[00:00:05] Speaker A: Welcome to the Short Term Show. The show about short term rentals and long term wealth with real property owners hosting real properties who are crushing it in the vacation and short term rental space.
And here's your host, Avery Carle.
[00:00:29] Speaker B: Hey y'.
[00:00:29] Speaker C: All.
[00:00:29] Speaker B: Welcome back to another episode of the Short Term Show.
We are in the fall now of 2025. Real estate market is really weird but picking back up and we are hiring agents in multiple markets. So Orlando, the Smoky Mountains, Emerald coast of Florida, the Poconos, Myrtle beach and Branson.
So email us if you think that you might be a fit to be a part of the team. We're hiring because we have a lot of buyers in these markets and not enough agents to be able to take care of them. So email us at Careers at the short term shop.com if you think you're a fit. Also, don't forget to download the Short Term Shop plus app. It's free. A lot of cool stuff in there and you can find that or more information about
[email protected] now let's get into it. Today we have Annie Lee of hello Host. She's a co founder of hello Host which is an AI platform platform for short term rentals and she's gonna give you a lot more detail, better detail on it than I can.
But I'm very excited about this little corner of the short term rental world.
AI is big. Obviously a big buzzword and topic across all industries right now. But since this is our industry, this particularly interests me. How's it going Annie?
[00:01:48] Speaker C: Darren Wells, thanks so much for having me on the podcast.
Yeah, thanks for having me and happy to share about hello Host but also about AI in the industry.
[00:01:59] Speaker B: I want to hear all about it. First let's introduce yourself. Give us a little bit about your background and how you ended up coming to co found a company in the short term rental AI space.
[00:02:10] Speaker C: Yeah, for sure. So I joined the short term rental industry back in 2014 just as a Airbnb host. In 2022 I also acquired a lakeside retreat a little bit outside of Toronto with multiple units and these have just been sort of passion projects professionally. I come from a background of management consulting as well as early stage tech startups. So just helping to grow and scale across various roles inside the tech industry. So when I saw the opportunity to fuse the two together, both the hosting side as well as sort of my interest in technology, I decided to essentially start the company. It really was inspired by a personal problem I was facing in terms of guest communications. At the retreat we Had a general manager who left. So a lot of the guest communications fell onto my shoulders as well as my husband's shoulders. And so as a result of that, saw the opportunity to automate this using AI.
That's in a nutshell, but happy to dive into it.
[00:03:21] Speaker B: Awesome. Yeah, love it. Tell us a little bit about what your tool does because I think a lot of people have that very same need to fill. Tell us a little bit about what it does.
[00:03:32] Speaker C: Yeah, at the moment it's very much focused on guest communications. We see that conversational AI is definitely the most advanced of all of the different multimodal types. So think like the visual generation audio. But of all of them, conversational AI is definitely the most advanced.
And so the hello host essentially plugs into your property management system. So generally for hosts who are managing five plus units, they're typically using a PMS. So think like guesty or host away hospitable, etc. And we connect directly to your PMS and automate all of the messages that are coming in. Guest message comes in, you set a response time, this is completely customizable and then it is able to take care of it for you.
It is on autopilot with hello Host. What that means is that there is no opportunity for the user to go in and review a message and change up the draft and send that message out. Just starting from day one, hello host is going to be sending it back to the guest, which means that there is such high standards for message quality and accuracy.
[00:04:42] Speaker B: Okay, so it's truly automated. It's not checking with you and saying, hey, here's what I've drafted. You have to hit send. It's totally communicating for you.
[00:04:51] Speaker C: Yes, exactly.
And this was a decision that we made. We think that this is a very different problem to solve as compared with, let's say just having a draft message for you to approve. Because ultimately you're still the blocker in those situations. You still need to be on call, you still need to be on when the guest is messaging you and you still need to respond very quickly to them. Having on autopilot means you can be hands off. And I think you're ultimately solving for two different problems. In the first, you have to, you know, essentially the AI company is not responsible for the quality of that message, nor is the is the company responsible for what happens if AI gets this message wrong. Whereas if it's on autopilot, then again that responsibility lies within the AI's message.
