The Direct Booking Revolution: The Rise of HostBuddy AI with Jay Ullrich

Summary and Highlights

Jay Ulrich, CEO and Co-Founder of HostBuddy AI and COO of Select Stays, is on a mission to shake up the short-term rental (STR) industry. After launching his own property management company in 2021 and scaling it to 50+ rentals across San Diego, CA, Jay saw firsthand the cracks in the system—especially the dangers of relying too heavily on platforms like Airbnb. That experience inspired him to co-create HostBuddy AI, the market-leading messaging platform built to streamline guest support, slash operational costs, and empower hosts with smarter, tech-driven solutions. Today, Jay is redefining what success looks like for property managers by helping them take control of their bookings, their brand, and their bottom line.

🛠️ Game-Changing Lessons from Jay

🔥 Turning the Tables on Airbnb

• From Platform Dependency to Power Moves: Jay breaks down the risks of relying too much on OTAs, sharing real-world stories of listings tanking overnight due to Airbnb policy shifts. HostBuddy AI was born as a safeguard, giving hosts the tools to build stability, security, and profitability through direct bookings and it’s changing the game.

🎯 The Magic of Micro-Niching

• Stay Narrow, Win Big: Jay swears by the mantra that “broad is broken.” Instead of chasing massive markets (like general inbox management), Host Buddy digs deep into the short-term rental (STR) space, crafting tools that speak directly to hosts’ pain points—from PMS integrations to task tracking. His advice? Own your niche first—scale later.

🌐 Tech + Hospitality: The Perfect Blend

• AI That Works for You: Jay reveals how Host Buddy’s AI is built to do the heavy lifting think seamless guest messaging, smart booking widgets, and friction-free pre-booking convos. By weaving AI into the guest experience, Jay’s platform is driving higher conversions and freeing up hosts to focus on what matters: stellar guest stays.

🚦 The Roadmap: From STR to Boutique Hotels

• Scaling Smarter: While STRs are Jay’s playground now, his vision doesn’t stop there. Once Host Buddy locks down its niche, the roadmap leads to boutique hotels and bigger fish in the hospitality pond. His strategy? Nail the niche, then widen the net.

🛎️ Lessons from the Trenches

• Adapt or Get Left Behind: Jay’s journey is a masterclass in agility. In an industry where Airbnb can tank your listing overnight, he’s laser-focused on future-proofing his business and helping hosts do the same.
• Local Leverage: Beyond tech, Jay taps into community-based marketing and loyalty-building, like his “Premier Membership Club” that keeps past guests coming back through personalized outreach.

🚀 3 Power Moves to Steal from Jay

1. Niche Like a Pro: The tighter your focus, the deeper your expertise and the stronger your brand.
2. Build Resilience: Diversify your booking channels early to protect your business from OTA curveballs.
3. Automate + Convert: Invest in AI that truly understands your industry to optimize guest engagement and grow your direct bookings.

Jay Ulrich’s vision is crystal clear: empower hosts with tools that don’t just work they win. Whether you’re a solo host or scaling a property management empire, Jay’s blueprint is all about control, consistency, and growth on your own terms.

Transcript:

Jay: Make sure that you don’t send retargeting messages directly through Airbnb so that Airbnb sees it, because we did that a few times at the very beginning, and they will immediately remove your listing. So that puts you in a kind of a bad position. You gotta be kind of sneaky about it, but if you wanna look for direct bookings, find a way to collect that.

Guest information. There’s a lot of cool tools out there. Guidebooks, the phi. Great, great tool. People can collect their information for direct bookings. Find a way to retarget these guests, ask them for their information, and that way they can feel like they’re, you know, part of something, part of your business, and that they know you personally and then they’re happy to consider you and they come back to, to the city that you’re hosting in.

Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring in top operators in the STR space to share their experiences in marketing, guest experiences and operations to get books solid. On today’s show, I have JO Rich, he’s the founder and CEO of host Buddy ai. I met him last year at the STR Nation Conference.

At that point, he was just starting off his company. He was just growing it. And what they’re really trying to do is really help host automate their guest messaging so that they can spend more time on other things and have a very consistent guest experience. I have seen and have used their product. It’s a very phenomenal product.

In this show. We get to pick apart why he started the company in the first place, where the problems that he wanted to solve, how he has built host buddy, and why it’s different than some of the other Chi Chat agents and kind of where he sees AI going, where he’s taking the company. And some of the things around direct bookings as well too.

Jay is actually going to be a customer of ours pretty soon. He’s gonna be building his direct booking stack on top of craft his days, and he’s looking to collaborate together on how direct bookings and his chat agents are able to kind of work together. So tune in on the show. I think there’s a lot to, to kind of dive into and learn about really AI in general by someone that’s specifically building AI for the industry.

So I’m excited to have him on.

Gil: Hey Jay, welcome to the show.

Jay: Thanks, Gil. Appreciate you having me.

Gil: Yeah. I’ve seen you a bunch of times at many different conferences. I know you just came back from, uh, from your leg abroad. Um, so definitely welcome to the show. Um, for folks that don’t know who you are, do you mind giving, uh, folks an introduction on who Jay is?

Jay: Yes, so I am a property manager first. It’s usually how I introduce myself because. It’s probably the most important part of everything that I’m involved in. It’s, it really fuels my, um, you know, my vision for creating the software that I’m involved in and also the business. Um, so kind of taking it back to where I got introduced to short term rentals as in 2021, um, I began managing.

Jay: Short term rentals in San Diego, California with my business partner, Sam. Um, I started as a civil engineer right outta college and just tried to find a way to kind of get outta that. I really wanted to own my own business and take it a different direction. Um, and short term rentals was that path for me.

Jay: So in about nine months, I was able to quit my job and go really time into short term rentals. And, um, from there, just, you know. Listened to all the podcasts, found all the right tools, talked to the right people, and just kind of fell in love with the automation process of scaling short term rentals. So, um, and around 2023, I was looking for ways to automate our guest communications.

