Transforming regular bookings into Repeat Bookings with Jessica Fernandez

Summary and Highlights

Doing it all from being in active military service to civilian life can be a daunting task, but Jessica, a military veteran, has embraced this challenge with the same strategic mindset that defined her career. In our recent podcast, Jessica shared her inspiring journey of moving from the military to becoming a successful short-term rental (STR) host in Virginia Beach. Her story offers valuable insights for anyone looking to make a mark in the STR community.

Strategic Property Selection: A Tactical Approach

Jessica and her husband, both seasoned entrepreneurs, embarked on their post-military venture with a clear strategy. They chose to invest in real estate with a focus on short-term rentals, specifically targeting properties that would attract steady clientele. One standout example is their property in Annapolis, Maryland. This particular location was chosen for its appeal to midshipmen parents and alumni, ensuring a reliable flow of repeat customers. By zeroing in on this niche market, Jessica has successfully tapped into a consistent demand, which is a critical factor in her business’s success.

Elevating Guest Experience: A Five-Star Commitment

In the competitive world of short-term rentals, delivering an exceptional guest experience is paramount. Jessica’s approach to hospitality is reminiscent of high-end hotels, where the focus is on creating memorable stays. From luxurious touches to meticulous attention to detail, she ensures her guests receive a five-star experience. This dedication not only garners glowing reviews but also fosters repeat bookings, which are essential for sustaining a profitable STR business.

Effective Communication: Building Trust and Comfort

Jessica understands the importance of communication in enhancing guest satisfaction. She maintains a personal touch by reaching out with pre-arrival text messages and staying available throughout their stay. This proactive approach helps build trust and ensures that guests feel valued and well-cared-for, leading to positive reviews and increased likelihood of repeat stays.

Harnessing Technology: Streamlining Operations

Technology plays a crucial role in Jessica’s business operations. She utilizes tools like Market My STR and a virtual assistant to manage guest communications effectively. This not only helps her maintain high standards of quality control but also ensures that her guests receive prompt and attentive service. By leveraging these tools, Jessica can focus on growing her business while maintaining a high level of guest satisfaction.

Ensuring Legal Protection: Clear Agreements

A comprehensive rental agreement is part of Jessica’s strategy to protect both herself and her guests. By setting clear expectations through detailed agreements, she minimizes potential misunderstandings and legal issues, creating a smoother experience for all parties involved.

Direct Booking Strategy: Encouraging Future Visits

Jessica actively encourages guests to book directly for future stays, providing them with her direct booking information during their visit. This strategy not only helps her build a loyal customer base but also maximizes her revenue by avoiding third-party booking fees.

Leveraging Referrals: The Power of Networking

Referrals play a significant role in Jessica’s direct booking success. Many of her new bookings come from previous guests or her personal network. This word-of-mouth marketing is a testament to the quality of her service and the strong relationships she has built with her guests.

Commitment to Continuous Learning: Staying Ahead

Jessica’s commitment to professional growth is evident in her investment in coaching and attendance at industry conferences. By staying updated on best practices and emerging trends, she ensures that her business remains competitive and adaptable to changing market conditions.

Mindset and Long-Term Vision: Building for the Future

A key element of Jessica’s success is her mindset. She focuses on controlling what she can and letting go of what she can’t, which helps her navigate the challenges of the STR industry with resilience. Additionally, Jessica views her STR business as part of a broader financial and tax strategy. Instead of seeking immediate cash flow, she aims to build long-term wealth and legacy assets, reflecting a thoughtful and strategic approach to her investment.

Jessica’s journey from military service to becoming a successful short-term rental entrepreneur is a testament to the power of strategic planning, exceptional guest service, and continuous learning. Her story provides valuable lessons for anyone looking to thrive in the world of real estate investment. For more insights into Jessica’s successful strategies and to hear her full story, be sure to check out our latest podcast episode.

Transcription

Jessica: I get their phone numbers and their emails. And I also have a card that I made up with like a little like gift that basically says like, Hey, here’s our website. You know, if you ever want to come back, just email us or, or go on to the website and you can book through there and get a discount. So we’ve had multiple people while they were there.

Message us and say, Hey, like we want to book for these other weekends because there’s specific like parents weekends and football games and alumni weekends that they already know those dates for. So I can book those out in advance and I can just fill in with everything else.

Hit me! Hit me!

Gil: Hey folks, welcome back to Direct Booking Simplified, where we break down the strategies and tactics to win in direct bookings. On today’s show, I have Jessica Fernandez. Jessica.

Jessica: Yeah,

Gil: good. It was, uh, really good bumping into you at, uh, STR Nation. Uh, this was a week ago. I feel like it was a week ago.

Jessica: I, I’ve lost track of time. Like I’m quasi retired right now. So every day is like a Saturday. Uh, yeah, it was funny. Cause I was like scrolling through Instagram and I was like, Hey, wait a minute. He’s. I was like, I

Gil: And we, I don’t think we met in person. So I didn’t know, I had no idea how you looked like, or.

Jessica: actually walked up to somebody else cause like, I knew you were of Asian descent. So

Jessica: I was like, Hey, and you said you were sitting in the back and I was like, Hey, are you a girl? And they were like, no,

Jessica: but I think he’s here.

Gil: Yeah. I think that was, uh, that was Jeff. Uh, I, I got to know him. Uh, I think he’s investing in like West Virginia. Um,

Jessica: Yeah. I think I found him on Instagram too shortly thereafter or had like seen it. And maybe that was what I was like, confusing. Um, he was like, was he a doctor?

Gil: uh, he was, no, he wasn’t a doctor. I think he was a paramedic. I think he was a 

Jessica: Oh, okay. 

Gil: Yeah. Yeah. Yeah. So he’s, he definitely switched careers and he’s like all in on, uh, STRs now. How’d, how’d you enjoy the conference?

Jessica: I was good. There was a lot of, um, different types of people. I was really surprised at how many first time and or, uh, people who haven’t bought or invested yet and where they’re just absorbing and learning the, the like absorbing knowledge and learning. So it was really cool to talk to everybody.

