How a 25-Year-Old Host Scaled His Short-Term Rental Business with AI and Direct Bookings – Chad Harker

Summary and Highlights

👤 Meet Chad Harker

He’s 25. He owns multiple short-term rentals. He’s not flipping arbitrage leases. He’s buying real estate. Renovating it. Renting it. Managing it. Growing a brand.

Chad Harker didn’t wait for permission. In the early days of COVID, while most people paused, Chad bought a fixer-upper, moved into a spare bedroom, and listed the master suite on Airbnb. One listing turned into multiple units. One property turned into a management company. Today, he’s building a sustainable STR brand in Edmonton, with cash flow that’s compounding.

💡 What You’ll Learn in This Episode

If you’re a host who wants to own more, automate smarter, and stop relying on platforms that don’t care about your growth, this episode is your blueprint.

We unpack how Chad got started with zero connections and built his first STR through house hacking, and how he applied the BRRR method—Buy, Rehab, Refi, Repeat—adapted for STRs. That first home eventually became his launchpad for scaling, thanks to HELOCs and consistent reinvestment.

Chad also reveals how he gets direct bookings without gimmicks by designing guest-first experiences that leave a lasting impression. (Hint: it’s the same principle behind why guest-first design converts better.)

He doesn’t just talk branding. He backs it with systems—like QR codes for guest reviews, UTM tracking to measure traffic, and email funnels to rebook returning guests.

🧠 Mindset from a 25-Year-Old Who Gets It

“It’s not about how much money you’re making. It’s about how much you keep.”
Chad’s financial discipline runs deep—from manually renovating his first property at 2 a.m. to allocating profits like a CFO using a Profit First approach.

And when it comes to tech, Chad’s team isn’t guessing. They use HostBuddy AI to manage guest comms and streamline their ops—freeing up hours each week while improving response quality.

For hosts starting from scratch, Chad’s advice is simple: focus on retention, guest loyalty, and starting direct bookings now. Don’t wait for a perfect funnel—start with a solid stay.

🧰 Tools, Tactics & Templates

Chad shares how his team uses custom GPTs, AI automations, and simple workflows to:

• House SOPs in searchable GPTs for internal training
• Keep guest experiences consistent across multiple listings
• Capture emails and retarget past guests using owned data

His long-term thinking shows in how he manages LTV—lifetime guest value—and runs his business more like a boutique hotel brand than a side hustle.

📚 Book Mentioned

Profit First by Mike Michalowicz — If you want your business to stop running you, start here. Chad uses it to budget taxes, op-ex, and owner draws.

📲 Connect with Chad

• IG – Business: @ecoescapes780
• IG – Personal: @chad_harker780

🎧 Listen to the full episode now to hear the exact playbook Chad uses to build guest-first, tech-enabled, high-cash-flow stays in his 20s. Then visit CraftedStays.co to build your own direct booking brand—no custom dev agency required.

Transcription

Chad: It’s not necessarily about like how much money you’re making, it’s about how much you keep. And you could have the guy, uh, working, you know, at McDonald’s making minimum wage. However, they’re saving more of the money they’re making than the attorney that’s working at a prestigious firm and they’re spending all of their money on like all the luxury things, the cars, the home.

Chad: I feel like if you’re able to set up a system where you’re taking a certain percentage of your income, then you’re gonna be in a really good position to like. As you increase your income, like you’re also able to maybe increase some of the rewards you give yourself, but you’re also able to increase your savings and how you’re gonna use and invest that money based on whatever your goals might be.

Gil: Before we bring on my guest, I wanted to talk just a little bit about something that I’ve been hearing a lot from Host. I keep on hearing the same thing. I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it. Here’s the thing, you’re letting all these marketing strategies, you’re driving traffic and you’re putting it all to work.

Gil: But if your site isn’t really built to convert. You’re basically lighting your energy and money on fire, and even if you could afford an agency build, every time you want to test something or make a change, you’re having to pay them again. You can’t iterate, you can’t test, and you really can improve on things.

Gil: You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I build Crafted Stays. It’s purpose built for short term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings and you can keep on testing and improving as you learn, and you can make changes all on the platform.

Gil: You don’t need to learn something new. So if you need some help or you wanna get started, go ahead and go to Crafted stays.co and start your free trial. Now let’s bring on our guests and dive deep into hospitality and marketing.

Gil: Hey folks. Welcome back to the book, solid Show, the podcast we’re bringing top operators to discuss marketing, revenue management, and the guest experience to drive towards being booked solid. On today’s show, I have Chad Harker. He’s one of the youngest guest that I was able to bring onto the show, but he has grown his portfolio in an amazing way, especially for his age.

Gil: There. He’s not doing arbitrage. He’s not Well, he does, he is doing a little bit of coasting, but he took the more sustainable path of doing acquisitions, for his short term rentals. He’s grown his portfolio, he’s grown his management company. He has a wealth of knowledge to share around just what he had to do to get to where he is right now at such an age.

Gil: But also he had a lot of good nuggets to talk about, specifically around direct bookings and some of the foundational pieces that he puts in place that I think is applicable for any type of vacation rental. So I’m very excited to have Chad on the show. And I just absolutely love just him as a person and the conversations that we had.

Gil: So let’s bring him in.

Gil: Chad, welcome to the show.

Chad: Yeah. Thank you for having me go. I’m excited to be here.

Gil: I’m excited to have you here. Um, we mentioned this during the beginning of the call or right before this, but I think you might be, at least for now, you’re one of my youngest guests on the show. Um, and it seems like you’re not taking the shortcuts like a lot of young folks that are getting into short term rentals.

Gil: Um, you have a kind of different mindset. On kind of how you’re approaching your portfolio. So I would love to kind of dive in deep there. Maybe let’s start off, who’s Chad?

Chad: Yeah, so, um, I have a management business here in Edmonton. I started out with, um, just the real estate investing side of things and got into the short term rentals, more or less by accident especially, uh, being younger, you’re kind of limited for. How many properties you could have or at least, uh, with myself and I’m sure a lot of, uh, your audience, you don’t have like unlimited money to, you know, be buying up apartment buildings at the start.

Chad: So I just really wanted to find a way to get the absolute most out of every property I did have. So that’s what kind of directed me to the short-term rental side of things.

