. How do you market and how do you draw people into even know about your place?
Skyler: Yeah, absolutely. So we did sort of establish the brand of, for the love of Upstate, and so that is kind of like where all of our properties fall under, um, our website is now finally live. So you can actually learn not only about like our investment opportunities, but also um, we have direct bookings that flow through our website as well.
Skyler: Um, so you can see where all of our properties are. Um, but yeah, when you’re operating in like these, these remote markets, um, thankfully again, kind of going back to like there’s not a lot of comps in these markets, which means that there’s just not a lot of short term rentals for people to book and. When there’s not a lot of short-term rentals for people to book, there’s definitely not a lot of luxury short-term rentals for people to book.
Skyler: And so, um, not only in some of these markets are we the only option. We are by far the best option. I’m not saying that to brag, but I’m just saying like, take a look at upstate New York and you’ll not find a lot of great short-term rental properties. And so again, that was all part of kind of our thesis around this area is, yeah, maybe we can’t provide our investors five comps as to like why we’re gonna hit a certain revenue number.
Skyler: But in that same light, we can also say, Hey, there’s literally zero other luxury short-term rentals in this market that house 14 overnight guests. Right? So clearly there’s something missing here for someone to step in and, and do this, right?
Gil: Yeah. Yeah.
Gil: And, and I have your, I have your site up right now too,
Gil: and if you can kind of look at it, you can kind of see that there’s a certain feel that
Gil: you want to get across. You guys are using certain tones of color
Gil: to provide that, like the sense of luxury there even shows in your website. I’m sure that that comes through in all your photography that you, that you have on your listing.
Gil: It
Gil: comes in on how you design the space as well too. So there, like, there’s a bit of brand cohesiveness that, that you’ve been able to establish.
Skyler: Yeah, I appreciate that. I can, I will definitely not take the credit for that. That is all Maddie, my wife. She is, um, I mean, that’s. To me, she does great, great work with deal analysis and all of that and getting us legally on the right foot when we’re opening up like new LLCs. But by far the best thing that she is amazing at is the design of the properties.
Skyler: And um, it’s funny ’cause my specific job is typically like the median between Maddie, our designer, and our construction crew. So I’m always like trying to make, uh, agreements, like maybe we won’t use like an exposed shower head for this one, but maybe this shower we can use it or, or something along those lines.
Skyler: Or, this tile is very tricky to install. Can we go with the easier tile to install in this bathroom, knowing that we’ll use the harder, nicer looking tile on this bathroom. So there’s a lot of, uh, a lot of backend, uh, conversations with stuff like that. But no, I appreciate it. I mean, that was kind of our number one thing when we started to do this.
Skyler: We knew we wanted to do it. In the most amazing possible. And with that comes a lot of, you know, major stress as well. We try and keep our investors as passive as we possibly can. We try our absolute best and we’re, we pride ourselves on never having to go back and get like, another round of investment from a particular investor on a property.
Skyler: If Maddie and I wanna use a $5,000 wallpaper when we know we could do the same thing with a couple cans of paint that typically would come out of like our personal finances to make sure that we can go that extra level to make that house look even better. Um, so yeah, we try and keep investors at, you know, at the dollar amount that we originally agreed upon.
Skyler: And, um, if anything has to come out of our own pocket, um, we are more than happy to make that happen, to make sure that that house feels as luxury as we possibly can make it.
Gil: Yeah. Yeah. Well, kudos, kudos to the, the growth that you guys got there.
Gil: It’s, it’s, it’s amazing.
Skyler: Oh, I appreciate it. Yeah, I mean, started from scratch, you know, I mean, started with buying Ikea furniture in San Diego, you know, and now we’re, uh, getting brand deals with Amber Interiors. So it’s like, it’s crazy to see the last few years and how they’ve, you know, un unfolded in that way. But, um, it’s one step at a time, right?
Skyler: Like, we would know nothing that we do now without taking these steps to get to this point.
Gil: Yeah.
Gil: I think that’s, that’s very, very true. Like every single one of these like phases in your invest investment career has taught you a whole lot to be able to tackle some of these more audacious projects where you’re taking a lot more risks, you’re going into markets that people didn’t know about.
Gil: You’re
Gil: making designs decisions that, um, are not like the norm of that market there.
Gil: Um, so that’s, that’s, that’s quite a bit.
Gil: Um,
Skyler: percent. And like we, we try and, um, I don’t know what the right word is, but we try and like make it all feel okay. ’cause at the end of the day, we know we’re in the short term rental business, but. Also we’re in the adding value to a home business, you know? And so we never scoff at, you know, we’re, we’re really early on in this stage, like, to give you a bigger picture of this, like our first ever property that we raised capital for, we’re just about to hit the year mark of one full year of revenue with that property.
