Do you want to make informed real estate investments for short-term rentals? Learn from successful women in the industry as they share their strategies for achieving profitable real estate investing in the short-term rental market. Hear from guest Stacey St. John as she provides insights and solutions to help you achieve success in your real estate investments for short-term rentals.

I think one thing to keep in mind is there are so many opportunities in this industry. Whether you own a property, whether you are looking to co-host, whether you’re looking to do an arbitrage or a Master lease, you can acquire a short term rental portfolio in several different ways. – Stacey St. John

In this episode, you will be able to:

My special guest this week is Stacey St. John. Stacey is the founder of the Short Term Rental Virtual Summit for Women and has made a significant impact in the real estate industry. Her journey began with long-term rentals, and she transitioned into the short-term rental space during the challenges posed by the pandemic. With a portfolio of ten short-term rentals across different markets, including Myrtle Beach, South Carolina, and Ohio, she has showcased her prowess in property management and co-hosting. Stacey’s commitment to sharing her experiences and coaching others highlights her dedication to empowering individuals in the industry. Her advice and insights are valuable for those considering entering the short-term rental space, making her an influential figure in the real estate and hospitality sectors.

Sign up for the STR Virtual Summit for Women: https://mydbs.live/STR2024

*Purchase your ticket before January 19th, 2024 and get $100 off your ticket!*

Follow Stacey on Instagram: https://www.instagram.com/stacey_st.john/

Schedule your FREE Strategy Session: https://staceystjohn.com/success/

The key moments in this episode are:

00:00:08 – Introduction to Short Term Rental Journey

00:04:40 – Advantages of Short Term Rentals

00:08:38 – Empowering Women in Short Term Rentals

00:12:02 – Real Estate Investing in Short Term Rentals

00:16:33 – Building a Brand and Direct Bookings

00:17:32 – The Vision Behind the Short Term Rental Virtual Summit for Women

00:20:18 – The Start of a Women’s Facebook Group

00:24:42 – The Three-Day Learning Extravaganza

00:27:26 – Direct Booking Success and Guest Verification

00:32:23 – Generous Offer for Business Planning Session

Show notes are available at: https://directbookingsuccess.com/podcast/

Follow Jenn on Instagram: https://www.instagram.com/directbookingsuccess

Join Jenn’s free group – the Marketing Hub Free Facebook Group: https://www.facebook.com/groups/marketinghubforholidayrentals


00:00:31 - Jenn Boyles

Hello and welcome to another episode of the direct booking success podcast. I am so glad you are here with me today. I'm Jennn Boyles, your host, and today I have Stacey St. John with me. Stacey is the founder of the short term rental virtual summit for Women, which is happening this month, actually next week. So welcome, Stacey.

00:00:54 - Stacey St. John

Oh, my gosh. Thank you so much for having me. I'm so glad to be here.

00:00:58 - Jenn Boyles

Great. So let's get into how you got started in your journey with short term rentals. How did that journey start?

00:01:05 - Stacey St. John

Well, it actually started with me initially investing in long term rentals in the real estate world. So I was in the long term rental game, shall we say. And when I started investing, I got my real estate license and I learned how to flip and do wholesaling and all the things right. And during COVID we were actually finishing up a flip. And when I say we, my husband and I, we invest together. And we had intended on purchasing another long term rental from the profits from our flip. And when Covid happened, there were all these eviction moratoriums that popped up. And here in the states, landlords were really put in a very tough position if their tenants didn't pay. And so he and I just kind of looked at each other and said, well, gosh, what if we pivot and purchase a property that is a short term rental versus a long term rental? And that got me started in learning about the short term rental industry. And we purchased our first property after about six months of me just soaking in education. And as we all know, you can have fabulous training, but until you're actually in it and doing it yourself, it's a much different story. So, such a fun thing that I've discovered, and I've absolutely fallen in love with this industry. And so it's really changed my life. Yeah.