Gil: Yeah, so I’m guessing you started off on the long-term rental side of things and then you moved your portfolio into the short-term rental.

Chad: Yeah, I actually, well, I still have one long-term tenant. Uh, but yeah, that’s how it kind of got the ball rolling. And it started with like, uh, house hacking, if you’re familiar with that. I, I, I thought like, you know, you hear so much about, uh, Airbnb’s and short-term rentals and until you’re really in it, you’re. Pretty much your whole understanding is what’s portrayed on the media, which. Isn’t necessarily always the best. So I was like, okay, there’s only really one way to find out. And that’s when I was like, okay, I’ll make the sacrifice and move into, uh, my spare bedroom of the first property I purchased. And then I rented out, uh, the master just as a room on Airbnb to kind of get a feel for it and understand how the platform worked and if it was something that was actually, you know, a, a viable, uh, option for future investments. And that’s when it, I was like pretty blown away with the results of the one bedroom. So I was like, okay, like what would happen if we tried this out on a larger scale or a full property? So that’s kind of how I initially got into it. Actually,

Gil: Well, so, so was that a per a property that you purchased or were you renting, um, the house and you were taking the spare ribbon? Like is it your, your own or did you rent at that point? I.

Chad: No, that one, I, I actually purchased that, uh, property during CO and uh, I was like, maybe a little bit of luck and also like, I think there’s something to be said just about taking action. ’cause at the time, like that was like the beginning of COVID and no one, everyone was like, really not sure. It was right before, like, the huge influx of buyers kind of flooded it out when the interest rates dropped.

Chad: So I got in with the lower interest rate, but it was like right at that. F initial time when no one was really buying anything either. So I was really fortunate in that sense that I was able to get a lower purchase price and a lower interest rate. And that’s when I got that first place. And we did a, like a legal suite.

Chad: So we added a A unit and that’s when I long-term rented it. And then I just wanted to see like how. I could really make the most out of this place. ’cause at the time I was like pretty much break even in terms of cashflow for that place. I was still living there. But then when I rented out the room, that’s when I was like, wow, now I’m like netting between 1,015 hundred a month of cashflow for this place and I’m living there for free.

Gil: Wow. So how did, at that point, you’re in your early, early twenties there, like how did you save up enough to do that first acquisition? I.

Chad: Yeah, that one was, well, it was a relatively low, uh, down payment because. Well, first off, I have to give a lot of credit to the, uh, realtor I was working with ’cause they were incredibly experienced. So they helped me out a ton and they had a larger investment portfolio, so I was really able to like, leverage their knowledge and skillset. So we were able to find a really awesome place in a, it wasn’t like, I wouldn’t say the best location, however it was, it was still a good, good spot and relative to the price point. So, yeah, I was pretty much just like really scraped up enough. And, uh, also, uh, if you are younger, uh, you know, maintain a good relationship with your parents.

Chad: ’cause they, they helped me out, uh, like with a little bit of the initial down payment and I paid them back. So maintain a good credit score, not only with the banks, but with your parents or, you know, any investors for that matter. So that, that’s what helped me out a lot. So.

Gil: Wow. And I’m guessing, so it sounded like you did your first acquisition, it was a primary home for yourself. You rented out long term and then figured out, oh, maybe I can house hack and do this with short term rental units, cash flowing, um, about a thousand dollars a month. How did that pick up from, from there?

Gil: How did you get to your second organization? How long was that journey there?

Chad: Yeah, so that one was actually as soon as we completed it and uh, I was able to save up enough with that. Uh, cashflow that we were collecting, we were able to move pretty quickly. ’cause with the, the time I purchased it, the, and the renovations that we did, I think that’s also like a very valuable component if you are gonna plan on purchasing your own investment property.

Chad: See like not only what you could do in terms of like amenities for short term rentals, but how you could get like the highest appraised value and the best return on your. Money in terms of like the renovations and if you could combine that, combine them both with, you know, like the best return on your investment in terms of, uh, like the bank coming to do an appraisal and on the short term rental side as well, you’ll be in a really good position to do what we did, which was get like a really nice, uh, home equity line of credit. And that’s what I was able to use to really help fund the next deal, which was, uh, a, a couple, a few years after.

Gil: Wow. So you, I don’t know if, if you, if this like qualifies, but like. You, it sounds like you successfully, um, did the burster method of like, buy, rehab, rinse, repeat on an STR. That’s amazing. That’s amazing. I.

Chad: Yeah. Yeah. So the, the pretty much, essentially that’s, uh, what we did, and that’s exactly what I did on the, the next one as well, and. If you are gonna do this method, I feel like, um, if you are able or the property allows you to add another unit, it’s gonna help a lot in terms of the short term rentals.

Chad: ’cause you could do the parent child listing to really get the most revenue. And from the investment standpoint, the banks will look at that as a higher, like, they’ll offset more of the mortgage.

Chad: I know like there’s different, um. Qualifications with other lenders or even different countries. However, with I feel like no matter where you are, if you have more units and you’re able to get a higher, uh, like market rent, you’re gonna be in a good position to qualify for more on your next purchase.

Gil: Yeah, yeah, yeah. We had, um, Ashita on the show, a couple, a couple weeks back, and she’s, she does like a lot of custom design and, and, and work, and what she focuses her attention on is really those value adds there. So she’s. Knocking down walls, building out extra space, and like one thing that she tries to do is to maximize square footage that is Permittable, square.

Gil: Square footage is, and what she thinks about is like, not just how do we amenitize the place, like you said, but how do you build it so that it has equity built in so that when you do need to do a reappraisal, or if you’re trying to do a HELOC or a line of credit, you’re able to pull more money out there.

Gil: It sounds like you’ve. Executed that. That’s, that’s amazing. I am curious where the education came from, because like for me, similar, like 20 18, 20 19, I was consuming a bunch of BiggerPockets podcasts like that. What I probably listened to. A hundred to 200 episodes. Um, and that’s where I learned, I think first off, is like really managing your money more effectively, being in tech for a decade prior.

Gil: When you make good money and you don’t have good financial stability, you just spend what you, what you have in there. And I wish I had kind of the mindset that you have right now in your mid and early twenties there, where you’re able to apply these much earlier in your career. And by the time you get to my age, like, dude, you’re gonna be, you’re gonna be living the life of your dreams.