Skyler: And so, um, we’re still very early on, but everything seems to be going really well. But now hitting that year mark, now we’re in talks, okay, when are we gonna do the cash out refinances, taking a look at interest rates, when’s the right time to do this and that. So, um, we always have that in the back of our mind.
Skyler: And if buying a little bit more expensive of a light fixture or something like that could eventually add to that equity, we typically are always making, you know, that decision.
Gil: Yeah. And, and when you’re taking on investors there, I’m guessing they’re per property. Um, I don’t know if you have plans to eventually raise for fund, where you get a little bit more flexibility on how you kind of distribute that across a bigger portfolio.
Skyler: Yeah, we’ve definitely talked about the fund environment before. We, there’s pros and cons to, you know, to the way we do it and doing it as a fund as well. We like the way that we do it where it’s like one property per LLC is kind of how we’re structuring at this point. Um, but over the last couple months and right, like we’re still very early on.
Skyler: We’ve done this for five years in total, but only doing this capital raising for the last year and a half or so comes with its own learning process, but. Um, ultimately because we do them on one property per LLC, some of the learnings that have come from that is now, we’re now Maddie and I are structuring new businesses like for the love of Upstate as sort of like a, if you’re familiar with like the summer LEDs of the world or like these larger design companies.
Skyler: So that pretty much how we operated it is like an LLC owns the property and then Maddie and I, and we have a couple other business partners that own for the love of Upstate. And so we actually funnel the renovation, the design, um, the furnishing everything through for the love of upstate. And that does give us a little bit of flexibility if we want to spend a little bit more on something we know, okay, that’s coming from, for the love of Upstate, that’s not necessarily coming from the property LLC to buy this, you know, more expensive wallpaper or things like that.
Skyler: So that’s, that’s helped us from a bookkeeping perspective, an accounting perspective, and also helped us kind of like get to more, again, that luxury, you know, point that we want to get to with these properties,
Gil: That’s interesting.
Gil: That’s very, very, I, I, I haven’t met someone that’s, that is doing that type of LLC structure because I’ve, I’ve heard a bunch about like the umbrella LLC and having
Gil: individual properties in there. Um, but I think you guys are in a unique place where you guys are doing a lot of sweat equity on there as well too.
Gil: So you guys are making sure that you structure your business that’s separate from the actual properties themselves.
Skyler: A hundred percent. And technically the way we do, and this may be getting even a little bit too granular, but for the love of upstate, LLC owns zero equity in any of the properties that we do. So Maddie and i’s equity in these homes are completely separate from our business, but that gives us the kind of flexibility with, for the love of Upstate as an entity, to kind of go wherever we want with it if eventually we wanna stop doing our own deals.
Skyler: Okay? Now we have a construction crew, a designer, we have all these different components where if we wanted to end up going out and taking on client work, even through for the love of upstate now, it gives us that flexibility to go out and do that side of the business as well.
Gil: Yeah. Yeah, that’s, that’s pretty cool.
Gil: Um, how’s, um, how have you seen the regulations specifically in your area? Because I know in the metro areas all around you,
Gil: it’s not a place that you wanna be.
Skyler: Oh yeah. Thankfully. I mean, upstate New York, I always kind of joke about it ’cause we have a lot of friends in Michigan specifically, and Michigan I feel like is just getting hit left and right. I mean, I feel like every single week I’m hearing another story from another friend. Oh, my house just got shut down.
Skyler: I’m having to sell it. All these things, knock on wood. Thankfully at the moment, upstate New York is very lax about short-term rental regulations. Um, it gets very complicated like it does in a lot of places. But it’s like you have, you know, you have your county, you have your city, and then oftentimes in these more rural environments, you have like your town of the city and there’s different towns within every city.
Skyler: And so oftentimes our properties fall in those smaller towns where. I mean, I’ve even had it where our building and zoning officer works Tuesday, Thursday, and then another property that we own. And he works in that town Wednesday, Friday. So it’s like very, very small town vibes. And again, going back to this whole thing of there’s not a lot of short-term rentals in New York right now, or in upstate New York, if you will.
Skyler: So they haven’t really had a huge reason to add regulations. ’cause it’s not like it’s a, you know, a problem like it is in New York City where you’re taking an apartment from someone that could live there. We’re, we’re really just not having that problem yet. So we’re trying to take, you know, a strong front foot.
Skyler: A lot of times when we start purchasing properties in this town, we always get it in writing over like an email. Like, Hey, you’re totally fine. There’s typically not even like a permit process with a lot of the towns that we work in. Um, but now we’re trying to, you know, emphasize the fact that, you know, a permit process isn’t the worst thing in the world, right?