Jay: So my business partner Sam, came to me with the idea of, you know, automating with ai and we started exploring some different options, but there was nothing on the market at the time to really. Take care of all the guest messages that were coming through our property management system. So decided to team up with our software developer friend and create a tool called Host Buddy ai.

Jay: Um, so that’s a new tool on the market as of May, 2024. We’re just about a year old. Um, but growing very quickly and um, yeah, trying to solve as many pain points in the industry as possible. Along with being a host myself, we scaled up to around 50 properties now in San Diego.

Gil: Wow. Did you, uh, as you’re scaling up to the 50 properties, at what point did you realize we can’t do this ourselves now and we need help from, from ai? Like what was that inflection point for you?

Jay: Yeah, so we, we hired our first va, uh, probably way too late. Honestly, like we, I think we were messaging all of our guests until we had about maybe 10 or 11 properties. Um, and at that time we hired a va. She took over guest communications for. I think just six hours a day. So like the first like checkout shift and then the check-in shift in the afternoon.

Jay: And so we used, um, her support up until uh, we think we got up to 20 or 23 units and we were like, there has to be some way because we really like this VA that was on our team. She still works with us today. She’s amazing. Um, but we were like, we can’t afford to just hire somebody overnight to, to cover our guests.

Jay: ’cause we had so many things popping up like. Hey, I can’t check in. It’s late at night, or I don’t know how to use the AC or the TV’s not working, and if we have to be rolling over in bed to answer guest messages on our phone in, in the middle of the night or answer, uh, phone calls. It was just, it’s not something that’s scalable and it was ruining the, uh, the quality of life that you look for as a Shortterm mental host.

Jay: So from there we were like, you know, there has to be another way. And we were kind of playing around with AI in the beginning of 2023 is really when, like chat GPT, I think 3.5 came out and. It really changed the game as far as the capabilities of, um, you know, customer service. So. We thought something could be possible to, to implement into our, into our business.

Jay: And, um, luckily there wasn’t anything there. And now we get to, uh, create it ourselves. So, um, yeah, I think by now I mean we have 50 properties. We only have two VAs now it’s, it’s really just covering from, uh, 8:00 AM to 10:00 PM So one does the morning shift, one’s does the evening shift or afternoon shift.

Jay: And then, uh, overnight we don’t have anybody, but we have host buddy available. So the host buddy is responding to every single guest message that comes through our property management system. Um. Every hour of the day. And so the VAs now get to focus on all these other things like listing optimization, air cover claims, um, reviews, you know, improving our properties and working with our operations manager to do so.

Jay: So I think by now, if we didn’t have the ai, we would’ve had to hire several more VAs. So it really saves us a lot of time and money, and it’s improved our property so we can stay competitive.

Gil: Yeah, yeah, yeah. And so, so I’m, I’m a user myself. I, I, I started using you quite a while ago, and I remember in the very early days, I was very hesitant to even relinquish. Guest messaging over to, to host buddy, and I know that you guys have like this ability to, um, not have auto respond and actually like generate the responses for you and then use those, um, as a base to, to whether or not you send. me a while to figure out like, okay, actually it’s responding better than I have. And I think it was like the 10th message. I was like, okay, maybe I should just lead this on auto. I, I’m curious on like what, what your experience is and, and how you’ve seen hosts really adopt it and kind of get comfortable with it.

Jay: Yeah, so our goal from the very beginning was to make sure that the AI could respond efficiently to the majority of your message, like 90 plus percent of your guest messages, and even more now, I mean, we have hosts that are automating a hundred percent just by including the right SOPs and giving the AI the right information, right.

Jay: Um, and so from the very beginning it was like, how do we make sure that it’s not just a draft so that the host doesn’t still have to be involved and just like hit approve or edit the message and then send it out. Like we want them to trust it, obviously. Um, but I think a year ago the story was a little bit different.

Jay: I. We got our first testers with the software and the STR industry moves so quickly, and that’s what I love about it, is people adopt new tech so quickly and they’re willing to use ai. Um, and so about a year ago it was, it was definitely a different story. People were a little bit more, um, hesitant to use it and people still are in general.

Jay: I think there’s a lot of, I mean, there’s so much market to, to still cover as far as automating the, the guest messaging, but. Um, yeah, we find that at least providing a little bit of an option for users to at least have a testing ground to see how AI would respond in a real scenario, and then also manually generate those messages in a real conversation as well.

Jay: Um, but we didn’t want to give them like, uh, training wheels that they never want to take off really. So we, uh, we made it so that, you know, we kind of push people to really just schedule it, see how it responds, and then that trust is sort of built from there. But what we’re finding is a lot of our customers are coming from word of mouth.

Jay: Um, a lot of organic inbound, uh, customers come to us. So it’s, it’s friends saying, you know, this has automated such a tremendous responsibility in my business, and they’re recommending it to their friends, which is really great.

Gil: Yeah. Yeah. You mentioned, uh, SOPs there. So for me, I have my, my touch day. Uh, PDF like uploaded in there and I was actually pretty impressed with that. It was able to like, pull in all the information from, from those guidebooks. Um, I think you guys do something a bit different where you’re actually not relying fully on standard like. Legitimate SOPs, but you also read past messages and how guest responds to, How host responds to different, um, different things, common things that come up of like how you turn on the fireplace. How do you, how do you get the hot tub to work? Like you’re, you’re able to actually like go through past messages to figure out like, okay, is this something that’s similar and can I respond to it?

Jay: Yeah. That’s a really helpful part, um, to making sure that AI can respond efficiently. So first of all, it’s going back in your past conversations. We take six months of conversational data, so it’s gonna realize like, have you already provided information about local recommendations or troubleshooting instructions on how to work the tv or how to turn on the water heater, fix this, fix that.

Jay: Um, so it’s using that information and then storing it. In the database for future use, and that’s all within the property profile is what we call it. So you’re able to go and see where that information’s stored, edit it when things change. Um, and then, like you said, yeah, download specific, uh, documents like, uh, like digital guidebooks and things like that.

