109. Start a Short Term Rental Side Hustle in 2024

0:00Today, I'm talking to Jamie Inlow of Be Still Getaways. Jamie used a$2 ,000 loan to turn a neighbor's unused apartment into an Airbnb rental and grew it to a seven figure business. On this episode, Jamie goes deep into what it takes to run a property management business and how she was able to do this with such a small startup budget. Be sure to listen to Jamie's tip about the structures that perform really well, no matter where you live, and how she was able to start this as a side hustle while raising a baby and working full-time. Stick around until the end to hear her method for building a team to successfully scale.

0:32I'm Alex Freeman, and you're listening to the Upflip Podcast, where we uncover how great businesses are built, how they run behind the scenes, and how you can replicate their success. Each week on the show, we interview an entrepreneur where we first get into the backstory, learn about startup costs, budget, profit margins. Next, we'll go into our FanBlitz questions that come from our YouTube community. And finally, we'll get more into the nitty gritty of what it takes to run a team, their marketing tactics, and what business regrets our guests have. Let's get into it. Jamie, welcome to the show.

0:59Thank you. Thanks for having me, Alex. Let's start with your story. When and why did you start Be Still Getaways? Yeah, great question. I can't not quote Taylor Swift here and say that it's been a long time coming. So I think this has been just a fruition of everything that I enjoyed when I was younger from, you know, making dollhouses out of cardboard boxes in my parents' basement to growing up playing The Sims on our family desktop. And then as I got older, you know, watching my friends move into the short-term rental space and purchasing properties, watching them flip them, turn them into STRs.

1:33I was working in higher education at the time, but I was watching my friends do this. I had recently had a baby and I was, you know, regularly working like an eight to five job. And it just it was not what I pictured for motherhood. And, you know, we made a decision to move our family back to Virginia from Boone, North Carolina. And I was able to work. I was working like a part time contracting role in higher education. And still, you know, short term rentals were on the forefront of my brain for something that I thought would be a really great endeavor for me. And then truly the most perfect opportunity fell into my lap when my new neighbor, I found out that my new neighbor had a beautiful horse barn and it had a beautiful finished apartment up above it.

2:10I went through it and I wrote a proposal asking him, you know, hey, what do you think about starting a short term rental out of this barn? Here's what the commission split would look like. And he was all about it. And the rest is history. It was just truly being in the perfect place at the perfect time to make my dreams come true. So let's talk about that first property. Is this the neighbor that also provided the$2 ,000? Yeah. So this is really funny thinking back on this because I'm like, okay, I furnished this entire apartment for$2 ,000. So know that that is doable. This was a one bedroom apartment with a bathroom, living room and kitchen.

2:42And I did the entire thing for$2 ,000 linens included. I was driving all over the state of Virginia for Facebook marketplace fines. I had sent my husband to like Richmond one day to pick up a mattress. And that is really funny to think about because now I purchase like bed frames that cost$2 ,000. But yeah, I told him$2 ,000. He gave it to me cash and I built his listing and essentially he gave me the money to start a short-term rental out of his barn. And then, you know, I created an entire business out of the short-term rental that was really profitable for both of us. That's incredible. Obviously what you just touched on is that the upper end of the budget to kind of getting these properties ready, preparing them for flips, etc.

3:22can become much more expensive. But like if you were advising somebody who was going to get started from scratch, what is kind of the budget you might recommend to them to plan for? Yeah, that is such a good question. So the first thing you want to analyze and the first thing that I always analyze when I'm working with a client is what is your desired nightly rate? And this means looking at your market, you know, analyzing what are the nightly rates that people are getting around them? And what do you want to do to be a standout? Are you going luxury? Like what kind of linen do you want? Or are we talking like a$99 per night barn rental?

3:54And if that's the case, then you know,$2 ,000 if you want to go Facebook marketplace is really reasonable. My budget, my kind of like mid grade budget that I shoot for is roughly$7 ,000 per bedroom. That's kind of where I'm at with like a Wayfair budget, Amazon. But you know, like I said, you really have to think about that. Like what is your desired average daily rate? And then from there, your budget can be decided. If you want to make more money per night, you're gonna have to put a lot more money into it. In your experience, how quickly does a new property become that first property? How long did it take you to get to profitability?

