
Ever wondered how to break free from OTAs and take control of your bookings? Sarah Pell did just that. She went from teaching elementary school to managing a thriving short-term rental portfolio using a mix of ownership, arbitrage, and co-hosting. In this episode of Direct Bookings Simplified, Sarah reveals the exact strategies she used to scale her business, build a strong direct booking system, and maximize profitability—without overcomplicated tech.
Summary and Highlights
Building a Portfolio with Three STR Strategies
“Arbitrage really opened up my world. Just within a year and a half, I had acquired four. Compared to saving for a single purchase, it was a game-changer.”
Sarah’s path to STR success wasn’t conventional. After getting into real estate through house hacking, she realized that long-term rentals weren’t providing the cash flow she wanted. Instead, she turned to vacation rentals. She initially purchased a condo in Orange Beach but quickly recognized that saving for down payments would take too long. That’s when she discovered rental arbitrage, allowing her to scale faster.
Within a year and a half, Sarah went from one STR to four through arbitrage, while also co-hosting for other owners. Balancing ownership, arbitrage, and co-hosting has given her a well-rounded perspective on managing STRs and optimizing guest experiences.
Direct Booking Strategies That Work
Sarah emphasizes that while starting on platforms like Airbnb and Vrbo is essential, building direct bookings is what truly allows STR owners to scale. Here are some of the strategies that have worked for her:
1. Leveraging Facebook Groups for Direct Bookings
One of Sarah’s biggest game-changers was tapping into Facebook groups to promote her listings. Instead of relying solely on Airbnb, she joined vacation rental and travel-related groups in her market.
“I found that Facebook groups were like a secret sauce. I would join groups for vacation stays in my area and respond to travelers looking for dates with a direct booking link. That was a huge boost early on.”
2. Using Repeat Guests to Drive More Direct Bookings
Sarah actively encourages repeat guests to book directly. She offers a 15% discount to returning guests who book through her direct website and includes promotional business cards and magnets inside her properties.
“We text every guest after their stay with a promo code they can share with friends and family. It’s a simple way to encourage direct bookings.”
3. Capturing Guest Emails for Long-Term Success
Sarah initially collected guest emails manually but later streamlined the process using her property management software. Her team now sends email campaigns and promotional offers to past guests through MailChimp.
“Even before I had MailChimp, I was manually emailing past guests with BCC. You don’t need a fancy system to start—just start collecting emails.”
4. Setting Up a Strong Direct Booking Website
While Sarah started with a simple site, she’s now investing in making it more streamlined and guest-friendly. She plans to integrate better search functionality and branding to make it easier for guests to find and book her properties.
Automation vs. Personalization in Direct Bookings
One key takeaway from Sarah’s journey is that automation is helpful, but personal connection matters. While she uses automated text and email follow-ups, she still handles guest communications manually to ensure a personal touch.
“I still handle my guest messaging personally because I want to interact with them. It helps me understand their concerns and improve my guest experience.”
Scaling Direct Bookings with the Right Tools
Sarah’s experience shows that you don’t need a complex system to succeed with direct bookings—you just need the right mindset and simple, effective strategies. Whether you’re just getting started or looking to scale, her approach proves that taking small steps, like leveraging Facebook groups and collecting emails, can make a big impact.
If you want to hear Sarah’s full journey and her step-by-step direct booking tactics, listen to the full episode of Direct Bookings Simplified [link to podcast episode].
Join the Community Want to connect with like-minded STR owners focused on direct bookings? Join our community, where we discuss strategies, share insights, and support each other in building sustainable short-term rental businesses. [Link to community]
Looking to optimize your direct booking site? At CraftedStays, we help STR owners create high-converting, mobile-optimized direct booking websites. If you’re ready to take control of your bookings and maximize revenue, check out CraftedStays today.
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Transcription
Sarah: Part of my direct booking as well is Facebook groups. So I do have a business Facebook page and you wouldn’t even need to do a page. I’ve done it even just personally. And I will have a little message with my direct booking link. And so what I do is join these groups. So like, um, you know, vacation stays of orange beach, and I will go in there and I will look for people that are searching for dates to come and I will just copy and paste my little message about my condo and.
I have found that was like a, in the beginning to a huge boost in like my direct bookings is I found that a lot of people would find me on Facebook and then reach out on my direct booking website. And so I would say that, uh, I feel like Facebook groups are kind of like a secret sauce. I mean, cause you can find co hosts, you know, arbitrage, properties, direct booking clients.
Like it kind of, it’s all, all there.
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 Sarah Pell. Sarah, welcome to the show.
Sarah: Thank you, Gail, for having me. I’m excited to be here.
Gil: Yeah. As we get into it, do you mind giving folks a quick introduction on who you are? Folks may have seen you on Instagram or other places, but yeah. Introduce yourself.
Sarah: Yeah, of course. So, I’m originally from Pierce, South Dakota. That’s where I was born and raised. And then I went to college to be an elementary education teacher in Sioux Falls, South Dakota. And I graduated in 2015. And I began teaching there in elementary ed. Um, doing English as a second language, so K 5.
And that is where I met my husband, and he is a journeyman electrician, and he was, I guess, an apprentice at the time. And he was house hacking when I first met him. Um, but surprisingly enough, I wasn’t that interested in real estate or cared, because I was kind of doing my teaching thing. Um, and then We got together and he was doing a FixNFLIP as well, and then we got married, and that’s kind of then when I started to become interested in it.
And we actually decided to go on the road and travel with him, um, through his work with Journeyman Electrician. So, for the past six years, actually, we Have been traveling. So I quit teaching in 2019 and we thought, you know, it’d just be a couple years and we come back to Sioux Falls, um, where we were living, but we did not.
And so we had a duplex there long term and was renting that with a property management company. And then, yeah, we hit the road and I just worked odd jobs and then, um, in 2022 is when I bought my first short term vacation rental, which was kind of due to the property management company of our long term and how they were handling that.
But that’s just kind of me in a nutshell.