Gil: Yeah. And you, I think on the other end of that, like we had some pretty big players there that have been like in the industry for a very, very long time. So it was actually a very good mixture of folks. And I think like almost like a good portion of the hospitable host team was, was there as well to, um, or the group there, it was really actually good to, to meet them.

Gil: Um, I met them all like kind of virtual. I met a lot of them virtually, but meeting them in person and getting to have lunch with folks is like, it’s just a very different experience.

Jessica: yeah, that was, um, you know, my husband’s always like, why are you going? I was like, I just want to meet people and then be able to like, talk to them in person. It’s a little different than, you know, even listening to everybody on podcasts and stuff. So, um, yeah, I feel like you can get a little bit more out of the 1 on 1 or just. Talking to random people that are also there.

Gil: Yeah. Did you attend any of the other conferences this year or even previous years?

Jessica: I feel like I did all of them except for the one in Colorado. Um, so I started with STR wealth

Jessica: in Nashville. 

Gil: Right. I was there too. That one was so busy. I felt like I was running around the entire day. That was exhausting.

Jessica: lot. Um, I think, I think they start, like, I remember they started at like eight or.

Gil: They did start early.

Jessica: super early. And I was like, man, all right, let’s go. Um, that was my first one.

Gil: Yeah.

Jessica: and I was not expecting that many people there.

Gil: Yeah. Yeah. It was a, it was a big party.

Jessica: Yeah. And then I went to level up your listing in Scottsdale with Natalie Palmer and Tatiana. Um, and that one was great too. I think that one was really good.

Gil: Yeah. That one was pretty female heavy, right?

Jessica: yeah, it was, I, I wouldn’t say like, I’m surprised, but there was, You know, males in attendance

Jessica: and some women were even like, I didn’t know I could bring them and Natalie and Tanya were like, we were not going to turn you away, but, you know, we are gearing towards the female audience with how we have things set up.

Jessica: Um, I would say like, it wasn’t. You know, there was no like male bashing or anything like that. Um, yeah, my husband’s like, well, I don’t know if I would go to something like that in, and I was like, but it’s really just like knowledge, but nicer. Like both of them were very different, but they both provided a lot of, um, learning experience and like the people and individuals that they had on stage and brought on stage to talk. Um, Was they, they were both very well done,

Gil: Yeah. Yeah. It almost feels like, and I don’t know if Natalie’s pulling this one out of like her hosting hat, but like, it almost feels like, you know, your guest avatar and who you want to attract and your branding is so spot on that.

Jessica: yeah.

Gil: Like we talk about this all the time. Like if you’re trying to market to everybody, you’re going to market to nobody.

Gil: And she’s taking the opposite approach of like, okay, I’m going to market to a very specific group. And she didn’t. Maybe intentionally like let leave out men, but I, when I looked at it, I was like, okay, maybe this is not the right conference for me this year, but that’s what I, well, that’s why I like when I, when I was considering which ones to attend, I was like, okay, maybe not this one.

Jessica: Did you go to any other ones?

Gil: I did go to wealth con. I felt like that one was really big. It was good to kind of meet a lot of folks there, but I felt like it wasn’t as intimate as this TR nation. Um, Like STR Nation, you get to sit down with the same people for like multiple days, whereas I think on WildCon, just because there’s the sheer number of people in the venue, how big it is, you’re constantly feeling like you’re, you’re speed dating.

Gil: You’re trying to get to that next person. You’re trying to make those connections, but like almost reflecting back to it, those connections were at not as meaningful as more intimate conversations that I got to have at STR Nation. I don’t know if you felt the same way.

Jessica: Yeah. I would say that the smaller I, I mean, I’ve learned my through going to different events and stuff that, you know, everybody kind of like scoffs at the VIP, you know, tickets and stuff. But I feel like with bigger events, that’s where that comes into play. And like, you actually get. The closer intimate, uh, conversations, like you said, in the smaller rooms. Cause that was kind of my takeaway with, uh, the STR wealth. Um, it was a lot of people, but I would say like the, the last day when we got to do kind of a one on one with Bill and Mike,

Gil: Yeah.

Jessica: I took a lot more out of that. Cause there was only about 20 of us in the room. Um, Not to say like, I, you know, I made contacts and like my coach, Marilyn was there.

Jessica: So I got to also walk around with her and kind of like settle if like the celebrity star going

Jessica: through and people coming up and talking to her. So I was like, you know, got to listen to a lot of conversations that way as well. But, um. You know, comparing it to the smaller intimate group level. If you’re listening, I would say it was very similar to because there wasn’t as many.

Jessica: Um, I would say, like, it was like the medium between,

Jessica: um, STR nation and STR wealth. Um, so it was a good, I feel like I hit kind of. this year.

Gil: Do you have any more lined up?

Jessica: No, um, I forget what, there is one other one. I had thought about the one out in Colorado, uh, where that was WealthCon. Was that the WealthCon one?

Gil: Well, Walt’s con was Nashville. I don’t know if they have another smaller one coming out. I think they thought about having one in Vegas, but I don’t know if they ended up. still doing that.

Jessica: Yeah, I, uh, it was, mm, the Robinsons,

Gil: Oh, I know. I don’t know where 

Jessica: that was the one that was in Colorado

Jessica: that I thought about going to, but then I ended up not because I had some other travel kind of sandwiched in between, and I was like, that would be too much, um, for me to be gone that long.

Gil: Right. And I think Rob built has his host con in sometime in late summer in Texas, Austin, probably.

Jessica: Yeah, I think I was looking at that one too, but I feel like I’ve got some travel around that timeframe. So,

Gil: It’s also going to be like a hundred something degrees there.

Gil: I’m a San Francisco, so we don’t really get much of a heat storm here. So it’s, I think I would melt it out there.

Jessica: yeah,

Gil: Well, Jessica, do you mind, uh, giving folks an introduction on, on who you are? We went pretty deep in many other things, but kind of give an introduction to yourself.