4:28Well, the first property, literally one month because we put$2 ,000 into it. The pandemic was really starting and we were just in the perfect place for everyone was coming down to DC. They were looking for farm stay getaways that were completely off the radar. It was truly absolutely perfect. So I mean, we don't see 100 % occupancy numbers anymore. In that time, it was just like we were booked every single night. So in the instance of that unit, it made back what we put into it in one month. We have a lot of units where we'll spend half a million to$1.5 million on them. And then you're looking at years to get back what you've put into it.

5:06So it really depends what a property owner is looking for, what kind of property it is. There is no standard answer. There's so many numbers to analyze before are, you know, committing to the outfit of your short-term rental. So going from that first property,$2 ,000 invested, it's you and a partner to today. What does the revenue look like in a typical month? And kind of what are the profit margins on that? Sure. Yeah. So depending on the month right now, obviously we're in low season. So things are a little bit painful, if you will. It's like we come off October where we're making, I think we finished October with$390 ,000 in bookings for the month.

5:45which was fantastic. That was wonderful. And then you kind of start to move into the holiday slump. So our revenue on a monthly basis is anywhere from like 200 to, I don't think we've broken 400 yet, but 200 to 390k per month. And then as a management company, our profit margin, you know, we take 20%. So that's kind of what a typical month would look like on our end. Okay. So we've got apartments in a barn. We have tiny house in a sheep field. Where does the business thing go from there? What is the first year of the company look like? Yeah. So from there, we really, we took off. And so I was living in Scottsville and then we ended up picking up a few properties here in the Shenandoah Valley.

6:25And our third property was also extremely unique. It was an old tea shop and we call it the storefront, but it looks like a bar downstairs because it was previously a tea shop. We left it as is, as an inverted floor plan with a kitchen upstairs instead of downstairs. So that was our third property ever. And that That was a great one to get because it was so popular. It had been renting for over five years by the time we acquired it. So that was a wonderful one to add to our portfolio. Really good exposure for Be Still Getaways. And so from there, truly, Alex, like wildfire. I was really pouring into our search engine optimization, listing ourself on the internet everywhere that I could, pouring so much into our website and our social media that people were just finding us like it was a very word of mouth situation.

7:07So I think I finished year one with maybe eight short-term rentals, eight to 10 short-term rentals after that first year of business. And what was that doing like revenue generation wise? I mean, how does that translate? Yeah, at that point, it wasn't a lot. I think we finished our first year, man, in bookings. We're talking about these were all like$90 per night units that I was listing at that point. And so I think maybe I finished my first year under six figures, 100 % under six figures. So our growth beyond that year one was just absolutely crazy considering that we didn't even clear six figures in year one.

7:42Wow. So I want to kind of just hang out in year one for just a little bit longer as I think a lot of our listeners will maybe find themselves in year one a little bit in the near term here. So what's the most challenging part of starting a property management business and how did you overcome that? I think any entrepreneur can speak to this, but you kind of decide to leave your nine to five because you work too much and you want to be home more. And then you decide to be an entrepreneur so that you can just work 24 seven. So I think the most challenging part of starting a property management business is that in order to make a lot of money, you need a lot of properties.

8:16And in order to hire more people to help you, you need more money. So I was just kind of a one man team for so long. I was establishing protocol for Be Still Getaways. I was the cleaner. I was taking my baby with me to clean these properties. Like it was so much and I was the only person hosting. So I had to have my phone 24 seven to be able to answer guest messages. And that was really, really exhausting. Truly a grind. I mean, a real, real grind. And I really had to keep my eyes on the fact that like I wanted this to scale. I wanted this to be big. It was exploding. And I wasn't feeling like, you know, I think some people might naturally feel like, oh, I kind of want to like pump the brakes.

8:50Let's like we're growing too quick. Let's slow down a little. I never felt that. I was like, yeah, let's go. Let's go. Like, let's do more. Let's do more. And that was exhausting. It was absolutely exhausting just from the sheer, you know, ability of having to be on 100 % of the time, like no downtime. That was hard. What's the biggest mistake you feel like you made in year one that you might advise somebody else to avoid? That is such a good question. Yeah. In thinking about year one, I wasn't keeping my numbers as tight as probably I should have because I think as most people are when they're starting a business, it's like, what am I doing?