Gil: Yeah. So, so you first did a lot of LT, it sounds like LTRs, house hacking, the combination of you, uh, you and your partner. It gives me a lot of, like, early vibes of, like, BiggerPockets and listening to a lot of that.
Sarah: Yeah, no, exactly. Yeah, it was more him, like I said, I was just kind of like there, like, I was living with, like, house hacking, and like, whatever, like, I was in college, had roommates, no big deal, um, and yeah, I even look back to, and like, will ask him sometimes, like, about his numbers, like, of the deals, cause, like I said, I did not care at all, and was like so oblivious.
But yeah,
Gil: Is he now in the STR side, or is he
Sarah: um, so he definitely likes it. We go down and vacation in Orange Beach where our STRs are But not so much like in it. Um He just does a very small portion of short term rentals. He’s definitely more hands on and so like computers and like You know, that sort of thing doesn’t really interest him. He likes furnishing them, um, and like kind of doing that work.
But we recently, um, just this past summer took a course on fix and flipping. And so we’ve have a fixed input property. And so he’s definitely way more involved in like that aspect. And I’m still kind of just in my lane per se with the vacation rentals.
Gil: Yeah. And you didn’t, I don’t think you mentioned this, but you’re also pretty big on arbitrage as well, too. Talk to me a little bit about that.
Sarah: Yeah, yeah, I really like that strategy. Um, which I found it a podcast with Jorge Contreras He has the real system And teaches co hosting arbitrage and owning but yeah after we bought our first vacation rental I really fell in love with like hosting and hospitality world But it took us 25 percent to save up for that condo.
So it was like Okay, this is gonna take forever to get the next one and then I found the podcast and yeah The arbitrage really opened up my world. Um, just within a year and a half I had acquired four so I was like, whoa, you know really like Room forward compared to saving up for that one. Um, I do have two with a partner actually So I found my partner.
I was gonna or I did co host for him And then he brought me this arbitrage opportunity. That was two units in Wilmington, North Carolina And so I was like, yeah, that’d be awesome And then I have two units by myself per se, but yeah, arbitrage is a great strategy with low, um, entry, like low capital and you still get to run it.
Like, you know, it’s yours and you’re obviously an Airbnb host, um, and get to host people on vacation.
Gil: I don’t think I’ve met many folks that have done a mixture of the three. Uh, I, I meet a lot of folks that do, like, They’re the owners and then they get into co hosting, um, or folks may even dabble in arbitrage, but not so many folks that have a good proportion of all three, all three methods there.
Sarah: that actually, now that you say that, that is probably true, because you do see like someone like really take off with arbitrage and scale up, which that’s kind of, yeah, I’ve thought about that, and I actually this next year would like to get probably three more arbitrage units, um, not that I’m opposed to buying, but it just kind of, I like kind of the fixed expenses more so, like, our insurance with our own has been crazy with like hurricanes and stuff that like, When you kind of look at our numbers, like, they’re not bad, but then you look at arbitrage, and it’s like They’re a little bit sweeter and I’m kind of like, you know, you have that flexibility per se to if it’s not working out Just to not sign the lease and kind of walk away
Gil: That’s true. That’s true. As you’re thinking about, you mentioned a little bit about picking up more arbitrage units as, as you’re looking to scale, how does that change or your, your acquisition strategy? Are you looking now to do more arbitrage and continue to do that? Do you want to do that for a little while until you start owning?
Like what’s, what’s, what’s your strategy there?
Sarah: Yeah, that’s a good question. I would like to do it a little bit too Yeah, I guess just a little bit more cash flow to purchase again Um, we just purchased the condo in march actually of last year. So 2024 um But yeah, I would like to get a little bit more cash flow built up to purchase again Um, because obviously owning assets is where your wealth is built But we are currently also just wanting cash flow right now So for us our kind of strategy is cash flow over like appreciation or maybe even tax benefits And I just feel like arbitrage gives me that cash flow that I’m looking for over Like I said, we’re beach people, so we’ve gone to a beach market.
I know if maybe we tried like a mountain market, then we wouldn’t have the HOA and like the high like insurance assessments. Um, and so that could maybe balance it out better.
Gil: Yeah, that’s, that’s interesting. And I see that a lot, especially in the bigger pockets group where in the very beginning, you’re really focused on cashflow because cashflow is, it builds up your wealth to start to be able to acquire larger properties. Um, even at least in the long term rental side of it, it allows you to do multifamily as well too.
Um, but it sounds like you’re, you’re really now focused on possibly in the next year, really beefing up your arbitrage units, getting more cashflow, maybe doing more STR acquisitions.
Sarah: Yeah, that’s what I really like. Um, I don’t mind like the fix and flip in the long term rentals. Uh, but there’s just something about hospitality and hosting the people and the guests and like hearing why they’re visiting and just making their stay and like memories part of like where they picked to stay was my house.
And so I really just like that a lot. And yeah, I definitely naturally just gravitate towards that and like with the acquisition side.
Gil: Yeah, it’s funny because I think I’ve been a lot of hosts now and It’s not necessarily an even split, but you definitely have a lot of folks that either really love the hospitality side of things, or they get into it, they don’t like the hospitality side, and they focus more on like the operation side, and they’ll find other folks to either partner up with or hire in their team there.
But it’s definitely a big part of like, if you want to be in the short term rental side of it, you’re you definitely need to have a strong passion for hospitality and the guest experience there because it, it percolates everywhere. And we will talk about direct bookings in a little bit, but like if you don’t have a strong passion to deliver really good guest experiences, it starts to hurt your ability to go independent and drive more direct bookings as well too.
Sarah: that is such a great point. I mean, your repeat guests are huge, um, and essential to your business, especially, yeah, credibility is everything. Like your reviews are everything. That’s why, at least in my experience, you know, you always start out a bit slower because you have no reviews, no credibility, um, until you start building that.
And then it really, it seems that, you know, skyrocket up, especially with the repeat guests that loved your stay.