Skyler: So we’re oftentimes even having conversations with these towns of like, Hey, we come with a lot of experience. Like if you’re ever looking to implement some type of permit process, like we’re happy to like lend a hand. Talk to you about what the best way is to do this, show them examples of other towns, um, that have done it the right way, things like that.
Skyler: So thankfully, again, knock on wood, not a lot of problems at the moment. Um, I know New York City just got hit, I think it was what, last year where Airbnb just got completely banned. But that really hasn’t trickled its way up into upstate New York quite yet up.
Gil: Yeah. Yeah, that’s, it’s awesome that you’re having that relationship and you’re actually. Extending your hand out there to have those conversations about regulation because, and I’ve been talking a lot about this probably in the last few weeks, but folks in the industry, at least in your folks feel like the regulations is the scary thing, but it’s actually the other way around
Gil: where when you do have regulations in place, it means that there’s some thought and foresight about like how we want vacation rentals to be enforced in the area and the
Gil: rules we, because when you don’t have that, it means that depending on who’s in office for that particular year, it can go in either directions
Gil: there.
Gil: So having some sort of stance saying like, yes, we support short-term rentals, but you have to abide by these rules, these regulations. It’s not a bad thing.
Gil: It’s not a bad thing whatsoever.
Skyler: and I mean, we’ve seen it, especially you and me being from California. I mean, we’ve seen it time and time again like Palm Springs, big Bear, all these places where it becomes such a big problem, then that’s when you see like a, a ban or an ax and no questions asked. Right. And that’s, that’s the worst case scenario for everyone involved.
Gil: Yeah. Yeah. I think at the beginning of the pandemic, like there’s like all these ordinances that are going up and
Gil: it’s, it’s a scary thing
Gil: because you spent hundreds of thousands of dollars in down payment. There’s a
Gil: lot of equity that you already put in there, and if you were to resell it as it, it might still work out in your areas there.
Gil: But for these vacation rental markets like Big Bear for instance,
Gil: you can’t sell that home at the same value if you end up having all the permits taken away.
Gil: This huge influx of all these cabins being back on the market, like
Gil: who’s gonna buy all of them?
Gil: It’s not gonna be investors.
Skyler: no. And as much as I love Big Bear and I grew up going to Big Bear, like I wouldn’t consider Big Bear as like a luxury market, you know what I mean? And so like when you know, economic times hit the fan and you know, regulations come into play and things like that, like you’re not thankfully here in upstate New York.
Skyler: And again, the techniques and the reasons as to like why we do specific things to properties, the fallback plan, whether it’s regulations or maybe we just didn’t hit the numbers we thought we were gonna hit as an Airbnb, we always have that backup plan of like. Okay. Maybe some rich New York City person is gonna come and love this house and just purchase it from us at a crazy, at a crazy dollar amount.
Skyler: So that’s always kind of the backup plan with a lot of the houses that we’re working on too.
Gil: I mean, you are in a market that like that. I, I, given that you don’t have a lot of short term rentals, the potential buyers are probably home buyers of anything.
Skyler: Oh yeah.
Skyler: Absolutely. Yeah.
Gil: do you or have you met either David or Dana from Rent Responsibly?
Skyler: No.
Gil: You should, you
Gil: should definitely get a chance to meet them.
Gil: Um, and we can talk about this afterwards, but,
Gil: uh, they’re part of Rent Responsibly and they’re all about really trying to figure out how do people band together to talk about rules and regulations and giving people the resources to code to their state, their county, um, in an orderly fashion kind of bang together should do this.
Gil: And I think like you probably, since you don’t have a lot of investors kind of investing in your area, that’s probably less beneficial. But
Gil: I think that some of the things that you’re doing about, like being forward thinking on the type of regulations that you think the city should put in place, like I think those are, those would be really good partners and,
Gil: and really kind of putting that structure in as early as possible.
Skyler: Yeah, absolutely. I mean, it’s needed it, we don’t need to be operating in the wild, wild west of short term rentals anymore. Like we can have some type of permit process and it not make people pull their hair out, you know?
Gil: Yeah.
Gil: Yeah,
Gil: I mean, I’m, all my properties, all of my properties have some type of permitting process. I have fire marshals coming to my property
Gil: every single year. They’re making sure that our property is safe. They’re making sure that
Gil: the, the pools that we have have pull alarms. We have fire extinguishes in, in all the places.
Gil: Like, that’s not bad. Like those are good things
Gil: for, for us all to abide by.