9:22I'm literally figuring this out as I'm going. Like, how does anyone know what they're doing in this? So, you know, there were a lot of commitments that I needed to make to like, you know, for my first hire of a turnover. When I first hired turnover staff, I was like, oh, wow, this is like a lot of money that you need to pay turnover staff versus I was used to keeping that money in my pocket. So, you know, I wish in year one, I would have, you know, had a better grasp on my finances or hired someone to help me with finances like from day one. And I didn't do that. Now, I'm sure that this is maybe different now that the business has grown and is in a different position than it was in that first year.

9:59But in that first year, you're starting this company, you're doing kind of some of this other contract work, you're also, you know, raising a new child. How did you manage the time and energy and stress to make sure you didn't burn out? I think I have a very high aptitude for a high workload and working makes me very happy It gives me a lot of purpose. So I do start to get antsy when I have idle time You know, it was those moments especially being a mom when it's like, okay, well, you know Babies don't keep they grow really quickly And so I really even now I have to practice this because the things like nag in the corner of my brain being like You should go do this.

10:33You have this thing waiting for you You need to work on this and I have to be like be present in this moment because it's very fleeting This is not going to last forever. And so a big part of that management for me now and then was screen time limitations and just like choosing to put on do not disturb, which is something I practice so hard now. I absolutely have to. If you're itching to dive deeper into the world of e-commerce and entrepreneurship, you're going to love what we're about to share. You know how we're all about practical advice and real-world business insights, right? Well, we found a kindred spirit in the unofficial Shopify podcast hosted by Kurt Elster, a seasoned Shopify partner and the brain behind EtherCycle.

11:10This isn't just another business podcast. It's a goldmine for anyone using or planning to use Shopify for their online store. It's a straightforward, no-nonsense podcast with real, actionable advice for starting, developing, and managing your Shopify store. Check it out wherever you listen to podcasts. The link is in the show notes. As the show continues to grow, we'd love to get your feedback. Would you mind taking a minute and clicking the link in the show notes and let us know what you think of the show? We want to make sure that we continue to bring you the very best interviews, and the best way for us to do that is to get your opinions via that survey.

11:40So take a second, click the link, fill out the survey real quick. We really appreciate it. And thanks for listening to the Uplip Podcast. Jamie, what's the number one piece of advice that you might give to someone who wants to start a property management business as a side hustle? Sure, yeah. So I speak to a lot of potential co-hosts that really, really want to start this as a side hustle. And the question is, how do you even begin to do that? One, you definitely should know someone with a short-term rental or considering purchasing your first investment property and starting a short-term rental there.

12:11Having credibility is everything. having some type of work to show for your skill is crucial. It's really, really hard to build something from nothing. And so, you know, having at least one property in your portfolio, if you know someone with a short term rental, reaching out, maybe having them mentor you like, how do you do this? How did you get into this? That is so, so important. I talked to so many potential co-hosts that are like, I'm a teacher, I'm a nurse, or I do this and I want to get into property management. And there just kind of needs to be that first step for you to take, whether your friend is a real estate agent, whatever, look for that one connection that you have to the STR world and grasp onto it.

12:48And that's a really great start to beginning in property management. And when did you know that it was time to make Be Still Getaways your full-time focus and not a side hustle? Yeah, I always wanted it to be from the day that I started it. I'm an Enneagram type three. So I go into things very seriously, fully committed, and I have really big ideas for the things that I create. So when I started Be Still Getaways, I was like, this is all I want to do. I love this. I'm so passionate about this. This is all I want. But it was slow for me. I mean, slow. Some people might not think it was slow. It was, you know, within a couple of years, I was able to quit my job and do this full time.

13:24But I needed to be able to scale. And that means that I really needed to be able to pour money into growing my team. And sometimes that meant not paying myself so that I could pay the salaries of others so that we could grow and have the help that we needed to be able to take on more properties. And I know that you've got a lot of properties on Virginia's coast as well. You recently acquired, I guess I don't quite know how recently, but two years ago at this point, but Cape Charles Escapes. Talk to me about that acquisition and kind of how that opportunity came about. Yeah. And this is kind of like one of those great examples of, you know, a time where maybe I should have pumped the brakes.