Gil: Yeah. Talk to me a little bit about that first story where you said that you got a long term rental and you ended up switching that to a short term rental or that at least the property management company, uh, helped you decide to switch that into a short term rental. What was the story behind all that?
Sarah: So I didn’t actually switch it to a short term rental, but I started looking at other ways to make, um, just the investment make sense and cash flow, uh, unfortunately, so we grew our portfolio in Sioux Falls of long term rentals and a property manager. The big companies aren’t just going to take care of your property like you would, um, especially, you know, when maybe they have 1, 200 units.
And so we were sadly losing money and not really getting the cash flow that we wanted from those properties. And so BiggerPockets, I started listening to podcasts and Avery and Luke Carl, I heard their podcast, The Short Term Shop, and they just talked about cash flow and how amazing it was and they self managed on their phone.
Um, and I was like, I want to do that. And so that kind of mind shift and like pivoted me to saying like, okay, instead of purchasing another long term rental, which my husband was very much like gravitating towards, I said, I want to try vacation rentals. I said, I want to buy an STR and I think I can manage it from my phone.
I said like, if grandma and grandpa can, you know, like before Airbnb, before apps, like I sure as heck can now that I have all this technology. And so, yeah, I just, that was kind of the switch. And I went all in with reading and listening, um, and working with the short term shop and like their management Monday.
And so, I mean, yeah, they really set me up for success with that and getting the right technology from day one.
Gil: Yeah, I followed a similar path there and I think that they do provide a ton of resources like market analysis. They will show you the numbers specifically in their markets. Uh, Luke’s, I think Luke’s management Monday or his, not his courses, but like his, uh, his calls. He runs through like how to run numbers, how to do the enemy method.
That’s like a huge help in the very beginning.
Sarah: Oh, yeah, for sure. Like, I, yeah, still stuff that I use, you know, every week to, you know, do my analysis or different stuff when I’m talking to owners that are, like, unsure about their revenue or their property management company, I’m like, yeah, Enemy Method or, like, have you looked at, you know, AirDNA or MassFed, yeah.
So there’s like so much out there.
Gil: So now that you’re operating three different modes, how do you think about like the guest experience? Do you treat the guests any different or, or have different? Ways that you process things, if it’s an arbitrage unit versus a co, like co hosting business or your, your own, or is it all the same where no matter what guests is booking with you, do you have the same processes to, to manage all of them and so on?
Sarah: Yeah, that’s a great question. Um, I do try to treat them all like my own, even though I know I do have like not just the guest to think about, but the owner as well, like with managing. Um, so in terms of like guest books and like communication, that’s all pretty much the same, like consistency throughout.
Um, so I keep that all relatively the same and the same formatted. Um, but when it comes to like maybe maintenance or like, um, if a guest is requesting a refund or unhappy, that’s where I do, uh, change between like, My arbitrage and my own pretty much stay the same because they’re mine But like between myself and the owner because now I don’t have to just think about how I would handle it I really have to consult with the owner as well.
I do my best to give advice But at the end of the day, I do allow them to make the final decision because it is their home And so then I would relay that like back to the guests Same with maintenance, you know, um, everyone deals with their maintenance differently. Some people, you know, might like to defer a little bit and group it together.
Some like to handle it right away. Um, I probably treat arbitrage and owners the same with maintenance just because arbitrage is not mine. And so again, I have to really think about costs at times with paying rent. Um, and like I said, like I Can’t put a new, you know, like kitchen in your house. That’s not mine.
Like I’m just not gonna do that And so I do do a two hundred and fifty dollar Maintenance like I cover each month to be enticing for my landlord And so I will spend, you know, small amounts of money for maintenance and whatnot. Um, but if it’s anything bigger than that, I’m reaching out to my landlord to cover that.
Where, obviously, my own unit, I have to like, just spend the money, unfortunately. And I try to address the issues as soon as possible. But sometimes I will like, group it. Because maybe I’m running tight on cash with like my arbitrages or I’m waiting for the landlord to get back to me
Gil: Yeah. So for your co hosting side of it, if there’s an, like a small issue, are you normally the one that handles scheduling the maintenance or do you put that back on the, the owner?
Sarah: Yeah, that’s a great question. So I do offer like I will hire Um cleaners and like work with their schedules obviously and then same with maintenance So I do say like if you have your own maintenance person that you want to use that’s fine But if not, i’ll find someone so yeah, I will find maintenance.
Um people and then I will schedule that as long as it’s minor, when it starts getting bigger, I do offer like quotes, like I’ll look for quotes and then end up putting that in the owner’s hands to like call and make the final decision. But yeah, I will handle small maintenance requests.
Gil: How about like, uh, replenishments and furnishings? Do you, do you take on that stuff regardless of the ownership type or is it mainly only for your arbitrage and you’re self owned and you’re on your coasting side, you have your homeowners take care of like all the upgrades?
Sarah: You mean like bit like if like a couch or something like a big upgrade or
Gil: yeah, yeah. I don’t know how much you furnish, but like when we, when we do our furnishings, uh, when we take on a property, we, we, we invest pretty heavily, like tens of thousands of dollars to, to furnish a new place. And it may be different because we have a lot larger property, single family homes, um, But I’m curious, on your side, when you’re bringing on a co host, like, what’s the expectation that you’re setting with the homeowner there?
And, like, how do you make sure that, like, when you’re taking on their home, that it’s at a quality bar that you feel comfortable of actually putting back on the market, um, to get the returns that they want?
Sarah: Yeah, okay. That’s an awesome question. I I understand now. Um, yeah, so I will have that discussion I’ll kind of like audit their listing if they have a listing if not, then i’ll ask for just photos obviously Um, but yeah, I will audit their listing and kind of suggest design or different aspects on what I think they could change Um I try to be budget conscious too, just cause I am, I guess.
But again, if you know, we’re talking like a big property that’s going to eat and the owner’s like, I want to charge a thousand dollars a night. Okay, well then we obviously need design and furniture that reflects that. So I do take that into account when talking with them. And then I would obviously again, leave it in their hands.