Jay: But the second thing that the, um, that the past conversations does is it’s gonna read your tone and kind of analyze how you normally speak. So it’s helpful. A lot of times, you know, property managers, they’re either. You know, sometimes they’re a lot really lengthy with their responses. Sometimes they’re rather short.

Jay: Um, sometimes, you know, they don’t respond to a simple thank you, but other people do. So it’s, every business is different. But if we’re able to mirror that host tone at the very minimum, um, that allows you to kind of feel like an ex, it’s an extension of you. And then when you hop into the chat to say something, uh, you know, after host buddies already responded, it doesn’t really sound like it’s two different things.

Jay: You know, it’s an extension of, of yourself, which is really helpful.

Gil: Yeah, actually that that leads to one of the questions I had for you around just generally ai. We’ve seen AI used pretty prevalently now across. Many different use cases and, many times it feels a bit robotic and it feels a bit, um, scripted there. And I’m curious on, like you guys what, what you’ve done, and it sounds like you’re using that, the, those past histories.

Gil: The tones, and using that to kind of, um, train your model to figure out like how should your, your AI respond to you so that it feels authentic.

Jay: Yeah, I mean that’s like. I think the, the base tone that we’ve created within Host Buddy is extremely hospitable. It’s the best on the market in our opinion, as far as like the most human-like AI that you’re gonna find. Um, and it, it didn’t happen overnight, so we, we spent a long time perfecting that language so that it was gonna sound like a super host.

Jay: Um, and we wanted that, you know, Superhost quality language and tone and cadence and all that. So. We had basically an unlimited testing ground with our own property management business to run all of these guest messages through our AI and make sure that it was responding right? So we were looking at this every single night.

Jay: Every morning when we wake up and we’d see all these messages that had come in overnight. How did host buddy respond? And this was between, this was before we even launched the product. So we wanted to make sure as soon as it went public, that everyone was gonna have access to the best AI in the market and it was gonna be immediately effective.

Jay: So that’s our advantage compared to some of the other AI tools in the market like. Right off the bat, we found that people were coming to us from competitors just saying like, I didn’t like the way this person was, or this AI was responding. It was hallucinating, which is, you know, a major problem in general, um, that we eliminated.

Jay: So, um, yeah, the, the, the trust component of that is just, is, it’s so important. Um, it, so as hosts ourselves, we were able to kind of use our own perspective to develop it the best. And obviously our, uh, our CTO is, is really talented with AI development. So, um, you know, he, he basically made it happen.

Gil: Yeah, I’ve, I’ve, I’ve had a chance to, to meet Michael and, and even just, just talk to him because I’m, I’m on the side doing also AI development, not, not within our STR space, but just generally playing with. How the technology works and how, how it all pieced together. And when I chatted with them about. of the complexities that you guys had to go through of creating a host buddy and what the AI infrastructure is there now. Like you’re still having to build a lot of pieces. You’re having not just the the dashboard, but the connections into the PMS and just how you provide the context that it needs to do.

Gil: There’s actually a lot of infrastructure that happens behind the scenes, and I think a lot of folks now may feel like, oh, AI makes it so much easier to make development happen, but it’s still product development at the very end of the day.

Jay: Yeah, and I think the term that people sometimes use is, like, for the software is like that. It’s a, it’s a wrapper of another LLM and for us it’s, it’s a lot more than that. There’s, there’s pretty. Deep engineering that, that goes along with it because it, you know, then, then that’s, that’s a, that’s the main reason why like the PMSs haven’t been able to develop something like what we’ve done.

Jay: You know, a lot of them have tried and a lot of them have simple AI autoresponders or, uh, draft message messaging. And, um, it just comes down to understanding in those situational, you know, testing environments, you know, every single business is different. Every guest is different, every property is different, so.

Jay: If there’s so much testing and engineering that goes into it, it’s um, it’s definitely a project. It’s not an easy thing to, to accomplish.

Gil: Yeah, I, I think what you mentioned earlier about you guys being property managers or yourselves, you being host yourself, I, I have a lot of empathy towards, that type of founder. Me being like, craft estates came out of me trying to build our own direct booking websites and kinda getting fed up with all the, the platforms out there.

Gil: And when you’re building it yourself, I found that. You really get to one, you’re dogfooding it like you’re, you’re, you’re having to, to live and taste what, what the product is actually doing and whether or not it’s doing what you wanted to do. that iteration cycle is much quicker because you know what you’re, what you’re trying to accomplish, you know, the challenges that you’re going through is just, I think like founder led, like products are that, that, that have the same problem, really rips through that learning curve really, really fast.

Jay: It’s amazing. I mean, going to these conferences and being able to speak from the perspective of a host and, um, really understand like deeply those pain points that property managers are experiencing. And it’s not like we only manage like one property, two properties. Like we have a, a, a solid size portfolio where we get.

Jay: A good understanding of how to scale and how to limit your, your expenses and, and really slim down your, your tech stack so that it’s most efficient. Um, ’cause there’s a lot of options out there, you know, like you said, there’s just like a lot of people creating a lot of software. Um, and it takes time for the, uh, you know, the industry to kind of weed out the ones that aren’t super effective and, um.

Jay: Hopefully I can speak from the property manager manager’s perspective authentically, and people understand that, you know, I’m not just somebody in the tech space that came in here trying to fit into an industry. I don’t understand. Um, and there’s two of us, me and Sam, you know, that’s our entire life is managing properties for short term rentals.

Jay: So, um, yeah, super helpful and I love kind of having that dual perspective and continuing to scale our, our property management business. Like we were at 38 properties at the end of last year and now. We’re at pretty close to 50, so we’re continuing to get opportunities and, and be able to take on them when, when needed, just because we’ve been able to automate all the repetitive tasks that, that are within our business.

Jay: Like I really only spend a couple hours on the property management per week. Um, but we’re still involved, like with our team, we have team meetings and we make sure that things are running smoothly, but we put the right things into place so that they have the right resources, the tools are running efficiently.

Jay: When things need to be updated and host buddy, our team knows how to do it. They’re, they’re very familiar with our tools. So, um, bringing all those things together and just seeing it run like a well-oiled machine is, is really cool.