Jessica: sure. Um, so like I said, I’m kind of quasi retired right now. I spent 20 years active duty in the military. Um, so this September I will be officially retired and, um, just have traveled the world, done a lot. Um, Out of Virginia beach and my husband and I here, we own a business here as well. Um, so we’ve been kind of entrepreneurs for a long time now. Um, and now that I’m getting to a point where I don’t know what I’m going to do after I get out. It’s like. We had started talking about how do we figure out like our tax strategies and what’s our legacy look like. And so that kind of led us back into real estate. Um, and so we had a long term rental for years ago, kind of what the military typically do, where you buy a house with your VA loan, you stay in it, you end up moving locations, you keep it, you rent it out, um, We ended up not leaving Virginia Beach, but we still rented it out.

Jessica: And then 2020 happened and we were kind of looking at it right in the beginning phase of everything going on. And we were like, I don’t know what’s going to happen. Like, I don’t know if we could float having that mortgage in this house. Um, so we kind of freaked out and sold it. And. You know, now looking back, we were like, dang, that was a bad idea.

Jessica: We just bought it and figured it out. Like we, we figure everything out. So we would have been able to figure it out. Um, so, you know, long story short, that led us back into the real estate. And then we started looking at the tax strategies and how do we fix what

Jessica: we’ve been doing and create something that we can give our kids later on.

Jessica: So, um, yeah, We really started looking at the short term rentals. Uh, well looking at rentals again and then nailing it down with like the short term rentals. And so, uh, about two years, no, two and a half years, almost three years ago, we started a partnership with our friends down in Texas. Um, they ha it’s just outside of Port Aransas.

Jessica: They’ve got a couple of rentals

Jessica: there as well as a primary house. And so we had, Been visiting with them and talking about how we wanted to get back into real estate. And he was like, I kind of don’t want to do this by myself anymore. Do you guys want to partner with me? And since they already had the processes and contractors and

Jessica: everything in place, we decided to do that.

Jessica: So that one was a built from, you know, the ground up, um, we purchased the land, built it. Contractor took. Exponentially longer than what we had expected to, and now we’re hoping that that will finally be in service this next year or this this month. Um, excuse me. And then we also listed it just to kind of see, um, because the whole play was to.

Jessica: You know, purchase the land, build it and then do a cash out refi once we got it appraised.

Jessica: Um, so we’re kind of looking to see maybe do we just sell it and 1031 exchange it to something else, um, that would potentially start giving us a better cashflow. Um, so that is a completely separate business. Um, but we’re still involved in that.

Jessica: And then in that meantime of trying to figure out like, what did we want to do? We ended up buying a place up in, uh, Maryland. So I actually got my real estate license in Virginia, hoping that I could utilize that as part of like, you know, use my commissions for some of our investment strategy, but ended up purchasing out of state.

Jessica: So, so that we actually have owned for a year now and purchased it. Closed, um, end of June and then I had it launched. I had a 2 month goal to launch it in September and I ended up launching it September 1st last year.

Jessica: Um, so we’re almost one year into all of it.

Gil: How has it been?

Jessica: Um, it’s good. It’s a, it’s a work in progress, but, um, I kind of, you know, I went at it with like the higher expectations of, This is what I want it to do.

Jessica: And what is it want it to be? Um, I went in, you know, I also went into with like, I want to provide the five star experience. I want people to love the house and come back and, you know, and share that with their friends.

Gil: Yeah.

Jessica: so we really, Kind of looked at it from that aspect of it and, and not necessarily the cashflow piece of it.

Jessica: So, you know, a lot of people get into it because they want to replace their, their daily incomes. And, and we looked at it more from a utilization of like a tax strategy and then a legacy piece. So like, that’ll be a house that, you know, in our financial goals will be paid off in the next, like Under 10 years, I’m hoping seven. Um, and then, then it’ll be significantly cashflow at that point,

Gil: Yeah.

Jessica: but also a point like a, you know, something that we could give our kids as like, here’s something, if you want to utilize this as, you know, income for you, you can keep it or you can sell it and, and do something, you know, do a 1031 exchange into something else.

Jessica: So

Jessica: that’s kind of what we’re utilizing our real estate portfolio, hopefully. For,

Gil: Yeah. What’s next for you? What are you looking, are you looking to continue to expand? Are you looking to do more of the new builds? What are you trying to, what do you think is like the path that you,

Jessica: I don’t think I’ll do any more new builds right now. Although I have a friend here locally, um, she’s a little bit further West out, uh, in Suffolk and they started doing that by purchasing some land and like, uh, building, but they’re building to sell.

Jessica: Uh, so I, yeah, I probably stay around away from that, but. When we started looking at real estate and like what we wanted to do, uh, we kind of went opposite of basically what everybody was saying. Like you should do, um, they’re like, you know, look for the cashflow or like, uh, we don’t like, I want it to break even at least, um, you know, cover all of the expenses.

Jessica: Like I don’t want to be dumping money into it every month. And they were like, you don’t necessarily need to look at where you want to go. And I’m like, I want to go visit where, where I have my house. Um, and so we’re looking in Florida right now, uh, because my husband’s family’s from down there and. We’re like, well, if we want to go visit down there and everybody seems to be moving down to Florida too.

Jessica: I was like, it just, yeah, so we were, we were looking to add this year, but our accountant after going through everything and like what happened last year and how we utilized it, um, we used the cost seg and, and what our financial situation looked like. He’s like, how about you hold off on doing that this year? Um, Especially too, so I’m still W2 from the military until September, um, next year, I won’t have a W2. So I would be able to get long term rentals as well. If we wanted to go that route

Gil: Oh, yeah.

Jessica: I was like the rep status. Um, because I, I’ve been managing mine. Um, you know, myself,

Jessica: this this past year, the last year, um, And so if I wanted to do that, I, we, we could utilize that and then in different situations.

Jessica: So there’s a couple of options. Um, but yeah, like I’d probably go back to school and then like maintain, like looking at some rentals and trying to figure out like how many more we want, how many more we need to get to, like, I want to be officially, officially retired at 50.

Gil: Yeah. Sounds like, sounds like you’re on the right track already. Or at least definitely the mindset as well too.

Jessica: We’re trying.

Gil: So you, you mentioned that you don’t follow some of the, the common, uh, What’s it called? The common patterns of people that recommend like, Oh, buy out of stage, doesn’t have to be where you, where you want to go and, um, even buy for cashflow. Why do you think the opposite? What’s the mindset for you?