But I have had to make some tough calls where I’ve just decided that we’re too far apart and I cannot proceed any further with you. Um, Just because yeah, I didn’t feel like it would perform as well as they would and or I’ve dealt with it Needed like a lot of work to not just furniture And same with my arbitrage my arbitrage.
I like to spend between ten to fifteen dollars per square foot when I’m furnishing so that kind of keeps me in check as well and not to like go crazy because Again, it’s not my home and they can List it if they want and then you’re stuck with all this furniture Um, so that’s kind of what I gauge when I do the arbitrage and then how I handle Like the co um, my co host is I normally audit their listing first.
Um prior to us even like really getting too far down the road
Gil: Yeah, I’ve noticed that with folks where As folks mature into co hosting, their standards have gone up and also finding the right fit because a lot of times when you’re finding a client out there in the very beginning, you’ll take whatever you get to really like help you get the experience out there more than anything else and cashflow, obviously, but like, it’s really about the experience, but as you start to get more units and actually talk to more and more homeowners, you start to understand, like, What type of homeowners are really a good fit for you that actually molds into your processes, your standards and so on, where after after a little while, you end up becoming not picky, but you know who fits your avatar and who you actually can serve the best versus someone that could be served in by someone else.
And I’ve even seen like a lot of co host will actually refer folks to each other, um, to their own peers because they’re like, Oh, well, actually, I don’t serve that market or whatever. Yeah. That demographic doesn’t fit my, doesn’t fit my portfolio. Uh, and they could serve them. It’s just that it’s not a good fit.
Um, and yeah, I, I just seen that over and over again.
Sarah: No, i’m glad you brought that up because that is a great point because that’s kind of me I was like green at the beginning and just doing whatever but yeah, you’re right like The more I’ve worked with owners it is like we have to be a good fit for each other. Um, Because yeah, I just feel like if you don’t really want to you know Like engage with me or like if it kind of gives you anxiety like I don’t want that on anyone either And so yeah, making sure you are a good fit, especially like communication wise because yeah, you’re handling their asset Which is a big deal and you want it to perform like they want to but that’s such a good point That I feel like sometimes co hosts don’t think about is like the owner like yes the property But how do you you know, how’s the owner too?
Gil: yeah. And I’m glad that folks are actually like walking away and finding like, Oh, let them know, like, as actually not a good fit. It doesn’t, it doesn’t work for me. And I’m sorry that like, we not wasted your time, but like, it’s not, it’s not worth us for for us to pursue for it. Because what you don’t want is like a few months now down a few months down the road, you end up finding that like, you’re asking them to do maintenance changes, and they have a different schedule or different way of wanting to do things.
And you start kind of like, Not biting heads, but you start having a bit of tension there that is not healthy.
Sarah: Right. Yeah all great points
Gil: Yeah, I’m kind of moving to like the second segment of the show around direct bookings. Talk to me a little bit about kind of your strategy and some of the things that you do on the direct booking side.
Sarah: Yes So I will admit at first I just kind of again took luke’s advice But she’s always like just start off on the airbnb and burbo and then work later on your direct booking. So I did that Um, but then we did get a couple repeat guests and I was like, Oh, shucks. I would have loved to, you know, just worked outside the platform.
So yes, I, um, was using hospitable and then I switched to guest. We actually, because at that time they offered direct bookings instead of hospitable. And so I created my. Direct booking website, which is super easy. It’s just a payment through stripe. Um, and then set, you know, my own house rules as well as collecting security deposit directly from the guest and requiring their license.
Um, and then also what I like to do with my guests is send them. A little you can have coupons. So like a or promo code I guess and so I do like to text them after their stay Um, just as a little reminder and thank you for staying with us and next time share with your friends and family Even this promotional code and you’ll get 15 percent off So I like to do that with all my guests just again to direct book and then I do within the units to some marketing and have Um, business cards as well as like magnets just to my website.
So I did make a website, um, where I have like co hosting services and my properties, um, as well as then I’ve started an, uh, newsletter or like a mail, uh, email campaign.
Gil: Yeah. Okay. I’m going to unpack, unpack that quite, quite a bit because you, you mentioned a few things there. Um, I think you mentioned in the very beginning you were using hospitable and you moved over to guesty. I think actually now both of them have pretty good direct booking platforms there. Um, hospitable has actually been beefing up their system quite a bit in recent, um, where they actually have some pretty decent features on the.
Uh, direct booking side, but also on a lot of the management side of things, because I think like a lot of folks know hospitable as being like the, the PMS that’s more for smaller managers and not necessarily co host, but more recently, like I’ve attended a few of their town halls and I was surprised to hear like, not surprised, but it’s actually good to hear that they’ve actually been investing pretty heavily on like more, uh, co hosting type of customers and, and owner portals and all those things.
Yeah. Yeah, um, you mentioned security deposits and requiring a license there, um, we do the same. I’m curious on your side, like, what’s the feedback from guests? And for us, like, it’s actually been really good. We’ve always, from the beginning, always required a security deposit. We’ve asked them to upload the ID.
And every once in a while, we get guests that will come back and say, like, that seems odd. Like, I’ve never had to do this before. But Yeah. Honestly, like, I’ll let them know, like, if you’re not comfortable with that, I’m, I’m okay cancelling the reservation as soon as long as it’s not like they’re, they’re checking in like the next week, but if they’re far enough out, I’ll be happy to help them cancel it, the reservation and, and I think them on things, but I’m interested in hearing kind of like your experience given your properties on a very different area, different demographics.
Sarah: Yeah. No, I’m kind of with you too. So I haven’t had really a lot of kickback with it. Um, I have had to like, in my frequently asked questions, or even some of my language and my messages, like change it a little bit. Um, just to help with that, because some guests would be like, uh, Like why do I have to do this or you know at the beginning I guess per se with a license showing the driver’s license Um, but I just have in there that they have 48 hours to send me it Um either texting or emailing me Um, and then, if they don’t, the reservation will be cancelled.
