Building Long-Term Wealth With Short Term Rentals

Stephen S. (00:02.531)
Welcome back or welcome to the Real Estate Pros podcast. I am here with Jessica Fischer today. And today we’re going to be talking about short term rentals and Jessica’s expertise within managing these for herself and other people, the technology and everything that goes into it. Here at Investor Fuel, we help real estate investors, service providers and real estate entrepreneurs.

2 to 5X their businesses to allow them to build the businesses they’ve always wanted, to allow them to live the dreams they’ve always had. So Jessica Fischer, thank you so much for being here. Welcome to the show.

Jessica (00:38.756)
Thank you for having me, Stephen.

Stephen S. (00:40.851)
You bet, absolutely. I’m super excited today to talk to you about everything Airbnb and short-term rental, STRs. I think a lot of people that I’ve met don’t realize that when they talk about short-term rentals, it encompasses not just Airbnbs, and I’m sure you face quite a bit of that. just tell us a little bit about yourself to get started and what got you into real estate and what got you into what you’re doing now.

Jessica (00:48.833)
Yes.

Jessica (01:06.463)
Okay, well a few years ago, we ended up having a bankruptcy and a foreclosure on our own personal house. And the sense of insecurity was crazy. I had two babies at home. We had to pay for our IVF. It wasn’t covered by our insurance. You don’t expect to have special needs babies when you do finally have them. So I ended up hitting a really financial low point.

Stephen S. (01:13.859)
Hmm.

Jessica (01:33.228)
So a few years later, I kind of went into money hoarding mode. I was terrified to spend money because I didn’t know what was happening next. So I just started saving and saving and saving. And then one year we got a really good tax return because our finances were so poor. So I said to my husband, I’m taking this and I’m gonna buy a house. And he’s like, we’re moving? And I said, no, absolutely not. I’m gonna buy a house and I’m gonna rent it. And he’s like, you’re crazy.

And everybody else told me that I was crazy too, but I knew that I needed to purchase another piece of property after reading Rich Dad Poor Dad like everybody else did. But I live on Long Island, New York, and we couldn’t afford anything there and the taxes are too high. So was able to buy a condo in Murrell’s Inlet, like right south of Myrtle Beach. And I started managing it. And of course, a month to the day after closing, COVID hit.

And then we couldn’t rent it. And I was like, I am not losing another house. This is not happening. So I joined a few mastermind groups on how to run and manage short-term rentals. Cause I couldn’t really trust anybody else with my baby. And that’s kind of how I got started. And then my business coach told me I was really good at it and that I should start managing for other people who didn’t have the time to do the learning curve of the technology and the pricing and.

just the hospitality, so I work for some physicians and some flight attendants who can’t answer their phone all the time because we do get rated on how fast we respond. So that’s where I come in.

Stephen S. (03:14.605)
That’s incredible. So you actually provide a really impeccable service for busy professionals as well that are buying properties that don’t necessarily have the time to do all those support things, which ultimately affect how much money they end up making with the investment. Wow.

Jessica (03:31.274)
Correct. If you were planning a trip with another family, you don’t want to sit there and wait to see if that’s available that day. You want to instant book it. You want to be ready. You want somebody to be on the other side to answer your questions. And if there’s no one there, you’re to move on to the next house. So that’s why we’re quick with our responses.

Stephen S. (03:48.621)
Sure, yeah.

You know, it’s funny you say that because I actually the first time I ever used Airbnb and this was you know, granted like nine years ago I was So broke I was in Denver, Colorado Needed to find a place to stay ended up finding a short, know Just a room stay with someone else and I was able to book it But the host never got back to me. No details were ever sent to me

Nothing, so I already paid Airbnb was impossible to get a hold of to get reimbursed for it I ended up sleeping in my car in Denver, Colorado in the middle of October 45 degrees out all night and So like that response on I think things have greatly improved now with like the platform

Jessica (04:30.912)
no.

Jessica (04:35.228)
Yes.

Stephen S. (04:37.447)
But that security, anytime I go to book a short-term rental now, that always plays in my head. I didn’t use it for another five years after because it was such a horrible experience. having that level of service and being able to offer that, I can’t imagine how valuable that has been to your investors as well. now you not only, you not only,

Jessica (04:46.609)
I bet.