Jessica: Um. So, I mean, like to be, to be frank and like totally honest, like we don’t need the cash flow. Like, would it be nice? Yes. Um, do I need it to replace my income? No. Uh, you know, in the military and like, now that I’m going to be like 20 years, I’m going to get a pension and we’ll get disability benefits. And, and I will actually be making more money retired. Then I am now, um, so we kind of looked at it holistically from like, all aspects of it was like, yes, I probably could probably could have bought a cheaper place. Um, or, uh, a more cash flow, heavy place, but we probably wouldn’t have got the cost segregation on it. Like, we did. Um, and I, I feel like a lot of those places.

Jessica: Well, you’re, you’re going to pay for it 1 way or the other, I guess. Um, so you can go for that cashflow heavy place. You’re either going to be paying exponentially and or have to bring in somebody else to help you with that capital unless you already have that capital. Or you could go find something that, you know, is a little bit less cashflow heavy that you can manage, um, and maintain, but still like somebody else is paying my mortgage down. I kind of look at it like it’s not making me money, but it made me a lot of money last year, just in the cost of a loan.

Gil: Yeah. Yeah. So you, if I’m capturing this right, you’re thinking about your whole entire life situation. You your upcoming income is pretty much well taken care of. You did this when you had a pretty steady W2 income that you want to offset taxes. So for you. It made a lot of sense to get into STRs because you wanted to offset that W2.

Gil: You want to do the cost seg depreciate it, take that against your income, reinvest that. And that’s where a lot of your savings is coming from. And the way you’re thinking about it is like longterm. Yes. You can pay down less of your mortgage and get it done in like 30 years. But honestly, like you don’t need the cashflow necessarily.

Gil: And you rather have the equity in, in, um, And the property taken care of, having that paid off. And really like that, that to you seems, seems to be where you’re comfortable and what success looks like for you. Is that right?

Jessica: Yeah, yeah, I’d say that’s pretty dead on. Um, yeah, a lot of people, you know, I feel like it caught up in the, I need to make more money. I need to make more money. I need to make more money. And you just, you really just need to look at your expenses. As they are and then look down the road and see, like, what is that going to look like for you in the future?

Gil: Yeah. That’s an interesting conversation. Like I was talking to a couple of STR hosts the other day and like when we go to the conferences, it’s all about scaling and building up your portfolio to however big you might want it. And, and, and. That actually works out for a lot of folks, but I think there’s a counter to that where some folks actually don’t need a really big portfolio and they are very happy with having a nice, decent sized portfolio that helps fuel their lifestyle and that they can spend their energy on other areas of their life.

Jessica: Yeah, I, I agree with that. And I think to, um, some people get wrapped around, like, the numbers piece of it as well. Like, you know, and if you want 100 doors. And love to tell people that you have a hundred doors. That’s, that’s your thing. That’s not my thing. Like, I would rather have 5 or 3 and be content with providing the, the, you know, the experience and the stays that, that we can in those 3 and 5 and still have my. You know, portfolio where that legacy will continue on, like, financially for us. Like, if we, whatever happens, like, in that sense, like, it was an interesting conversation I had with 1 of our friends to the 1 that we got into Texas with. So he’s a doctor. His wife was a nurse. They got into it too, because they were like, how do we. You know, deal with the tax situation. And I remember asking him about, um, life insurance policies. And he was like, I don’t have any life insurance policies. I was like, I’m like, we’re not that old, but I was like, why I was, I always thought I was like, that’s what you do is like, you just get a life insurance policy and that’s like, you know, covers.

Jessica: And he was like, I don’t need one. And neither does she, because if something was to happen, she could just sell one of those houses and, and have money.

Gil: Yeah.

Jessica: like, Oh. And that kind of got our wheels turning of, like, oh, there’s different ways to go about. You know, feeding your finances and setting up your retirements, then just dumping money into a 401k or an IRA and letting it sit there or finding a term life policy that, you know, you might get. Or your, you know, your children or family might get if something was to happen.

Gil: Yeah, yeah, you’re almost taking control over the, where you want to be spending your money, where you want to be putting it, where you want it to grow on your own, rather than trying to follow everybody, follow what the norm might be.

Jessica: Yeah. I can go on a whole other segment about what that might entail outside of like real estate with like whole life policies and like the IRA. Like, yeah. Um, and I’ve dug way too much into that. Um, but it was, you know, it was interesting to learn. And I think the real estate piece of it. Kind of fit our thing and what we wanted to do.

Jessica: And we had a really good accountant that kind of directed us and was just like, just find one, one thing, go into that. And then once you, you know, figure that out and get that going, then you could look in like to going into other things if you want to.

Gil: Yeah. Um, on the hosting side, are you on the camp of, I’d rather be hands on and really have that Taylor experience. I want to be, uh, really crafting that. Or are you more on the other side where you’re, you’d rather scale up a team and leverage that and have people take on different parts of the business.

Gil: Like, and maybe there’s a huge happy medium in between, but I kind of, where do you fall? Yeah.

Jessica: of those two. Um, I, old Jess, years ago would have been like, I’m doing everything myself, nobody else is gonna do it better than me. Um, new Jess has gone through a lot of therapy and work to figure out, like, there are other people who can do things better than you. Um, and then it’s okay, even if it’s not the way that you would do it. Um, it allows you to give that time back. And be able to do something else. Um, and I think a lot of that too, was having kids and

Jessica: realizing, like, there’s things that change and there’s things that you’re gonna be able to control and you’re not going to be able to control some of those things. Um, so I, I hired a coach when I first, um, uh, got our, uh, Our rental in Annapolis, and because we had another business and I realized like going through all of those experiences of standing everything up, building the processes, setting up the, you know, how do you respond to emails, blah,

Jessica: blah, blah, that.

Jessica: Um, I wasn’t about to recreate all of that and happy to pay somebody else to copy what she did. Um, so it, it ended up being perfect and we were able to like copy. I was able to just take everything that she had massage it to what I and how I would say things, um,

Jessica: and then put that all into play. And then I met Stephanie, uh, Figaro’s at actually my graduation from that.