Chad: Uh, yeah, hopefully. I think you’re absolutely right though. It’s not necessarily about like how much money you’re making, it’s about how much you keep. And you could have the guy, uh, working, you know, at McDonald’s making minimum wage. However, they’re saving more of the money they’re making than the, the attorney that’s working at a prestigious firm. And they’re spending all of their money on like all the luxury things. The car is the home. I feel like if you’re able to set up a system where you’re taking a certain percentage of your income, then you’re gonna be in a really good position to like, as you increase your income, like you’re also able to maybe increase some of the rewards you give yourself, but you’re also able to increase your savings and how you’re gonna, you know, use and invest that money based on whatever your goals might be.

Gil: Yeah. Have you, uh, read the Cashflow Quadrant by Robert Kawasaki?

Chad: Yeah, that’s a classic, hon. Honestly, I feel like that’s one of the go-to books that, and um, the first one he wrote, A Rich Dad, poor Dad. That’s another except, and, and the bigger Po Pockets, uh, podcast is also phenomenal. Like, I remember I was a big listener to that one too, and I remember like. You know, staying at that property, doing a lot of the renovations myself at the time, because I didn’t have the financial means to, you know, be paying contractors.

Chad: So I’m like staying there till like two in the morning and, and it was, uh, and that was the reason I was able to get that property. I was, it wasn’t in the best shape, so I was able to. Add some of the value. Like it wasn’t even really livable when I, uh, purchased it. So I was like doing a commute from my parents’ house to this property, like every day.

Chad: And, uh, staying till like two or three in the morning, like just scraping, uh, the uh, uh, pet, uh, the ceilings and, you know, doing all the painting, the flooring, the baseboards, the trim, so. But there, and, and listening to the BiggerPockets podcast, like the entire time I’m doing all these, like just to stay motivated and like, I thought it was a, it was a definitely a period where I had to make some sacrifices, but looking back at it now, it was, it was totally worth it.

Gil: Yeah, I, I think that BiggerPockets, that whole, the whole podcast series, not just that one, but they have a bunch of different series now, but like. I think it’s opened the, opens people’s eyes to like what’s possible, because like you mentioned, what people consume on media is kinda what the norm ends are becoming.

Gil: But there’s actually another cohort of, I would say, like us, where you may not be consuming mainstream media and you’re looking at different avenues, but I think that BiggerPockets is one of those where they built a community and the media that they produced helped shape people’s lives in a very positive manner.

Chad: Yeah, I, I couldn’t agree with it more, and especially like even on your, you know, like your newsfeed on, uh, Instagram or Facebook, if. If you actually train the algorithm to give you a little bit better content in terms of like the education or what you want to see, like I, I like my newsfeed is like all these like crazy unique stays or some of the renovations and like creative approaches that you could do with these properties. You could consume media in a lot healthier way, like listening to a fantastic podcast like yourself.

Gil: Yeah, I, I, I didn’t consider like, um, your newsfeed being, uh. Kind of a, a reciprocating way of like for you to reinforce, but it is actually probably the most natural way for you to enforce some of the, the things that you care about because you’re naturally gonna click on those videos. You’re naturally gonna look into it.

Gil: And, uh, meta’s gonna reward you with feeding more information like that. So if you’re a liking posts that are like the Alex Hormo, the Dan Martel’s, or um, any of those like go-getters out there, um. You’re gonna get more of that and it’s, it’s gonna fuel you more. But it also can go on the other side as well too, where if you’re looking at other people’s lives and, and so on, you could be admiring others and you’ll have a very different experience of how to use social media.

Gil: I never thought of really that way. I.

Chad: Yeah. Yeah, no, I, I found it’s, uh, very helpful and you, I also just try to like, uh, be a little bit more intentional with my time using, ’cause it’s pretty easy to get like, uh, stuck scrolling or, you know, get sucked in. But if you are able to kind of train the algorithm or use it for your own content creation, like we have, uh, tabs where we’ll have like ideas for future posts or like really cool transitions with some of the reels for properties. So you could really use it to your advantage if you use it the right way.

Gil: Yeah, I haven’t found a good way to, to organize that and pass it over to my team, but, uh, if you have any tips on that one, I would love to hear it.

Chad: Yeah, we, well, uh, you could have like a shared, um. Um, like saved lists. So that’s one that I, I use with, uh, some people on our team so we could like each be saving certain ideas for reels or transitions or, and like, it’s really good if you have a social media page or a brand for your business or a management company. So you could always be thinking of like, you know, cool hooks or creative ways to. You know, make the, make that amazing content and showcase your property and the experience of your location even.

Gil: Yeah. Yeah. I need to do a better job at figuring out the hooks for me. Maybe it’s because the podcast, but like I’m all about more on the education slash value side of it. And I, I forget that like, oh, if you want to go viral or if you want that, that education to be seen by more people and benefit more people, you do have to shape it in a way that brings people in.

Gil: And that hook is actually very necessary. And that, but that to me, it’s not very organic. It’s like not organic to me. So I kind of had to like force myself to think, think of that matter. I haven’t trained myself to do that yet.

Chad: Yeah, no, you’re absolutely right. The hook is the most critical aspect. I do feel that, um, a lot of it could be super clickbait. Um, however, if you are able to make a compelling hook and you’re, you just make sure you deliver on it. Like maybe don’t, uh, say something like, this is how I made a million dollars in two days, or whatever, and it’s, you don’t have any context to support the hook that you’re saying. Uh, but if you are able to like, deliver on the hook and do so in like a way that’s educational, I think that’s like the best, the

Chad: best way. 

Gil: Um, on the content creation side, or maybe even more broadly on running your business and your personal, are you using, uh, like this is, we’ve seen this a lot, but like there’s this big wave in AI right now. Are you using AI much at all in your business and, uh, are you doing anything special with it that you feel like is, uh, unique to you?