[00:05:46] Speaker A: With AI from the hardest working gal in real estate, Avery Carle. We now have a new book, Smarter Short Term Rentals, available wherever books are sold.
Build a dynamic real estate business and out host the competition that's Smarter Short Term Rentals. The book.
[00:06:10] Speaker B: I have so many questions. So how does it learn what you need it to say and do? So you know, each, each property, each host is going to have different ways of doing things. They're going to have different FAQs that the guests always ask and then different processes for how they answer that. So how does it learn these things?
[00:06:30] Speaker C: Yeah, there's multiple sources. I would say one of the most important sources of the past conversation history. A lot of the guest questions that are being asked, hosts have answered not just once or twice, but just possibly a hundred times. Every single, for every single guest, right? Like, what's the WI fi password? Where can I park? The AI is able to essentially easily deal with these types of questions. I think the more interesting question comes from, like, what happens when it's a more dynamic situation or a particular exception where you have a particular operational process.
For these cases, we generally split up. Like, we help you define what kind of permissions you give the AI to do. For example, if a guest is looking for additional replenishable items or supplies, do you, do you even allow the AI to promise that or do you allow the AI to promise that they're going to contact maintenance and then, you know, inform you, inform you of this need from, from the customers or from, from the guest?
So essentially looking at past conversation history, looking at the listing information, determining permissions that you're giving to the AI.
Just like how you might train a member of your team to be able to communicate with guests. Similarly with our platform, a lot of it is self learning by the AI, but you can also train it. You can also give feedback which will further like refine and tune the responses.
[00:08:05] Speaker B: All right, my question now is going to be one of those more dynamic situations that it's like a, you know, a one off where let's say a guest is really unhappy about something, maybe they showed up and the property wasn't clean. And that's like, you know, a red alert when it comes to short term rentals. So in that case, how does it know where the line is of okay, let me tag in Avery. It's time for her to handle this rather than me.
[00:08:31] Speaker C: The AI software, Right.
In this case, this is going to be interesting, but it's going to behave like a person and make a judgment call.
It is not like code, so it's not programmed If X, then Y type of a situation, but rather leaving the AI to make a judgment call. And this is a very.
Because the guest is going to be pretty upset over the situation. The AI is able to detect the sentiment of the guest and that helps to inform the next steps it's going to take, which is obviously to notify the host and then communicate with the guest in an appropriate way.
[00:09:13] Speaker B: Got it.
You train it to tell you when it gets to a certain point of okay, this I need to let the actual host know now so they can take the appropriate steps.
[00:09:27] Speaker C: Actually, you don't even have to train it. It's already trained as an experienced vacation rental operator. So on the situation that you just described, the AI, you don't need to like use the software to do this. You don't need to tell the AI to do this. It will just know that.
[00:09:44] Speaker B: So it'll just note, wow, this is so crazy. And I feel like all of this has happened. I know this was years and years in the making, but just in the last two years have we just made these leaps and bounds of, okay, now we have this AI that actually makes judgment calls and handles situations like a human would.
It's a little creepy to think about.
[00:10:06] Speaker C: Yeah, we've seen a ton of progress. In the very beginning it was kind of just tapping a generative AI model for an answer. So think like you get the guest message, you send it to ChatGPT and it comes with a response that would be like the earliest version of this. And back then the models were also not as fast as they are today. Now you're talking about multi agent systems that are working together using multiple different models that have different access to tools. Right. So it's going to be able to look at your calendar and read it. It will be able to go on the Internet and like look at, look up information that the guests might be asking for. So like where's the Uber pickup location and where. What are some recommendations for restaurants nearby? It can utilize all of these tools, including your data sources, in order to better answer the question, wow.
[00:10:57] Speaker B: So let's just go over some basic things that a potential user of this product would need to know. So we know it, it can act like a human.
But if I'm just somebody new who's like, maybe on your website looking at, well, should I, should I sign up for this or not? What are some of the basic things that people need to know?