So, I feel like I kind of have that as stronger language, and that kind of, you know, gets them like, Okay, I need to do that. I have, though, had a couple of times to remind someone. And, like, you, as long as it’s not, like, the next week. If they didn’t feel comfortable, I would for sure cancel it just because I feel like again, like I like your profile picture You just need that idea.
It’s the safety of like other people as well Um, like maybe in your neighborhood or anything like that and then for the security deposit um Again, not really kickback. I think just people don’t always read sometimes so they’ll be like, um this charge of 500 just came out of my account when I already paid, you know at this date And then I just had a lady actually say that to me and I said, I said, yes, I understand.
I said, it is our security deposit, which we do know in our messages and like it will be refunded to you in five business days as long as there’s no damage to our property. And then they’re like, okay, thanks.
Gil: Yeah, yeah, it’s, I think more and more, it’s becoming more common on, on the OTAs and I think a couple of years back when we started hosting, like it’s very, very foreign to folks where we’re probably the first person to ever ask them to fill out a rental agreement, uh, upload their ID. Um, I’ve even had cases where like, I didn’t notice it, but the, you know, everybody has their profile picture and the profile picture is like nothing like it wasn’t them at all, um, which threw me a surprise.
Like I didn’t cancel the reservation, but like it has me inspect the property a little bit more after post a to make sure, um, because our cleaners typically don’t message us or don’t, don’t, don’t mention anything unless it’s like severe damage there. Um. Yeah, so when there are cases where it’s like something suspicious, then I’ll just give my cleaners a heads up to let me know if there’s anything bad, but usually it’s actually, it’s not ill at all.
Um,
Sarah: No, that’s good. Yeah, I feel like most guests are pretty good. We have, uh, when you say that, like, yeah, pictures that, like, don’t match. I will then ask a few more questions. And like you said, just kind of, like, yeah, heads up to the cleaner about it. Um, but yeah, I don’t, I, I know, I feel like Airbnb’s kind of recently starting to crack down on that.
And Verbal, I mean, doesn’t even have it. So it’s kind of, like, still the wild west out there. But.
Gil: Yeah, it’s true. That’s true. I never realized that. Uh,
Sarah: I know like you don’t think that because sometimes I’ll be like, oh they like I need you know You’re Airbnb picture or whatever.
Gil: Yeah. Um, talk to me about the effectiveness of some of the coupon codes. So you mentioned that you generate coupon codes or you give, you provide them with the coupon code and you, you text it to them. Are you manually texting it to folks?
Are you using some type of system? Like, how are you doing that?
Sarah: Yes, so the guessy I’ve only texted to them, I guess, if they reach out because of past, but no, so I don’t mass text from my personal phone. I do, Guesty has a feature on there that you can send an email or text, and so I just send a text message. It’s from a Generic number their number. Um, but yeah, so we like to do that throughout the year Different holidays maybe in different stuff.
I changed the promotion like Black Friday. We did one And yeah, we’ve gotten good responses Definitely pretty good from like just the generic. Thank you one like I’ve had, you know, friends or family members of a past life Which I love that they’re sharing. Um, we did get, though, like, yeah, Black Friday, we get a few folks that do it.
And I try to obviously do it, like, in advance as well. So, like, if the code is in November, you can still use it, you know, for, like, January, February, March. So, like, future dates as well. But, yeah, it seems to work well. Um, Yeah, like I said, so I just text from Generic, and then I do email, too, and when we send newsletters, I’ll make sure to include the code in there, as well, if we have, like, a promotion, or if I just want to remind guests, like, hey, you can use the thank you code.
Gil: Yeah. So when you’re doing the, actually, before we actually move on to that, on, on the texting one, are you running sequences or are you like automating it or are you actually going in there and you’re actually like, You’re selecting people that you want to send a message to.
Sarah: Yeah, so unfortunately, it’s not automated, and I know MailChimp, which I need to look more into this, so I do have a virtual assistant, um, and so she is the one that does it, um, and we do our mail, emailing from MailChimp, Right? Like I said, I haven’t looked in the text one yet, but yeah, so she’ll go in there and select manually.
I mean, you can select like per property, so it’s not as tedious. Um, but yeah, she’s doing that and then just inputting like the name tag. So it says their name and then just a message that is pretty short, obviously, because it’s a text. So I don’t want to like bore them with it. And then, yeah, just sends it that way.
But my virtual assistant is the one that is doing it.
Gil: Oh, that’s good to know that like, even, even manually, you can have some pretty good effectiveness and it sounds like it’s not super cumbersome where it’s, it’s prohibiting you from actually running those types of, of campaigns.
Sarah: No, I would say like, I know a lot of people say it, but ChatGBT is like the best friend. Um, and so that’s kind of, yeah, if you need help thinking of it, like I’ve plugged in, give me a 12 month touch campaign texting for like holidays. And, and you can even say, put it in an Excel sheet. And it will spit it all out for you.
You could add emojis. So, I mean, it, it makes it pretty simple that I feel like there’s no excuse not to do something like to remind your guests, Hey, you know, remember me, come back for me even once a month when, yeah, like I said, you could just use chat GPT and it spits it out so quick.
Gil: Yeah. Are you using chat GPT also beyond your SMS campaigns also on your emails, your weekly newsletters or your quarterly newsletter? I think it is.
Sarah: Yeah, I mean so Yes, I yes, I will admit that I do the idea and I do a general format But they do polish it up for me or it does so yes, we use it for that as well Um, I mean I’ve used it in all aspects honestly like guest messaging reviews Yeah, even Yeah, for direct booking. Yeah, just how, like, write me, you know, an email to remind guests about, you know, myself, like, and my properties, and yeah.
Gil: Yeah. It sounds like it sounds like chat GPT has really helped in really. Speeding up the process of you figuring out what’s the right things to say and so on. Are you using any tools beyond ChatGPT, like the actual interface? Are you using any, like, AI tools or any review systems, automated messaging, any of that stuff?