Jessica: Uh, she came and did a talk and was talking about VAs and my husband had used a VA for his business at one point. And we started kind of talking about it. So being in the military and my job, like I couldn’t have my phone on me all the time and I couldn’t necessarily be at the computer and part of, I think, providing a, uh, a five star experience.

Jessica: If you’ve ever been to one of those types of hotels, it’s like they are an almost instant response. Um, and that was kind of what I wanted to do. So I started talking to Stephanie about bringing a VA on and I was like, okay, well, I’m just going to start copying, like how I would And do things. So that’s where I say, I’m kind of that happy medium is like, I, and she actually helped me to like build out all of the like FAQs and like, if this, then that, you know, sort of happens. And she basically has all of that now. And can I can literally walk away for a week or two and know that it would be fine because she has everything now, you know, do I want to oversee and see kind of like, you know, do you like a quality control? Yeah. And like, that’s where I think like the medium is, is like, I wouldn’t ever fully, I think I’m off of it, but I also think that that’s not being like a good owner

Gil: Yeah.

Jessica: Um, cause you need to, you know, QC what’s going on. Uh, otherwise you have literally no idea what’s happening in your business.

Gil: Yeah. And I’m picking up like small world hints, but you’ll, it sounds like you also enjoy the hospitality side of things as well, too. You mentioned five star experience. It doesn’t seem like it’s just purely for the business and getting the revenues and hitting those targets. It sounds like you also really enjoy being a host and actually creating those really good experiences that keep guests coming back to you.

Gil: Silence. Silence.

Jessica: you know, any other venture we get into it, that like transparent, like that is what happens.

Jessica: Like, I want to be able to provide that. And I think a lot of that comes from is like, I know how good that feels when I go someplace and get that treatment. And, and, you know, having traveled around the world and then all over in different cultures and, you know, stayed in little fricking hut houses to, you know, more than five star like hotels, um, The service, like in the way that you feel, like when somebody gives you that, like, that’s what I want to provide, um, in any business that I like end up getting into or doing or being a part of, like, even if I was to go and try and get a new job, like after that, like, that’s what I would want to be a part of.

Gil: Yeah, yeah, I’m, I’m, I’m in the same camp as well too. Like I, I don’t, I have a VA, but I don’t actually have, I have more working on the business, but I don’t have them working on specifically the STR guest messaging side of things, which I actually thought about, like, should I transition and have him take on some of that stuff?

Gil: Um, but honestly. I really love hosting and I don’t know what it is in my, my, my previous life that makes me enjoy it. But like reading the reviews, talking to guests, helping them prepare for their trip, like those actually bring me a lot of joy. Um, so like, If we were to scale our portfolio, like I will definitely have to like, pull myself out of the business and really work on work on the business, not necessarily in it, but there’s a part of me that wants to keep that connection and figure out like, how do I stay connected to my guests, make it very personable.

Gil: Um, but without like that, that, that overhead or the not like the overhead or the time it really takes when you’re constantly on the clock.

Jessica: Yeah. I, I would challenge you. So I would say like one of the other things, and this would be the challenge is like allowing somebody else to have that feeling too.

Gil: Oh, interesting.

Jessica: So I was talking with somebody else recently, too, and I was like, I also in like, now enjoy being able to employ other people who love doing what they do.

Jessica: Um, and that goes same to our CrossFit gym. It was like, uh, we want coaches who love doing that. And it used to be like, I’m the, you know, like I said, like old me was like, I could, I do this the best. Knew me is like, I get the joy now too, of seeing other people having and loving what they’re doing. And he was like, oh.

Jessica: He was like, ’cause I, you know, if I look at like everything that I do and even some of the things that I’ve let go of, like our cooking, like. I like we have somebody else who helps us cook dinners, not every night, but it’s a majority of the night because she’s a chef and she loves cooking. I sometimes just don’t like it. Like, I don’t want to think about having to make a dinner and like I can come home and I have this awesome meal prepared and all I have to do is heat it up. I love knowing that she loved making that for us. And

Gil: good point. That’s a very good point. I never considered it in that perspective of, like, growing your, your, like, if your STR business is like really passing on that joy. to someone, your employees, um, I’ve thought of always about it, like I’m creating this brand. I’m that’s very, very me. Um, and I want to like gift every guest that comes through a really good experience, but you’re, what you’re saying is like, really like leverage the team to really Really have them shine in the areas that they are doing well, but also give them that joy of that experience that they’re providing the guest.

Jessica: it may take finding a few people and going through all of that to like find somebody who meshes with you and you trust and you create, like, you know, they show that they’re responsible to withhold your brand. Um, So I’m saying to is like, don’t hold on to somebody like you think you’re like, oh, man, this, you know, this isn’t working, like, let it go. It is a work, but then, like, once you find those people, like, those are the ones that stick around forever and they build your team and they become part of you. I feel like they become part of me. Yeah,

Gil: Yeah, I agree on that part. Um, I started doing this with my VA more recently. It’s like I journaled for him to consume. Um, which was very interesting, um, because I felt like I was keeping a lot of stuff in my head and all the stresses and the things that you have to think about on, on a very daily basis.

Gil: And I was like, okay, maybe I’ll journal to kind of get out of my head, but also like, it’s a good way for me to translate what I’m thinking to, to my VA so that he can empathize with what I’m doing and probably take things off my plate too.

Jessica: I like that.

Gil: Yeah.

Jessica: Yeah.

Gil: On, on your side, what are some of the big learnings of working with the VA?

Jessica: Um, I would say it’s all like you have to be prepared to teach them like what you need them to do. Like, I would say, like, don’t go in expecting them to understand, like, you need all of this stuff done. Um, and then I’ve worked with Philippine and U. S. Yeah, those are the only two. I know that there’s like some like African and some other countries that, um, they utilize, you know, VAs out of, but, um, there is definitely a difference, although it’s not that big of a difference. Um, I don’t, let’s say like some of the U. S. ones tend to be a little bit lazier, uh, in the sense of like, I feel like I was always kind of having to pull. And from them instead of them, like asking, uh, where the Philippine, um, ones, like they were kind of, yes, yes, yes. They’re like, always kind of like, what do you need?

