Welcome back to another episode of Into The Airbnb, where we chat with Airbnb hosts about their short-term rental experience.
Our guest for today is Jaylen Cromwell, an Airbnb host from Boston who is about to launch his remotely managed listing in Houston, Texas. Jaylen already got started on Airbnb in the past, but failed on the attempt, in this interview, he gives out valuable advice for other Airbnb hosts to not make the same mistakes as him. He’ll also share with us the best insights and tips to have a successful and fresh start in the business.
This episode is sponsored by Airbtics, short-term rental analytics for high return investments, comprehensive data for insights, ideas, and inspiration. Go to app.airbtics.com to find precise Airbnb data such as occupancy rate, revenue, average daily rate, and so on. So, without further ado, let’s get into it!
Into The Airbnb Podcast S2 EP 52: Started off bad on Airbnb but came back from round 2 – Projecting $7k for their first quarter live, remote hosting in Houston, TX
Delia:
So can you tell me how did you get started on Airbnb or short-term rentals?
Jaylen Cromwell:
Yeah, so I started my junior year of college, it was kind of, my college experience kind of got like messed up due to the pandemic. So it kind of got split in half and I was kind of just looking for ways to make money at the time, I was taking a stock course, I was learning more about the stock market, how to invest and how to day trade. And then one of my close friends from my marketing class actually messaged me and was like, “hey, like, check this course out” and so it’s an BNB simplified course with Justin Richardson. And I’m the type of person who likes to get things started right away. So she sent that to me, I think the first of February we got started forming and see and all that. Relatively, like quickly, probably like the night after maybe the day after that, but it was like I jumped right in, I took all the notes. I did the course in like a night, I did an all nighter, took all my notes, reviewed my notes in the morning, and just jumped straight into action.
Delia:
And how was the experience getting started like that?
Jaylen Cromwell:
I was taking a stock course and I kind of did, I had the same approach with the stock course where it was like, you know, I didn’t waste time paper trading with like fake money, I jumped in with real money. So as far as like the experience, it was an interesting experience, because it was a new form of investing for me. But I just knew I was hungry and I knew I could find a way.
Delia:
And can you tell me a little bit you started like right in, how was your investing process? Did you decide to buy a property? You’ve started subleasing? How did you start it?
Jaylen Cromwell:
So we went the rental arbitrage route and we found a complex that accepted corporate leases at the time, we had just started our business. So we didn’t have as far as like a sheet of business statements or bank statements. So I actually signed the lease in my name and then my business was also a part of that and they knew like it’s a new business. So they allowed me to not only use my name, but also like in parentheses around it, also have my business name as well.
Delia:
Okay, can you explain us a little bit more about how did you use your business name to get this rental?
Jaylen Cromwell:
Yeah. So normally, when you’re approaching complexes about running your business through one of their units, usually, if you’re going to apply for the apartment complex via a corporate lease, they would want to as far as financial statements go, they would want you to at least have some type of bank history, but because we were so new, when we started, we didn’t have that. But as far as being able to speak to them and let them know, “hey, you know, we’re just getting started in the business and we’re just trying to find a place to, you know, set up shop. Is it okay if I sign the lease personally, and then also include my business name as well?”. But it’s really just a simple conversation. I don’t think it takes any sort of swindling or anything like that, but really just having an honest conversation with these people.
Delia:
So they agree right away with that?
Jaylen Cromwell:
Yep.
Delia:
That’s great. And how was your experience with rental arbitrage then? How long did you keep this listing?
Jaylen Cromwell:
So I kept that listing for six months and it was very interesting. It was definitely a good test property to get my feet wet in the in the business and experience what it was actually like, versus just seeing somebody else talk about what they’ve done. But to go out and actualize, well, this class is taught as a concept, but to go out and actualize it, it was exciting, you know, in college, I have a property that I don’t even stay at, but that brings in money, so it was cool. But I would say, as far as the complex went, there were a lot of things that I didn’t recognize when I stayed there. When I was in the middle of furnishing and stuff like that. I stayed there for almost a week, trying to furnish everything and have everything taken care of and I felt very safe and I felt very comfortable in that complex. But it was like the moment I left, I don’t know if they started moving people around us, but or if they changed workers, but maintenance was always a trouble, our washer and dryer would always break down and we’d always submit requests, and it’d be like the same issue over and over again. Our neighbors were really disruptive and it didn’t provide an environment that felt safe for our guests. We had a lot of people who would show up and be like, “hey, the neighbors are really loud and, you know, there’s smells coming from their apartment and, you know, I just don’t feel safe having my kids here”. So there’s that and then as far as the upkeep of the grounds, you know, I have my cleaner cleaning off the entire level that we’re on because, you know, people aren’t taking out their trash when they’re supposed to and they’re missing that valet trash that comes around every night, which is Sunday through Thursday. So they’re missing those days and when they miss those days, you have an abundance of trash on there. So I’m having to unpin my cleaner extra to take care of their trash, sweep everything up. So it looks like a presentable space before you even walk into the place.
