How Scott Sherin Turned Claude into a Super VA for STRs with Hospitable MCP

Perfect. All right, everybody, welcome to the podcast. Uh, I've got a really, really exciting guest to my left or my right, however you are watching this, uh, podcast or listening to this podcast. And it's somebody that I've just been watching on the Facebook groups the past sort of couple of weeks talking about how they are adopting AI into their business. And it's phenomenal to see documenting the journey as we go, and I wanted to get him on just so we can just delve into the posts and the use cases and what he's been doing and just get a bit of more context to it. So Scott, thank you so much for joining us. Really, really appreciate your time. Can you just give a bit of background of who you are, where you are in the world, your property journey, and then we'll get stuck into the good stuff with AI?

Yeah, sure thing. First of all, Mark, thanks so much for having me. You've been a legend in the space for a long time, so it's an honor to be invited on. A little bit of background about me. I'm a real estate investor and also operate a short-term rental co-hosting service, which is essentially just a property management company with some pretty nuanced differences. So I have my majority of my portfolio located in Delaware, in the Delaware Beaches area along the entire coastline, but I'm also spread out a little bit into some other markets, mainly focusing on growing the portfolio in Delaware. And essentially, I'm sure your listeners know by now, but what I'm doing is acting as a secondary host on existing Airbnb accounts for my clients and helping them become completely hands-off and maximize the revenue that their properties are earning through combination of strategies and practices that I'm sure your channel has gone into detail all about. So it's a little bit of background on me.

Amazing. And give a quick shout out for the, for the business, the domain, if anybody wants to reach out, because we've got a wide range of people that tune in.

Yeah, sure thing. So the domain name is trustedstays.pro, not to be confused with another Trusted Stays, which is actually a UK-based business. I've been trying to work through, um, you know, trademark names and whatnot. But yeah, trustedstays.pro is, is the name. And I'm also very active on, on Facebook if you ever want to search my full name and chat shop there. That's where I do a lot of the, you know, blogging, so to speak, or talking in forums. So that's probably the best way to get a hold of me for anyone who's curious about anything we're talking about today and just wants to chat shop a little more.

Yeah, well, you may have— if you're in the Facebook groups, which I know a lot of the audience have, are in a lot of the Facebook groups, and, you know, they may be in the same ones, and you may have seen Scott's post recently about how he's adopting Claude with Hospitable. That's where I first came aware of your post, was in the Hospitable Hosts Facebook group. So could you just, like, lay out sort of when did you first get started, what was like the first sort of aha moment, and why did you get started when it comes to adopting AI in, into your business?

Yeah, absolutely. So I just, you know, I've been aware of this new emerging technology and watching a lot of videos about how can help people save time, how can help people generate revenue. So instantly I'm thinking, all right, how can I apply this to the business that I'm in. So just started with essentially just a curiosity about technology and artificial intelligence, and then started hearing this term come up a lot that was confusing to me at first and still is, which is an MCP server, which for my fellow non-techies— and people can correct me if I'm wrong in the comments if I'm misdefining it— but it's essentially a way for different tools and applications to be able to connect and talk with one another, right? So started hearing about this idea, and then Hospitable, which is the property management software that I'm sure many of your listeners are listening to— are using, rather— and myself as well. I've realized they released their own MCP server, which essentially is allowing Hospitable to connect to different AI tools, and just started getting curious, started asking Claude what some of the possibilities were with this MCP server, started making my own connections, and From there, was able to build a few interesting workflows that have already paid dividends for my business. So that's kind of how it started, a little curiosity and then just experimenting.

I think I remember seeing the first post in the group. It was round about April 1st, 2nd, or 3rd, and you saw about Claude and the hospitable MCP. Maybe was it a town hall or a post? And you just asked a very simple question. Where curiosity is everything, right? So who's building cool stuff? Who's got good use cases? And you tagged in Pierre, which is one of the founders of Hospitable, and that post got so much comments. And I think like your curiosity matches what a lot of hosts and business owners and just people online are sort of also mirroring as well. Because I think for the last 3, 4 months, we've seen people talk about OpenClaw, and then we've seen people talk about like, say, MCPs, and now Claude is doing what they're doing, and all these different LLMs are playing, playing catch-up. And what was like the, the driver for you? So you did the post, you, you learned about the connection. What was the driver for you to stop being somebody that is just reading to actually taking action? And then what were those first steps? What was the first things that you did?