Jessica: Like, but, um, they do have, like, uh, I would say, like, there is probably a little bit more of a mentality of. You know, yes, I can do this. And then I’m not, but not asking the questions. So I found with them, like asking upfront, like, okay, do you understand this? Okay. Repeat that back to me. Let me see, you know, or show me that you can understand what I need you to do. Uh, and then like following up frequently or giving them a deadline that was very helpful. Um, but it’s, you know, it was, it was a learning process, but I feel like. It all is person like dependent too.

Gil: Yeah, that’s true. Uh, definitely there’s like differences in culture there. I feel like the, the VAs in the Philippines, they have a pretty high work ethics. Um, then they, they really, um, They put a lot of heart into their work. Um, it may take some, some training because they’re, they’re not familiar with the culture as much or the norms as much.

Gil: Um, but they’re really hard working folks, at least from my experience.

Jessica: Yeah. I mean, I, I had, I think I had to like tell my ones once or a couple of times now, it was just like, Hey, like it’s your off day. You don’t need to respond. Like I got it. And she was like, Oh, but I saw it. And I was like, it’s okay. Like, thank you though. Like, I appreciate it. But she was like, yeah, like I’m ready.

Jessica: Like, let me do it. And I was like, it’s okay. I was like, I got it. It’s your day off. Take your day off.

Gil: Yeah. Yeah. Um, moving to like the, the next portion of our, of our show, I, you, you have a direct booking site right now. Um, you’re driving traffic towards it. What have you seen as being the most successful tactic that. Um, it was driving, uh, quite a bit of direct bookings for you.

Jessica: Um, so I would say probably all of our direct bookings have come from a referral, either being there, like, having somebody having come through another booking website and staying there or like a friend, uh, like, I would post on my social media and they would be like, hey, I want to go stay or I know somebody who’s going to stay up there.

Jessica: Can you send me the website? So that’s, you know, probably not the greatest, um, piece, but yeah.

Gil: You mentioned before when we were just chatting earlier, um, that you have a lot of repeats that come through as, as well, too, and they’re, they’re driving. Can you talk a little bit about what types of repeats you get and how do you like, like nourish that? Silence. 

Jessica: is there and then, um, they also have massive sailing, um, there’s, Two or maybe three, at least two sailing weeks where a lot of vendors come in and everybody brings their boats and they have the marinas right there. Um, so the entire week people are staying there going and checking out the, the, um, the event. Um, But my big draw was for midshipmen parents, um, and, or St. John’s alumni who are coming back for, for training and stuff there. And so the parents, like, you know, your kid’s going to be there for four years. Um, if you can find a place to stay that, you know, already, and it’s nice. And you know, the experience that you’re going to get, I, you know, I wanted it to be like the Marriott’s and the Hilton’s, um, but they don’t have to get two rooms.

Jessica: Or get someplace with a double bed. Like I was able to fit a king bed in one of the bedrooms and a queen in the other. So parents get to stay in the king bed and the mids get a queen bed, which is much way bigger and nicer than their beds in campus on campus. Um, so when they either come through via BRO or Airbnb, I have a contract that they sign.

Jessica: I get their phone numbers and, um, their emails. And I also have a card that I made up with like a little like gift that basically says like, Hey, here’s our website. You know, if you ever want to come back, just email us or. Or go onto the website and you can book through there and get a discount. Um, so we’ve had, you know, multiple people while they were there. Um, message us and say, Hey, like, we want to book for these other weekends because there’s specific like parents weekends and football games and alumni, uh, weekends, um, that they, they already know those dates for. So I can book those out in advance and I can just fill in with everything else

Jessica: or all the other.

Gil: Nice. Nice. Did you realize that when you were purchasing the property, did you have that in mind or did you kind of serendipitously kind of fall into that? Silence.

Jessica: when you have off, um, because otherwise, like, they’re just left on campus.

Jessica: And, and, you know, if you’re, if you’re, you know, On any sort of school. It’s like, it’s not like a regular school where you can just go leave and do whatever you want, whenever you want. It’s basically you get the weekend off and that’s it. Um, so their daughter actually went to school and then came back as a realtor.

Jessica: And I started messaging her when we were looking for our areas that we were thinking about. And her and her now husband had run kind of an Airbnb arbitrage right before COVID. And so she was super familiar with the area and was like. I know exactly like what you guys need. And this would be, um, like this would be awesome. And it was, it was someplace that we wanted to go back to and utilize as well. So my goal going into it was finding a place that would be able to fit parents and a midshipman or two couples, um, you know, within our price range that was in this area and when she found the house, she was like, Hey, we got to jump on this right now.

Gil: Yeah, so you had, you had a vision in mind, you had some goals in mind when you were purchasing the property. Um,

Jessica: I would rather have repeat customers who I, I know and are going to take care of, like, well of the place. Um, then a bunch of like individual randoms, like coming up.

Gil: yeah. Yeah. And especially after years of doing this, you’re going to get a heavy repeat base that you’re Can pretty much cover your mortgage at that point. Like you’re not going to have to worry about the OTAs all that much because after they stayed with you once, you build a good report with them over a couple years, you’re, you’re building up a pretty good volume that can sustain your revenues.

Jessica: Yeah. At least get that, you know, if they come in for, you know, indoctrination, like now I’ve got them in my system for at least four years.

Gil: Yeah. Yeah. Are you doing any, uh, email marketing campaigns or are you looking to get more into that?

Jessica: I am, um, I have been trying, so I, I utilize market my STR, but I don’t utilize it to the extent that I should. Um, I have been trying to figure out like how to build out those emails now that I have, you know, at least. Uh, I don’t even know how many stays, probably 30 stays, you know, you know, so 30 different emails in there. Um, that is on my list of things.

Gil: Yeah. Yeah. Market master is pretty powerful, especially if you know how to do it. And also there’s actually a lot of other tools that I’ve come across and I can’t, I, I come from the e commerce industry, so like I know. What folks are using on building e commerce stores and like even like simple tools like MailChimp and Klaviyo are highly effective tools and probably even a bit more simpler because they’re not quite a quite as feature rich as Markham STR or GoHighLevel So yeah, but definitely I think collecting the emails in the first place is probably the biggest, the biggest like service you can do for yourself for building a sustainable business.