Skyler: Literally, I, I, I almost, I still can’t fathom it here is like, you know, I mean, thankfully we do things the right way and we, you know, we’re putting the smoke detectors, the fire extinguishers, all of these things and taking precautions. We have proper for our short-term rental insurance policies, things like that.
Skyler: But I can’t believe towns allow you to even rent to a long-term rental with some of these, like, inspections not being done. It doesn’t make any sense to me from a safety perspective.
Gil: Yeah. Yeah, absolutely. Uh, let’s go, let’s switch gears a little bit and
Gil: talk about, um, your direct bookings.
Gil: Uh, we talked a little bit about kind of like how you do your marketing there, but help me understand kind of like what are some of the things that you feel are really important to kind of start thinking about as you’re thinking about building out your short term, like your direct booking engine.
Skyler: Yeah, and this is a great conversation. We are just kind of hitting that stride of like starting this whole direct booking process with our properties now that we have a few kind of within the, for the love of upstate portfolio as well. So I would say the number one thing is like branding of our properties.
Skyler: And I don’t mean branding in a way where it’s like, here’s a QR code or a postcard kind of telling you who we are. We want people to like walk into our homes every time and know like, okay, if I’m either at one of our houses, it’s called the river retreat. If I’m either at the River retreat or if I’m at the Pearson house, or if I’m at the right house, I know that this is a, for the love of upstate property by just like walking in and looking at the furniture, seeing the types of wallpaper.
Skyler: I know I joked with you before this call, but even the toilets that we put into properties are all the same. So we always want guests to have like that consistent feeling and then. Taking that next step and being like, oh, if you really loved your stay at this particular property, like you should check out all the others in our portfolio.
Skyler: Because if you love this house, you’re for sure gonna love these others. ’cause it’s gonna have that same look and feel that you’re getting every time. And so we’re just kind of starting that process. Um, thankfully Fede, who is our property management partner, he is the guru of all software. So we’re finally have our website, uh, integrated with Host Away for people to start booking direct.
Skyler: So now, now we’re kind of going back through all of our properties and even doing things like putting, um. Sort of like vinyl si uh, signs on the front of our property so people know it’s a, for the love of upstate property, a lot of our houses are historical and have those names like the Pearson House, the right house.
Skyler: So we’re gonna be putting signs out on the front of the property, um, for people just to drive by and see them and, and be interested. And I would say one of the biggest things that we’re really going down the rabbit hole of for our bigger properties are, um, event spaces and specifically for weddings.
Skyler: And so, um, with that in mind, one thing that’s actually been huge already for this summer, um, we’ve gotten a couple of inquiries and I think one booked out for 2026 already. A wedding was from just a simple Google Maps, uh, search. So we’ve been adding our properties to Google Maps and um, I literally have my cell phone and I’ll get an occasional call every now and now and then from someone asking like, Hey, do you host a, do you guys host weddings here?
Skyler: Like, I’m a wedding planner, I’m looking for a client, all these things. So just trying to be as visible online as possible in. Sort of ways that you don’t really make synonymous with short-term rental properties, but for some of these bigger properties, they act more like a venue for some type of guess, instead of it being just a true place for people to lay their head at night,
Gil: Yeah.
Gil: Yeah. Yeah. That’s, that’s amazing. Yeah. So it sounds like it’s really about like making sure that the guest understands and feels that they had a really good experience, a high class experience
Gil: there. And it sounds like in your case, you’re not actually pushing the brand like that heavily. It’s really about more the properties brand that you’re, that you’re elevating out and, uh, maybe like small little cues to have them remember that it was for the love of, uh, for the love of Upstate,
Gil: um, as, as the umbrella brand.
Skyler: Yeah, a hundred percent. I mean, I think it comes from like. It’s a holistic approach, right? It’s like the guest communication is more important than them knowing that we have another listing and, you know, the, the s’mores kit laid out in a nice way is more important than me asking them if they wanna book another property of ours.
Skyler: So I think it’s, you know, set the experience and set the standard for what our property provides and wait for the guest to reach out and say, Hey, I’m coming back here next summer. Or, Hey, do you have any other listings in the area that, um, that look and feel the same way? So we try and always put that, you know, experience first for everything.
Skyler: And we’re not perfect, believe me. Like our house is sometimes, you know, we miss a, a, a roll of toilet paper now and then and things like that. But we try and make sure that everything is as perfect as possible for every single guest so that it’s not us reaching out to them, it’s them reaching out to us, which makes that point of sale so much easier for that next booking.
Gil: Yeah, that’s, that’s amazing.
Gil: So now that you have kind of like your, your website.
