Moments with an M.E.O.

Short Term Rental Investing, with Courtney Ross

June 17, 2022 Britt Lanza Season 3 Episode 125
Moments with an M.E.O.
Short Term Rental Investing, with Courtney Ross
Show Notes Transcript

With sites like Airbnb creating trusted brands and the cost of living rising, you may be asking yourself about rental investments. Is rental investing right for you? What goes into rental investing? Courtney Ross knows! Courtney is a military spouse who has a marketing business for short term rentals. Episode 125 of the Moments with an MEO podcast is all about short term rental investments. 

In this episode, you can expect to learn: 

  • Courtney's journey from climbing the C-suite ladder to starting her own marketing agency.
  • What rental investing is and how it works. 
  • Why military families are the best candidates for short term rental property investing.
  • What goes into being a rental owner, including marketing and ideal client work. 

Connect with Courtney Ross:

Connect with Britt:

Links Mentioned:
Ideal Client Episode
Facebook Ads Episode
Book: Building Your Brand Story

Check out MilSO Box here:

Courtney Ross  0:00  
When we talk about brand consistency, really what this means is making sure that you're using the same fonts, color palettes, the same type of imagery, that everything that surrounds your brand stays very much in line with how you started your company and who you want to connect with. It should always be incorporated. From really your mission statement and your goal from your company. That's how you start your brand. You're trying to solve the problem, right? The brand is the ethos and the visual that you get of your mission.

Britt  0:40  
Welcome, Courtney to the moments with me. Yo, podcast. How are you?

Courtney Ross  0:45  
I'm doing pretty good. Brett. How are you doing? I know, it's what 5am Over here. How are you doing? It's in the afternoon, right? Yeah, it's

Britt  0:54  
the afternoon over here. And I am so excited. So I want to read your bio for our listeners. But today's conversation, you guys, today's conversation is going to be awesome because we're talking about short term rental investing what? And we're talking about the importance of branding and marketing your business and there's no one better than Courtney Ross. So Courtney Ross is the founder of sawgrass marketing, which is a luxury marketing agency supporting boutique hotels and vacation rentals. Since opening in 2017. sawgrass marketing has served over 30 clients across the United States with curated marketing strategies, bespoke branding and custom web design. How awesome. In addition to leading sawgrass Courtney serves as the Marketing Committee for the vacation rental Management Association. Try saying that 10 times fast and mentors, the military spouse entrepreneurs. She currently lives in Japan. It was it will Cooney me. That's right. Yeah. Oh my gosh, with her husband, who is a US Marine pilot and her two kiddos. So, Courtney, I am so excited. And I cannot wait to dive into investing. Because to be quite frank, I feel like when women hear the term investing, they go oh, that some that's a man thing. Or like, oh, that's for like C suite executives, or, Oh, that's for like, when I'm so successful, I don't know what to do with my money. But that's not really the case. And so I know today we're talking about rental investments. And I'm really excited to dive into that. But investing can look like a lot of different things. And I 100% believe that women and just quote unquote, ordinary people should totally be doing it. So let's start at the very beginning, and then we'll get to the really juicy stuff. How did you meet your Marine?

Courtney Ross  2:58  
Oh, man. So Eddie and I met gosh, almost nine years ago, in Washington, DC. He was at TBS, the basic school for all the other marine corps spouses. And I was working my way up the corporate ladder. I had moved there two years prior from Florida, and was just completely head into my work. We ended up being completely smitten with one another. And you know, with TBS, they'd go out in the field for two weeks, and then they'd come back. So we were really seeing each other every weekend we could and going to the Smithsonian museums and the Kennedy Center for my first opera. And it was just like a really fun courtship. Then TBS graduation came and we started four years of long distance dating. It wasn't easy, because when he went into flight school, he was moving everywhere. He started in Florida, and then went over to Texas and was out in Nevada and California. And then once he got his wings, he was stationed in North Carolina. over those four years, I was flying at least like once a month to try and see him. And I won't lie, like we broke up a few times. Because dating long distance is hard. It's it's very humbling. It just tests your communication and your patience and your selflessness. It feels almost sometimes that like, you're the one that's always giving because their schedules don't bend. And ultimately, like we ended up knowing that we always wanted to be together and we were supposed to be together. So about four years after we met Eddie came to Washington DC. He ended up proposing over a nightcap at the quill at the Jefferson Hotel. So cute. We finally finally ended the long distance. Gosh, and 2017 2016

Britt  4:49  
Wow. So I'm curious what you wanted to do before you met Eddie. Like what was every woman has a plan like what was the plan? And before you met your spouse,

Courtney Ross  5:02  
oh man, I was like, on my way up to be a C suite executive. I was like working my ankles sitting on committees. I was getting promoted every year in DC, like I was the girl that was showing up early and staying late because I was hungry to get to the top. Obviously, I didn't understand at the time that becoming a military spouse would kind of change that trajectory. And, you know, I thought it was possible. But once I moved to North Carolina and saw that the job market was very different than what I had experienced in DC, I had to shift. So I started sort sawgrass, shortly after moving to North Carolina to be with Addy. I'm sure like other military spouses, I saw that I was facing like a 50% pay cut with the move. And pretty much starting over and losing six years of my work experience in DC to an entry level job. So that wasn't something that was comfortable sitting with. So I ended up starting my own company.