Gil: Yeah. One of the things I found interesting as, as, as a founder that’s pretty deeply involved in the product development, um, and, and kind of serving your clients is really love to latch onto really. Innovators in our space, customers in our space that are trying to push the envelope on things and trying. I love those like really big vocal clients, those enterprise clients that have hundreds of doors and they’re looking to do a whole lot. And I’m, I’m interested in hearing from you whether or not like you’ve had the opportunity to like work pretty deeply with one of your clients and seeing like what things trying to do and, and how that has evolved your product.

Jay: Yeah, that’s a amazing question. Um, because I think. Like, that’s something where for like as you, I can understand, like you as a, uh, a software founder, like that’s something that you’ve experienced and that’s something that I don’t, I don’t get to discuss enough, is just that iteration process and refinement of, of the product for different portfolio sizes and.

Jay: Making sure that you’re fitting it into the market properly. ’cause short term rentals is crazy. Like you have a customer that comes in with two properties and they’re able to automate the guest messaging and they’re so happy they did it in two minutes, and then you have somebody with 200 properties and they’re like, whoa, this is gonna take a lot of time.

Jay: Um, and that’s kind of what we faced within the first few months where we had some people interested who had managed, um, like a hundred plus properties. Um, and we realized that our onboarding process was set up so that. The autofill feature from the property management system just wasn’t super streamlined.

Jay: Like it was a bit more managed or manual of a process to go and enter in that information. Um, so we made it really easy. So that Right, right, right. When you connect your property management system, all that data’s gonna come in. Um, it makes it super simple. There’s so many things that we want to continue adding though.

Jay: It’s like, um, just a never ending list of. Of requests from, from users, and we’ve prioritized that and we, we have a product roadmap on our inside of our portal so that people can kind of vote on, you know, what’s their most, um, interested, what are they most interested in, in seeing out of us. A lot of times it’s mobile app, um, additional integrations.

Jay: Um, just additional functionality and all that’s being worked on in the back, in the background right now. So really excited to, to release some of that stuff. But, um, yeah, no, especially at the beginning, we worked directly with a lot of our users just to make sure, like how. Where are we missing the mark?

Jay: Um, right, because we built the pro, we built the, the system to work for our own property management business, but it’s not the same as everybody else’s. Um, so yeah, everyone else has different resources. Everyone’s got like an SOP guide in a different software that’s like, um, you know, living in a different place and they all have their systems connected differently.

Jay: So we’re really involved in the process and like. Sam and I are still involved in, in a lot of the customer service aspects of things because we want to understand what people are asking for and how to solve those issues. And, uh, just being aware of kind of what’s going on in the industry has been really, really helpful.

Jay: And, and every day there’s like a new tool that I hear that somebody’s using that’s like, do you guys connect with this? It’s like maybe in the future. Um, but there’s like hundreds of them. So it’s, it’s hard to tackle everything, but we really have, I mean, we started with the PMSs and we connect with now like.

Jay: I think 13 or 14 of them. Um, so obviously that’s the most important part, but there’s always more down the line that we want to include, like operations, management, software, and, um, you know, digital guidebook companies and things like that. So, um, yeah, lot, lot more to do. Um, but we have a, a pretty clear, uh, timeline and, and pipeline of, of development that we’re working on.

Gil: Do you, do you recall any like big clients that you’ve worked with that has shaped maybe like large portions of your roadmaps?

Jay: That’s a good question. Um, I would say

Gil: You don’t

Jay: yes at the beginning there was, there was some that were like, we need this or else we’re not gonna use you. Like, it’s just not, it doesn’t make sense for us, um, with. 200 properties to, to implement this if we’re not gonna see this one feature. One of those things recently has been the, uh, WhatsApp communication.

Jay: Um, so, and this is really popular outside of the us It’s definitely something that, it’s an issue in the US too, but, um. With property management companies that have, uh, like a business phone number, a lot of times it’s through like open phone or WhatsApp or something similar, a different VoIP. And we wanna make sure that guess who messaged the host directly through there?

Jay: And it’s not through the PMS, those messages aren’t missed. So if we’re automating all the messages through the PMS, we wanna make sure we’re also automating the messages that are coming through Your personal or your, sorry, your business phone. So WhatsApp is really, really big, especially in Europe. Um, and, and other places outside of the us.

Jay: So. We wanted to make sure that we implement that. And that’s being released here really soon. So it’s gonna be an even more unified inbox with all of those external resources. Um, and that’s a big one for those larger property managers that are saying, you know, we get these messages late at night, people are just messaging us directly on our business line, and they’re not sending us a message on the PMS.

Jay: So, um, from there it opens up a lot of doors to, um, you know, making sure you have that, that full coverage. Then, um, also just like a lot of retargeting for just having the guest off platform too. So essentially if, if a guest sends you a message and it’s not even the phone number that’s assigned to them on their reservation, you can assign that number to a specific reservation.

Jay: A host buddy that way host buddy, knows exactly who this guest is, who they’re staying with and stuff like that. Um, and then you can choose to send a message to them on the PMS or, or on WhatsApp. Um, kinda gives you a lot of flexibility there.

Gil: Yeah. Do, do you guys, uh, currently integrate with emails as well too, or mainly on just the channel messages?

Jay: Not email now, um, that’s planned in our next inbox rollout. So that’s, that’s kind of our, that’s part of the, the, uh, the new phase of inbox revamp, um, to include all those external resources. So email, yes. And the idea is that. You can also include vendors and clients and people that are outside of just your guests, um, to also automate those messages and just have visibility into it too.

Jay: So now your team, if they’re working inside of Host Buddy, they see an email that comes into your host buddy unified inbox, and it says it’s from this address. Um, you can name the, the conversation, add notes to it, generate a response with ai, um, assign it to a property, things like that, and then vendors too.

Jay: So if you have a specific maintenance person that sends a message about like, Hey, I just finished up this, um, this task. I know it was an open action item or whatever that they received. Um, and you can kind of have everything live in one place, which is really helpful and kind of manage things from there.