Yeah, excellent question. So I guess I'll start with the first thing I did and what I would recommend anyone would do, and which I'm sure you're doing as well, Mark, is when you're not sure really which direction to go, just brainstorm in one of these LLMs, right? So I, as soon as I connected the MCP server to Hospitable, which again, if you're not, I have no idea what that is. It's really simple to set up. I don't want that to be too intimidating of a concept. I just asked, hey, I just installed this MCP server. Like, why don't you list all of the capabilities of it and cross-reference what you know about my business to Help me understand how I can apply it to save time and earn additional money, right? So just brainstorming within the LLMs, I think is a great idea. And then, um, your other question about wanting to transition more from being just like a reader and a spectator to an action taker is, I think that for me at least, I was a little nervous to be outspoken in these Facebook groups because One, I didn't feel like I was an expert or didn't really know what I was talking about compared to some of the industry experts. And I would like to push back on that notion because we're all just building things and figuring it out in real time. So I think getting curious and getting others engaged is— and just building in public, being willing to make mistakes, talk about your mistakes is a lot more of a fruitful conversation than needing to be posing as an expert. Or, you know, just hoping to learn things from others without actually experimenting yourself. So just building in public, being willing to make mistakes, being curious, asking others. I think this is just creates a little bit of community amongst the short-term rental hosts and is conducive to learning for, for all of us. And I recommend—

amen, absolutely. I would never, uh, ever, ever shy away from anybody documenting the process because If you look at the term expert, it's just knowing more than the person that you're speaking to, right? And 10 years ago when I started Boostly, I literally stood in front of 6 people in a room in my little town of Scarborough in the United Kingdom, and I had the biggest imposter syndrome ever because I was like talking about how to get direct bookings. And you know, if I hadn't done that and then talk about it in Facebook groups, then Boostly would never be here today. So there's amazing things that can happen on the back of it. And I would— anybody who's got that imposter syndrome feeling of why should people listen to me, especially when it comes to all of this new technology? Please don't. Just do what— take Scott's example, because again, I now associate hospitable MCPs and experimenting with Scott. And, you know, and this is what made me reach out, which is, which is awesome. So I want to talk about one of the case studies. Um, I believe it was last week you talked about turning Claude and the hospitable MCP into your Rebook past guests engine. This is something that tweaks my inquisitive nature in this because it's very easy with OpenClaw AI Claude to just to create a very expensive hobby. What do I mean by that is that a lot of people are doing it to, you know, read podcasts or, you know, enhance their inbox or whatever. But what I really love seeing, and which is what I've done, is turning it into something that makes money. Because if you're going to spend all this time setting it up, you want to have money coming on the back of it. Now talk to me about what you did. Talk to me about level 1, level 2, and just explain for the listeners and the viewers what you did, please.

Yeah, absolutely. And I like the point you made about making sure that you're not just tinkering, you're actually putting forth tasks that are revenue generating for your business. So essentially what I did is I ended up consolidating into a Claude skill, which is essentially just like a Kimpact direction set to be able to use hospitable messages, use some of the MCP connections such as the ability to read past conversations, read through reviews, read your calendar dates, consolidate all of that information to be able to reach out to my past guests through the Airbnb/VRBO platforms and write them highly customized welcome back, essentially invitations to rebook them for future dates and have these messages be, you know, hyper-curated based on something that they mentioned in their review, something they mentioned throughout the duration of their stay, what was their, you know, sentiment overall, what was something they loved about the property, a bit of an analysis of the things we talked about or questions they asked. So being able to really add context to your outreach message instead of just the generic, hey, we'd love to have you back, we have some dates open. We're actually writing messages that feel like, you know, I really remember their individual stay. I remember all the things we talked about. So the real difference between just adding them to like an email drip campaign or just reaching out to chat with them is being able to add all these layers of context that otherwise you would have to literally read through all the conversations. To have that same level. So being able to layer that context on top of your outreach message and then the step further is being able to cross-reference that with your future calendar availability, check actual dates that you're looking to fill. How does it line up with the last dates they stayed in? You're layering in all this context to be able to craft something really personalized and something really useful. So that's kind of the best use case that I found so far for the MCP server and continuing to enhance that and make it run more intelligently.