Chad: Um, well, I feel like you, AI is gonna be a critical component and it’s gonna be an essential tool for any, any business like. Obviously use chat GBTA ton. I I do feel that if you are able to kind of curate the responses, like using some of the custom GBTs and how it allows you to add, uh, files that are specific to your business, that could be a huge, um, component that really help you grow and how it could curate the responses that are specific to your situation or your properties. So right now that’s, um, something that we’re working on and how, and we have some shared, uh, custom GBTs with our team for like, some of the internal documents with our business with like SOPs or certain procedures and like property specific things. So rather than like, uh, maybe searching through a Google Drive, which is still like, I think a great tool, you could have it, almost use it as like a search engine so you could. Have, if you have all of the information in a custom GBT, you could be like, what’s the procedure if a guest is asking for early luggage drop off or late checkout, or, what happens if this happens? And if we have something, uh, in the files for that custom GBT, it’ll be able to give you a, a really good response if you have it set up correctly.

Gil: Interesting. So, so it sounds like you have some custom GPTs on just like how to run your overall management companies and your process procedures there. Maybe you hinted to it, but you’re creating, or you have. Property specific gpt as well too, that kind of layer in on specifically like, where can I find this?

Gil: Or, um, like, how does a hot tub work? But you have like specific ones on just how, how that property is, is that right?

Chad: Yeah, and I think like having. Good property guides in place is, is super critical. ’cause you’re always gonna get those questions and obviously it’s something that could be built over time. Like, you might not necessarily be able to anticipate every guest question, but if you have like a good, uh, onboarding form that like that’s what we use when we’re taking on a new, new property.

Chad: Whether it’s one that I own or manage, just to have as much information as possible. So like if you have a team. It gives them the ability, especially if um, maybe they’re not from your specific city or you’re working with people overseas, then they’ll be able to have like a really good outlook of the entire property where everything is and how to answer a lot of those questions.

Chad: And if you’re able to also like, kinda make it as scalable as possible, like if you always have extra blankets in the closet. Make sure that that’s like a standard thing for all of your properties. So then anytime someone asks for extra blankets or some of those common things, it’s like a very like easy to answer question.

Gil: Nice. And, and are you uploading these files kind of manually and you’re updating these, like you’ll take down a file and you upload, upload a new one if you need to make any changes, but they’re, they’re pretty like static files. You don’t have any on automations that kind of inject those files in there.

Chad: Uh, we don’t currently. It is definitely something that we’re, uh, looking into. I maybe you have some good suggestions or, uh, feedback in that, in that regard. I know that there is a lot of, uh, great tools with, uh. Some of the AI automated messages. I know you use, uh, owner res for your PMS as well, and I know that their messaging is like, they have some really good custom triggers like, uh, and automations for like, if someone books with pets, then you could have like the custom messages go up for that.

Chad: But maybe you have some good, uh, suggestions or feedback on

Gil: yeah. Yes. So we actually use Host Buddy as, uh, as one of our ai uh, chats. Um, and given my properties are like a three hour time zone difference, it’s helped a lot in terms of like making me feel like I can rest and not have to worry about if a guest message is me nine o’clock their time and it’s six o’clock my time and I’m waking, I’m just waking up.

Gil: Um, it some, in, in some cases it had had flown full blown conversations with a guest to triage why the hot tub wasn’t heating up and it was because it was on, um, like eco mode there. Um, and just like troubleshooting with the guest. And basically what I do is I. Host body has all the content about what amenities I have, where my spare keys are, where to get spare blankets.

Gil: Um, it has tour guides, like all the different things, like best places to eat, where to get groceries and all that stuff. So any of those types of questions I’m having to now just feed it once and it’s already kind of in my, my guidebook. I was able to kind of like pull that all out there and provide it to host buddy and it’s able to then respond back on my behalf and it’s just.

Gil: It just allows me to be more present on where I need to be more present. So if a guest does have an issue, I’m able to spend a lot more time with them on it rather than trying to feel like I’m putting out fires that are pretty trivial in a, in a lot of ways, like probably, I don’t know how it’s for you, but 90, 90 to 95% of my messages are things that.

Gil: Isn’t an issue. They have a small little question that has a pretty canned response in there, but I, I do wanna respond by, like, I don’t wanna do, like if this, then that, but like using AI in this manner has been super effective on that.

Chad: Yeah, and from my understanding too, it’s also will pull some of the history and data from previous messages and responses, so. I, I feel like having a system like that where it could continuously be learning is super beneficial. And that would kind of answer, uh, your question with being able to automate some of that.

Chad: So it’s, instead of having to manually update a file or an SOP, it gives you the capability to just like it continuously learn on its own.

Gil: Yeah, and I think like with anything, the way that I would think about these agents there is that you have to treat it. Like if you’re treating a new hire on your team there, it might not know exactly what your pro procedures are. So you’re building these SOPs and you’re trying to teach it over time. But the great thing about using AI agents, um.

Gil: That’s different than a VA is that it scales infinitely. Like there’s no ramp up time. Like if you need to add more properties on there, you can provide the same set of instructions, change it any way, and you kind of know how it performs there. Where with the va there is this ramp up time. Yes, you’ll have your SOPs.

Gil: Yes, you’ll have your, your processes and your checklists and everything, but it takes time for someone to understand all the different parts of your business there. So like this, almost like supercharges it. I’m in no way of saying like. This is gonna replace VAs in any way. And if anything, like I have a couple VAs for across our, across our businesses.

Gil: And what it’s allowed us to do is allowed them to spend their time on more, more meaningful things that helps move the business, um, rather than really sustaining things. So it’s, I think like it’s more of a collaboration with AI and your team more than anything else.

Chad: I feel like there’s always gonna be that need for the. Real, real person or the personal touch. However, if you’re able to use it like a tool and um, a tool for your team to use effectively or allocate their time on more critical aspects that are really moving the needle for the business, that it, it’s, um, maybe AI’s not there yet in a certain areas.

Chad: In certain areas, then that’s like a really good position to be in. So.

Gil: Yeah. I think another way to think about, it’s like when you’re running a business, there’s a lot of things that you do over and over again. Um, but there’s also a lot of things that you are trying, new things to grow the business. And what I want myself and my team to be spending their time on is trying different things out.

Gil: So if they’re doing a repetitive task, um, try to figure out some way to automate that. It’s, it’s, it’s. It’s never been easier to do that. And so I want them, them spending time on like different ways to approach the business, um, and spending their time on more knowledge work. And I think like the overall quality of what they, what they grow their skills on is gonna be much more meaningful that way.