Gil: Yeah, that’s actually something interesting that I noticed, um, that I, when I was playing with host Buddy and I was also playing with some of the other, um, AI agents as well too, that you guys actually had a task management system in there. And I was like, what is it? What is this? In the very beginning, and I started getting messages come in, I started noticing that like. Host buddy was actually creating tasks for me to follow up with, with the cleaners or the handyman, or anyone that had some sort of question on things. Um, I, and that I’m, I’m guessing that that really came out of your own needs first. Like you having to, when you have 50 properties or 30 something properties out there, you’re having to keep track of all the different things you need to do. It makes a lot of sense in hindsight that, that you guys did that.

Jay: I think our first version didn’t include the, the action item tracking, so it was really just. Automation. Um, we had this thing’s called a transcript page. We didn’t even have an inbox. So like we had a transcript page initially that was just like, it was just a, a record of your conversation so that you could see what host Buddy had said to your guests.

Jay: Um, now there’s a full inbox that looks like your PMS, right? Um, but we’re also tracking like guest sentiment. We’re tracking open issues and sometimes they’re not even like major issues either. It’s just things that host buddy feels like you need to stay in the loop on. And so, like you said, you can get action item notifications.

Jay: Sent to your phone via SMS or email or Slack. Um, if you work on a team, the Slack integration’s really cool. So you can just have a specific channel where all those notifications go to, and then your team can kind of send messages back and forth on Slack to say like, Hey, I’ve taken care of this. I’ve coordinated it.

Jay: So on and so forth. Um, but yeah, that just allows you to kind of stay in the loop on things where, where like maybe a guest says, Hey, I just entered the unit. Um, notice there’s like a dent in the wall, not a big deal, but just figured out. I would let you know. Um, doesn’t need to be fixed now, like, do it once you check out.

Jay: So it, the AI will summarize that issue and then put it inside the, the action items page. We’re adding a lot of additional, um, functionality into that tool pretty soon that I’m really excited for. So kind of, um. Allowing the user to, uh, mark the progress of the task as well. So take it from. Um, you know, uh, received to in progress, to finished add notes.

Jay: Um, so if you have different users on your host buddy account, you can have one person say like, Hey, I reached out to the vendor about this. Uh, the maintenance person’s gonna head over at this time on this day and kind of keep everybody in the loop. Um. So kind of, yeah, allowing it to be a little bit more like a task tracking sort of thing.

Jay: Right now it’s essentially it’s incomplete or it’s complete. We do do, uh, the sorting, the automatic sorting of if it’s a cleanliness item or a maintenance item, or a guest request. You can kind of sort it that way. And then you can also actually send those items to specific people on your team. If you have one person that takes care of cleaning, one person that takes care of maintenance, like you can have those specific action items that are generated for just maintenance specific sent to your maintenance guy or your maintenance person.

Jay: So, um, yeah, I think there’s a lot more to be done as far as the operations management. Side of things, but this just allows you to never really miss things that are coming through your inbox. Um, so I mean, ’cause if, if host buddy was just having conversations all day, and maybe the guest is still happy, but they’ve mentioned a few things like, Hey, this, you know, the, there’s leaky faucet, or like this, this chair’s a little wobbly.

Jay: Like, these little things are always gonna be tracked and it’s easy for those things to fall through the cracks if you’re not using a, a tool to really like, um, track these things.

Gil: Yeah, so what I kind of gather out of what you guys are, are really focused on. really around one, really making sure that the guest experience is something that you can deliver very, very consist consistently over time. two is really to make sure that your properties are at a quality standard that you also wanna deliver consistently as well too. As you think about kinda like the overall vision of Host Buddy, what, what do you see that being two, three years from now? What’s, what’s your focus areas?

Jay: I think we’re gonna continue applying, um, AI improvements so that the, um, problem solving capabilities are always improving. Um, I think that’s, that’s always gonna be something where I. There’s like nuance situations where a host buddy just doesn’t understand how to fix a specific thing at a certain property, and that’s fine.

Jay: Um, a lot of times, like hosts, they wanna be involved. If, if someone says, like, you know. There’s, I don’t know if it’s something very specific about your property where it’s like, Hey, I’m trying to use the grill and it’s doing this specific thing, and the AI can actually troubleshoot with them even if it doesn’t really understand exactly, you know, like the model and make of the grill or the, whatever the appliance is.

Jay: Um, it’s gonna be able to take general worldly knowledge, which is great and, and really try to troubleshoot. Ultimately, if it can’t solve it, it’s gonna push it onto the host and say, Hey, I’m gonna contact the rest of our team and get right back to you. So. Um, it’s done a great job. We’re doing a, done a great job making sure that it can do that, but I think there’s a lot more opportunity to, to improve the, the problem solving.

Jay: And in general, I think AI is gonna continue improving in the future, so it’s only gonna get better and we’re gonna keep working on our things on the, on this end. Um, but I think the operational aspect of things just, and, and that’s pretty broad, but bringing in your, uh, the rest of your team to make sure that everyone’s looped in on, um, action items because things happen at your unit.

Jay: Um, obviously hosts don’t want to have to deal with a lot of little issues like cleaners messing up a little bit each time, uh, or every, every once in a while. Um, but being able to kind of bring everything into one place and, and like I mentioned, like the task tracking kind of. Making it into a full operational management tool.

Jay: Um, we don’t want to take the place of a PMS. I think PSS have their place and, and we operate really well by partnering with them because we’re able to access really anybody’s property management portfolio now as long as they’re connected to A PMS and it’s one of the major ones in the market. So. A lot of people ask us like, are you gonna become a PMS?

Jay: Like, you’re almost getting there, right? Um, and we’re pulling all that data in, but it’s not something that we’re necessarily interested in doing now. Um, our focus from the very beginning has always just been providing the best AI agent possible. And, um, I think we’re still sort of in the process of convincing the STR industry, um, and hosts, uh, in this industry, that you can actually improve your guest experience using ai.