I love that. And you're right, so many people struggle to get repeat bookings or get the guests to come back or refer a friend. And the reason being is they set up their automations, whether it's in Hospitable, whether it's in Hostaway, Guesty, wherever, to go where, okay, 3 months after checkout, you're going to send this templated message. And templated messages, they look templated, they look generic, and they don't grab the attention of the user. But what you've done is you've gone, right, this is all my data from, from here, this is all the guests that stayed, and then you get it to read all the context of the stay, what they've listed in, like, like I said, the review, and then it will create a hyper-personalized custom outreach. And the keyword is custom. Customized marketing, customized ads is going to be the thing. It's like if you ever watch Minority Report with Tom Cruise and he's walking down the street and every billboard he looks at is customizable to him and it's different to what the next person sees. That is where we're walking to in the future, like highly customized ads on a mass scale. And you're doing it at a very simplistic level, but it's so effective because I guarantee 99% of your competitors in the area or in your town or in your state are not doing that. They're sending the bland generic one. So that's a phenomenal, uh, case study. And am I right in thinking— did I read that it actually resulted in a booking?

Yeah, several since that post has been made. I've, I've been now creating it as like a scheduled task because I try to not do 100 at once to tell Airbnb that I am using a bot of some sort, but what I'll do is I'll just send out like 5 in an afternoon. Next afternoon, I'll do another 5. I've actually gotten several bookings. I think at this point, 3 or 4 with maybe 50 to 60 messages sent. So the return is tangible. It's not just another cute tool that we can tinker around with and tell ourselves we're being productive, but actually seeing additional booking revenue come in. It's easy to tie this activity to real revenue. And I think that's the most important part that I would like to take— I'd like your listeners to take away from this is it's actually real revenue generating activities and the setup is so simple even if you never used it before. So that's something really helpful.

Amazing. Well done. So again, it's simple. You just connect it, get it to read it. Don't spam these platforms because they will go, hang on a second, what's Scott doing here? You break it down into a skill. And a scheduled task. And if any words that we're saying right now start to confuse you, all you need to do is go to the transcription of this YouTube video, wherever you're listening to, copy the whole transcription, paste it into Claude, and just say, okay, explain this to me like I'm a caveman, explain this to me like I'm a 10-year-old, and then get it to go, right, build this for my business. And literally AI will do that for you, which is, which is so cool. So I love that example. Have you got any other examples of anything else you've sort of figured out and worked out with the NCP and Claude? Anything else cool you want to sort of share with the audience?

Yeah, I'm still definitely in tinker and experiment mode. Another one that I've been using is essentially have something on a schedule that goes out and looks at same concept, but specifically for orphan gaps. For future bookings. So orphan gaps, essentially when there's like a small amount of gaps between two existing bookings that are unlikely to get booked, right? So for example, you have a guest checking out on a Sunday, another guest checking in on a Wednesday. Booking a Sunday to Wednesday stay is maybe not, not super likely depending on your market. So what my orphan gap filler skill did, I guess we can call it that, is goes in and is going to send messages, pull context from the conversation. So it's not going to want to say something if it contradicts something we've already talked about in the message thread. So pull context from the message thread, determine if Claude thinks that this guest might be a good candidate to invite to start their stay early or check out late, and then it'll go ahead and start sending those messages out. And we've had some success with that as well. We've had a Sunday checkout extended to a Monday. We've had several Friday check-ins that have decided to check in Thursday as well. So fill these orphan gaps, you know, even if you're just getting a few successes out of, out of dozens of messages sent, then it already becomes a tangible return. So the orphan gap filler is an interesting one. And then doing a bit of work with how I export financial data, being able to move financials into my client statement portal more easily without having to do any import and export. So Fill orphan day gaps and being able to move finances around in an intelligent way that saves me time are a couple of my latest use cases that I've been working on recently.