Gil: I.

Chad: Yeah, I, I think that that’s a really good, um. A good element to try to focus on because if you aren’t able to, um, like auto, like if you aren’t able to delegate or automate, uh, something, then that would be a good role for a hu like a human or virtual assistant or other, uh, member on your team. But if you are able to automate or, or delegate it, then it gives you the time and capacity to focus on like the things that are really moving the needle.

Gil: Yeah, we, you’re talking about like, um, custom gpt and quite honestly, uh, I’ll, I’ll, I’ll admit this onto the show even like. Two, maybe three weeks back, I didn’t know what custom gpt were. And people were like, what do you mean? Like, we’ve been using this forever. And I was like, I’ve been using AI in different ways, but I haven’t learned about custom gpt.

Gil: And I started diving into it more recently and the, the test case or the use case that I’m doing on is to figure out like how I can be a more effective father. So what I’ve done is I’ve created a custom GBT that knows. All my parenting styles that I aspire to. So I, I, I kind of worked alongside Claude and JG PT to like figure out like, okay, what is my parenting style there?

Gil: And then, um, then to choose either books, resources, guides that can align with that parenting style and then. Using that to feed in as like you, you talked about your, your documents that you upload. So it could be full transcripts of books or it could be summaries of it. Um, but also then combining that with context about me as a person and where my shortcomings are.

Gil: So it has like all the things that I wanted to feed it from a knowledge standpoint, what I wanted to give back to me, but also layers in the context of what my kids’ habits are. What’s my parenting style? What are my. Like where the, the areas of opportunities for me to grow in and kind of merge that together so that when I ask it a question of like, oh gosh, kids are having trouble waking up and I’m trying to get them out the door.

Gil: Like, how, like how should I best approach it? And it knows how my kids react, it knows how I am, what I’m good at and not good at, but also knows like from the knowledge of like things I want to build towards. It gives me a very tailored response. And I was like, oh my God. Like this is, like, this is not possibly for.

Gil: So I, I, I, that’s, that’s, that was my use case in the cus custom GPT for the first time.

Chad: Yeah. And, and I, I feel like that’s a really good, uh, point to highlight. ’cause you could use it for, it doesn’t necessarily need to be on your business. It could be on the personal growth or maybe like a, if you’re trying to. Curate like a specific, uh, diet plan or a workout regimen. Like you could use all of these features so it knows you so well or the context that you’re providing it in and how you want it to respond.

Chad: Like it maybe there’s a, a certain author that you really resonate with. Or certain content creator, you could ask it like, be like, if you were, like you mentioned, uh, Alex Ram Moie. If you were Alex Ram Moie giving me advice on my business, what would, what, what advice would you give based on this situation?

Chad: So like, I think that’s one of the most powerful elements of using those custom GBTs as you could really tailor and curate the responses. So specifically to you and your situation or your business.

Gil: Yeah, and to kinda add, add on top, when you create your custom GPT specifically in this coaching scenario, like this is all about coaching and how to like coach you. Give it all the context of what resources you want, but also give it the context of you as a person or your business there. And when you ask your questions, you’re not having to, to redescribe your business to you.

Gil: So you can give it this big blocks of text or this and like 20 page markdown file about your business. And when you ask questions, it already knows everything there. And that becomes much more powerful. So like when you ask like, how do I get more leads using like. How do I get more leads? It already knows these are the tactics that you use.

Gil: These are things that does not work in your industry. Um, it’s able to give you a very tailored answer. So that’s, that’s freaking awesome. Yeah.

Gil: Um, Chad, moving on to like the, the second segment of the show. I would love to kind of hear from you some of the tactics that you’re using to drive up direct bookings in your business.

Chad: Yeah, for sure. Um, so I think, uh, one of the main things that we try to focus on is. Having such an amazing property that, well, f first of all, like if no one even enjoyed their stay to begin with, they’re not gonna come back and book with you directly. So we try to really make our properties different in a, in terms of like the branding and consistency. And there’s always gonna be maybe like certain variations depending on the property and location. However, like having like. We always like to have include like a really beautiful coffee bar and some kind of standout feature that makes it very marketable. So having those elements like built into your brand is gonna really help with, after someone stays, they’re gonna wanna come back and book with you again. So that’s where we will make sure that they know that they have the option of booking directly. We have some, uh, elements in our properties like. Uh, our website and some QR codes for like business profile to leave us a review on Google and things like that where they know and it’s very clear that there is an option to book directly and what’s in it for them to like how much money you’ll be saving and it will be end up being a little bit cheaper and you’ve already built that, uh, element of trust ’cause they’ve already stayed at your place and they, they like the property. So I think those are like. Some huge things that you know, first of all, making sure that you have an amazing place and people want to book with you a again, and then like letting them know that that option’s there and making it very clear and obvious, like on how to do that.

Gil: Yeah. Yeah, that, that makes a lot of sense. And I, I see that as almost like foundational pieces that you have. They ship put in place no matter what vacation rental you kind of have, it’s, it’s the same if you’re renting to business travelers or multi-generational families or young couples, like, I think those foundational pieces still hold true.

Gil: You wanna make sure that one. You’re providing a stay that people want to come back to, they want to talk about, and it goes above and beyond the whole Superhost badge or getting the five star review. It goes way beyond that. Um, people can tell the difference that you care about their stay and that they want to get their, like, you want them to come back and it’s not just for the review.

Gil: And then two, you make a good point of like, I’ve seen this more and more, and I didn’t realize this in the Be beginning, but more folks are actually. Going back to really old school vacation rental tactics of like leaving business cards at their property or some sort of signage at their property, that just signals to the guests that, no, you’re not just staying at an Airbnb.

Gil: You’re staying at a, at a branded and at a branded stay. And they know where to come back to. They want, you want them to walk away remembering that. Uh, they came from eco escapes and they’re not coming back from, from, from an Airbnb. I think that’s what you, that’s what I kind of captured out of what, what you said there.