Gil: In a place where it’s all connected the way you wanted to with phase health there, um, and you’re starting to brand these and you’re, you’re, it sounds like you’re also gonna be publishing or kind of making it more prominent, the brand within the, the property themselves.
Gil: What’s next for you? Like, what are some of the things that you’re looking to invest into from a, either a digital marketing side or more of a branding side?
Gil: What are you, what are you trying to amplify this year?
Skyler: Yeah, I think now like the, the digital stuff was always first for us. We never wanted to start promoting in property until we had the digital assets all taken care of. So the last few months actually, Fe’s wife car does all of our digital marketing and she does like all of our branding for properties.
Skyler: She helps with our website design, all of that. So now that we have all of that taken care of, which the website, I kid you not went lab I think two weeks ago or something like that. So it’s very recent. Now we’re gonna go back and start doing all of sort of that like more, in my opinion, the more simple in property branding, where we’re looking at the postcards, we’re looking at, you know, a QR code here and there, things like that.
Skyler: So that we just stay top of mind, especially. You know, that last day when a guest is checking out, you know, having a simple postcard, um, that’s for the love of upstate brand with a little picture of all of our other properties on there, um, can very easily lead to, you know, a future booking at another property as well.
Skyler: So started with the digital stuff and now solely but surely kind of moving into the in-person on the property type of branding. And hopefully we will roll that stuff out over the next three to four months or so.
Gil: Yeah. Yeah. And I, when I was talking to Fey, he, he also mentioned that, um, he’s investing into also the email marketing as well too.
Gil: Really capturing emails that come through
Gil: and nurturing that over time so that if they forget about it or they need to jot a memory of like what it was like to stay with you,
Gil: you’re kind of staying on top of mind so that the next year they’re thinking about a stay. You’re the first person that they think about if they’re looking for an escape.
Skyler: Yeah, a hundred percent. And I think that has done that brilliantly in terms of like, he knows it’s about the team too, like on the internal side of things. Like there’s so many things that need to get done, especially for a company like ours where we’re not only. Helping on the management side of things, but we’re also standing up new properties every single day too.
Skyler: So it’s like how do we balance the property management stuff and balance like full blown two, three properties at a time. Renovation projects as well. So building out the team, and I know Feta uses, um, Emily Leko, who is at Level Up your listing as well. She also does our marketing for short, uh, the short term rental book club as well.
Skyler: She is awesome when it comes to email marketing, so I think if it’s not Emily, you know, find yourself and Emily in terms of like doing that digital marketing, finding someone that can run your email marketing and things like that because there’s just so many things that need to get done to be. At the, you know, top tier of everyone’s game when it comes to, especially the property management stuff, that it can become very overwhelming.
Skyler: And even for us, we put off building the website for months and months and months. Every single day. Maddie and I are like, we need our website live. We need our website live for so many reasons. And finally it just happens. So now we’re just kind of trying to keep the ball rolling and if we have to hire someone to, you know, take care of a specific aspect of that to make it happen sooner rather than later, it is 100% worth it every time.
Gil: Yeah.
Gil: Yeah. It sounds like you’re big on the, the partnership and the who, not how type of kind of
Gil: mentality there of like building it, not necessarily all by yourself, but really who do you want alongside of you to kind of help you build towards your vision?
Skyler: Yeah, absolutely. I think Maddie and I have actually struggled with that, where it’s like, it’s certain points, we’ve even had friends tell us like, you’re giving up too much of the deal, like you’re giving up too much of your business. But for us, like. We come from a place where, I mean, thankfully, like we come from decent families, like if shit ever hit the fan, we, you know, we have a place to live.
Skyler: You know, we’re never gonna be in a point where we’re like homeless. So it’s like, in terms of sharing the wealth on every single deal on businesses, like not only can help alleviate the stress levels between Maddy and I about, you know, having to take care of all of this. Um, but there’s so much to go around, like on every deal.
Skyler: We look at it as a way there’s 100 percentage points to go around on every single deal. Now it’s about finding the right equity percentage for every single partner in the deal and make sure they feel taken care of, like they’re not getting taken advantage of. And same on our end. And so there’s plenty to go around.
Skyler: And if there is a hole in our game, we try and fill that with a person that could do it better than we can at the end of the day.
Gil: That’s awesome.
Gil: That’s awesome. Um, I wanted to, to bring up something that you mentioned just, just a little bit in the very beginning about the, the book club. I, I do wanna give a space because
Gil: it’s, when I found out about it, I was actually pretty jazzed up.
Gil: Um, can you talk to our listeners about kind of what, what is this book club thing?
Gil: What, what is this? What is a silly sounding book club thing?