00:02:46 - Jenn Boyles

And it's so interesting because I think everyone we talk to, you talk about, how did you get into this? How did you start? And it's kind of like, it just kind of happened. It's not like you woke up one day and said, yeah, this is what.

00:02:58 - Stacey St. John

I want to do something with my life.

00:02:59 - Jenn Boyles

It just kind of happened. And the pandemic has a lot to answer for because I know I pivoted in the pandemic, and I know so many other people did, too. And hearing what you've done as well is getting into it. So tell us more about your properties and your management business.

00:03:16 - Stacey St. John

Yeah, so I currently own ten short term rentals. They're in two different markets. The majority of my portfolio is in Myrtle Beach, South Carolina, which is about 10 hours away from where I live. So I live in Cincinnati, Ohio. The majority of the properties that I own are in Myrtle beach. And then I also have a property management and co hosting business. And the majority of the properties I manage are also 10 hours away in Myrtle Beach, South Carolina. And then I also own a vacation rental, short term rental in Ohio. And, you know, I have always loved the beach. I am a beach girl through and through. But there is something so magical about being out in the middle of nowhere and enjoying nature, and again, just falling in love with that market. And so I own property there and manage and co host there as well. And I've started co hosting in multiple markets around the country. And it is something that from a co hosting and management perspective, I really try to keep my investor brain on and we make sure that we're caring for the guests and the owners and the properties as if they were our own.

00:04:39 - Jenn Boyles

Yes. So you wear so many hats. You've got sort of the investing, hosting on Airbnb, the co hosting, helping others go along this path as well. What has given you the most success?

00:04:54 - Stacey St. John

Well, success is a really broad term. I will share with you. One of the things that I initially discovered when I joined the short term rental space is, oh, my gosh, I have the ability to help someone make a lifelong memory. And there is something very rewarding. Like, even when I say it, I get goosebumps. I just think that it is so cool that families are coming together in our spaces and they have the ability to make memories that last forever together. And again, the properties that I own and manage at this point in my career are primarily vacation rentals. Okay. That being said, I absolutely love what I do. I've got an amazing team around me that I couldn't do what I do without them. But one of the things that is most rewarding for me is having the ability to help other people and being able to coach other people and help them along their journey. Again, I can't really even articulate what that feels like. It warms my heart and it gives me chills just thinking about, wow, how cool is it that I could just share with someone my thoughts or opinion or my experiences, and it can help them change their future. And I know you know that, too, Jenn, with all the work that you do, I mean, it's absolutely incredible, right?

00:06:29 - Jenn Boyles

The best feeling. It is the best feeling. And I had Annie Holcomb on the podcast a little while ago, and we were talking about mentorship and that giving back and the exchanging of ideas and mentee mentor relationship. And it's just so important. And I really love what you're doing because you're not just a businesswoman and all these hats that you're wearing, but you're a strong advocate for women in business.

00:06:55 - Stacey St. John


00:06:56 - Jenn Boyles

How do you see short term rentals as an avenue for women to achieve their financial goals? What kind of advice would you have for those considering they're listening to this and they're like, this is something I want to do. What kind of advice would you have for those considering entering the SDR space?

00:07:14 - Stacey St. John

Well, I think one thing to keep in mind is there are so many opportunities in this industry. Whether you own a property, whether you are looking to co host, whether you're looking to do an arbitrage or a Master lease, you can acquire a short term rental portfolio in several different ways. And so one of the things that I love doing is helping people understand that some of the roadblocks or hurdles that they see in front of them to their goals are limiting beliefs. And when we can get those limiting beliefs out of the way, clarity is much easier to obtain. About, okay, how do I want to go about this short term rental game? What do I enjoy most, and how can I leverage my God given talents to find success? And again, that looks different for so many other people. But I think if you're listening or watching and just thinking, gosh, this short term rental stuff sounds fun, but I don't really know what to do or what I want to do. My biggest piece of advice is join a community or a series of communities and just listen. Just be a sponge and see what other people are doing and ask questions and attend things like Jenn's summit. She just provides such wonderful education for folks. Soak all of that in, and you may not know right now what your future looks like, but it will come. As long as you keep feeding your brain, you will end up with clarity. And I have to be honest, I prayed a lot early on. Like, okay, God, give me clarity. Okay. But for me, that was impactful and helpful. Whether that's impactful for other people, I don't know. But if you believe there's a higher power out there. They will help you as well.