Sarah: So just do the property management software Guesty has. Um, I don’t do anything like AI further than that. Guesty does a really great job of automated messaging. Um, and then does great with the reviews. So, I have it on that a day after the guest stays that it’ll automatically review them from a pool of questions.
As long as, you know, there’s no issues. You can easily turn it on and off, so you can have that control. As well as, um, for, uh, Five hours after they check out I send an automated message with a little picture of like the five Please review us with the five star chart of like what it means and how it’s important And then yeah, I mentioned earlier We also send out 15 days after they check out a message to stay with us again with that promotion code Of thank you.
Gil: Nice. Are you sending that via email or are you sending that through the channel messenger? If they’re like, if they book on Airbnb, are you sending that
through a Yeah, yeah, it’s through um Texting it’s through the text. So I think yeah, this is the one I chose You can either text or email, but yeah, it’s not on platform. So, the review obviously request is, but no, the inviting back is, um, off platform.
I see, I see. Yeah, I’ve actually been surprised, like, over the last year or so, I don’t know how long Guesty has had it, but, the AI reviews is phenomenal. Like, I’ve seen some of the platforms use it. I think a lot of the PMSs now have reviews where they’re AI driven and it’s actually a lot better than I can write.
Mainly because AI, they’re actually going to parse through all the messages that they that we’ve actually um, sent back and forth to each other. They know how many people are staying, which property is So they’re able to actually craft a much more personalized message where I feel like sometimes when I’m doing my reviews, I end up having to do like five to 10 reviews at a time and matching it.
And I run out of things to say, and I’m not going to go back into each message and say like, Oh, thanks again for letting us know about this or like particular things that they, um, that we messaged back and forth on, uh, where AI is, is able to parse through all that stuff and is actually able to craft a much more personalized message.
Sarah: Mm hmm. Yeah. No, I agree. That’s so true.
Gil: You mentioned that, uh, you are sending out messages or emails through MailChimp. How are you collecting your, your emails?
Sarah: Yeah. So, I was doing it more of a manual style, where in just my messaging, I was saying like, to complete this reservation, please share your email address with me. Um, Oh, and to receive future promotions. I know that there’s, like, StayFi and technology out there to use. Um, I have not invested in that. Um, I just have, so far, been very DYI, to be honest.
Um, but now I’ve recently Started using Guesty has a forum so you can send an attachment with the forum and then they can fill it out and then they’ll include their email address. Some of them will include the other guests email addresses, which is nice. Most of the time it’s just their own, unfortunately.
Um, but that’s how I’ve been collecting it. And then my virtual assistant once a week will go in and like filter. Either in Guessy and look for those or go on like Airbnb and just type in like Gmail in the search bar and stuff and then she collects those and enters them into MailChimp. The phone number and email.
Gil: Yeah, I like how a lot of the tactics that you use to even generate the, the direct booking volume you have right now is, it doesn’t require a very sophisticated systems. And in many ways, it sounds like you. Already know of a few things that you want to improve throughout time to help automate some of those things, but that’s not necessarily stopping you from actually building out your own direct booking engine.
Sarah: Yeah, I mean, I know there’s definitely easier ways and especially as I scale like I know the DUI I can’t last forever Um, that’s why I mean i’ve have a virtual assistant now to definitely help me and i’d love to start scaling that and even Making that more streamlined for her But yeah, I feel like for anyone really you just need like google excel And because I did that for a long time.
I honestly didn’t get mailed chimp until I think september just this year I got it In September. Before that, I was manually emailing people, just batches, the BCC, and just emailing them. So, yeah, I mean, it doesn’t take a whole lot. I don’t, definitely do not have a sophisticated system, um,
Gil: Yeah, I would say for like our listeners here, like if you’re sending out personalized messages using your own email is fine. Uh, when you’re starting to do a lot of mass and you’re starting to collect a lot more emails, um, then I think that’s where a lot of ESPs, email service providers, really help in making sure that, like, you are having opt outs and automating some of those flows in there.
But I think in the very beginning, like, if you’re starting off and your messages are very personalized, where you’re actually, like, you sending someone else a message there, A one to one email sounds very, very natural, and it doesn’t really scare a lot of folks off. Um, and you, and as I, I think probably the most important thing is like, starting to collect emails early on as much as possible.
Because, for instance, if, if you collect a whole bunch of emails, and you start messaging folks, if they don’t want to hear from you, they’ll let you know. Um, and you can definitely just manually, either manually remove them, or if you’re using ESP, Give them the unsubscribed link. Um, but as long as you’re adhering to just them opting out of it, however way they want to, um, and respecting their time and privacy, like I think that’s that’s fine.
Sarah: Yeah, no, that’s such a good point. Yes, definitely. Yeah, if they say like stop or yeah, don’t don’t email me Yeah, for sure. Then we respect it. And yeah, I remove them for the list But that’s why yeah, MailChimp’s nice now because they can just unsubscribe
Gil: yeah. And they do actually have a pretty decent SMS campaign too. So like if you’re entering a contact in there and you have their emails and their phone numbers, you can do some interesting things where you’ll actually text them first and then you’ll then lag and then email them following that. So it feels very natural there where you’re like, Oh, I just sent you an, or I’m sending you an email tomorrow about a promotion code.
So you’re giving them a heads up or you can remind them as well too. And we all know like the text message open rates are close to 99 percent where everybody opens up. All the text messages, but they don’t always see their emails or may not notice it. So like combining the, the SMS and the emails together, especially putting them into one platform really helps mixing a lot easier where you’re not having to like jump like, Oh, did I message them on, on, on another system already?
And like, can I email them? Yeah.
Sarah: Yeah, no that I know I need to look into that for sure because that would be very cool and like you said more organic
Gil: Yeah. And I think they actually will. You can even get a, like a, your own number associated with the two. I forget, uh, I know, I definitely know that they do the short codes, which is like the five or six digit code that, that, that folks email from or text from. But you can also register your own, your own phone number as well too.
I know other, other providers like Clavio and some of the other ones definitely do. I forget whether or not MailChimp does that. I expect them to at least.