Skyler: Yeah, so the book club, so it’s called the Short-Term Rental Book Club. It is a monthly subscription for, uh, like a book club membership, but it’s a little different. Like I think in a typical book club, you’re really just, you know, you’re buying the book of the month or whatever and you’re reading it and you’re probably talking about it with the other members.
Skyler: But the only difference is your subscription price with the rental book club includes the, also the book getting to your doorstep. So you can either choose, we have a hard copy option, an audio book option, or a Kindle option, and you’re always welcome to kind of switch between those three options depending on, you know, if you’re traveling and wanna get an audio book instead.
Skyler: Um, so it’s been a really fun time. We launched it in March of, or probably February of 2024, so we’re a little bit over a year. We’re up to about 150 members. And so it’s grown more rapidly than we ever thought it would. Um, and it’s. At the end of the day, it’s a networking group. Like I think people get a little bit daunted when you hear about, okay, we’re reading one book a month at the end of the month, we all hop on a Zoom call to discuss that book.
Skyler: Me being a founder of the book club, I can honestly tell you you do not even need to finish the book to be a part of the book club. Like if you are just
Skyler: wanna read a few
Gil: say that. You can’t say that.
Skyler: It’s totally fine. Like the zoom meeting at the end of the month is what makes the short-term rental book club. The book club.
Skyler: And at the end of the day, what that means is the members of the book club make it what it is. And so whether it be, I mean, we’ve had already only been been around for a year. We’ve had members partner on properties together by finding each other in the book club. We’ve had people partner on property management companies together.
Skyler: Like, so it’s just a really great low cost. It’s $30 a month, like short term rental group where you can be around like-minded people once a month. And if you’re an avid reader, it’s, I don’t need to sell you. You get a book sent to you every single month and you get to read that book along with a bunch of other, you know, investors and hosts in the short-term rental space.
Skyler: But I think overall it’s just a really, you know, low risk, low cost space for, you know, like-minded people like that. We all are in the short-term rental space just to be able to discuss everything from my house flooded this week to, I had my first booking on my new Airbnb listing and it’s just a really positive group that I think.
Skyler: Most people have very much enjoyed, like myself, the last year being a part of,
Gil: yeah.
Gil: Remind me. I’ve, I, so I, I’m very new to it. I only
Gil: signed up during Level Up. Um, so I’m a new member and I missed the last, uh, meeting because I was at, um, the SDR Hospitality Summit when we had
Gil: the last meeting of the month
Gil: or the, the meeting of the month. But
Gil: is there also a group that goes along with like a chat group, or is it mainly kind of
Gil: within that cohort?
Skyler: Yes, so reach out to us. So on our website, it’s just info at the short-term rental book club. You can email that, uh, email and we’ll get you all hooked up. So we have a Facebook group that everyone is involved in. And then we also have on Instagram, we do close friends on Instagram. So you’ll see like just stories, uh, between members show up on there.
Skyler: Um, so there is a couple of like, digital places for us, all of us to interact with over the course of the month. Um, so yeah, reach out, reach out to the email address. Maddie’s brother, Nick, uh, helps us run the, the
Gil: Yeah. Yeah. Remember.
Skyler: So yeah, you’ll be talking to Nick. So, um, but yeah, yeah, so we have, we have a couple digital spaces for people to kind of communicate throughout the month.
Skyler: And then, um, if you’re super unfamiliar with the book club, that Zoom meeting at the end of the month. Typically one of the last days of the month. So everyone has as many days as possible to finish the book. Um, but that Zoom meeting, it starts off with sort of like a live q and a. So either Maddie or myself typically host the meeting.
Skyler: Um, and then we have a kind of like a guest host come on. And so it’s kind of like a live podcast for the first 30 minutes to 45 minutes. And then the back half of the meeting is what everyone I think really enjoys, which is we break out into small breakout rooms on Zoom. So instead of it being, you know, 50 faces on your screen, you’ll break out into about a five person room.
Skyler: And we have predetermined questions that, again, if you’ve read the book, great, but if you haven’t read the book, they’re still typically questions that you can participate in and, and really just get to know, um, specific members of the group a lot better in those smaller breakout rooms as well.
Gil: That’s awesome.
Gil: Yeah.
Gil: And for, for folks that aren’t in the book club, the, the book that you guys are reading, we all reading for the month of May. I think
Gil: this podcast will air probably after that, but the May book, it’s actually one of my favorites. Buy Back Your Time. Um, it’s funny that when I pulled this out, I didn’t, I I, I hadn’t like, saw what was coming up
Gil: on, on the Instagram, but when I pulled it out, ironically, I actually had another copy already on my desk because I was, I was one of their like, pre-orders of that book.