Britt  6:08  
How awesome. I'm curious what it was like, emotionally and even within your relationship. When you were like, Okay, we're gonna do the thing, like we're getting married, we're gonna make this life like this is gonna be awesome. And then like getting smacked in the face with the realization of what employment as a military spouse is like, compared to what you're used to. What was it like for you making that shift? Like actually doing it? Because I know, for me, it was hard. It was hard.

Courtney Ross  6:41  
Yeah, oh, my gosh, Brett, like, I think I dragged my feet on putting in my two weeks notice at my job in DC, because I had so much fear around being unemployed. Like I knew I did not have another job lined up as much as I searched and interviewed. I was even considering jobs and Raleigh and commuting two hours from Wilmington, just so I could have the position that I wanted. But Edie and I had some really honest conversations back then. And he really reassured me and said, you know, your career is not your end all be all, I'm here to support you. You know, you really have to make a personal choice and decision. Now I'm not a professional one. And he was right, like I needed to focus on on me for once and not so much on my work. So if I knew then what I know now, I think, you know, I wouldn't have any hesitations just moving forward. But the transition from DC north to North Carolina was definitely an emotional one.

Britt  7:45  
Yeah. Everybody who's ever started a business knows that. Making those boundaries, both personally and within your work can be really, really hard. And I know that you were mentioning earlier how hungry you were to climb to the C suite. You know, you were working really late getting in early. What was it like when you actually created your own business? And how was it setting those boundaries for yourself?

Courtney Ross  8:14  
You know, when I first started, I feel like my work ethic was very similar to my corporate life. You're building everything from scratch, right? You need a website, you need a brand, you need to figure out who your ideal client is, what industry you're going to support. And you know, when you are, you know, engaged or recently married, you have the time to be able to put into it. You know, I was chugging away on my laptop, probably for the first six months and got I think, three or four clients in the door, you know, at a very entry level rate, because hey, it was beginning right, you got to start somewhere. I realized quickly after that, that I was pregnant. When I found out that we were expecting our first daughter McKenna, I knew that something had to change that the work hours needed to shift. And it was really having the candidate that kind of shifted my mindset from like, grind grind, grind to Okay, we got to find a balance. I took off two weeks for maternity leave. And I realized after having McKenna that that was completely bonkers. I hired on my first employee right before she was born and Katie Ketchum, who's been with us, you know, since day one. I found that I cannot do everything myself and having a team and a community to support me has really helped me grow and scale my business.

Britt  9:39  
I love that. Okay, so you went from climbing the C suite ladder to starting your own marketing company. And now you do short term rental investing. So let's just pause and talk about like, Okay, what is short term rental investing? Exactly.

Courtney Ross  9:57  
If you think about any vacation rental that you ever stayed out whether it's on verbo, or Airbnb, all of those properties, have somebody funding them right or investing in the property to rent them out. So short term rental investing is, you know, finding this unique property that you want to profit on and rent out to other travelers, we really stepped into this because we knew that as a family, we wanted to have a beach house somewhere in North Carolina to come back to with our PCs to Japan, it gave us the opportunity to be able to invest in a home before we moved here and make income while we're over here. So being a military family really positioned us perfectly, to be able to have a little bit of extra cash, because we didn't have to put in any down payments with our VA loan on our home. And then when we had the extra cash to be able to throw into a second home, North Carolina was an area that we became very familiar with. Luckily, we were stationed on the coast and found a perfect home, the rent is actually paying for the mortgage. So it ends up you know, being a great financial decision for a lot of military families.

Britt  11:15  
So if someone's like, okay, cool, like this sounds awesome. I want to have my own Airbnb or my own vacation rental, like, Where would they start? Besides just like, obviously finding a property and purchasing it?

Courtney Ross  11:30  
Sure. So you know, running the numbers is very important, because you want to be sure that it's it's a profitable and smart decision for your family. And there's a lot of new legislation that's coming out that is impacting the short term rental industry. So I think the the hottest topic right now is Honolulu just passed a law that says that short term rentals can no longer rent for 90 days or less. So they're really trying to push out investors from the area and support their local community. So if this is something that you're considering, and you have an area or location that you have your heart set on, be sure that you're looking into local regulations and laws, obviously, Hoa considerations as well, because this could drastically impact where you invest.