Jay: We see people report increased communication scores all the time. Um, so it’s, it’s happening every day. And I think people still think like you’re sacrificing the guest experience and the quality if you’re substituting ai, um, for a human. And that’s true in some circumstances. But as far as communication, we’re, we’re in a really cool spot now where like their capabilities are beyond what you’d expect and, um.

Jay: I think that’s just, that’s just been our mission from the beginning and we’re gonna keep focusing on that and, um, making sure that we can improve the guest experience. ’cause long term, if people continue seeing that they can charge more, they can have higher occupancy, better reviews, um, and, and everything, your entire business continues to, to flourish.

Gil: Yeah. Yeah. Um, where, where have you seen the biggest advancements in ai, particularly in our space, outside of what you guys are doing?

Jay: outside of what we’re doing? That’s a good question. I think there’s just a lot of tools right now, chat, CPT and Claude are two that I use like every hour of the day many things. I haven’t done a full like analysis of the tools in the market quite yet outside of the guest communication.

Jay: And I know there are some, um, one that I’ve been relatively interested in. Um, and I think listing optimization is, is something that I think I. Can be done and is being done right now. And tele hosts is, is one where I’ve, I’ve, I’ve worked with them a little bit and their products seems great. I can’t necessarily speak to it quite yet.

Jay: Um, but there’s just like, once you, once you automate that guest messaging process, you’re able to open up so many doors for your team to go and figure out. How, how can I now optimize the rest of our business, um, outside of the messaging. Um, and there’s just, there’s so much opportunity. We, we allow our, our team members to, to use AI every day and not just in the responses now ’cause they’re not really handling the responses, but, uh, the new chat GPTs, uh, image, basically.

Jay: Generation, um, is really cool. I mean, some of that I, I think, is going a little bit too far if you’re gonna be editing every single one of your image images to make it seem better than it actually is. Um, but there’s, there’s really cool things that you can do with that. And I think, like, ultimately the algorithm, Airbnb’s algorithm and a lot of the OTAs are gonna take a lot of that stuff into account.

Jay: So, um, yeah, I think like there’s still a lot of things that are developing here in, in the STR space when it comes to ai, and I’m excited to continue exploring those things. Um. But I wouldn’t say there’s any, necessarily any other AI tools that I’m like crazy about right now.

Gil: Yeah. Yeah. So at at least, how about as you as a founder there? You mentioned that you use, uh, Claude and chat PT on a regular basis. Are there any AI tools that you found as being helpful as a founder? I.

Jay: Honestly, the ones that I use the most are, are really just Claude and Chat GPT. We’ve trained them. I, I use it, I use it every single day to, to draft. I mean, I, I basically, I write blogs with it. I write emails with it. It knows everything about Host Buddy and everything, about all of the content that we’ve ever written.

Jay: Um, I’ve been trying to find a really good inbox solution, like an email solution. Um, it’s funny, I’ve been like realizing that like this is something that we could just build ourselves, um, if we had the time and the resources with host buddy. Um, because I find myself answering a lot of emails every single day and like, I just haven’t found a good tool.

Jay: I’ve tried a few of them, uh, to answer, to answer emails and, and like draft AI responses. Um, but I, in general, like I, I’ve just trained the, um, other LLMs to, to know everything about my business and me and it’s, it cuts down hours and hours of the day.

Gil: Yeah. yeah. Um, I know, I think it was Sam, he was using Fixer before.

Jay: Yeah,

Gil: is, is that, has that worked out well for him or has he abandon ship on that one?

Jay: he abandoned ship, but I can’t remember why. Um, I think it just wasn’t as efficient as he wanted it to be. Sam built out a custom GPT for. That same purpose and we kinda, we’ve done the same thing, um, to we, I mean, it’s not as efficient ’cause you still have to copy things over. It’s not just like in your inbox.

Jay: But, um, yeah, ultimately, like if there’s a solution like that, that, that we love, we’re gonna stick with it. And I think he dropped off for whatever reason.

Gil: Yeah, that’s actually the, the, the, the project that I was talking to, to Michael about was actually in that space is. As a founder, you’re having many different priorities thrown at you at many different sources, I just needed some way to have a second brain for me to distill things down to and respond to things and just act on my behalf, even if it’s gate, gate kept by me, even if I have to approve of every single thing that has to go out. so that’s the thing that I’ve been toying with on, on the side.

Jay: Nice.

Gil: in, in ai mainly it’s a, a brain exercise more than anything else.

Jay: I would love that.

Gil: And you know, as a, as a, as a founder, like, uh, or especially in tech, like, you see problems all around and you’re like, oh, I want to, I want to tackle that one. Um, and it’s hard not to tackle that.

Gil: And I, I think that that’s kind of why, like craft estates ended up kinda living, or, or being birthed in the first place was like, I was, I saw a problem. I found a, i, I, I knew I, I had some solution towards fixing it. And it’s evolved quite a bit since my, my first inception of things. But like. When you turn on that side of your brain, it’s hard to turn it off.

Gil: Um, and so you wanna, you wanna tackle those problems if, if you see it’s feasible.

Jay: I think you can definitely, uh, I mean there’s, there’s always advantages and disadvantages to different, uh, projects and different markets. I think it’s a big risk to, uh, to try to tackle such a big market. If you just go to like inbox management. General, like that’s way bigger than the STR space. Um, and it kind of takes away from your direct focus in, you know, optimizing your own tools for short term rentals.

Jay: So we’ve kind of experimented and had those thoughts to like, go different directions and we’re just like, oh man. I mean, it, it would open up so much opportunity, but a lot more competition and then it would take away from, you know, what we’re focusing on here.

Gil: Yeah. And that, that’s a good point of like, I think it’s actually very helpful to be very niched down and I think that those are the software companies that are being successful today, especially in, in the AI space. There’s a lot of AI applications that are, I. broad in terms of the usability and the capabilities there. And they spring up and they fall down just as quickly because it’s hard for them to get the adoption because they’re serving such a wide market, such a wide use case. But I found that the, the companies both in the general product space, but also in the AI space. That do really well are the ones that are very niche.