Stephen S. (05:01.321)
manage your own properties, but you also manage for other people as well. Do you see with your long-term vision with what you’re doing, having a large portfolio of other investors, buying more of your own properties, or what does that look like when you think about it?

Jessica (05:16.711)
So I ended up getting into a little niche. In the Myrtle Beach area, there’s lot of condo, condotels that people think are hotels and resorts, but there’s really, they didn’t want to run the risk of owning these empty units. So what they did was they subletted or sold their hotel units to personal people. So we try to…

get back as soon as we can and we try to like get those investors to get their money and to get the rentals as quickly as they can. So they fill out rental agreements with us because people are known in vacation rentals to trash the units. So when we have a security deposit and we have a rental agreement and we have a driver’s license, it provides safety for the investor. They feel more comfortable renting out their unit.

I would like to grow this to the point where when I can no longer do my W2, this is my full-time side thing that becomes my full-time.

Stephen S. (06:19.617)
Right. Now, have you had the same to move towards that, you know, in the future of being just full time real estate investor, property management for short term rentals? When when when you were going through all those challenges, when you got started right before Covid, when that hit.

Were you still working the same job that you were back then? Like what was that? I know you got the huge tax return, but what was it in your brain back then that sparked like I’m a busy mom, special needs child, which I relate to because I have a special needs son myself. What was it that prompted you to do that? Was it reading Rich Dad Poor Dad again? Or what was like, I’ve got to do this and make this my thing long term so I can be free. What does what does that look like?

Jessica (07:08.398)
I didn’t expect it to grow the way it did. After reading Rich Dead Poor Dead, I realized that I needed to own some type of real estate. And after losing our home, having a piece of real estate gave me a sense of security that if anything ever happens again, I have this house. And it was nice to have other people be able to help me pay for it and to be able to learn the tax deductions. So then when I started learning that, it just sparked something in my brain.

And then I was realizing the people, I’m a physical therapy assistant full time. I’ve worked at the same two part-time jobs for 20 years. Because of the kids, I wanted to be able to take them to doctors and stuff like that. So then I realized the Apple watch, I get the notifications right away. I talked to both of my bosses about the situation that I’ve worked for them for 20 years. And when they decide to retire, I’m going to walk away with nothing. So I had to do something to protect myself and my future.

Stephen S. (07:50.531)
You bet.

Jessica (08:08.047)
And I didn’t know how to pay myself properly because these are all things that people don’t even think about learning when they start a business. It starts as a hobby and then you’re like, crap, this is actually a business. So I had to backtrack and I realized the first three years I just collected all the money. didn’t pay myself at all. And then I started realizing I have enough money in the bank to possibly buy a second property. And I love the Myrtle area, but weather is a very big.

issue and people don’t want to be at the beach when it’s 20, 30 degrees. So then I wanted to buy something in a different market. And we looked at Branson, Missouri, once again, a thousand condos. And I was like, I don’t want to be run by an HOA anymore. So I met up with an investor that told me that I could build a unique structure for less than I could buy a condo for. So we ended up building an A-frame.

on Table Rock Lake and we’re dog friendly and it’s been going fabulous.

Stephen S. (09:09.495)
Wow. Now, what type of systems and processes have you had to put in place over the last five years? Because for where you live, if I remember correctly, when we got started today, you’re in New York and you’re talking about Myrtle Beach, South Carolina and Branson, Missouri. So what type of systems do you have to put in place to actually be able to manage those properties well and effectively and know people are showing up to clean them and all that kind of stuff?

in order to have a seamless integration to where you’re not waking up with an oh shoot moment, you know, in a phone call at 1130 at night for somebody in Branson, Missouri. What does that look like for your processes and systems? Sounds like you’re an expert at that.

Jessica (09:51.329)
There’s a very big learning curve with technology that I don’t think people account for or have the time to necessarily learn. So we use one app called Owner Reservations that merges our Airbnb and our VRBO bookings and our direct bookings. So this way we know when the property is occupied. We use a tool called Price Labs to help us with our pricing and we can set parameters based on

actual competition so we can see what the competition’s doing and where our pricing is and where their pricing is. And we use an app called Cherno in order to see the cleaning so the cleaners can see the calendar so they see same day check-in same day checkouts. And in order to get paid, they get paid the same day that they clean so they prioritize our units because they don’t have to bill it, they just get paid as soon as they’re done, but they have to submit pictures.