Delia:
And is that the reason why you decided to leave that rental?
Jaylen Cromwell:
Yeah, it definitely is because it came to a point where we were getting bookings, but it started to negatively reflect on our account. So like a lot of people would make complaints via reviews and comments. But a lot of their complaints had to do what was going on around the unit versus what was going on inside the unit. So to anybody who’s. you know, taking these courses, when they say like location is key and distressing location, location, location, like it’s bigger than just “oh, how far are you away from NRG? How far are you from Toyota Center?” No, it’s who’s in this complex? Who are your neighbors? Who’s running this complex? And are they taking heed to your request as a tenant?
Delia:
That’s right. Sometimes you hear some guests complaining with these things that have nothing to do with your rental, but yeah, the location is very important. Sometimes we pick the right location and, you know, the complaints are going to keep coming.
Jaylen Cromwell:
Oh, yeah, like it would happen so often. It kind of got sickening at one point where I would be, I’d be looking at my camera as my guests are getting ready to come in. They’re like, “Hey, we’re here” I’m like, alright, great, send them over their code so they can unlock the door. And I remember sitting in my driveway, because I went to school in Washington, DC. I remember sitting in my driveway one evening, and I was watching the ring camera as my guest came up the stairs. I’m like, “Yes, you know, we’re checked in, we’re ready to go”, I watched this person get to the top of the steps look left, look right, look down and I immediately got a message from Airbnb, before they even got the chance to unlock the door, they said, “We are not staying here because the grounds just look terrible. We don’t feel safe”. So we had a couple of instances where that actually happened.
Delia:
And like when you were staying at that place that one week, did you feel safe, did you recognize any of these troubles that your guests were having?
Jaylen Cromwell:
I did feel safe, but also at the time there weren’t neighbors on either side of us. There was one family that lived all the way at the end. But as far as the units directly to my left, and to my right of my unit, there is nobody there.
Delia:
So you’re going to start again soon. You haven’t started again with Airbnb, right?
Jaylen Cromwell:
Yes.
Delia:
And this time, are you going for buying a property or are you going for rental arbitrage again?
Jaylen Cromwell:
Rental arbitrage again, but this time, we’ve decided to go through a private landlord, mainly because we just have a little bit more control of the area ad we don’t necessarily have to rely on whatever agency is controlling the complex to take care of certain things, where if something needs to be fixed, we can be the one to fix it. If landscaping needs to be done, we can make that request, you know what I mean? Versus a company wide thing where there’s a company running a complex, and they’ve got 100 other tenants to attend to and it may not always feel like you’re always top of the list especially, is a huge difference when you’re trying to run a business versus these are tenants who are traditional tenants and who live here.
Delia:
Okay, I understand and can you tell me what was the process to select the area and also the complex where you’re going to be doing Airbnb?
Jaylen Cromwell:
Yeah, so as far as the process goes, I just started looking at places on Zillow and I adjusted my filters. So between Zillow and apartments.com really adjusted my filter. So I really wanted a two bedroom, anywhere between two bedroom and up and two bathrooms and up and we also put for rent by owners. And that kind of narrowed down the search and made things a little bit easier. And as far as where we want it to be, we want it to be close to Midtown, in the Montrose area, and we were able to find the perfect property that it’s appealing to the eye. It’s one of those properties where if you’re scrolling on Airbnb, the cover photo will catch your eye because it’s lovely, bright colors, it’s a different kind of architecture, when it comes to in comparison to like apartment complexes. Apartment complexes, you know what you’re gonna get, you’re gonna get the SkyRise buildings are like five different floors, pool somewhere in the center area. But this place is a little bit different, you know, we’ve got a nice sized balcony that overlooks the street. On the backside of it, you can see the city line downtown.
Delia:
And what are the other unique like amenities or unique things that you’re going to offer at this new listing?