00:09:29 - Jenn Boyles

Definitely. And for those who are like, we all come into this space in different ways. You started investing, you were doing the long term rental and pivoting to short term rental, and you already owned those buildings that you started with and then went into co hosting for those that maybe are on the co hosting side, and they love being managing and looking after other people's property, but they want a bigger piece of the pie. Do you have any advice there how they can sort of pivot into investing into their own property?

00:10:06 - Stacey St. John

Yeah. My biggest piece of advice is to learn the art of real estate investing. And I see so many people, quite honestly, that have gotten into the short term rental space and are in trouble because they have bought what I call consumer brain. And the consumer brain is, oh, my gosh, this house is so cute. It would look so good on an Airbnb. And I can see an exit wall right there and they're buying as if they're going to live in the property. And let's face it, we're human. I'm not here to fault anyone for that, but when we are investing in real estate, it is incredibly important to make sure that you are using data and running a proper analysis of a property to know, does this meet my investing criteria? I had a student of mine come to me not too long ago about a property that she was so excited about potentially purchasing. And she said, can you just help me make sure that my numbers look good? And I dug into it, I've got a financial calculator I give my students. I dug into that and I was like, okay, we forgot this over here, and we need to address this right here. And sure enough, in a matter of a couple of minutes, what she thought was a great buy was, oh, whoa, I'm going to be losing money every month. I probably should wait, right? And so, again, learning how to invest in real estate, analyzing a deal, knowing when you should buy and when you should walk, is really important, and not getting emotionally involved absolutely would be so hard.

00:12:02 - Jenn Boyles

We're human.

00:12:03 - Stacey St. John

We are so human. And let me tell you, just like anyone, when I go to the beach, I'm like, oh, my gosh, look at the view. It is gorgeous. Look at this adorable kitchen. But if you have an investment first priority, now, there are folks that want to buy a property at the beach as an example, or in the mountains for their family to enjoy. And in those scenarios, maybe they're just looking to offset the cost to subsidize their second home. Well, in that scenario, it doesn't necessarily matter potentially that you're cash flowing because your priority is different. So if you have an investment first mentality, it is really important to make sure that you're running your numbers and analyzing your deal accordingly.

00:12:58 - Jenn Boyles

Yes. No, I think that's really why. So a lot of people do have these second homes and they're like, okay, we're not getting there as much as we could or want to. Let's just stick it on Airbnb and get some bookings in and that kind of thing, which is totally fine. It's totally fine. But it is different than buying this as an investment to create a brand, to create a business for people to come to. What are those numbers? I think that is really good advice.

00:13:28 - Stacey St. John

The other thing to point out, if I might add, is for the folks who are just looking to subsidize their vacation rental and throw it up on Airbnb. I just said throw it up. That's gross. Put it up on Airbnb. I shall say. But I think it's really important that you, as much as you can, professionalize the way that you are hosting. And sometimes that is, again, soaking in education, sometimes that is bringing on a co host to help you have a level of professionalism. The more that we can optimize our listings on Airbnb, the better our properties are going to perform. And again, if we want to maximize the amount that we are subsidizing, it's really important that we are playing our cards right when we're on the otas. Really good advice.

00:14:32 - Jenn Boyles

So now we're in 2024. I think it's ridiculous. I think time is just speeding up so fast. What are the things that you're going to be doing this year with your business, with your management business? Where's your focus?