That protects us on multiple ways. One, if a guest says something’s missing or wrong or not clean, I have photo proof of what time and when the cleaner was there and exactly what the unit looked like. And then on the other hand, it lets me see that the cleaner did everything the way that we wanted it to do. So even though I’ve had great cleaners, I’ve had to train them on the processes of how to take those pictures. I need the refrigerators open. I need the…

microwaves in the oven open so I could see that it’s actually clean, not just like the front of a refrigerator. So there is a process to training them on how to take the photos properly.

Stephen S. (11:28.267)
Now, how did you learn to put those things in place over time? I typically find we learn things when we make mistakes. And I’m sure you have plenty of stories that you’ve experienced in your five years here of doing this. So what was it that led you to having a lock solid process like you do today?

Jessica (11:51.09)
I joined a few masterminds. I was the brokeest person in the room. I didn’t even feel like I belonged in those circles, but I got to learn from those people. I paid for a few courses. I showed up in person and I just got to learn everything that way. I invested a lot of money into my education with this because I didn’t feel like I had room to fail. As I said, I was not losing another house. And then it became even more important when I was dealing with other people’s money.

Being so broke and financially strapped at some point, I think I relate to my clients more than they may think that I do because I don’t make money unless they make money. So I want the best for them because that’s what I would have hoped would have been done for me. But when I first started, I hired some of the cheaper, bigger name brand companies and I ended up having to refund three cleanings, my first three cleanings.

because they weren’t done properly and that’s when I decided this wasn’t gonna work and that I had to be the one to match.

Stephen S. (12:56.043)
And so using the tech that you use now in those apps you mentioned, that’s how you’re able to have a solid SOP, standard operating procedure for how that goes so it’s all smooth.

Jessica (13:07.527)
Correct, but it is also a relationship with my cleaner. I have to recognize that they’re more important than me because if the unit isn’t clean, it doesn’t matter how friendly I am. So we need to have good communication and we need to get along. It’s a relationship between me and my cleaning team.

Stephen S. (13:26.509)
How have you, over the years, how have you vetted your cleaners to know that you’re working with somebody that’s quality, shows up on time, gets the job done, other than obviously some of the checks you’ve put in place with the pictures, training them on how to do that properly. How have you built those relationships to find the right people or vet the right people for somebody that’s maybe just new into this, maybe wanting to do it for themself and not knowing where to start?

Jessica (13:53.871)
I do have FaceTime phone calls with them. I want to see their engagement. I want to see how much they’re invested into the property. And I do choose cleaners that tend to own their own company because then they realize that if they screw up, it’s coming out of their pocket. We have a 24 hour turnaround guarantee where if something was not done that it was supposed to be done, you’re going back within 24 hours.

Stephen S. (14:01.495)
Mm-hmm.

Jessica (14:20.666)
I’m not paying you a bonus for doing what should have been done in the first place. So I really hold them to high standards, letting them know that this is coming out of their personal pocket. So when you use these bigger companies, you could have anybody come into your home and you’re not gonna recognize if all of a sudden my Keurig’s missing or something’s missing because you’re not familiar. So I like having the same people in the home and I understand that everybody needs support staff.

but I like them going and training their support staff. And it’s worked pretty well for me right now. I stay invested in my cleaners. They get bonus for a lot of the things that they do, but I don’t bonus them on each clean, because it shouldn’t be expected. A bonus is a bonus. So when we’re busy and we get a few five-star reviews and I’m getting some extra money in, then I send them a bonus. They get birthday presents, they get Christmas presents.

I want them to know that I’m invested in them personally. And I ask, what can I do to make your job easier? Is there anything that you need from me to do your job better? Because if they’re happy, then they’re going to take pride in that unit. And then we’re going to get better cleaning scores.