Jaylen Cromwell:
Right. So as far as like the amenities go, we’re still working on that, we’re actually thinking about putting a fitness center in the garage area. But that kind of allows us like the freedom to do something like that, because it’s a house not necessarily an apartment complex that already has these amenities built into the complex. But we can make spaces for that, where we can even have an outdoor fitness center on our patio, or you know what I mean? And but as far as like special perks and stuff, because we’re a new listing, we’re looking to entice people, so we’re giving our first three guests, three in home massages for one hour. We also have access to a Personal chef, and event coordinator, somebody if you’re coming to have a girls night, you know, guys night, baby shower, graduation, gets together or just for the family. Like we have somebody who can curate that event for you. In addition to that, we have two different types of massage therapists, we have a female and a male massage therapist based on our guests preference. And then also, we also provide a list of places and date night ideas, so we have brunch places, we have lunch places, dinner places and then we also have places within the area for date night ideas. So we make those suggestions to our guests as well. And then later in the future after we booked a couple of guests and we begin to see some more revenue, we’re actually going to put a hot tub on the back patio.
Delia:
Oh, that sounds actually nice. So you decided to go a little bit high end for this property, right?
Jaylen Cromwell:
Absolutely. It’s one of those properties where you look at it, and you just assume it has the work. So for us as business owners, we want to give the consumer exactly what they’re looking for.
Delia:
And what inspired you to pick this type of listing for your future listings?
Jaylen Cromwell:
I think, for me, as far as why we chose this one, it had a lot to do with what’s going to catch the eye of the person when they’re on the platform, what’s going to catch the eye of somebody or the guests. This one, it was really the color and the architecture that set itself apart from other homes, that set itself apart from other homes in the area and then also other listings on the platform.
Delia:
Really unique.
Jaylen Cromwell:
Exactly. It caught my eye and as somebody who uses Airbnb often when I travel, I actually really thought I was like this is a place that I would want to stay at. Just based off of the look. Yes.
Delia:
That’s great to look at, you know, your listing with the guest eyes, that’s a really good thing to do. And can you tell me a little bit about the investment you’re doing right now with this listing?
Jaylen Cromwell:
Our projected investment is anywhere between, it’s about 3,000 to 6,000 because I’m including the security deposit and first month’s rent. But take those things out, our investment total investment so far, is about 2,500 a little bit upwards of 2,500 mainly because we have a lot of the staple, like furnishing pieces like the couch and the beds and the dressers, we had all of that stuff in storage from our previous unit, so that took out a bulk of those costs. And as far as projections go, in the first quarter, we’re looking to make upwards of 7,000 for the quarter, based on how we priced. So we’re looking to at least at the very least break even in the first quarter.
Delia:
That’s great. And you talked about how you’re going to price right now, I would like to know if you have any particular pricing strategy that you’re thinking of?
Jaylen Cromwell:
So for us, our pricing strategy is very simple. At a base, we know that it takes $160 on a 20 day calendar month, if we use 20 days as a staple, in 20 days, can we make our money back for the month, it takes $160 a night for us to do that. So with that being said, we’ve added 50% markup.
Delia:
And how did you do the market research to choose the market that you’re going to be hosting in?
Jaylen Cromwell:
So as far as market research went, I didn’t use AirDNA or any of those platforms, but I did research for the area itself, like by zip code and I also cross reference that with other listings in that area.
Delia:
So when you were no planning to open an Airbnb again, did you do the research, you usually do in the area like contact other hosts in the area? Ask them how it has been around there or not?
Jaylen Cromwell:
No, I don’t really contact other hosts. I’m a part of the Facebook group BNB simplified. I’m also in the Houston Airbnb Facebook group. So if I ever wanted to, I can contact other hosts in the area, people who actually live in Texas, and maybe from Texas and have rentals in Texas. But for the most part, I think I have a pretty good idea as far as the area that I’ve chosen, and how it could benefit our business in the future, just based on its proximity to all of Houston’s hotspots. It’s literally a 15 minute drive anywhere you want to go and that’s like, that’s at the max, like, that’s as far as you’re gonna get. It’s 15 minutes to get anywhere.
Delia:
Okay, that’s great strategically location there. You told me before that you were located in Boston, are you from there, you’re going to do remote hosting?
Jaylen Cromwell:
Yeah, so I have a co-host down there. She actually started out as a cleaning company that we hired for our previous unit. And we had a lovely couple who was helping us co-hosts. But I think moving into this next unit, we really wanted somebody who made this their priority. So our current co-hosts like she’s a self made entrepreneur, absolutely lovely. She takes care of the cleaning and she also takes care of the co-hosting aspect of it. So she’s really a one stop shop for us and that made the communication a lot easier.