00:14:46 - Stacey St. John

Yeah, such a good question and such, I think it's an exciting time. We are continuing on the management side of things. We are continuing to expand our client base, both in Myrtle beach as well as in the Hawking Hills area for what I would call full service management or co hosting. And then in other markets outside of those two key markets, we are supporting owners with what I am calling a hybrid hosting scenario. So the way that that works is we are managing, think of a restaurant the front of the house, we are managing the dining room, shall we say, where we're welcoming guests and taking care of everything that is guest facing, where our owners are taking care of the kitchen, the back of the house, where again, they are the ones responsible for sourcing the cleaners or calling the plumber when the toilet is overflowing. My team is a, we've got folks that work 24/7/365, and so we really feel like that's an asset to be able to offer to host, to allow them to have a guest facing experience that is five stars. And at the end of the day, they retain control and have the ability to make sure that their properties are maintained in the best way possible. So what's cool is we can do that service for hosts or, I'm sorry, for owners. Right? And so I'm really excited about that because it allows us to serve people all over the place.

00:16:33 - Jenn Boyles

And I know that you're not just listing on Airbnb. You have your own direct booking website, you have your own brand. So what are you doing there this coming year? How are you building your brand and getting new guests into book direct?

00:16:47 - Stacey St. John

Yeah, well, one of the things that we have done from the start is have a social media presence. So that will continue to be a priority for us. The other thing that we are focusing on is our email marketing and being able to cross promote our different properties. And so again, I just mentioned that we've got a pretty broad portfolio in the Myrtle beach market, but we're able to serve hosts all over the country. And how cool is it that we can welcome travelers? We can gather their email addresses and then encourage them to go check out other locations across the country. That is so fun to me. So that is a huge priority for us in 2024.

00:17:37 - Jenn Boyles

That's great. And we've got to talk about next week. So next week is the short term rental virtual summit for women. This came to be. How did you start this?

00:17:50 - Stacey St. John

I am very much a visionary. I'm a visionary and an integrator. I'm kind of a hybrid. But I love thinking about how I can level up all the time. And it is so incredibly rewarding for me to have a community around me that I can be a conduit of information. And when my Facebook group started, it just kind of occurred to me one day, like, wow, well, what if we could do this? What if we could do this? And the first year that I thought about it, I thought, you know what? I don't have the right resources around. This is. It's like a full time job preparing for a summit, as you well know. And so actually, Tracy Northcott, who, I don't know if you know Tracy, but she's amazing. Okay. She lives over in Japan and she hosts a regular meetup inside the STR sisterhood she said to me, and I had mentioned to her about having a summit, and she's like, you know, I know somebody that I think could help you produce the summit. And she connected me to a lady by the name of Lauren Summerly. And Lauren is still on my team today. She not only helps me produce my summit, but I'm like, Lauren, I love you, I adore you, and I need you. Okay. Will you come work with me more often than the summit? So she and I work together, and she's located in Africa, so I truly have a global team, which is so fun.

00:19:28 - Jenn Boyles

You realized she was amazing.

00:19:31 - Stacey St. John

Yeah. So it's really the power of connections and leveraging the sisterhood that we have together, that the summit even came to life to begin with. And so this is our third summit. It happens every January, and every year they get bigger and better, and it's such an amazing experience, and nothing that I could have imagined ten years ago I'd be doing.

00:19:58 - Jenn Boyles

I can't wait. I'm speaking this year, and it'll be my first year attending as well. And I can't wait. It's going to be so brilliant. But I have to ask, why women only?