[00:11:16] Speaker C: Yeah, I think I'm just going to talk about the biggest concerns that I've noticed. Users have which is this idea of being intimidated. Can I really trust the AI?
Can I really trust the AI to get the messaging correct or get it right?
When you think about that question right now, that's being done with people, right? So like you might, if you hire someone new, you're going to have the same question, but because it's AI, you're just going to be a lot more cognizant or careful of the responses. What we have seen in our system is at this point the AI is performing as well, if not better as compared with manual responses. If you have a large team of communicators right front facing staff that is just focused on guest comms, you're performing, the AI is actually performing better and you don't have to, you know, like there are consistencies in the message in terms of response times, in terms of how professional it is. The tone of the AI can be tweaked so it can be more professional or more casual.
But still they could make mistakes. It is not Perfect. It's not 100% of the cases it's going to be perfect. But humans are also not perfect. What we're looking for is that the AI just needs to perform better consistently. And so we do see that. And if there are mistakes, at least with our system, what we can promise is that we can trace exactly the data source for a particular guest question. So if a guest is asking about the crib or asking just amenity in general, we have seen the AI make a mistake, but it's also because the listing information is not up to date, we generally can trace it and we generally see that here human error, whether that was a wrongly added FAQ or the listing information not being, not being update updated, that's leading to a potential mistake. Otherwise I think you can expect AI to behave as you might imagine. So it's going to sound exactly like a person like yourself responding to the guest.
It's going to respond very quickly. So the response times is customizable. It can speak multiple languages, including the guests language and it's able to read your calendar, it's able to know all of the information, you don't have to train anybody. All of this data and it can just come in.
We essentially have a 30 minute onboarding call and then we said go late, go live, date and time. And so you essentially can start a free trial just like that.
[00:13:56] Speaker B: Wow.
So have you ever had, you know, I think the biggest complaint with people from guests or customers, when people take actual people out of roles, they're like I want to talk to an actual person.
So this is going to be different than, you know, like a phone tree where you're dealing with that. But have you seen guests ever realize that they're talking to AI and get mad about it? And then what, what do we do in that situation?
[00:14:21] Speaker C: Right. So I think what's very unique about conversations in the short term rental industry is that hosts are oftentimes jumping into conversations alongside the AI. So the AI needs to detect like, is the host involved in the conversation?
If the host is responding, does the AI need like essentially the AI needs to stop responding as well. They definitely can do all of these things. And for your specific question, you know, if guests like, do guests recognize they're speaking with AI? Generally speaking, if there is an important decision that needs to be made by the human and the human is not jumping in, the AI doesn't have additional information or it doesn't have additional data to help this guest in those cases. We have seen that happen. Generally we just reduce escalations or essentially stop the AI from responding. But we generally just recommend host to enter into the conversation and make a decision such as like no refund is going to be provided. Otherwise you might see like 10, 20 guests messages from the guests and the AI sort of trying to manage the situation, but they still are not making the decision.
[00:15:31] Speaker B: And how do you know as the host when it's time to jump into something? So if this thing is on autopilot but it needs you, how do you, how is that notification received?
[00:15:42] Speaker C: Right, so just send you a notification through Slack or through WhatsApp group or through SMS, just whatever you're already, you know, most useful for you and then you can look at that notification, click on a link, jump back into the conversation.
[00:15:57] Speaker B: Wow.
So it's like an actual person. Because RVAs are slacking us all the time. So it's like an actual.
[00:16:04] Speaker C: Yeah, it kind of behaves in the same way.
[00:16:06] Speaker B: So crazy.
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[00:17:26] Speaker B: Shop plus that this is all extremely cool. So does this focus exclusively on guest communication or does it do other little tasks within your. I don't even know what I'm trying to say. Other little things within your listing?
[00:17:43] Speaker C: Yeah, this is going to be dependent on the pms, but generally speaking it's solely focused on guest communications at the moment.
Specialized.
Cool.