Sarah: Okay, yeah, no, that’s great. I’ll have to, yeah, remember that and use that. Cause I do obviously now have like a Google voice number where I can like disassociate myself and I put that on a lot of places, but no, that would be great too, even just on MailChimp. Mm
Gil: Yeah, I mean, technology is a lot easier nowadays where you can automate a lot of things and make it feel a lot easier where it’s not such a big burden, um, but I’m kind of actually glad that you’re doing it manually, even starting like this business here, I have to say is in the very beginning, it was a lot of one on ones and We didn’t start, we didn’t start doing any type of automations until probably a lot further into it.
But when you start emailing, start texting, and start like just messaging folks manually, you start to understand like how people are responding, what are they saying in return, and really like you get to tune the messaging a lot more than if you were to go like straight automated in the very beginning without doing some tests along the way.
You could be ignoring some of the feedback that you’d be getting and just setting a campaign that might be ineffective.
Sarah: No, for sure, yeah, that is, yeah, great points, yeah, definitely. Because and that’s why actually I still do I haven’t had my virtual assistant even do my messaging to guests because I still like that feature Of like getting that interaction and getting to how they’re like, yeah just how they respond but definitely also with the on mail campaigns and sending it out and Yeah, it’s just way more personal.
Like, I know different guests that come, repeat guests, and like, when they come, so now I can, like, definitely tailor my messages when I send marketing out to them.
Gil: Yeah. What are, uh, given that you have a lot of things that you’re, you’re thinking about expanding on, what’s some of the, like, the, either low hanging fruits or the, like, the next big thing that you want to invest into to really help amplify your direct bookings?
Sarah: I feel like what we talked about, obviously, previously, but, like, something, like, with your, um, company and your, like, website with, so I have a website, but, yeah, it’s just making it more streamlined for the guests, Where you can come to my website and select like what dates you’re looking for. And then because I invest in so many different markets or manage in different markets to see like, okay, these five properties work.
And like, is that of interest of me and my family or, you know, whoever. So I definitely think that, and then I’ve been working with a brand like a marketing or branding. And I think that would help too is Yes, I send to repeat guests, and that’s great, but even, you know, if it’s, like, I just had someone reach out who hasn’t been with us for two years, and now they’re rebooking, which is awesome, but just, like, making sure they can easily find me, um, even if they just type in, like, our name and our company, so, I guess, because I do feel like there’s some difficulties still with that, even with my website and all the marketing that I’ve been doing, so I think that would definitely help improve my direct bookings.
Gil: Yeah. And I think what you’re facing is probably not too dissimilar to a lot of folks who are, If you’re on the coasting and arbitrage side, you need to have a website to be able to showcase. So a lot of times you’ll end up building out the website with that being the lead in there. And then as your portfolio grows over time and you’re trying to get more direct bookings, and I think even a lot of homeowners they actually like to know that you can actually book directly because they send that to a lot of friends and families and so on.
Um, but having two different, Like use cases, it’s rather hard to bring them together. So we’ve actually seen like a lot of folks that sign up for our service that have like co hosting pages or management pages alongside their booking page. So if you were to go onto the website, it kind of leads with the booking side because that’s where most of the traffic comes from is people wanting to direct book with you.
But then you also give opportunities to talk about your management services and. It’s actually a nice way to even advertise to new homeowners too, because they see like, Oh, wow, this person is, these are the properties that they manage. This is the caliber that they operate in. Um, so it allows you to kind of like leverage that not just for guests, but also to acquire new, new co hosting clients.
Sarah: Yeah, I think that’s a great point too, because I have, um, gotten, yeah, like just, yeah, hosts that come, you know, stay repeat times. And so that would be a great way to be like, Oh, maybe I could use a co host or, you know, cause yeah, you get a lot of. Obviously, like, I travel, so I stay in other people’s Airbnbs, too.
Okay,
Gil: Yeah, yeah. Awesome. Sarah, we usually end the show with two questions. Uh, I’m changing it up this time around mainly because I’ve been doing a lot more reading. I would love to kind of get your input on this as well too. Um, so two questions. One’s, uh, kind of a very typical one that you’ll hear on a lot of podcasts, but I’m interested in hearing what is one of your favorite books that’s really changed your life, um, either recently or in the past.
Sarah: yeah, so recently, or right now, I’m currently reading, uh, Robert Kiyosaki’s Cash Flow Quadrant. I did just finish, maybe a couple months ago, the Rich Dad, Poor Dad, and I think that I, I like the, the sound, like, reading it, like, how he’s written it, and I think it’s very applicable to a lot of people in your mindset, and I’m big into, like, my mindset and my mind, um, how I think, uh, with changing, you know, different habits.
But earlier on, I would say the influential was taking Dave Ramsey’s course, which I know he has a book too. So I’ve never read the book, but, um, just doing that was huge. Like taking responsibility for my finances, definitely like set me up to be who I am today. Um, because I think without that, I don’t know, I don’t think I’d be very financially responsible and, and even be able to have, you know, Asset, let alone take care of other people’s
Gil: Yeah, you’re probably the first person I’ve heard that reference Dave Ramsey that’s in the short term rental space because I don’t know if folks know, but Dave Ramsey is very against short term rentals. So it’s interesting to hear you kind of say that.
Sarah: I know, but yeah, like I don’t, he, like I said, it was really influential and I know, like I, I feel like you too, obviously with anything can grow out of stuff. So I do feel like a lot of, like what he says isn’t for me anymore. But like I said, it was like, yeah, that’s how I got, I mean, financially free, like paid off my loans, paid off my car.
Yeah, really changed, uh, changed the trajectory, I kind of feel, because even as a teacher, you know, I was still like Spending everything and just like, eh, it’s fine. You know? Oh,
Gil: definitely understand that. I think a lot of like, Dave Ramsey’s approach is really to get back to kind of neutral status where you have control over your funds. But I think like, I would agree like Robert, Robert Kiyosaki is like the next step up. If you’re looking to grow long term wealth, Robert Kiyosaki is a much better, like, idol to look after or influencer to look after to really teach and like, I’ve read Rich Dad Poor Dad many, many, many times.