00:20:10 - Stacey St. John

Well, it may not be as exciting of an answer as you want. Okay. How it started was I had my real estate license, and I had someone who was a fellow realtor from Texas reach out to me several years ago, and he said, Stacey, I've got properties for sale down in Galveston, and I have clients who are buying beach houses in Galveston. And they're asking me questions about short term rentals and vacation rentals and how to do all the things. Will you help me put together some information for them? And I was like, sure. Yeah. So I started to kind of make a list of what I thought would be helpful. And I thought, you know what? I've been doing this for a little while now. Let me go back and ask some folks who have never done short term rentals, like, what would be helpful for them to know? And so I popped into a Facebook group for women real estate investors and just said, hey, if you are ever going to buy a house at the, like, what would you want to find out? And the floodgates opened, right? So there were so many comments, and one of the comments was, you should start a Facebook group about, I've got. I can do that. I can start a Facebook group. And since I was in a women's Facebook group, I thought, I'll start a women's Facebook group. There you are. That's it. All began. There was a crazy plan in the beginning and then once I obviously had a community around me, I'm like, this is the most amazing thing ever because these people get me. These people know that. Oh my gosh. At the time I'm balancing a full time job. I'm doing this short term rental thing. There are dishes on the counter, my laundry is piled up. My husband is saying, can you schedule my doctor's appointment for me? My kids are saying, mom, by the way, I'm not going to do my homework tonight. Are you okay with that? All the things, right? And so it's so rewarding to be surrounded by a community of people who not only get you professionally but understand what you're going through in your personal life and can be there for you.

00:22:38 - Jenn Boyles


00:22:39 - Stacey St. John

That's why women, I think it's a great answer.

00:22:42 - Jenn Boyles

Don't worry, it's not full lady me.

00:22:47 - Stacey St. John

I'm asked that all the time and I feel bad. I'm like, oh, man, I feel horrible that this is not going to be anything exciting.

00:22:55 - Jenn Boyles

No, I think it is great because I know that in the coaching that I do. And even on a call yesterday, we were talking about our lives in ten years and talking about our vision and what we wanted. And a couple of the women started with, my child will be this years old. And I just felt, yeah, this is why I'm here. Because we're supporting each other and as women, we sometimes, I'm not going to generalize and say all the time, but sometimes we're putting ourselves second to the others.

00:23:30 - Stacey St. John

Oh, girl, let me tell you. Okay, I was at my computer until 11:00 last night and I got up at 04:00 this morning. Do you think I put myself first yesterday? No, but I got stuff done that I had to get done. Right. And that's what we do. Yes, that is what we do.

00:23:45 - Jenn Boyles


00:23:48 - Stacey St. John

But at the same time, I wouldn't trade that for anything. Right. And so I think being able to live intentionally, there are times where we have to give 120% because of what's going on in our lives, but we have to give ourselves permission to take a step back and allow us to enjoy a 30% day where, you know what? I'm going to go get a massage and I'm getting my hair done and my cleaner is going to do my dishes. Right. We have to give ourselves permission and be okay with that.

00:24:20 - Jenn Boyles

Yes. Very good advice. And another thing we need to give ourselves permission to is learning and learning more for ourselves professionally, personally, and so we can level up our businesses as well and grow. So tell me more about next week's event, the short term rental virtual summit for women.

00:24:42 - Stacey St. John

So it is a three day, I'll say, learning extravaganza. Okay. By the end of the three days, I will let you know right now that you will feel like you have been drinking from a fire hose. But the thing that is so cool is that folks will have two weeks to go back to the summit platform and watch replays of the different sessions. We have sessions covering every aspect that you and I can imagine from acquiring real estate and analyzing deals and investing with creative financing strategies. All the things with acquiring real estate, all the things with creating standout properties. We have interior designers galore on hand to not only share their learning and their expertise, but also help you on your property, give you feedback, give you direction. We have hosting education on how to level up your hosting. We have marketing education on how to level up your marketing. Hint, hint. Jennn Boyles. But again, it's women coming together from all around the world. And again, knock on wood, glass, plastic. I feel so blessed to have women supporting women, women helping each other. Again, I got goosebumps. But there's something. So it's just powerful and rewarding and yummy and delicious. I don't know what to say, but I absolutely love it. And what is really cool is people walk away and go, wow, I had no idea that this summit was going to be like this. This is amazing. Thank you. And then they come back the next year a different person.

00:26:37 - Jenn Boyles

Yeah. Wonderful. I'm going to put those links in the show notes. I'm going to put all your links in the show notes because there's things going up, but definitely for the summit because it's somewhere that I think you need to go have a look, see if it's right for you. Join up and come and yeah, I'll be speaking there about direct bookings and marketing and I just, oh, I can't wait. And I know that all of your hats that you're wearing, we keep coming back to that because you've got so many things going on. But I want to ask you about your hosting business, your property management business, and about how you're bringing in those direct bookings. And what does direct booking success mean to you?