[00:17:54] Speaker B: Cool. So what have, what have I not asked in terms of features? So I think that it's, you know, obvious we are using this to communicate with guests so we can kind of step out of the day to day responding to questions and things like that, which is huge, huge, huge. That's probably, I don't want to say the most annoying because I mean real estate investing is a lot of headaches and annoying things. But you know, this is going to be the most, most complained about situation for when it comes to short term rentals from hosts and owners is oh, I have to answer all these questions all day. So I think this solves like a really big major problem or gripe with short term rental owners that like oh, I have to, you know, this interrupting my dinner. I'm trying to be at the zoo with my kids and I'm trying to having to answer questions about TV remotes. So I think this solves a pretty huge issue here. But what else have I not asked about the platform that you feel like the listeners should hear about?
[00:18:54] Speaker C: Yeah, sure. I think the AI is also helping to these conversations with guests are really insightful for hosts. So if they're not in the day to day of messaging with the guests because it's being done by AI, they still need these insights. And then kind of going back to these notifications I was referring to these notifications are just the first step into like ultimately AI agents that are going to do a lot more than just purely GAS communications. So you're, you're looking at the host being able to send a message to their AI agent to accept the reservation or to alter the reservation or to collect a payment and to actually take actions across the reservation. I think that's the general direction that this is going that this industry will head towards, but more specific specifically for our platform. You're going to see a ton of different insights pop into notifications. Just things to know. Like these are the things that need to be fixed with this listing.
For example, you know you're going to get maintenance requests that came from a guest complaint related to something that happened inside the property. And being able to see all of that in a cumulative way with hello Host, I think is also a huge value add.
[00:20:08] Speaker B: Yeah, yeah, I love that. I love insights and things that you may not notice if you are actually talking to the guests. Like a little thing like they mentioned, well, the microwave wasn't clean so we weren't able to do, blah, blah, blah. But their real complaint is something else you forget about the microwave. So I love that because you can get humans can get distracted and you.
[00:20:31] Speaker C: Can even use this to kind of deliver really fantastic experiences for guests because they are going to be looking at all of the guest conversations, understanding the guest sentiment. You can say, okay, if the guest is happy in their stay based on the conversation, offer them xyz. Right. And it could be like something that you're planning for the guests in terms of experience or also any kind of upsell that you might have for the guest.
And we've seen a wide range of different types of upsells. Everything from equipment rental, like barbecue rentals, equipment rentals, to massages, to packages for experiences.
[00:21:07] Speaker B: Wow. Okay, well, I think that's a really good segue into my next question. So the beginning of the podcast you mentioned that you might want to talk about where AI is going as a whole in the vacation rental industry. So we've been really drilled down on this exact tool and the messaging piece and guest communication, which is probably the most important piece of hosting. But where do you see AI in the short term rental industry going?
[00:21:32] Speaker C: Yeah, I think I kind of touched on this, but I definitely see from a host perspective, you're going to see a lot of hostages, tools or softwares utilizing AI for various workflows. And a lot of these workflows are going to move away from just kind of SaaS software. So think logging into a software, clicking on buttons and more into conversational workflows whenever that's possible.
So think of a AI agent offered by a software that is going to allow you to communicate with it, to take actions using that software.
And then this is going to be interesting. But I think on the guest side, in the future, I think the guest will also have an A.
It could be a generalized type of AI assistant that's helping them make bookings, but also kind of acting as, I want to say, kind of like an ea. But it could be also pretty specialized for the travel industry. We haven't seen there are many different AI startups in the space that's trying to do this, but we just haven't seen sort of one that's leading the pack. So this is to be seen. So the interactions between the guest and the host might actually have additional filters. On the host side you see AI interaction, but also on the guest side you might see conversational AI taking over in terms of booking, helping to actually make bookings.
So here's one example. Instead of, yeah, instead of, you know, a person going to Airbnb and booking a trip, they might just ask something like ChatGPT book ChatGPT to book it for them in the future.
And this is not super like long down the line. This is probably going to happen within the next five years.