Chad: Yeah. Yeah, for sure. And I think, um, like you need to understand that this process, like of building up a good. A contact list with a previous guest. It’s, it all takes time. Like we were talking, uh, before the show about the, the restaurant thing. So like, if you have that really cool restaurant that is a, it, it gives you that amazing experience.

Chad: Like maybe they’re throwing some stuff in the pan doing the, you know, the ball of fire coming out or preparing something cool at the table. You’re creating that cool experience and people are willing to pay that premium price. For that experience and if, and you might not go and eat there every day. However, if you’re gonna be going there on like all your special occasions or a reoccurring birthday, if you build up enough guests like that, you’re gonna have like slowly build up like a really solid percentage of direct bookings for your property and your business. So just understand that it could take some time and, uh.

Chad: I feel like a very overlooked metric in this industry that I know is like they focus on a lot more on other businesses is like the lifetime value. So if you know that like a guest is coming every summer or they’ve like maybe mentioned in their messaging that they’re gonna be coming back, like they come back for this family trip or their, you know, their father’s birthday to this location every summer, it might be worth it to invest a little bit more on like. You know, providing a little something extra for that person and they’re gonna make, it’s gonna make it a lot more memorable, and they’re probably gonna be a lot more inclined to come back and stay with you at your place like every year. And you build up enough people like that and you’re gonna have a really solid contact list of guests that are gonna be consistently coming back and booking with you directly.

Gil: Yeah. You, you, you mentioned a lot of good points that I want to kind of tease out just a little bit. Um, a lot, like if you go to a restaurant, you may discover them on Yelp or Google or somewhere else. But the restaurants that do really good, you remember that restaurant’s name. Um, and, and, and that’s kinda like what I want people to kind of bridge there where they may discover you on Airbnb, but you want them to walk away knowing your name, knowing your brand there, and thinking about you the next time that they’re seeking for that type of experience.

Gil: I think there’s a lot of correlations to the restaurant industry. We’re both kind of in the hospitality space, but really making sure that people will kind of walk away with you. Um. The, the point that I kind of wanna like make is like you talk about the, the fancy restaurant that you might want to go to and the restaurant’s there to really make sure that like you’re building that lifetime value there.

Gil: Um, restaurants know, and specifically the high-end restaurants, they know that if you go to that restaurant at least three times, they have you for life. And so what they do is the waiter will ask you. Uh, have you been here before? Is this your first time? And based on your response of that, they will actually do something different that is very subtle that you may not even notice.

Gil: Um, but what they’re doing is if you say that you’ve been there, this is your first time, this is your second time, and they’re trying to get you over that cliff, sometimes they’ll leave a red napkin at your table. Or they’ll put some flight. The play setting and what that is doing, it is signals to all the other waiters and people that are servicing you to make sure that they take care of you because they know that if they get over you to the third, to the third stay or the third visit, you’re gonna go there over and over and you’ll be a lifer there.

Gil: So next time you go to a fancy restaurant, see if they, uh, see if they leave you a red napkin or a special place setting, or they put out a candle on, on, on your, um. On your table, um, and notice whether or not your, your water cup is always full. It’s never empty. They’re trying to make sure that you stay there and you, that you have a great experience.

Gil: That’s not to say that like. Once you get to it the third time and you don’t get that napkin anymore, they’re not gonna, they’re gonna treat you like shit. It’s like, that’s not the case. But you’re trying to really make a good impression where they want to come back to you. And you, you, you have that memorable experience.

Gil: Like when I heard that that’s, that’s such an amazing like metaphor that you can apply to pretty much any industry.

Chad: Yeah, for sure. And especially like, um, even though it might not necessarily be the same as, um, the short term rental industry, it’s still, uh, hospitality and you’re still, uh, serving a customer or a guest and there is a lot of, uh, transferable skills that you could, I. Pull and recognize, especially after being in this space, like, um, not a lot of people might, uh, even pick up on the napkin thing. And it’s, it’s pretty cool that you, uh, mention that. ’cause that’s something that, like, we actually make notes in our, uh, property management software. Like specific things about the guests. Like if they’re coming back for, if they mentioned that they’re coming for a wedding anniversary or something like this, and it could be a really good thing to put into, uh. Like a, your CRM for a follow up email. You could make a note and then you could, uh, you know, follow up with them, uh, maybe like at the beginning of the summer and say like, you know, we loved, uh, hosting you at your, uh, wedding anniversary or your birthday. If you, and you could be like, Hey, we have like a, maybe like a little offer.

Chad: We would love to welcome you back again and. I think that’s like a really good, uh, element and if you’re able to, you know, make a few notes on some of those guest profiles to really like, personalize the experience, it, it, it’ll go a long way. People will really appreciate, like you recognizing that I.

Gil: Yeah. Um, I haven’t found any good tools around this. You mentioned CRMs. I haven’t found a really good tool specifically for our industry that tracks. Guess their experiences, notes like that stuff, and kinda like how you tailor maybe your messaging towards them or the things that you do. I don’t know if you’re doing anything special there or you have any special tools that you’ve deployed that worked really well.

Gil: Um, but I feel like this is a huge gap in the industry that if it doesn’t exist already, like someone should be solving this problem of like making sure that we understand who the guest is and how to effectively message them, how to bring them back and make them lifers.

Chad: Yeah, I, I think you’re absolutely right. There is a, a little bit of a gap there. I, I know like, um, in, uh, our property management software, you can put custom tags. So that is something that we will do and we will have a tag for like repeat guest or some. Maybe like it was a special occasion or even like a problematic guess.

Chad: So we know like, uh, if they reach out to us again, we might not necessarily want to accept that booking. So I think that’s a really good tool. I think, um, there is a gap though, like in terms of like that customization. So if you do have like a property management, uh, software that allows you to make notes or apply those custom tags. It’s a really good thing to, for your team to refer to and be like, oh, this guest has like, booked with us a few times. Like maybe it’s worth, uh, tossing the red napkin on the table so everyone knows and we maybe, like, they’re coming on a reoccurring basis and the lifetime value might be a little bit higher, so it’s worth to, you know, maybe do a little something extra for that, for that person.

Gil: Yeah. Yeah, I like that. We’ll see the, the, the industry’s evolving quite a bit, so I, I wouldn’t be surprised 12 months from now, there’s this killer startup out there that’s trying to figure out how to merge all your booking data with their guest experience, making sure that your management team or your, your cleaning staff knows how to handle that as well, too.