13:57So a good lesson learned. But, you know, hosting can be very isolating. And so I have really leaned into like other co-hosts within my state that are doing boutique short-term rentals. So, and you know, we talk, we Marco Polo, we text because there are just some things that like guests do or, you know, things happen and you need someone who understands the world that you live in. So I had made friends with the woman who owned Cape Charles Escapes and she approached me when she was like, yeah, I can't do this anymore. Do you want to buy it? In that point of time, you know, I've always been in scale mode, but I was like, yes, let's do more.

14:32Let's do more. Let's do more. I'll take it. Let's go. And so actually, my Carriage House business partner and I, we purchased Cape Charles Escapes together. But plot twist, we actually just recently sold it last month. So tell us about the Carriage House portion of the business. I feel like every significant connection that I've made in this industry has been through Instagram, to be completely honest. So I was early on in Be Still Getaways. This was, I think, in year one of Be Still Getaways and a local realtor, Sydney Robertson, sent me a DM on Instagram and she was like, why don't I know about you?

15:06I feel like I need to know about you. You are a great asset for my clients. And I was like, oh, okay, great. And we got together, we had coffee and obviously everyone needs a resource to point their clients to. And when you have a lot of clients purchasing short-term rentals, which they were during the pandemic, it was so important for them to be able to point their clients to management companies. So that's what we did. We got together and she kind of really became a niche short-term rental realtor. And we were like, should we put an LLC on this? Because we were moving into a place where I was having guests staying with me who were sending me messages being like, wow, we have money to purchase a short-term rental.

15:44Who can you refer us to? So I was sending her clients and then she would pass them back to me for management. And it was just this really beautiful two-way symbiotic relationship where we were just referring clients back and forth to each other. So we decided to start Carriage House, which was one of the best business decisions that I have ever made because it's just a constant influx of clients, which is fantastic. Sydney has really become, you know, she is the short-term rental realtor of this area. Like it is totally her niche. Like this is what she does. And then she's able to give clients to me and they receive a great management experience and potential outfit and design experience as well.

16:20So her and I created Carriage House. That is really the acquisition side of things. now before, you know, I would get a DM from someone maybe being like, hey, I want to purchase a house. And I'm like, okay, please come talk to me after you have a house. But now when I get those emails or messages, I just send them straight to Sydney. She's able to pull all the numbers that they need. So that has taken that off of my plate as well. I'm not having to run as many numbers for clients. And then, you know, she finds them a great house, hands it back to me, and then we have a new house for our portfolio.

16:48It's been absolutely amazing. Highly recommend partnering with a local realtor. So it sounds like Instagram has been an important part of brand building, attracting customers and various industry connections. Was that a conscious strategy? What was your kind of strategy at the beginning to build that brand? Yeah, 100%. Absolutely. You know, obviously, I had been doing my research up into the creation of Be Still Getaways. I was looking at what existed in Virginia. What were they doing? Were they successful? How many properties did they have? I was also looking at nationwide companies. And the one thing that was very apparent to me and has always been apparent is that social media is really, really critical for the growth of your business and can really, really, it can help you, you know, get your brand out quickly.

17:33But social media has been huge and we really had to decide who is our audience. Is it property owners or is it guests? And I think I really worked to find a way to make our audience both. Like I wanted to be a place where property owners came and were like, wow, I want to hire her. But I also wanted it to be a space that guests could come to and be like, oh, I want to book one of those properties. And it took some figuring it out. But, you know, we've been really successful with our social media and I'm very happy with where it's at. Now, beyond social media, what other kind of advertising or marketing strategies are you employing?

18:05I boost posts regularly through social media. And you know, those push to Facebook and to Google, which is great. But you know, the search engine optimization was a huge piece that got us on the first page of Google, you know, I do a lot of local ad running. So you know, we've been in Scout Guide and Charlottesville, which you know, I think Scout Guide is nationwide. So a lot of you maybe know what that is. But you know, I also think just making partnerships and being in print where I can, as well as being featured, you know, in other large businesses, social media or whatever type of branding that they're doing has been really, really, really important for our success.