Gil: They understand the problem very intently. They’re trying to apply the technology for a specific use case and less like a general platform. and I think that that’s why we’ve been successful at craft days is because I. not just building a site builder, we’re building a specifically to drive conversion for direct bookings. And that allows us to really say no to a bunch of different things that we just don’t do or other people can do better in and say yes to the things that will lead to higher conversions. and I’m, I’m guessing the same way it goes to, to you guys, like you can create an AI application that helps you just respond in general for gen, more general use case, but. now diving so deep into this specific use case. You’re thinking about task management. You’re thinking about all the PMS integrations. You’re thinking about how to add additional context, know that problem very, very intently, and it, and it is able to create a much stronger specific niche product to fit that need.

Jay: Yeah, great point. And I was talking to somebody recently, it was different, um, industry colleague, but he was mentioning how like before, like you know, really when short-term rentals were getting started, a lot of the tools in the hospitality space were built for hotels and then they. Moved into short-term rentals when short-term rentals started get to get really popular.

Jay: And now it’s almost like the other way around. Like for us, like we’re gonna start looking into, after we obviously really tackle the short-term rental space, and this goes into boutique hotels and things like that. Anyone who’s listed on the OTAs, right? But then moving into this now applies to hotels and you know, maybe even like different industries of customer service.

Jay: So there’s a lot of opportunity outside of that. But once you’ve really focused in on that. Niche first, and you’ve shown that you’ve validated your product and it’s been really successful. I think, like you’re free to move on from there, but I think if you kind of spread it out, you’re, you’re, you’re, you’re not really focusing enough on, on one specific area.

Gil: Yeah, I, I a hundred percent agree with that. I, I think like. Our trajectory here at Kraft Estates is, is very similar where we started in the very beginning helping smaller hosts and as time went on, more established hosts have been coming to us because knew that our focus was so intent and we knew exactly what to build, and we just continually graduate over time.

Gil: And I could see like doing boutique hotels and doing even private hotels, uh, with many, many hundreds of doors being able to, to automate that.

Jay: Yeah.

Gil: but it, it’s a, it’s a gradual process towards that.

Jay: Yep, a hundred percent.

Gil: Yeah. I, I wanted to switch gears just, just a bit on, kind of like we, we had a, like a, a brief conversation the other day, uh, through, through messages.

Gil: Um, and, and you’re thinking about direct bookings, uh, a bit more intently. Talk to me about what kind of led you to, to reach out to me in the first place. I.

Jay: Yeah. So I would say, um, we’ve always understood the importance of direct bookings, um, with my property management business. So we created a website as soon as we started our business to list our properties. Um, and I think back in 2021, like I didn’t feel like. I didn’t have as much of a grasp on the industry knowing like what options were out there.

Jay: And since then, like other OTAs have been popularized and, and direct bookings have become a little bit more normal. Um, but from there, you know, we, as, from the beginning, we tried to make sure that we’re redirecting, retargeting our guests to come back and stay with us again. Making them feel like they, um, you know, they’re part of a.

Jay: We call it our premier membership club. It’s just really, you’re able to come back and stay with us because you have this specific conver or confirmation code and you’ve already stayed with us. Right? They just, we just had them send us an email and we keep their information and we can re retarget them that way.

Jay: Um, and I think we, so we, we built our website back in 2021 and we’ve been adding properties to our properties, uh, specific page on there ever since. And we realized like. Middle of 2023 is when we started building host Buddy. We haven’t even really reconsidered the, you know, the design of the website optimization for SEO, uh, really bringing people in for direct bookings.

Jay: We haven’t even thought about that for like two years. So it’s something where I contacted you because I know you have, uh, a lot of very, very happy clients, and I’ve seen a lot of the, the websites that you’ve built too. Um, and I think that’s, it’s, it’s amazing. Um. Night and day compared to what, what we currently have.

Jay: So I reached out to you ’cause I was looking forward to, uh, to hopefully developing our website into something that can kinda, you know, be a little bit more powerful than what it is now. And I think we’re blessed to be in such a beautiful market in San Diego, California that we’re not really, I. We’re not super worried about like, oh, we’re, we’re gonna have a 60% occupancy or a 40% occupancy and we’re gonna be screwed for this month.

Jay: Like, it’s pretty consistent and we get bookings a lot on Airbnb. But we found recently that, um, there, there have been some major changes to Airbnb and their policy and the way that they review listings and issues. And a lot of times the. The status of our listings is out of our control. Like one day it can be running totally fine.

Jay: We get a bunch of bookings, people are happy. One day a guest comes in and reports something, some issue, they gave us three stars, and now Airbnb takes our listing down and we’re like, shit, what do we do? Because now most of our bookings are on Airbnb. It’s, I think we probably have 70% Airbnb bookings. Um, which is, you know, better than some, but obviously we want to take that down a bit and be able to increase our direct bookings because it provides that security.

Jay: So started kind of thinking on that path of things and um, yeah, that’s why I reached out to you. I.

Gil: Yeah, I’m excited about the, about working, not just to build your website, but seeing kind of where you as a founder, thinking about how you wanna bring host Buddy back into. Another channel into the website itself, and we’ve talked about this. Me and your team have, have talked about, collaborating together about how AI might play a role in guest messaging on, on the webpage as well too.

Jay: Absolutely. Yeah, that’s a, that’s a great, um, a great source of just conversion for just pre-booking inquiries we found. So we created a, a booking widget on, on, um, host buddy that people can basically drop into their websites. And you were the first person that was able to actually, I. Successfully create it, um, from basically conception on our end.

Jay: Like, uh, we had the ability to do it from an external link. Um, and then it was, yeah, one of your, one of your clients, mark, that came to us and he was like, I really want to do this, so I’m gonna connect with Gil. And then you had it, you had it ready to go. And that kind of led us, uh, to. Make that process a little bit easier as far as embedding that into people’s website.

Jay: So it essentially now can be a, a window in the website. It can be a chat, a chat widget, um, that just, it’s always there to answer questions and it, it really helps just to, like, if people have any questions about like, how many bedrooms can this, how many people can this fit? Or, you know, whatever the question is.