Jessica: Yeah. I’d say one of the other things that I do that I picked up from Bill Faith when I was there at the, um, STR wealth conference in Nashville. Um, and I’d heard him talk about it before too, but was sending a text message prior to them. Um, Um, arriving. Um, and I found that that is also like a very useful, um, tool to, let’s say like get them off of the, the platform messaging, but, you know, at least show them that you have another number that they can contact you on.

Jessica: And not just through whatever other messaging system that they, you know, maybe both through.

Gil: Oh, interesting. Do you send like, I know Bill does like the, the videos, um, to welcome them. Do you do that or just a casual message, like introducing yourself?

Jessica: I love what Bill puts out and he has a ton of good things. And this is when I’m like my pet peeves about it was, he was like, you know, send a message. And I was like, cool. I got my mark in my STR. I’m trying to send messages through here. Like you can’t send a video message through here. And he was like, Oh, no, no, no.

Jessica: You have to use a different phone number. And I was like, I’m trying to make this simple and not also confusing for the guests, because I would be confused if I keep getting different

Jessica: numbers from buddy. Um, so he’s like, no, you have to send that personally. And I was like, but. I thought the point of having market my STR, you know, or go high level, whatever it is like to keep all of your stuff there. Like, it’s all in 1 spot now

Gil: Yeah, that’s true.

Jessica: and it now, you know, if I have somebody else, maybe I’m on vacation and somebody else needs to respond, you know, or now it’s on my phone and now I’m tied to that. Now the text messages is usually, I still keep that, um, like that’s always me. Haven’t turned that over to the VAs yet. Um, but it’s, they can see it.

Jessica: So like they’ll notify me if something comes in and I haven’t responded like, Oh, Hey, did you see so and so texted? And I’ll go in and take a look at it.

Gil: Got it. So you’re sending the messages through MarkMistr, not through your, just a 

Jessica: well, I just do a text message. Now I stopped doing the videos. Um, and I, and it’s still, I think, no, I think I would appreciate it too. It’s like when I get a text from, from somebody, um, I think I’ve only had one guest not respond.

Jessica: Um, he also didn’t respond on any messages after he like checked in. And I was like a little worried.

Jessica: Like that was the only one that I ever worried about, but then he still gave me a five star rating. I

Gil: that’s always the nerve wracking one, which is like, you go the entire stay, you send them the rental agreement, they just, eventually they’ll do it. And then you send them all the information about checking information that you do the mid stay and they don’t respond back and they check out, you’re like, okay, is this guy even like, did he, did he go, did he, is it, is it.

Jessica: can see like in my, like locks. I’m like, okay, you stayed. And I was like, I was like, yeah,

Gil: Yeah. So it sounds like, uh, you have, you have your tools built in, uh, you’re leveraging a lot of repeat customers or guests coming back to you. Um, and there might be even some room for like further optimizations with more, more email funnels that you might be looking into.

Jessica: I definitely know I can dig into that and, and utilize, um, At least the direct booking website more by sending that out. Um, I don’t, I don’t do that enough right now.

Gil: Yeah. Yeah. That’s a pretty powerful tool. Especially if you’re already collecting emails there, like it’s a, it’s a really effective way to get to repeat bookers.

Jessica: Like everybody’s like, you got all these emails. I’m like, yeah. Like

Jessica: I need 

Gil: well, I mean, at least you’re, you’re getting with what you have so far, you’re actually getting a pretty steady stream of folks coming back even on a manual basis. Um, so you can, what’s your, what’s next is really to amplify that impact there.

Jessica: I, I mean, I would say that a lot of that comes back to like our communication with the guest and then what we provide at the house. Um, yeah, I pretty much went through everything. I mean, like, we go and stay up there anyways. So it’s like, when we stay there, I’m like, what do I want? What do I need while I’m here? I don’t want to walk in and just have some blanket thing. And I don’t wanna have 95, like a list of 95 things that I have to do on checkout. Um, either

Gil: Yep. Yeah. I, I think what you just said is one of the most critical parts of direct booking is really the guest experience. I think that the hosts that create a really phenomenal. guest experience and consistently do that. And they’re not just like reaching for that five star on Airbnb, but they’re really, they care about the experience.

Gil: They’re trying to make it as perfect as possible. Something that people really like will want to talk about, to rave about, and really like want to come back to. Those are, I found to be the hosts that get the strongest direct bookings because those guests are likely to come back to you because not every stay at every place is always going to be phenomenal.

Gil: But if you have a really good experience and it was almost flawless, like you want to have that experience the next time, because there is a lot of stress traveling. There’s a, there’s a lot of stress, especially Like, you know this, but like traveling with kids and finding a place that really suits them that if you feel safe, that the kids feel safe into has all the amenities that they want.

Gil: Like you capture every single one of those moments in your brain. And when you check out, like you almost play that back of like all the great things that you did, but also like what might not have gone well, but if it goes well as a parent, you want to like, that’s an easy way for you to say, okay, I want to go back and give that same experience to my kids again.

Jessica: Yeah, I, I completely agree with that. And I think kinda where you were going with that and like how I feel about it is that it makes the guests feel comfortable with you. Like one, it’s not just a property management company. Um, cause I’ve stayed at some of those too, and they were very communicative, but I also kind of feel like it was shell ish, you know, it wasn’t necessarily, uh, I don’t know.

Jessica: It wasn’t like the best experience I ever had, you know, but I feel like when you can communicate and you can like accept some responsibilities, if something was to go happen, like there’s been, you know, a couple of times where things kind of went a little bit bad. And I, they still gave me the five star review, but they’re also coming back and booking again after because they understand, like, I’m going to take care of them. And I think some people will use the other, you know, booking websites, um, because now they feel comfortable that they’ve got a backup. If something was to go wrong.

Gil: Yeah. Yeah. And I don’t think that that’s actually exclusive to boutique hosts, like hosts that have, like, that they’re doing it themselves. I think it actually does scale to, I’ve known some hosts that have 30, 40 properties, but they systematically think through the entire guest experience. They get feedback loops, but they really do care about like every single guest that walks through and they, they’re able to create a system where.