And what is your current tech stack— is it for me to say tech stack— looking like? So you've obviously got Hospitable. From what I read, have you still got HostBuddy in the background? Is there anything else you've got going on but behind the scenes that powers the business?

Yeah, so of course using Hospitable for just like my, you know, centralized calendar sync and my like source of data. And of course now it has the MCP, it's even more valuable. I'm using HostBuddy for some basic like AI automation around answering guest messages. So essentially just answering guest questions based on information you feed the system. I only have it set up to answer basic questions because I still like to be relatively hands-on with the guests. Communication process to have that customized approach. I have a Claude Max plan, which is the— I'm paying $200 a month. For people who think, okay, I've given up, that's way too expensive, you can get the one that's $20 a month and still get, you know, most of the functionality unless you're using it all day, like I tend to be nowadays. Using Zapier to kind of be able to chain some of these different tools together. They also have an MCP server, which is another rabbit hole for people whose ears are lighting up about all this stuff. That's one I'd recommend checking out because that also connects to your Claude and, and everything else. And then I have a few just vibe-coded homemade tools. Like I have a whole accounting and revenue dashboard, so to speak, that I built using Lovable, which is just, you know, essentially a vibe coding tool that your viewers can, or listeners can, give a listen to. And then just recently created my entire onboarding, uh, flow and go-live portal for all of my clients from scratch using Claude. And that's one that I've been, been really excited about. So yeah, the tech stack is— feels like it's getting bigger by the day, but it's all giving me a return, so it's certainly worth it.

So, but again, I think if you were to, for example, that there's loads of these tools out there that will do this for you, but you're building it yourself, so potentially, yes, you may have the cost, but you are saving a lot compared to if you go to said company and go, right, I just want to use your tool. Which— so the whole software as a, as a principal business is— that's going to change a lot. A lot of software is going to change rapidly over the next 18 months because of this. Because, you know, as you, you admitted yourself, you're not a techie founder. I am not a techie founder. Everybody that I've spoken to on this podcast when we talk about things like OpenClaw and Claude, nobody has come to me and said, I'm a techie founder. So, but we're all figuring this out very quickly. And, you know, your story is probably many, many of people who are figuring this out or trying to figure this out, which is phenomenal. And so you've built tools, you're building onboarding procedures that, you know, this time last year you could have quite easily spent 5 times, 10 times as much tapping into that solution. So you're saving money, you're making money, having fun in the process, learning so much, and having the results to show. So brilliant. Really, really good. Before we let you go, is there anything else that you would like to share with the audience? Any other cool things that you're figuring out, or what is the next things that you're thinking that you want to figure out?

Yeah, sure thing. And thanks for the kind words, by the way. I think that the next layer for me, something I'm working on and something that Mark, frankly, you've been an expert in this space for as long as I've been hosting. So I'm sure as I say this, you're like, yeah, we're building or we have something that already does that. So, but is adding some intelligence to the way that I'm trying to get my direct bookings by what I'm doing right now. I've called level 1 is reaching out through the online travel agencies, but of Of course, the issue with that, which you know better than anyone else, is the service fees associated with it and how that can be an issue. So what I'm working on is creating a smart email capture layer of this where, you know, I can either through a QR code or through a rental agreement be collecting guests' actual information, real email addresses, real phone numbers, gaining their consent, of course, to reach out to them and be able to reroute them through a direct booking website instead of on the online travel agencies so that we're actually owning our own audience and saving on these service fees and having, you know, more control over the whole process, being less reliant on the big online travel agencies for these things. So still kind of perfecting that and something that I'll be deploying for myself soon, but having that as a layer where It's continued personalized marketing outreach, not through the OTAs, is something that once it's set up correctly is going to have a really tangible and palpable return for my business. So that's the thing that I'm still trying to make sure I get everything right and don't violate terms of service for these OTAs and just deploy in a way that's really scalable and simple.

Amazing. Music to my ears. And what is your CRM of choice? Where are you storing all this guest potential data, or have you not figured it out yet?