Gil: So I
Gil: was real and I haven’t had a chance to read it. So like this was actually a really good
Gil: forcing function for me to,
Gil: to go read it.
Skyler: that’s great. Buyback your time has been like on our shortlist since we started the book club. We typically, Maddie is pretty much the book selector, but we probably pretty much have like two to three months in advance planned out. But Buyback Your Time was one of those ones from day one that we’re like, we should read it.
Skyler: But I know so many people have already read the book that we, we were like holding off on it. But, um, even though this might come out after, after this month, we are having, um, it’s a company called Delegate. So we typically have a sponsor for the book club every single month. So you’ll hear a little bit from a sponsor at the beginning of the call, but they’re typically someone in the short-term rental space.
Skyler: But Delegate is actually a virtual assistant, virtual professional, uh, company that helps partner people looking to hire virtual assistants. And then they have a bunch of, um, of people looking for, for potential opportunities there. So they’re gonna come on, talk about delegation, and then Blendy, who is the founder of that company, is actually our host speaker.
Skyler: So he’s gonna be talking about. How to use a virtual assistant properly within your business and how to actually delegate things properly. So he was the perfect person to actually get buy back your time off that shortlist and into the book club.
Gil: That’s, that’s, that’s super smart.
Gil: Um, if you ever, uh, if you ever do the Five Types of Wealth by Sahil, that’s,
Gil: that’s the one I wanna, I wanna host for.
Skyler: okay. Five types of, okay, well, well, I’ll write that down right now. I
Gil: have you heard of that one?
Skyler: have not heard of that one now.
Gil: Um, that one’s on my bookshelf. I
Gil: haven’t like gone through it, but I follow IL’s, a lot of his like Instagram posts and what he talks a lot about is really, we talk about wealth and like the monetary, financial standpoint of like, like when you’re wealthy, you’re, you have, you have a lot of money.
Gil: But what he talks about is really like, there’s five different types of wealth. There’s time, social, mental, physical, and mental. Oh, sorry. Financial. And it’s really, these are the things that you wanna balance your life at, because what you don’t wanna do is over index on the financial wealth that you have, where in your later parts of your life, you start to deplete or not have enough equity
Gil: on your physical wealth
Gil: or your social wealth.
Gil: Um, so it’s, I I really just like the idea of like, it’s not like grind, grind, grind, and we want to get as like build up our cash flows and, and so on, but it’s really about like living a fulfilling life that has many parts to it.
Skyler: absolutely. That’s amazing. We’ll have to keep that in the queue for sure. That’s awesome.
Gil: Yeah. Yeah. Awesome. Skyler, we usually end the show with three questions.
Skyler: Okay.
Gil: First question, what better person to tell me about books than a founding member of the book club?
Gil: Uh, what’s a, what’s a book recommendation that you would have for me and the listeners?
Skyler: My favorite book that I’ve read this last year was, uh, it’s called Rocket Fuel, and the author is, I can’t think of the author right now, but it’s called Rocket Fuel. It’s pretty much an idea about are you as a person or as a entrepreneur, are you a integrator or are you a visionary of a person? And so the whole topic of the book is really like, okay, if you identify yourself as a visionary, you should go out and find whoever your integrator is gonna be within your business, and vice versa.
Skyler: If you’re an integrator, you need to probably go out and find a person that you can partner with. That’s the visionary portion. And I relate to that so much because with Maddie and I, the dynamic is so clear between the two. Like I’m 100% the integrator, and Maddie is 100% the visionary. And so as I’m reading this.
Skyler: I think a lot of times, especially for me, why it resonated with me so much is, you know, everyone has their mental health problems and things like that. And for me, like being an integrator has sometimes a negative connotation to it as like, oh, I’m not like a natural born visionary. Like I don’t have all these ideas when it comes to entrepreneurship, but I’m someone where it’s like, all right, if you wanna do this type of business, like, all right, like, I’ll figure it out and make it work out in some capacity and I’ll, you know, make the steps here if it’s needed.
Skyler: So it not only tells you kind of who these types of two people are, but also it helps you come to terms with whichever one of those are and why that’s not a negative thing about yourself and why that’s a positive thing. And you should really lay into that type of type of thing for yourself because it’s just gonna make you a better entrepreneur at the end of the day if you accept that role for yourself.
Gil: Yeah. Yeah. Does it talk about like flipping between the different roles or are you kind of ingrained of like these are the two paths and
Gil: kind of
Skyler: mostly is like ingrained in that particular role. Um, I would say, but, um, I don’t know. Like I think everyone knows there’s blind that are blurred occasionally, right? Like there’s sometimes I come up with a great idea and Maddie looks at me like, who are you? Like, is that guy? That’s amazing. So, and I think vice versa, you know, sometimes Maddie will come to me and like, oh, I just knocked out this, this, and this from our to-do list.