Gil: Like there’s gotta be some, there’s, there’s something in that space. There’s a void there that needs to get filled sometime.

Chad: Yeah. No, I, I, I wouldn’t be surprised, especially like you said, how quickly everything is evolving. Like if you think of like in context of like all the other business models, like this is a still a very new industry and I. It is evolving very quickly. So yeah, I wouldn’t be surprised if they had some, uh, if there was a new startup, like maybe they listened to our podcast and thought it was a great idea

Chad: and integrated in their business in some capacity.

Gil: Yeah. Yeah. Give, gimme a holler when, uh, when you guys get rich, whoever’s gonna create this.

Chad: Yeah.

Gil: Awesome. Um, you mentioned kind of one last point on the direct booking site. You mentioned Google business profile there. Talk to me a little bit more, more about that and why you think that’s important.

Chad: Yeah, I think it’s, uh, a really, really great, like low hanging fruit that anyone could implement right away is just having a business page set up. And if you have, like, you could have a custom QR code generated, which, what is what we do? And we say like, if you, you know, enjoyed your stay and. Would like to, uh, leave us a review.

Chad: Uh, you could scan the QR code right at the property and that’s going to help tremendously with, uh, SEO and building some organic traffic to your website. ’cause if people are searching, uh, on Google for a vacation rental or a place to stay in your specific location, it’ll bump you up in the rink and you, you could actually drive a lot of traffic that way. And also on the property management side, like if you have, uh, if you’re looking to get more clients and they see like they Google short-term rental property management, if you’re ranking high and you have a lot of good reviews, you’re probably gonna get, like, we get a, a good amount of calls from people who have found us on Google.

Chad: So, and always ask for reviews. ’cause if you, you don’t ask, it’s a lot less likely that you’ll get and don’t feel bad about it. Like if you gave people. An incredible experience and they had a great time staying with you. Or even if you had, um, you know, like a meeting or a ma management client that you’re working with and they’ve had a really good, uh, time working with you, and they, they’re happy with the results and their property performance, like, just ask them for a review and, uh, it’ll, it’ll help you out a lot.

Chad: So I think that’s a, a really good one that anyone could, uh, in incorporate and implement right away.

Gil: Yeah. Yeah. I think that that’s often overlooked and I think what’s happening kind of behind the scenes for any of our listeners here, for your webpage to rank highly on Google, we call them SEO, search Engine optimizations, but there’s like one specific type of search engine optimizations that this is really benefiting and it’s really around backlinks.

Gil: So Google will look at your webpage and see whether or not it performs really well on site performance. It’ll look at your page and see whether or not the content relates to the queries that people are looking for, the searches that people are looking for. Um, it’s also looking at, um, and because of that, how much if, how much time people are spending on the page.

Gil: Um, but it’s also looking at. How much authority this site has site authority. And the way that Google kind of ranks site authority is whether or not there are reputable sources sending traffic back to you, and vice versa. Are you sending traffic to others? And the more that you see, Google sees this connection, they know that it’s not just.

Gil: Some business that started up last week and um, is not known EL elsewhere. And so what you’re trying to do is you’re trying to generate back links. And a great way to generate back links is local businesses referring people to you, the Chamber of Commerce. Um, any pages that kind of link back to you, Google will index that and tie that back to you.

Gil: But what you’re doing is you’re actually using, in this case, a Google business profile. You’re actually using. One of the most highest sources of authority, which is Google themselves. And you’re saying, if Google’s business profile is pointing back to your homepage, then you’re actually gonna rank a little bit higher.

Gil: And that’s also why you wanna include your Facebook, your website, and your Facebook link and on your Instagram. That’s more links generating back to you. And when Google is that, it starts to slightly bump up your site authority. I don’t know if people knew kind of like why you should be doing these things.

Chad: Yeah, that’s actually really interesting because I, um, I knew that obviously it’s gonna help a lot if you have, uh. Links or partnerships with local businesses, and especially if like, maybe you have, uh, some of those, uh, favorite restaurants or cafes that are featured in your guidebook on your website, you could have the links directly to their site and, uh, vice versa if you have those good relationships.

Chad: So I think that’s a really good point, and I wasn’t even fully aware that that’s how, that, like it’ll boost your ranking that much. So that’s, I, I appreciate the advice on that

Gil: Yeah, that’s one of the benefits crafted. For those that don’t know, crafted stays. Is actually backed by Google. Um, so Google for startups actually, um, they pay for a lot of our infrastructure. They do, they give us a lot of training on just how to use their cloud infrastructure because our entire platform is built on, on GCP, Google Cloud.

Gil: But because of this relationship, it allowed us to seek out Google on how do we optimize our templates, our pages. To be highly SEO optimized, and we get to ask silly questions and really understand like if we’re helping our hosts rank higher in search, like what are the things that we can do internally within our site, but also how do we educate our hosts to do other things outside of us, like generating back links, that helps ’em as well too.

Gil: So that’s like one of the, the small little fringe benefits from being backed by Google.

Chad: Yeah, no kidding. And probably not a bad, uh, company to be backed by.

Gil: That’s not, not that company to be associated with. Definitely. For sure. Awesome. Chad, I absolutely love this conversation. Um, we usually end the show with, um, three questions. Um, so I’ll go with the first one first. What’s a good book recommendation? I’ve been looking for a solid book to, to read. Not that I have a lot of excess time, but.

Gil: I will make time for a good book.

Chad: Okay. Yeah, for sure. One that I’m currently reading and it’s actually, um, it’s one of the. Few books that I’ve, uh, reread a few times. It’s, uh, the second time now it’s called, uh, profit First. It’s a really good business on, uh, or a really good book on, on business and accounting and, and, uh, how we were talking about previously about having those, uh, allocations for your personal budget.

Chad: This is pretty much, uh, using it for your business, so like how you could allocate certain percentages for your taxes, operating expenses. Your owner’s compensation, which I feel like, um, a lot of businesses might not ha have that same, they don’t really, they look at more the general accounting practices rather than, you know, they just toss it all to their accountant and they’re like, okay, how profitable are we?