And I think at one point on my bookshelf I had three or four copies of it. These are relatively cheap, they’re not that expensive. Um, but I would have multiple copies on my bookshelf. And whenever I would meet someone that I felt like could benefit from the book, I would just give them the copy. Uh, and,
Sarah: that.
Gil: it actually worked out really well.
And I like, after like a few years, I connect back with the folks and they’re like, I love that book. Thank you for giving to me. I’ve like, I’ve switched how I manage money, how I think about money, how I think about assets. Because in the very beginning, if you’re not thinking about it, like it’s very natural for you to.
Buy what you want, spend what you want and live day in, day out. Just kind of like that, where if you, a lot of our listeners here have a very different mindset where the, the money that we earned is really used to help us grow additional wealth in the future. And that’s a lot of what like Robert and many of the others talk about in their books.
So that’s what if you listen to bigger pockets, that’s a big thing about all the bigger pocket stuff as well, too. I
Sarah: Yeah, well, and just like a lot of us, I will say, like middle class families, or you know, people that, that’s just how we think. So I feel like it’s very natural to be like, oh, yeah, it’s not a big deal. Just go buy like a new car. Or, you know, like without even thinking about how that’s not like an asset or like your primary home.
I just talked to some. He was a younger kid. He was 21 this weekend. And he was like so committed on buying a home instead of renting, because that was going to be an asset. And I had to tell him, it was not an asset that it was a liability, even though he said, well, my parents bought this home and it was 80, 000 and now it’s 400.
And like, look at that and all that equity. And I was. I was just like, you need to read Rich Dad Poor Dad. I did say that. I was like, read Rich Dad Poor Dad.
Gil: I mean, he’s, he’s not wrong and necessarily that there’s definitely a lot of equity growth, like however many times equity growth, but like if you can pull that money out and redeploy it to other places, it’s not an, it’s not an asset that you can, you can leverage.
Sarah: Right. Yeah. Exactly.
Gil: Yeah. Awesome. Uh, Sarah, last question.
What’s the tactical takeaway that you want our listeners to get out of today’s episode?
Sarah: Yes. And I realized I didn’t even really touch on it, even though I love it so much and it’s part of my direct booking as well is Facebook groups. So I do have a business Facebook page and you wouldn’t even need to do a page. I’ve done it even just personally and I will have a little message with my direct booking link.
And so what I do is join these groups. So like Um, you know, vacation stays of Orange Beach and I will go in there and I will look for people that are searching for dates to come and I will just copy and paste my little message about my condo and I Have found that was like a in the beginning to a huge boost in like my direct bookings as I found that a lot Of people would find me on Facebook and then reach out on my direct booking website and so I would say that I feel like Facebook groups are kind of like a I mean, cause you can find co hosts, you know, arbitrage, properties, direct booking clients, like, it kind of is all, all there.
Gil: Are you also on a lot of the big, uh, short term rental, like Facebook groups as well too outside of it where like we have other hosts.
Sarah: I’m on some, yeah, like, uh, short term rental. There’s, I’m on like, the STR Secrets. And better hosts. Um, so yeah, like a decent amount. But I, definitely on a lot of like, the property, just the, you know, vacationers looking for them. Cause, now I have my virtual assistant that does that. Um, looking for people.
But yeah, I do, I’m in a lot of Facebook groups.
Gil: Yeah, I think I did not expect myself to be that embedded in so many different groups prior to joining Short Term Mentals. But now it’s like, my entire feed is all Short Term Mentals. It’s either about Smokies, Branson, Uh, other, other hosts, other hosts talking about their entire experience, like, it’s all, it’s my entire feed now.
Sarah: But yeah, I mean, well I found cleaners on there. Found handyman, like muralists, like, yeah, it’s, yeah, it’s like a one stop shop for your short term rental if you need it to be.
Gil: Yeah, and I think if you find like a one or two different groups, and like, probably not spread yourself too thin, but if you find one or two different groups that you feel really comfortable with, those are, I think, the most valuable ones. Um, like, there’s a lot of like smaller niche groups that, Like you can be more vulnerable.
I’ve known, I know there’s a bunch of groups that are like females only that a lot of folks are like much more comfortable asking questions there. And I’m like, Oh, I kind of wish I had that type of group for males. But like there’s, there’s, there’s a lot of different groups for like different niches there, which I think is a lot more valuable than some of the bigger ones sometimes.
Sarah: Oh, yeah, for sure. Um, but yeah, you’re so right. And I think, too, you have to take some of the stuff with a grain of salt, you know, host and other stuff are going on. But, yeah, like, when I first started, too, like, I remember typing in, like, search bar, like, questions just to help me if I had a guest issue and, like, Didn’t really know who to like reach out to per se, but yeah, Facebook groups can be a lifesaver.
And then, like you said, even if the smaller niche ones, that’s even kind of better. Cause like you said, you can be way more vulnerable, um, with questions.
Gil: Sarah, where can folks find out more about you? How can they follow you? How can they, if they, if they decide that they need you for their management services, where can they reach you?
Sarah: Yeah, of course I’m pretty active on Instagram. So at Sarah underscore Pell underscore or at my website, www. cpvacationhomes. com.
Gil: Awesome. Sarah, thank you for coming on the show today and sharing your entire experiences, talking about all the different ways that you can get into short term rentals and how you’re balancing it all and the differences between them. And also. giving us a glimpse at kind of like how you run your direct bookings.
It’s, I’m actually very inspired by some of the tactics that you use and not like not having to figure out like everything has to be perfect and you have all the right tools. Like you just get started and it sounds like it’s doing quite well just for just with doing it manually. So I’m, I’m, I’m very, very impressed.
Sarah: Yes, yes. Thank you, Gil, for having me. This was a lot of fun. I loved talking about it.
Gil: Thank you. See ya. Bye.
Yeah. Yeah.