18:39But overall, social media has been my number one, without a doubt, the number one thing I have poured into. You've also had some really great PR opportunities, things like Southern Living, Make It series on CNBC, Last Call Live, etc, etc. How did you go about not only securing those opportunities, but making the most of them as they happen? I'm a big believer that networking is everything. So one of the greatest decisions that I made for my business is, well, one, finding a great property management system. Anyone getting into this industry will attest to the fact that that is absolutely critical.

19:12I cycled through three of them before I found the one that was the right fit for us. So I signed a pretty large contract with Avivo to be our property management system. And that was one of the greatest things I could have done because that was when I decided like, okay, I want to be a vacation rental company. We're not an Airbnb rental company. We are a vacation rental company. I want people coming to our website and booking direct. So I went with Avivo, which was expensive, very expensive compared to any other system that I had been using, but it felt worth it to me. And so, you know, along with that opportunity, Avivo has a fantastic PR rep in-house and he connected with me and he was like, Hey, I have this opportunity with CNBC.

19:50Would you be interested? And, you know, Jimmy with Avivo, he has just opened so many doors for me. He is so connected. He is amazing at his job. and with PR. So he opened me up to CNBC. And then the story was really successful. So this is going to bring us to a section of the show that we call our fan blitz questions. Listeners, these questions come from the YouTube community. So you can go to youtube.com slash upflip and post questions to future podcast guests. Jamie, we're going to try and get through five questions in about a minute. Are you ready? Okay, ready. All right. First one comes from MesoF, a collection.

20:24What factors do you look for to determine if a location will be profitable. Demand 100%. What's your occupancy going to be and what's my highest nightly rate that I can achieve? Do your research. This one from Make Your Own Buskets. What are some key things you know now that you didn't know prior to starting the business that maybe could have helped you reach your goals at a faster pace or with more efficiency? I feel like I moved pretty quickly, but I think team structure has been my biggest hangup. So I think if I could have like maybe planned organizationally a little better on that end, we would have had less hiccup as we scaled.

20:59At Asian Mac Adventures wants to know, how has the business model shifted since the pandemic is over? Sure. Yeah, it's still highly profitable. We don't see numbers like 100 % occupancy anymore. But overall, this market is very nice. We're not at a saturation point where I live. But you know, we're always trying to be the most unique rental out there. So you know, numbers still look great where I am. We're just It's not in a 100 % occupancy industry anymore. If you could change one thing about your business, what would it be? To be less connected to my phone. Last one here in the FanBlitz questions, why should someone not do what you are doing?

21:35Well, if you don't like every single day being different or flexibility is challenging for you and like rolling with the punches does not sound like something you would enjoy, this is not the industry for you. Listeners, our goal here at UpFlip is to bring as many entrepreneurs as possible, the knowledge they need to start and grow a business the right way. You can help us reach that goal by sharing, reviewing, and following this podcast. The more people who engage with our episodes, the easier it will be for other people to hear the valuable advice shared in interviews like this one. Thanks in advance for listening.

22:07And if you have a few minutes to leave a review, it's very much appreciated. Jamie, I want to ask about that team. When did you bring in the first employee for Be Still Getaway? And what were the first roles you were hiring into? Yeah. So, you know, turnover staff was one of the first thing that I hired when I was like, okay, I can't clean all of these units by myself anymore. I'm doing too much. This is crazy. So I pretty quickly, I think when we signed like our eighth property on, that was when I brought on an operations manager. That wasn't officially her title at the time, but she was really my key person.

22:39She was, you know, she became my person to hire turnover staff to train them. And she was really the point person for keeping our turnovers moving smoothly. That was my first hire that I ever made. How have you kind of made the choice that it is now time to add a new team member, add that operations person? And then from there, now we probably need somebody to do this. How are you making that decision that, okay, it's time to expand the team? It's very easy to overextend and work too much in this field. So it's been a very, there have been times where our team has been so overworked, plenty of times where it's like, we're doing too much, we're doing too much, you know, and it took us about two years before we had in-house maintenance.