Jay: It, it just helps to have that resource there. And we don’t have any data quite yet on the conversion rate increase, but I’m sure, um, in the near future we might, so.

Gil: Yeah, I’m excited about that. Um, so definitely folks stay tuned on just how AI will actually like influence the direct booking space as well too. And I’m sure there’s a bunch of other things that we can do together as well too.

Jay: Yeah, I think natural, natural language processing is one that Sam has been talking about for a while here too. Just having, uh, one text field at the, at the homepage where it’s like, I wanna travel to this location with this many people for this purpose. And then we run the, the AI and, and it, it gives you the best results.

Jay: It makes it a little bit easier and I think just people are gonna feel like that’s a little bit more normal coming into the next three to five years maybe. I think by that time people are just gonna feel like that’s just how people search, you know? It’s not like you have to like tweak all these settings anymore.

Jay: It’s, I’m just gonna type what I want. Um, and we’re seeing a lot of big tech kind of implementing that as well with Google and um, apple and things like that as well.

Gil: I, I mean that’s, that’s how search happens on Google. You ask at a question on what you’re looking for, and hopefully it responds back and I think we’ve just been so ingrained on. four or five different dropdown fields in Airbnb, check in, check out the number of guests there, but ignored so much about like what you’re trying to look for in, in your stay there.

Gil: Where I think when you’re talking about natural language processing or using, being able to use ai, it’s able to take in the context of what people are looking for and compare it around all the amenities. What people have said in the review is it kind of merge those two together. So definitely I see the potential there.

Jay: Yeah, I like that point. See what people have said in the reviews, their general experience, just talking about the property, knowing like somebody mentioned like, oh, it’s just a short walk down the street to the beach. Um, and we had a great time doing. This, this and that. Um, mentioned that there’s a coffee shop nearby or something like that and somebody mentions in their search like, I want something near a coffee shop that has this, this, and that.

Jay: Like, I don’t know, there’s so much I, I love, I love going down that path ’cause it’s just, it opens up so many, um, fun ideas, but I’m sure there’s gonna be some cool stuff that we create here in the future.

Gil: Yeah. Um, so I wanna kind of respect your time and kind of wrap things up as well too. We usually end with two or three questions. Uh, first on, what is one of your favorite books that has influenced your life?

Jay: Favorite books? Um, there are several, um, one that I, because I remember the title, and this is purely why, honestly, and also the fact that it kinda just has a good concept is who, not how. That’s a really good book that kind of led me to. Figure out who I needed in my team, not how to do it. Um, that, that really kind of escalated, uh, you know, the, the scaling of my property management business.

Jay: And then another big one that I read, uh, late last year was the comfort crisis. And that’s not as much, um, you know, like business related, but it’s more like human psychology and just like our tendencies to, um, you know, be attracted to, to comfort and the benefits of just putting yourself outta the, outta your comfort zone and into places where.

Jay: Fortune favors the bold is one of my quotes that I really like to, to, to kind of reference because, um, we found a lot of success in just taking risks and, um, putting ourselves out of our comfort zone and our business. And I think there’s a lot of, um, applications that kind of come from those, um, types of things.

Gil: Very nice. Uh, second question, what’s one piece of mindset advice that you would give to someone that’s starting something completely new?

Jay: Yeah. Um, I would say that nothing happens overnight. I always tell myself at the beginning of the week, like, take it day by day. Like I’ll look at my schedule and be like, I have a lot to do this week. And um, if you look out a month, you’re like, oh my God, I have so much to do in a month. And then if you think, what’s my goal for the next year?

Jay: Sometimes it can feel like you can’t get there, um, because it’s just so far out. But you take it day by day, focus on your short term goals. With the end in mind. Um, and that can be really powerful because there’s a lot of anxiety that comes with knowing that you have like these really big meetings at the end of the week where you have these, um, you know, just big events that are going on in your life.

Jay: And taking it day by day has always been great. That’s something that my mom always told me too, is just take it day by day and we’ll move, move on from there.

Gil: I love it. Love it. Last question. What’s uh, one piece of tactical advice that you would give to someone that’s. Either starting off on their direct booking journey or trying to boost or ramp up their direct bookings.

Jay: Oh yeah. Um, I would say a tip is to make sure that you don’t send, uh, retargeting messages directly through Airbnb so that Airbnb sees it, because we did that a few times at the very beginning, and they will immediately remove your listing. So that puts you in a kind of a, a bad position. Um, it, you gotta, you gotta be kind of sneaky about it.

Jay: But if you wanna look for direct bookings, um, find a way to collect that guest information. There’s a lot of cool tools out there. Um, guidebooks, um, even like, um, shoot, why do I always forget their name? The, uh, stay phi Great, great tool. People can collect their, uh, information for direct bookings. Find a way to retarget these guests, ask them for their information, and, uh.

Jay: And that way they can feel like they’re, you know, part of something, part of your business and that they know you personally and then they’re happy to, to consider you when they come back to, uh, to the city that you’re hosting in.

Gil: Awesome. Awesome. Jay, it’s been great having you on here. Where can folks learn more about you, uh, follow you or even try out host buddy.

Jay: Yeah, so you can find me on, uh, Instagram, Facebook, whatever. Um, just search JT Ulrich, JAYT, Ulrich. Uh, you should find me. Or just go to host Buddy AI on Instagram and you’ll see me all over that page. But, um, if you wanna learn more about Host Buddy, uh, host buddy.ai is our url. We give two week free trial to anybody who.

Jay: Signs up, so feel free to play around with it. We’re also the only AI messaging solution that puts the AI on our front pages of our website for people to try. So you can literally go on the tab that says Meet host buddy on a website, ask it any questions you want. It’s with a fictional property, but a lot of people have fun with that.

Jay: So, um, might as well suggest that for you guys. But yeah, thank you so much Gil. This has been great. Appreciate you. Uh, you have me on.

Gil: Yeah, absolutely. Uh, I’m, I’m excited to work together in the future as well too.

Jay: Absolutely. Sounds good.

Gil: Thanks, Jay. Bye.

Jay: Bye.