Britt  12:24  
That's really, really smart. So when it comes to investing in short term rental properties, who would be a good person to do this? Like, what does it take to do this? What do you need in order to be successful?

Courtney Ross  12:39  
Somebody that has a really like, all encompassing vision and positive attitude. When we purchased our property on Bald Head Island, we saw that there were areas that we wanted to improve in the house, but I don't think we really estimated Well, the sweat equity that we would end up putting into it. So you really do want to be sure that you can roll up your sleeves and my husband and his father ended up sanding down all of the walls and painting them. So not only is it like a time commitment to be able to put in the work for the renovations. But you also have to have you know, a vision of what you want your property to become and, and what types of guests you want to support as well. Because the decor you pick the property that you pick, really does impact who you're attracting to your home.

Britt  13:32  
That is such a good point, we've been talking a lot, at least at the time of this recording, we've been talking a lot about ideal client, we have an episode on how to identify your ideal clients. I'll link that in the show notes. And the episode right before this one is with Katie. And that one is definitely one where again, we talk about your ideal client and reference to Facebook ads. So just to kind of like really nail this into the coffin, do you need to have an ideal client when it comes to having a rental property?

Courtney Ross  14:06  
Absolutely. So this one impacts your reviews, you want to be sure that the person that is coming and renting your home aligns with what your home can support. So the property that we have is a two bedroom, two bath. So we really focus on young families, small families or couples who are trying to get away. So all the decor that you pick and set out obviously we have to pack and play for the young families. All of that really impacts how they experience your property and what their state is like. So yeah, before you even put that listing out in public, be sure that you're really thinking about who you're talking to, and how they're going to enjoy their stay at your home.

Britt  14:47  
Awesome. So when it comes to talking to like Okay, so I've set up, I've purchased this property, I've set it up to be inviting, we'll go with what you've got going on, you know with the young Families are younger couples just trying to escape for the weekend. I've got this image in my head, I know who my ideal client is, I know who I want to attract, I set everything up. But then comes posting it online and marketing it online. So let's talk about the importance of branding and marketing.

Courtney Ross  15:20  
Sure. So branding is really telling your story, right? It's developing this connection with the person that you want to come and stay. So really, what I like to do is I like to focus on the unique features, features that other properties in the area don't have or the experience that you provide, and how it fits into your brand story. I'll use our home as an example. We named it the Palmetto place. And the reason we chose the Palmetto place is because the home is situated on an island that has Palmetto poems everywhere. We also found out that the history of the island, it used to be called Palmetto island. So it allowed us to connect the sense of history and presence in the brand and the name. We also wanted to make sure that it was kind of like earthy as well, because the cottage is made of cedar shakes that has a lot of natural wood textures and tones. So when you're thinking about branding, just think about how your property fits in with the environment, how it stands out, and its location, and how you want people to feel when they're coming in. We want our guests to feel relaxed, natural and really appreciate the natural surroundings of the property.

Britt  16:45  
I love that. So when it comes to marketing and branding for your business in general, like doesn't matter if you've got a short term rental, if you've got a product a service based, a daycare center, a gym, it doesn't matter brick and mortar. Why does it matter? Why is it important to have branding? Like I hear the term on brand all the time, but like what does that really mean? And how does that relate to the success of the business?

Courtney Ross  17:11  
Branding is seeing a Facebook post or a website and knowing exactly what you're going to get from a company when you see it. So branding is really important in marketing, because when you're establishing consistency, you want to be sure that your potential client knows exactly what they're getting when they're coming either in store, or they're visiting your website for the first time. When we talk about Grant consistency, really what this means is making sure that you're using the same fonts, color palettes, the same type of imagery, that everything that surrounds your brand stays very much in line with how you started your company and who you want to connect with. It should always be incorporated. From really your mission statement and your goal from your company. That's how you start your brand you're trying to solve the problem, right? The brand is the ethos and the visual that you get of your mission. Now when you're marketing your business, branding comes into important play because branding is all of the assets that you create for your marketing. It's the visuals that you create for Facebook ads, it's the copy and tone that you have for those same ads, when you're really looking for you know, connecting either with your local community or with new prospects for the first time where you advertise your brand is really important too.

Britt  18:40  
I love that. So do you have any quick tips if someone's like, okay, maybe I haven't been on brand. Maybe I have not been doing the whole marketing thing. Or maybe I've kind of been slacking, like, where do you suggest our listeners start?