Stephen S. (15:33.537)
love that. That’s that’s incredible to hear too, because I think a lot with you know, even like the fix and flip market, you know, your subcontractors and your GCs are so important and crucial to your success as a business owner. And they also own a business. And so when things run seamlessly, and you take care of those service providers, they tend to do a better job tend to not cut corners, things along those lines. And ultimately, you know, all of it

Relays back to sales right and having people in the house and when you can create that with your team Your your end customer has a much better experience and you make more money and everybody makes it You know, there’s money at the table and so ultimately having having a solid team taking care of them I love to hear that because it’s applicable and not just with your cleaner, right?

Jessica (16:05.859)
Mm-hmm.

Jessica (16:15.96)
Absolutely.

Jessica (16:29.644)
Absolutely, every area of your life. The more you feel like your boss, I guess, invests in you, the more you’re willing to give back. Recognize that your people, if their spouse comes and helps and does me some handyman services, I’m very happy to pay them. I’d like to keep the money in their house and their family the same way I like to keep the money into my house.

Stephen S. (16:58.147)
Now one of the things you touched on here a few minutes ago as well is about the learning curve and you Wanting to not learn from just your mistakes, but also possibly the mistakes of other people So you were involved in masterminds paid for courses coaching etc. How important how crucial do you think that’s been? To your success and getting you to where you’re at now compared to if you just went out and did it all solo dello

Jessica (17:25.783)
Well, I started just doing it my own and my pricing was so uneducatedly bad. Then when my business coach is like, what are you doing? Why are you not using these tools? I’m like, I didn’t know to do so. So that became so important. In the physical therapy world, we don’t really have coaches in the same way that we do in the business world. And it’s been impeccable to…

Stephen S. (17:33.482)
wow.

Jessica (17:53.226)
have those relationships, not only with coaches, but just the other people that are in the same situation. If I call a friend and I complain about something in my house, it sounds like I’m bragging. It’s actually, it’s affected a lot of friendships because I’ve kind of elevated myself financially opposed to some other friends. And it’s not even that I have a lot of money because in the first few years you lose money in almost every business.

But when I’m talking about my vacation rental, it sounds braggy, even though I don’t own my primary home. So it’s nice to have those friendships from people that actually understand what you’re going through and they could give you a different perspective on your situation and just reframe the situation for you when you’re having a crisis. They might’ve been through something and could give you some tips. And that’s been a huge part of my success, being able to call certain people.

I’ve gotten my cleaners from people in my mastermind groups. I’ve gotten handymen from people in my mastermind groups. So it’s been very important to get those connections.

Stephen S. (18:59.2)
Absolutely.

Jessica (18:59.476)
It started with just a few classes and then it’s bigger conferences and then you start seeing the same people all the time and then you’re on a Facebook group and then all of a sudden you realize these people are my friends now.

Stephen S. (19:11.969)
Yeah, I love that. And you know, you when you filled out notes to be on the show, you mentioned your your greatest weaknesses, I guess, are just some of the biggest challenges that you faced is just basically growing a business by yourself, learning on the go.

trying to accept that you need to release control. What does that look like for you now today as you’re moving forward into this next season, Q2, all that?

Jessica (19:44.605)
Every time I think I have a process down, I realize that there’s a flaw with it. So we’re still kind of working on that. One of my weaknesses is definitely marketing, but there was a weakness along every path. There was a weakness with pricing. Now I’ve learned how to do that right. There was a weakness on having the systems and procedures in place, and then I’ve mastered that. So I feel like the longer I grow,

Each year I could kind of focus on trying to master one area. I am starting to try to relinquish a little bit of power, which is a little hard for me. But we’re doing it. I’m getting my husband to help me a little bit more on some of the things that I find overwhelming. I’m learning just different apps for billing. So this way it’s more.

transparent for my clients. I’ve had to learn documents and JOT forms and docu-signs to make our rental agreements easier and look more professional. Canva has been a huge help on getting a lot of my marketing stuff to look more professional without having the finances yet to be able to afford a graphic designer and I’ve created my own website so.

You just have to micro focus on one area until you perfect it and then move on to the next.

Stephen S. (21:11.843)
You Figuring out what fire to put out today. That’s going to push the needle 1 % forward. You bet.

Jessica (21:17.521)
Alright.

And I feel like a failure every day. As far as I’ve come, I’m very hard on myself with accountability and I make sure every day that I just do 1 % towards this business and then I’ll be better than I was yesterday.

Stephen S. (21:26.275)
Hmm.