Delia:
I see and you told me that you met her when she was your cleaning person in the other Airbnb, right?
Jaylen Cromwell:
Yep.
Delia:
So what are the things that you realize about her that will make her a good co-host?
Jaylen Cromwell:
I’m the type of business person who wants people like me on their team. So like I said earlier in the interview, I’m the type of person like if I have an idea, I start working on it like that second, and I get obsessed about it and she has that same kind of energy with her. Where if I say “hey, like, let’s rock out with a theme for one of these bedrooms” and if we’re gonna go with like a nature themes, she’ll start sending me stuff, we will start doing collaborations on Pinterest boards, just to really get the ideas flowing. She is like my creative muse, we bounce things off of each other, as well as with my partner’s in the business as well. But she’s a great person to have on the ground in Houston. When you feel like somebody is like your spirit person ad they’re like the other half of you as far as when it comes to like business, it provides you with a sense of security, where you can say, “I can trust this person to go out and do it” because that’s what I would do and that’s exactly what she’s going to do.
Delia:
I see. So you’re very lucky to find her then!
Jaylen Cromwell:
Yes, absolutely!
Delia:
What about the other listing? Was it located as well in Houston?
Jaylen Cromwell:
It was located in Houston, but it was on the Westheimer side.
Delia:
So you were doing remote hosting this whole time?
Jaylen Cromwell:
Yes.
Delia:
And what’s the experience like with remote hosting as far as it went for you?
Jaylen Cromwell:
It’s interesting to say the least, I think before our co-hosts, I think we just had like a little bit of a different vision and both of them also worked full-time jobs, you know, and they had kids. So it was like, there was a part of me where it’s like, I don’t want to interfere with their work, and I don’t want to interfere with their family stuff. So there’s some things that I may have held back on, and some things that they may not have been able to do. But needless to say, like they did an amazing job helping us get started, it was a great experience with them to begin with. But I think, as far as with my new co-host, and the type of energy that we bounce off of each other, it’s been more refreshing.
Delia:
Okay, so with this help you’re getting with your co-host is not challenged at all to do remote hosting.
Jaylen Cromwell:
No, no, no, no, it’s a breeze. She really takes initiative and it’s amazing to have someone who can just do that, where it’s like, at the beginning, it’s like, I don’t need you to tell me anything. If you see something, you don’t have to say anything, just take care of it and send me the receipt and then we’ll do it that way.
Delia:
And that’s exactly what you did?
Jaylen Cromwell:
Exactly.
Delia:
So would you say that the key to remote hosting would be to have great person, in-ground people like, a great co-host, for example, or a great team?
Jaylen Cromwell:
Yeah, I think it’s very important to have a very communicative team. And if you and your team are not in the city that you are trying to host then having someone on the ground in that city that you can trust, and you’ve built a relationship with and you can really, it has potential to grow even further and you have somebody who who wants to scale your business as much as you do. Like, that’s the kind of person you need to have on your team. I was watching a podcast the other day and one of the guys is basically like saying, like, “you don’t always need a team to do everything, like you need jobs to be done. But you don’t need to build a team with that person”. So being very selective about who you build a team with, like, I think I made the right choice. Like I got the first round draft pick like, she’s doing the great thing.
Delia:
Okay, see, that’s great. And one thing I would like to know is, what are the main mistakes you made? And what have you learned from them with the other listing?
Jaylen Cromwell:
I would say the main mistake that I made was probably the same reason why I got started in the business just moving fast. Like, I’m the type of person when I want it done, I want it done at that moment. So I’m gonna go and do everything I can and have it done at that moment. And at times that has caused me to move a lot faster than the rest of my team may be ready for and it’s something that I’ve noticed and partially it’s a regret. But, you know, I don’t necessarily like to live by regrets or learning lessons, you know, next time on the next unit, we’ll take it a little bit slower. For right now we gotta deal with the mess that we made.
Delia:
Yeah, I understand. So right now it’s better to start off a little bit lower. At least you already learned your lesson. And when you were hosting back then, was there any particular thing you find really challenging as a host?