00:27:26 - Stacey St. John

Well, I'm going to give you a pretty unconventional answer based on something I'm actually going through right now, because direct booking success for me means maximizing revenue and profitability. Okay. A very distinct challenge that I have incurred recently is I have been discovered and I have been discovered by a band of criminals and this band. Okay, girl, I didn't tell you to go, okay. I know. Yes. So we have had in Myrtle beach people booking direct and they have been using fraudulent credit cards. So lo and behold, 30 days after their stay, then I'm sure that the rightful owner of this credit card opens up their statement and they're thinking, I never took a trip to the beach. Why do I have this charge on my credit card? And they're disputing the credit cards. It has been literally like someone flipped a light switch and it occurred in September. We've taken drastic actions over the last few months to prevent this from happening in the future. So if you are listening and you don't have processes in place or resources in place to be able to validate the guests who are coming, validating their credit card is not fraudulent. We screen our guests, but of course, the guest isn't ever like, yes, I'm going to book with a fraudulent credit card. Are you okay with that? No, they don't say that. So direct booking success for me means maximizing my revenue and my profitability and making sure that I'm keeping that money in my owner's bank accounts instead of having it go back to the rightful owner of a fraudulent charge victim.

00:29:27 - Jenn Boyles

Oh, wow. I'm so sorry that you've gone through this. It's a question that I get a lot. I'm in a Facebook group, someone brings up direct bookings and they're like, how.

00:29:36 - Stacey St. John

Can I do this?

00:29:37 - Jenn Boyles

I don't feel this way, and I actually feel the opposite because I use guest verification for every single guest that I have, and I have for years because of this reason and I don't feel safe. Now, anybody can have an Airbnb profile. Anybody can put up a review. I don't know who they are. But my people that come to me direct, my guests I have worked with know your guest with, you know, guest verification is what all of my guests do, and if they don't do it, you don't stay. That's the bottom line, because I'm not dealing with the fraud afterwards or damage or whatever it is.

00:30:22 - Stacey St. John

Superhog has such a great product. And I will be the first person to say I made a big mistake because I've actually been in conversation with Superhug for a year and I was waiting for this one little teeny piece of integration with my property management software to make it easier for my team. And it's never a mistake to put your team first. That's not the mistake. The mistake was that I didn't just bite the bullet. The sign that says progress over perfection. I was waiting for the perfect solution. Yeah, but it's me and the buns.

00:31:00 - Jenn Boyles

It's human nature. And I'll put a link to superhog. Know your guest product in the show notes, too, because I think it's vital. And other products are available, I should say, out there, but I've worked with them for years and I just think I don't have problems. And I think that it's a peace of mind, isn't it? I think that's really what it is. It's peace of mind that the guests are who they say they are. I am who I say I am. And everyone can just get on with having a good day and making those memories.

00:31:32 - Stacey St. John

Amen, sister.

00:31:34 - Jenn Boyles

Now, if this isn't enough for everyone, all these resources and nuggets that we're dropping today, you also have an offer, don't you, that you want to extend to those listening?

00:31:45 - Stacey St. John

Absolutely. I just want to say that if you are watching or listening and think, man, I really want to take a step back and think about my business and how I can level up my business. Jenn, I was going to say you are so amazing at so many things, and I know that you have such amazing resources for your listeners and your viewers. But if you need a second set of eyes or ears and want to go through a business planning session with my team, I'd be happy to offer that at no charge. So I'm assuming we'll put a link to that in the show notes as well.

00:32:20 - Jenn Boyles

Definitely. Thank you, Stacey. It's very generous. And thank you so much for coming on today. I've so enjoyed our conversation and I can't wait for next week's short term rental virtual summit for women.

00:32:32 - Stacey St. John

I cannot wait to have you as a speaker, girl. Thanks for having me. Bye.

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