Unknown Speaker  18:57  
My favorite resource and I'm not trying to give homework. But my favorite resource is a book by Donald Miller called the building your brand story. It is the foundation that we use for our branding process at sawgrass. He walks through this narrative of how you identify your main character or your ideal client, what core problems they have. So the challenges that they're trying to overcome, and how your company as the guide helped them solve and overcome those challenges. So it's a wonderful resource if you're just getting started, and you really don't know where to go to help you build your brand story.

Britt  19:35  
I love that. And yes, it's actually right here on my bookshelf. I love the book. We'll put a link to the book in the show notes. I love that we've talked about not just investing in short term rentals, but also like what goes into a rental space who could fit and the marketing and the branding behind it and why it's important to have an ideal client no matter what business you Have, where can people connect with you if someone's interested in short term rental and they want to ask you some questions, or if they have short term rental properties and they want to connect about possibly getting you on their marketing side of things like where can we find you online,

Unknown Speaker  20:16  
you can visit us at sawgrass and k t That's our website and just hit the contact form. Or you can find us on Instagram. Our handle is at sawgrass and K T G. We'd be happy to connect in the DMS.

Britt  20:32  
That's awesome. So what does success look like to you, Courtney?

Unknown Speaker  20:36  
Oh, man, I really find inspiration for work and in my personal life through travel. So I think success would look like investing in properties around the world so that we're only a flight away from new experiences. My husband and I have talked about Italy and Ireland. And my goal would be to have a property that is like a six, seven hour flight away. So we can just travel the world and always have a place to stay.

Britt  21:04  
That sounds so magical. There is a Netflix show. I'm trying to think of what it's called. But basically, it's this group of friends. And they just travel the different Airbnbs. And they stay at like, like the most budget friendly, one right in the middle, and then a super luxurious one. And they just go like all over the place. And it is such a fun show to watch. Because just looking at, like how creative people can get with rental properties. I mean, like tree houses and condos, but they're like nests in trees. Like it's incredible the creativity that comes out of rental properties. And I could only imagine the fun that you would have creating rental spaces all over the world.

Unknown Speaker  21:54  
Yes, yes, I know the show that you're talking about. And it's one of my favorites. And I think it also, you know, gives a little bit of inspiration and hope to like what you can develop and have, right? Like the homes in Joshua Tree where the entire wall is made up of like mirrors and Windows, it really makes you want your property to stand out and be unique and have this whole experience that you really can't get, you know, in a hotel?

Britt  22:24  
Absolutely. Can you describe a time when you felt successful? Even if it was only for a moment?

Unknown Speaker  22:30  
I think it's right now honestly, like moving a company to Japan has been a feat working 13 hours ahead of my team. Is it incredible. And I think looking back at how hard I've worked for the past four years, almost five, sawgrass is just like, really taken off. And I love that I can one support the clients and support the growth, but also support my team. I don't think I've ever imagined that I live in Japan, much less run a business from a foreign country. So I think I think I'm pretty proud of myself right now.

Britt  23:15  
That is awesome. Well, I know so many people listening, including myself, also feel like you are totally successful. Because it can be very hard to PCs with a business even within the states. And the fact that you've taken it abroad is just incredible. Absolutely incredible.

Unknown Speaker  23:35  
Thank you so much for it. Yeah. It's it's always a challenge being a military spouse, but you know, entrepreneurship just provides so much flexibility. And this would not have been possible without, you know, starting my own business. So you guys can do it, too. It's it's achievable.

Britt  23:52  
Absolutely. So how do you embrace being an M E. Oh, and I feel like we're kind of talking about it right now.

Unknown Speaker  24:00  
Oh, my gosh, yeah. patience, flexibility. And honestly, like delegating and finding a team or community to support you. We've talked a lot about the business side of things. But there's a personal side to that you really need to be able to embrace moving here has been a very, very big adjustment. Japan has very strict COVID regulations in comparison to the states. And so we found it pretty challenging to find consistent childcare because of COVID closures. So really leaning in to my military community and finding a deep bench of babysitters has really allowed us to to stay on track with business and to allow me to work you know, the hours that I need to work so don't forget to lean on your community and be patient with yourself. growth happens gradually it overs overnight. Success, you know, may happen for some, but traditionally not for all. So just give yourself a little bit of grace and be sure that you're making time for yourself as well.

Britt  25:11  
I love that. Well, Courtney, I just want to say thank you from the bottom of my heart for sharing not only your morning, but also your cup of coffee with us to make this timezone thing work. I really, really, really appreciate your time. And this is a topic that we have not had on the podcast before. So I know people are going to be very intrigued. So thank you so much.

Unknown Speaker  25:32  
Yeah, absolutely bread and if anybody has any other questions that I didn't answer today, again, feel free to reach out. I'm happy to help you guys.