Chad: How’s the p and l look? But if you’re have that pulse on your business and you understand how much money you’re taking in and you’re making those allocations yourself. You’re gonna have a really good understanding of the actual profitability and how much you’re, how much is going to operating expenses.

Chad: ’cause that’s one thing that I think could, uh, get outta hand really quickly, especially as you’re growing.

Gil: Yeah, and I think like, because maybe you start off on the long-term rental side and you consumer of BiggerPockets, we do a lot of like. Por FMAs. And one of the line items that we almost always bake in are your reserves there. And I, I’m, I’m guessing like that has actually a very tight tie to profit first.

Gil: Because what you wanna do is you make sure that you’re allocating your budget for all the different things, especially in our space, just to wear and tear that our properties go through and the reserves. So you’re not just looking at cash flow, uh, and how much money is actually going into your pockets or your business, but you’re looking at like.

Gil: Does each one of these accounts have what it takes to have a very sustainable revenue for the long term?

Chad: Yeah, and absolutely, and I think that’s, uh, really critical. Especially in this industry and real estate is making sure that you have reserves in place for, you know, things that might not necessarily be accounted for or even, uh, for like having a budget for maintenance or some of the major, uh, items like your roof or your hot water tank.

Chad: ’cause these are things that won’t last forever. So, and if you’re not accounting for it and you ha get hit with a, you know, a few thousand dollars bill for one of the. Major capital expenditures for a property and you don’t have the money. It could be, it’s not a really good situation to be in. Same thing with your taxes.

Chad: If you’re not like, you know, setting some money aside to pay Uncle Sam at the end, end of the year, you know, you get hit with a huge tax bill and it might not be, uh, the fund and it’s not, probably not the best situation that you’d want to put yourself in.

Gil: Yeah, it’s, yeah, absolutely. You made me chuckle just a, just a bit because when I think of you being Canadian, I would not think that Uncle Sam was the term that you would be using to talk about paying the government, but it just cracked me up.

Chad: Yeah, well, uh, make it relevant to your audience and I think, uh, even most people in Canada could, uh, resonate with that analogy. So.

Gil: Awesome, Chad. Second question. What’s uh, one piece of mindset advice that you would give to someone that’s starting something completely new?

Chad: Yeah, I, um, I feel that probably one of the best things is understanding that it’s gonna take time. Like whether that’s building your direct booking, uh, list or, uh, scaling your portfolio like. It’s not gonna happen overnight and you’re gonna have to make sacrifices, especially being younger. I feel like a lot of the people that are maybe my age are just starting out want to like experience that, like rapid growth and of course like that’s ultimately the goal.

Chad: But you would probably, like, one of the, one of my favorite quotes is you will always, uh. Overestimate what you could do in a year and underestimate what you could do in 10. So having that longer term time horizon will be tremendously helpful with, you know, like if you’re going through a rough day, it’s just a period in time and you will be able to, you know, push through.

Chad: And if you know what your long-term goal or vision is, that that’s like what’s really gonna drive you and know that it’s not gonna. Just happened like super quick. So I would say that’s probably one of the biggest thing that’s has been like super helpful for me.

Gil: Yeah. That’s awesome. All right, last questions. We dug pretty deep into a lot of, a lot of tactics around direct bookings. What’s, uh, one tactical takeaway that you want our listeners to put in practice today? Either to start their direct bookings or to amplify it?

Chad: Yeah. Well I think one of the best things would be to. Uh, you know, implement the Google page and going back to the old school methods, especially with a lot of the changes on the OTAs with them being, and like the AI is advancing super, super fast. So they’re gonna be able to detect if you’re, I. You know, messaging anything or hinting to direct bookings and the message threads on those platforms.

Chad: So just put some, uh, material out at your property so like they know that they can come back and book with you directly and they don’t have to be searching for you on Airbnb or one of the other channels. So just doing a few things like that. So they are very, it’s very clear that, you know, you could come back and book with us directly and you’ll save them money. So like highlight the benefits to them and, you know, I think, uh, having like a sheet or like a form at your property, laminate it so something doesn’t get spelled on it. Uh, but it’s just like a very low hanging fruit that anyone could, could do right away.

Gil: Yeah, I love that. I love that. And it doesn’t take a lot of time, and I think like if you’re a Google business profile, you. Might have to do some verifications to make sure that you own the whatever you’re p onto the map there. Um, but it’s highly valuable for a lot of different reasons. You’ll solve, I think prob problem most importantly is you’ll show up and search more effectively.

Gil: So that’s a great tip,

Chad: Yeah.

Gil: Chad. It was, uh, really, really good to kind of walk through kind of how you’ve grown your portfolio at the age of what are you 2025 right now.

Chad: Yeah, 25.

Gil: That’s, that’s amazing. Just kind of walking through that journey, the sacrifices that you had to make, the, how you built out your team and you’re thinking about how to leverage AI and some, some good strategies on really how to get some really strong foundations around direct booking.

Gil: So I appreciate all the time and all the effort that you put into the show. Where can folks find out more about you? How can they keep in touch with you?

Chad: For sure, uh, probably we have like the best following and we’re the most active on, uh, Instagram. So we have, um, our page, which is our business page, eco Escapes, uh, 7, 8, 0, and then my personal page. Uh, is Chad Harker, 7, 8, 0. And yeah, we try to post as much value and like tips and what we’re doing and what’s working, what’s also not working where. So that’s a, a really good, uh, place to find us and get some good, uh, tips and tactics on, you know, things that we’re implementing or things that you could use in your business.

Gil: Awesome. Well, Chad, I, I can’t wait to. Kind of see how your portfolio grows and some of the things that you’ll be tackling over the next 10 years, uh, and even the next one. So definitely, I’m glad we had you on the show and all the knowledge that you shared.

Chad: Yeah, for sure. Thank you Gil. And I could say the same for you, especially with how much growth that your business has, uh, experienced in like the short time that you’ve been started. Like, it’s gonna be exciting to see where you’re at, like a year or two from now. So. Looking forward to it and uh, hopefully we’ll catch you at one of the cool conferences or events.

Gil: Yeah, likewise. I appreciate that. Thanks, Chad.

Chad: yeah, for sure. Take care. Thank you.

Gil: I.

Chad: Bye.