[00:23:14] Speaker B: I can see that because I know when I'm going to book like a vacation for our family and I'm using Airbnb or vrbo. The part that I hate the most is actually sorting through and finding the right place. Like I have a few things I always want to see king bedrooms in every single room and you have to click on each listing to see that.
And having some sort of AI assistant that could do that for me and say, okay, here are five properties in your price range and they all have this. That would be really helpful.
[00:23:46] Speaker C: Yeah. And there's a lot of companies kind of building working on this problem.
[00:23:51] Speaker B: It's interesting you say a lot of companies, so there's a lot of AI little startups popping up everywhere. Specifically since I'm a real estate agent, I get so many because real estate agents love signing up for tech. Any, like, any little thing, we will sign up for it. My husband's in the past has been like, you have 275 subscriptions to things that you don't even know what they are. So how do you, as a, let's just say a short term rental host, as a bunch of AI companies are popping up? How do you know, like, what are some questions to ask or some things to look at when you're weighing these options against each other of, okay, this is a serious company or this is like some guy in the basement who's just doing, you know, whatever and it's probably not going to be a real robust platform for me. Like I don't feel like I'm putting this very well. I feel like there's real companies being started and then there's like people who want to be influencers who are like, look at this AI thing that I made and it really doesn't do anything.
[00:24:52] Speaker C: Right, right. Of course. I think you can ask specific questions about how the AI works. Like what kind of models are they using, what's underneath the hood, how do like as I mentioned before, I think there's a huge difference between companies that are simply, you know, connecting your guest messaging to ChatGPT versus building something that is multi agent with multiple LLMs standing for large language models interacting with each other. I think the technical component here is something that you can just simply ask about and see if they have a clear explanation for that. And now also beyond that, looking at, you know, when the company was founded, where it's based and of course what other kind of customers do they have advocating on their behalf.
[00:25:45] Speaker B: Yeah, I think all of that is. So you say where it's based. So what are we looking for and where it's based? Like we want it to be based in the Bay Area and not like Gary, Indiana or what does that mean? Exactly.
[00:25:59] Speaker C: Yeah, I think you're just gonna have like these companies will have access to the best talent if they're based essentially San Francisco, you know. Gotcha, gotcha.
[00:26:08] Speaker B: Okay, that makes total sense. I, I like that because yeah, I think that there are a lot of people out there who are really just connecting things to chat GPT and then calling it a startup.
[00:26:20] Speaker C: Yeah.
[00:26:21] Speaker B: And there's a difference.
[00:26:22] Speaker C: There is a huge.
Awesome.
[00:26:25] Speaker B: So all right, we're getting, getting to the last few minutes of this show. Thank you so much for coming on by the way. This is, I'm really excited about this tool.
What are there any, anything that you feel like the audience needs to hear that I have not asked about? Hello, host.
[00:26:41] Speaker C: Yeah, I think, I think there is a general concern, perhaps a concern or this feeling of like, what's my role?
What's my role? Given the advent of AI obviously in GAS communications, but also in the entire industry as the as a whole, I think that's not just happening within the short term rental industry, but I think it's happening to every single industry out there, whether it's engineers or designers. Right. Everybody's looking at their own jobs and going like, can I possibly be replaced by AI? I think that's something, that's an interesting topic in general. But when hosts look at this question, I think ultimately you have to understand that this is a human Business. Right. Like, there are people who are. There are travelers who are visiting actual space and they want the comfort of home kind of in this new place.
Ultimately, it's still a people business, and that component cannot be automated. Right. Creating and crafting, the need to create and craft a great guest experience is not going to be automated. That drive will come from humans. With that said, I think whatever.
Whatever I can do from a manual perspective, we should try not to do it. The AI is only going to get better in the. In this space. So focus on the areas that are true value add from a.
From a initiative perspective. So being able to do different tasks for gas, crafting that experience, but then using as much automation to automate it will kind of position you as a host in general to succeed over the long term, longer term.
[00:28:27] Speaker B: Awesome. Love that.
[00:28:28] Speaker C: Yeah, I definitely see some just last word, but I definitely are kind of like fighting this, the rise of AI or just.