Stephen S. (21:35.683)
So if you were to go back to the beginning of when you just got started and push yourself back in that state for just a moment

and knowing what you know now five years later, which, you know, most businesses, fail in the first five years, right? And you’re already over that hump. So now it’s a matter of getting it where you want it to be so you can do it full time, not have to worry about anybody else’s stuff with stretching people out or anything along that lines with physical therapy. So, you know, if you put yourself back in that state for just a moment and you know what you know now, what would you do differently?

and what would you do the same?

Jessica (22:24.164)
I don’t know how much I would have done differently because I think I needed to go through each one of those challenges to be better. I think if I would have passed it along, I wouldn’t have made the income in the beginning that would have got me through some of the slow seasons. I think people make really good money during busy season and they expect it to last all year. And because of my financial hardships in the past, I knew that I had to make that money stretch.

So I had to learn everything my own and I’m kind of glad that I did because now when I hire somebody, I’ll be able to train them and I’m kind of in control of what goes on. I was always scared of somebody taking advantage of me for my financial weakness or my lack of knowledge. So I feel like I did need to learn each one of those phases for myself to be able to teach it to somebody else the way that I want it done and to make sure that I wasn’t being taken advantage of.

Stephen S. (23:22.595)
Hmm.

Jessica (23:22.687)
I really work hard on transparency with my clients. I give them access visually to their full calendar. A lot of property managers, they bill people once a month. And then the money comes in only one time a month. My clients get paid on the same day that their guest stays. They can see my conversations with the guests. A lot of people don’t do that. So it’s actually made my job a little harder because by being full transparency,

the owners of the properties that I manage, they have a ton of questions. Where if I was just the property manager and you just got a bill and you didn’t know what happened, that would be a lot easier for me. But I feel like I need to be transparent and there needs to be trust and they need to see how quick I’m responding. They need to see the way I’m responding. And I feel like that’s what made the relationship with my owners so good because they feel like they have…

some control, they know what’s going on, but they do tend to ask a lot more questions because now they see things that they hadn’t seen with their other fails property managers. But I also feel that gets me a lot of business because they want that visual because they also are nervous about getting taken advantage of. They’ve heard horror stories as well of a property managers booking their units and not paying them. So with me, there’s no question about money. They see everything.

Stephen S. (24:50.039)
you bet. And so if you were to have somebody new, just completely new, but kind of had an idea that they wanted to do something similar to what you’re doing, where would you have them start?

Jessica (25:06.598)
It’s hard because what we consider property management is also called co-hosting in the Airbnb world. It’s an Airbnb term for co-managing. I think maybe if they had their own property and they kind of watched me, I’ve had a few clients that called me and they’re like, can you manage for a year and ultimately train me? And that’s fully fine with me because I feel like you can’t learn everything all at once.

So I think mirroring somebody and kind of asking those questions along the way, why do you respond this way? Why did you do this? How did you do this? I think that would be a good hands-on learning situation. I could read a book a thousand times and not process it. So I think it’s about your own learning style, somebody that has to do it in order to learn. So I’ve had clients where I’ve said, okay, on this date, now you’re going.

to take over and I’m gonna shadow you for three months. So this way, if you have any like emergency questions, I’ll essentially be your coach, but you’re gonna do the pricing and you’re gonna do all this stuff. And then they gain the confidence to start managing their own unit, but feel like they have me as a safety net for those few months in case there’s something that they weren’t prepared to handle.

Stephen S. (26:24.291)
You bet, love that. Well, I know we’re coming up a little bit on our time here. Where can people find you to connect if they’re possibly looking for what you offer? Where can people find you and connect with you more, Jessica?

Jessica (26:41.961)
So the properties that we manage, that website is happyplacevhr for happyplacevacationhomerenzels.com. I learned I had to abbreviate that. So that’s where the properties are listed and where people could book with us directly. And the name of the management company is the Coastal Co-host, because I manage pretty much all along the East Coast. So that’s how they could contact me.

Stephen S. (27:07.701)
Okay, awesome. Well, Jessica, thank you so much, everyone. I hope you enjoyed today’s show. I’m your host, Stephen Schmidt, and we will see you on the next episode of the Real Estate Pros podcast. Talk soon.