Jaylen Cromwell:
Dealing with negative reviews. Yeah, that was probably the hardest thing where it’s like drawing art and having somebody tell you, it’s bad. With the situation with our last unit, there was a lot of stuff that we couldn’t control. So it hurt that much more where it’s like, you don’t even know how much time, effort money, blood, sweat, tears went into this unit, and you didn’t even open the door. But I get it though, because as a guest, I probably would have done the same thing. So being able to take a step back and really sit and look at it from the guest perspective, like, it’ll definitely have you humble yourself.
Delia:
Yeah, that’s right. It’s very important that you actually listen to those complaints and saw that it was not a safe place for your guests because maybe some other hosts or other landlords would have say that “They just complain too much” and just keep doing Airbnb there, right?
Jaylen Cromwell:
Exactly.
Delia:
So any particular tips that you’d like to give out for any person who is thinking of getting started on Airbnb?
Jaylen Cromwell:
Yeah. First tip, stack your bread. I would just say because I’m the type of person like I said, because I’m the type of person who jumps in like headfirst like, I didn’t necessarily have all the money that I should have to start. I was just kind of going based off of the money that I was making that summer from my internships. I worked three jobs last summer when we were doing it or not last summer, sorry, the summer before that, when we were doing it, I was working three jobs, I had two remote internships and I had a part-time job on the weekends, like, I’m taking three texts, dropping it straight into my bank account for the business like, and I’m just doing that by weekly. So I would say like, take a couple months, really forming an LLC, take that time in the beginning to like, build your business credit, like you don’t always have to just jump right into it. And I wish that was something that I had told myself when I first started like, “hey, like, I know, you’re excited about this, but like, take a beat. Let’s work through like the smaller steps first” where maybe in the future, if I had worked more on building my business credit, I could have a business credit card where I don’t have to come out of my pocket to furnish the place where I could put it on credit, you know what I mean?
Delia:
Yes, I understand completely.
Jaylen Cromwell:
So like taking smaller steps like that stacking your money, having money like in the reserve. Like so for when I went back to school, after we had got the unit up and running, when I went back to school, I wasn’t working. So the the cash flow kind of stopped and that was because in my head, I had it made up that, “oh, this place is going to make a ton of money”. So I don’t like, it’s gonna pay for itself and when you’re getting these bad reviews, and you have guests canceling, you got to do refunds, it’s not making the money that you thought it would. And now you’re not working. So they’ll still gotta get paid.
Delia:
I understand. One last question that I have for you now that you mentioned something particular, when you were looking at the Airbnb business, did like someone sold it to you like it was going to be some easy money and that’s why you thought that you had to do it fast? Or was it just like yourself?
Jaylen Cromwell:
It was really FOMO, to be honest. Like, I realized it was the same problem that I had when I was trading, you know, it’s just FOMO, that fear of just missing the wave. And I’m sitting there, I took this course and you know, over the pandemic and watching the news and the Airbnb comes out. And they’re like, “when we come out of this pandemic, we’re gonna need a boatload of hosts” and I’m like, “What sense would it make for me to have this information and not be a part of this movement?”. So it was a little bit of FOMO. And truthfully, it was really weird, even with bad reviews, like the place still got booked and that’s exactly the reason why I came back for round two, because it’s like, the business makes money, but it’s that location, location, location thing that they stressed from the beginning.
Delia:
Yes, that’s right.
Jaylen Cromwell:
I was just excited to get a yes and get a pair of keys, you know, but taking it a step further the second time around where it’s like, no, I want a little bit more control over the space that we’re in. I don’t want to have to leave it in someone else’s hands. And I’m getting bad reviews because of things that I can’t control.
Delia:
Yes, I understand completely and it’s really great that you will learn from your mistakes and you decided to start again and this time, with the right food. So that was it for today. Thank you a lot for being my guest today. Thank you a lot for your time and for your tips. It has been amazing to hear about your experience!
Jaylen Cromwell:
Thank you. I appreciate you having me on your show!
Do you want to maximize your profit?
As a professional in the short-term rental industry, you’d definitely know that there are intense competitors who are probably obsessed with maximizing profit & exert efforts to promote Airbnb listings. What are their unique tools, you ask? We say:
A super-accurate & reliable data analytics tool.
Looking to earn more money within Texas county? Read more about Airbnb Rental Arbitrage in Texas and start receiving loads of cash without owning a single property!
Designed to showcase accurate short-term rental analytics data, not only does our app help you optimize your listing, but it can also provide VERY useful data for simulating cash returns using the Airbnb Calculator. try looking at real-time data from Airbtics & stand out among your competitors!