Yeah, so I was using Notion, another, another tool in my tech stack that I forgot to mention, which essentially just like database tool, note-taking tool, to-do list tool, a million different things tool depending on how you configure it. But now I'm experimenting on just essentially like building my own homemade dashboard, um, within Claude Code, which if it sounds intimidating, it's totally not something you need to do. You can use a spreadsheet, you can use a Notion template. There's so many different options, but I'm someone who wants to have all my tools work in a really particular way. So I'm starting to find that I like to just build my own mousetrap. If the tool that I'm using, I feel like there's an element of it that I don't like or that's not conducive to my business. So switching from just Notion databases to a bit of like a homemade CRM system that I'm working on getting connected up.

Nice, nice, man. Well, I'll, I'll reach out to you afterwards because I'll give you a free version of GoHighLevel, which is a very cool CRM tool that we use at Boostly. I think a lot of those things will have been built into there and you can just build on top of it. It has its own CP into cloud as well. So I'll give you a free version of that after this call and I'd love to see what you can build with that because Hospitable syncs straight into there as well. So all of your guest data will come straight into there with the new Connect tool that we're launching next week. So I'll be very excited to see what you can build with that. So very, very good. Listen, thank you so much for joining us. I'm really encouraged for everybody to take this and figure out what you can do, you know. Um, please, if you're in the Hospitable Hosts group, go and look out for Scott's, um, for Scott's posts. His last name is spelled S-H-E-R-I-N. Is there any other Facebook groups that you're documenting this journey in outside of the Hospitable Hosts one, or, um, is it mostly in that group?

Yeah, it's, it's mostly that just because it's specific for A lot of my posts are specific to the Hospitable MCP, but I'm also in Bill Faith's Build Short-Term Rental Wealth Facebook group. I know there's a— it's a very popular one, and sometimes I'll just write something in the Hospitable group and like cross-post it to just a bunch of other kind of like generic Airbnb host tips and tricks groups. So I'm sure if you're in any of the, any of the bigger ones, then you'll, you'll come across my stuff. And I love talking shop about this. So like if anyone is curious and wants to you know, just swap some ideas, just, just reach out and, you know, we can chat. I love it.

We're gonna have to get you on Substack. We're gonna have to get you like your own, uh, platform because it's such good stuff and it's just behind these gated, these gated walls. So yeah, we're gonna have to work on that. Uh, definitely get you posting more because it's fantastic what you're sharing. Uh, just out of interest, how many people are in your inbox? How many people have been messaging you, asking you questions? Uh, has it been kind of busy since you started posting?

Yeah, I do get, I have had a fair amount of people just like sending me direct messages who are kind of in the same spot as me, right? They're like, I've just started hearing about this technology. I'm starting to tinker around with what I can build, but I don't really know what I'm doing. Seems like you're kind of figuring it out in real time too. Like you want to hop on a call and just swap some ideas. So I've had one or two. I've got a couple other scheduled of, again, it's not like to sell anything or to. Have any type of— it's just literally swapping ideas and, you know, putting brains together. Because of the— at the end of the day, you know, rising tide raises all boats. So we're all just—

love it—

a big community trying to help one another.

I love it. We, um, we did something in London about 3 or 4 weeks ago where we— again, we just put— we found a venue, we got 15 people together, they all traveled down from wherever they live, and we got— we got in a room for 6 hours and we did the same thing. We just sort of figured it out. Swapped stories, did some presentations, like a mini buildathon, a little mini hackathon, which was really cool. And it's the power of it. You're absolutely right. I love what you're doing. Keep doing it. Um, I'm going to be over in America in the summer, so hopefully we get to meet up. And we're looking at doing like a big buildathon, hackathon-y thing in Nashville in October, um, for Verma International. So if you want to be part of that, let us know. So it's going to be something— cool things happening this year. Appreciate your time. Thank you very much for joining us, uh, and we'll let you go. For everybody that's tuning in, please jump in the comments, thank Scott, go find him on Facebook, go find him in the groups, and we'll work on getting that Substack, uh, as well. All right, Scott, buddy, thank you very much for joining us.

Thanks for having me, Mark. Thank you.