Skyler: And I’m like, that has nothing to do with what you would typically do, but awesome job. Like. So I think, I think it’s, you know, it’s really just coming to terms with, with those types of roles and you know, that everyone has a specific place in entrepreneurship if you want to be an entrepreneur.
Gil: Yeah. Yeah. I, I like the framing of it as well too, because it’s often, I think like it’s being talked about from like a, this is the leader versus follower or, or, or, or whatnot. Which, which has this like imbalance to it as well too. Like you’re feeling your subordinate to
Gil: whoever the leader is. But what you’re saying is it’s actually not like that.
Gil: Is that, like these are two almost equal roles
Gil: that has its value in its own ways, um, and their own expertise.
Skyler: Absolutely. Yeah. It even goes into depth. Like I know there’s another concept in that book where it’s like the difference between like a superstar employee versus like a rockstar employee. And like it talks about a superstar employee. You can typically, um, you can typically get them to work harder when they get a, uh, like a upgrade and title for example.
Skyler: Like they’re, they’re wanting to work harder for that next title that they can get to and the next title they get into. Whereas like a rockstar, you could picture as kind of like maybe a quiet, uh, engineer that is super great at writing code. Maybe they get, they don’t want a higher title, maybe they don’t wanna manage other people, but they just wanna be really good at writing code.
Skyler: And if you pay them more, they’re gonna write code for you for 30 years if that’s what it takes, right? So they’re a rockstar. They wanna stay in their specific position, put their head down and just work. Whereas again, a superstar is someone where it’s like you can throw a bunch of stuff at them, but what’s really gonna make them motivated is like, okay, is this gonna get me to that next level in my career path?
Gil: yeah,
Gil: Yeah.
Gil: I. Having, having been been in that specific environment, I,
Gil: I completely can see that.
Skyler: Absolutely.
Gil: Um, awesome. Second question.
Gil: What’s a one piece of mindset advice that you would give to someone that’s starting something completely new? I.
Skyler: I feel like I’m a, I’m, I naturally have a lot of anxiety and stress in general, so I feel like as someone, if I was telling you when you’re starting new on something, like don’t get too like scared of the stress and anxiety that might come up. Like what I’ve learned the last few years, especially the last year or two, as we’re raising capital for the first time, like doing something stressful and having something give you a lot of anxiety oftentimes means you’re probably on the right path on doing something and it’s super scary and super shitty.
Skyler: And it might be cliche to like say these things, but. When you’re doing something hard, it’s supposed to feel hard, you know, and it’s gonna give you that stress and it’s gonna give you that anxiety. But at the end of the day, you really have to kind of take a step back and I, I have to do this daily and I have techniques that I have learned to make sure that I’m not going crazy daily, but in terms of just like, you know, it’s gonna be okay, at the end of the day, it is just work.
Skyler: At the end of the day, it is just money and investing and things and, you know, making sure you’re doing right by other people. But this doesn’t define who I am as a person. And so allowing yourself to like, understand your stress and understand your anxiety and kind of just be able to live with it, but know that you’re on the right path is, is a good thing, even though it may not feel like it in the moment that you’re feeling those feelings.
Gil: Yeah.
Gil: Yeah. That’s awesome.
Skyler: Yeah.
Gil: Um, third and final question, what’s one piece of tactical advice that you would give to our listeners that’s either trying to get started in direct
Gil: bookings or amplify it?
Skyler: Ooh, focus on your product. Like the, the direct bookings will come if you have a product that is worth the direct booking.
Gil: I love that.
Gil: I love that.
Gil: Skyler, it was awesome having you on the show. Uh, definitely fulfilled kind of like the expectations that I had for the show when we
Gil: first met and I, um, but yeah, I love what you guys are doing. I love how you’re kind of not necessarily going against the grain, but you’re not following like the Brighton bright and shiny paths that everybody’s doing.
Gil: You’re doing it the hard way
Gil: and you’re putting your sweat equity into it. Um, you guys are doing amazing.
Gil: Well done.
Skyler: it. Thank you so much, Gil. Thanks for having me. I appreciate it.
Gil: Yeah, and I’m excited to keep on being part of your book club and just following along your ride.
Skyler: Yeah, absolutely. Yeah. Join book club if you haven’t.
Gil: Absolutely. I’ll, I’ll be sure to include the, uh, the link in our show notes.
Skyler: Perfect. Cool. Thank you so much.
Gil: Awesome, man. Talk to you there.
Gil: Bye.