Gil: It feels very personal. Still. Um, they are taking care of them. They have post stay checkout. We had Annalisa on the show just, just a few weeks back. And it actually was really good to see, like, you don’t have to get rid of that really tailored experience as you scale. Some people actually do figure it out.

Jessica: Yeah. Yeah. I definitely think that. It’s not, know, not doable. Um, it just becomes more difficult once you start getting in kind of like what you

Jessica: were saying was like communication piece of it and, and allowing you to take the reins off and give somebody else the opportunity to do that and be you. Um, you need to be a really good leader to give and pass that information down.

Jessica: So it’s definitely doable. And I think you can still, I mean, I, you know, I can tell you like the, the resort experiences and like some of the, the hotels that we’ve stayed in, it’s been a very personal, like we rolled up one time and like, we got to the gate, we checked in with the guy at the gate. By the time we got to the front desk, they were calling us by name.

Gil: Mm. Yeah.

Jessica: of the 1st times I was like, holy, what just happened is just the communication that they have and their systems that they have set up that I was just like. We literally just drove five minutes from there. And like they, the guy, the valet opened the door and was like, hello, Mrs. Fernandez, Mr.

Jessica: Fernandez. And I was like, how do, um, so it is, yes, it is definitely doable. And then, but it’s, I would say it’s been experiences that like that, that I’ve turned into, it was like, wow, it was like, that felt really good.

Gil: Yeah.

Jessica: would go back to that resort in a heartbeat.

Gil: Yeah. That’s true. I think the matter is to like, as a host, the, do you care more about like scaling your portfolio and racking up those numbers of properties you have or is consistently giving a. Really good five star experience as important to you as growing your portfolio and the folks that do keep that pretty high bar, no matter how many numbers of properties you have, we’ll be successful at that.

Gil: So I don’t, I don’t, it is harder. You do have to put a lot more effort because like you as a solo host. You get to see everything that comes in. You get to do everything yourself. So like it doesn’t rely on systems as much, whereas you scale, you have to rely on systems in order to really keep that, that high quality bar.

Gil: And like you said, it, it takes really good leaders and people that really care about the hospitality.

Jessica: And yeah, and I, and I would go back to that like comfort piece, where it’s like, if you’re going to be comfortable enough to drive somebody to your direct booking website, they need to be comfortable enough to trust you that you’re going to take care of them.

Gil: Awesome. Jessica, we went pretty deep in many different areas. Um, I, I enjoy talking about, um, really your journey up until this point, what, how you leverage direct bookings, how you think about scaling your portfolio. I usually end with two questions. Um, one’s a mindset question and one’s a kind of a tactical takeaway.

Gil: What’s the one takeaway from this? So going with the mindset question first, what’s that one piece of mindset advice that you would give to someone that’s starting something completely new?

Jessica: Oh, completely new. I would say I always come back to this one all the time is like control what you can control and let the other stuff go. Like if it is. I like take a look, like if you’re freaking out about something and you have control over it, then fix it. If you don’t have control over it, then let it go.

Gil: Awesome. Awesome. All right. And the last question, uh, what’s, uh, what’s the one big takeaway? What’s the one tactic that you want our listeners to put into practice today?

Jessica: I would say the tactical, uh, piece of advice, because it was probably the most, uh, for me was learning from my coach, um, was utilizing the contract. Um, and if you don’t have one, I would check her out. Like Marilyn Taylor. Um, she, she gives you her contract that she has had written. Um, and she’s been many years in the experience, but a lot of people don’t think that you can use it on anything.

Jessica: But especially if you’re doing a direct booking website, you need to have a good contract in place. Um, a lot of people freak out about it because they’re like, but you know, it’s a lot of things to read. It really isn’t anything different than if you were to go to a hotel and

Jessica: sign something at a hotel, saying that you would be responsible for anything that happens at the hotel. Um, and I have never, like, I’ve only been doing this for a year, but she’s been doing it for a long time. Like in my year of, of guest stays, nobody has ever complained about having to sign it. Um, and in doing that, you get their email, you get their phone number. You get their address. If you, if something like I’ve had people leave stuff and I just pulled it up and I sent it back to them from their address on, it was like, is this address good?

Jessica: And they were like, Oh yeah.

Gil: yeah, yeah. That’s a good point. Yeah, we, we also do contract ourselves and it just, it sets a expectation as well too, because we’re very clear on like how we want them to treat our home. And it allows us to like, not stay Stuff the listing with all of that information that might scare or give the wrong impression when someone’s checking out your website.

Gil: Um, but when right prior to check in, we’re very clear with them like, okay, these are the things that we expect you to do. Um, and to take care of our property. Um. And so far it’s kind of likewise. We haven’t really had much issues. I had probably had like one person, maybe two that didn’t want to sign it.

Gil: And I was like, okay, if you want, we’ll, we’ll reverse it. And you guys, you can, you can cancel your, your, your stay. And for me, like, I’m very comfortable with that because like, I would much rather have someone that doesn’t stay at our property than someone that, um, stays there without writing, like signing the agreement, because like, that means that they don’t respect my property.

Jessica: Yeah. And I, I feel like explaining to them, it’s not like just covering me, but it’s also covering them as well. Um, then, you know, people are also more inclined to be like, Oh, okay. Yeah. Like, um, I understand that.

Gil: Yeah. Yeah. Absolutely. All right. Well, Jessica, again, it was really good chatting, chatting with you again, um, to, to meet with you week after week, um, where can folks find out more, more about you? How can they follow you? How can they follow your journey?

Jessica: Um, so I mainly on Instagram, I don’t do any of really, I’m on Facebook as well, but mostly posting on Instagram. Um, and it’s just Jess period Fern one, um, on Instagram. And then that should link to my Facebook page as well. And then our, um, direct booking website or whatever is, um, or are not direct, but our short term rental is the restriction retreat.

Gil: Okay. Nice. I’ll, I’ll be sure to include that into our show notes, uh, so that folks who click through, um, but Jessica, it was really good having you on the show. Uh, I look forward to seeing kind of how you grow, um, both your portfolio and you as a person, it sounds like you’re consistently, uh, spending time and effort into growing yourself.

Gil: So I appreciate you sharing that.

Jessica: Now I appreciate you having me and allowing me to share the story.

Gil: Thank you. All right. Bye.