[00:28:37] Speaker B: I don't think you can do that.
[00:28:39] Speaker C: Yeah, I don't think so either. So just recognizing how do I leverage AI into the business, how do I automate things, how do I save costs, and how do I focus on areas that will truly tailor a customized, interesting experience for guests is important.
[00:28:56] Speaker B: Yeah. And I mean, at the end of the day, like, just AI can never be the house that you're providing.
[00:29:03] Speaker C: Exactly.
[00:29:04] Speaker B: You can use the tool to make the experience better always. But the AI can't be the rehab of the house or the accommodations itself. So, you know, you still have. You as the human, have the asset, and the AI is just helping you do the best with that asset that you possibly can.
[00:29:21] Speaker C: Exactly. And you are pro. You're in a position to, like, lead and essentially train and manage the AI.
That's. That's something that's important for our operators.
[00:29:34] Speaker B: This is completely off topic, but we know. We're just talking about the, you know, the relationship with the AI and training and leading and managing it as if it is a person.
Did you see the guy recently who says he's in a relationship with his AI assistant and he has a wife, but he likes his AI assistant better?
[00:29:52] Speaker C: I haven't. I have not seen this specific scenario, but I'm not surprised. And I've seen many similar stories now.
[00:30:00] Speaker B: Crazy. I mean, they did. There was that Joaquin Phoenix movie a while back. What was that?
Simone, I think it was called, where he was in a relationship with his AI chatbot before that was actually like a thing.
[00:30:13] Speaker C: Yeah.
Anyway, black people are crazy in real life already.
[00:30:17] Speaker B: Yes. Yeah, I haven't finished the, the most recent season, but oh yes, I did the one where he's talking to the little rabbits in the game.
It's pretty crazy.
[00:30:29] Speaker C: Yeah, every episode is pretty mind blowing, but it's crazy how some of them are kind of in the process of being realized.
[00:30:36] Speaker B: Oh yeah, the one, the one that freaks me out the most is where you, you review people in real time as you talk to them like you're, like, I just talked to you. Five stars.
[00:30:47] Speaker C: Yeah, it's kind of crazy.
[00:30:50] Speaker B: Anyway, we're off topic. Annie, thank you so much for coming on. So we have three questions that we ask every guest at the end of the show. And first question is what advice would you give 20 year old Annie if you knew then what you know now?
[00:31:05] Speaker C: I would say trust yourself, don't keep doubting yourself and then just keep walking the path that you're walking.
[00:31:13] Speaker B: Great advice.
And number two, what advice would you give a new short term rental investor who's looking to get started today?
[00:31:23] Speaker C: Definitely utilize, understand the landscape, especially in AI and look for opportunities to automate your processes. Look for opportunities to incorporate it into workflows.
I think you have to go and find that for yourself. I don't think it will just come to you naturally.
[00:31:42] Speaker B: Also great advice. And last, this one's a little bit more fun. What's your favorite book that's impacted your mindset?
[00:31:48] Speaker C: So many books.
[00:31:50] Speaker B: The hard one.
[00:31:51] Speaker C: Yeah, I would say one that has made a particular impression on me is Zero to one by Peter Thiel. And this is just about starting startups like creating something out of nothing versus and in my past career I was always focused on the 1 to 1010 stage. Right. Like getting something that's already created and improving that over time. So personally being able to start something from scratch as an entrepreneur, what does it take? What does that, what kind of market are you looking at? Some more technical things in that book have just been super helpful for me.
[00:32:26] Speaker B: Great one. All right, and last but most important question, how can our followers find you and your tool or follow you on social media? Any of the above.
[00:32:37] Speaker C: Yeah, I mean, hello hostai.com you can go ahead and book a demo. Can also email
[email protected] and now also you can find us@IG ellowhost. AI.
[00:32:51] Speaker B: Hello host AI. All right, well Annie, really, really interesting conversation. Thank you so much for coming on and listeners, we will talk to you next week.
[00:33:01] Speaker C: Thanks so much Avery, really appreciate your time.
