AI in Hospitality: Autopilot or Assisted Control?

All right, good morning, good afternoon, good evening, and welcome. We are gonna go live for our second day of the boost your bookings summit, the booster bookings bootcamp, Obviously. Tomorrow is book direct day, which we're really looking forward to here. I hope you are looking forward to it too. I've got a lot of more information to give you later on today about the book dark day and what we're going to be doing. But before that, we're going to be cracking on today with something really cool and a topic that I think everybody needs to be paying attention to. I've put it in the. In the. In the WhatsApp group. I've put it in the Facebook group. Today we're going to talking about Human first, AI second. It's a really cool title. Before we do get going, though, can you just please let me know that you can see this by saying hi in the chat? And I don't know we're going until we are live until someone says hi in the chat. As soon as you say that, I know that we are good to go. There we go. We've got a few hellos coming in there, which is good. Right, before we get going then, let me just quickly share my screen. Little bit of admin. Now, I keep mentioning about a Facebook group and I'm gonna be talking about a Facebook group at some point during today. Oh, hello, everyone. I can see you better. Let me just remove you for a second. This is the Facebook group. This is where all of the action happens. This is where all of the replays are stored. This is where all of the cool little features I will talk about in a second are announced. If you are not in the Facebook group, simply go to Facebook and type in boost your bookings special virtual summit. It will come up. Let me just move my face out the way. Request to join and one of the admins will let you in in there. What we did today is we announced the winner of the prize draw that we've been running for the last 24 hours. Congratulations to Charles, Nicole, Karen, Maureen, Linda and G. You won a copy of the amazing Airbnb optimization playbook by Eli. If you are not a winner, go and grab a copy. Very, very cheap. I'm about 60 pages in now. Very, very good book if you want to optimize your listing. And obviously as well, this will be where I put the highlights. We've got Frank last night. Um, again, we've got some great highlights in there and all of the things that you need, including this little Dropbox folder. Which I want to talk to you about very, very quickly. Tomorrow, obviously is Book Direct day. I encourage everybody to post about direct bookings and why it's important on all of your socials. Whenever I say this, people always go, but Mark, I don't know what to post. So I've come up with a full Dropbox of content for you for free. It's, it's social media, it's videos, it's images, it's everything that you could possibly need. Plus email templates. It's all in there, it's all for free. You can literally grab it, download it, post it on your socials, you name it, TikTok, Instagram, LinkedIn, Facebook, Pinterest, whatever, go and post it. And then you've got the email templates as well that you are more than welcome to use for absolutely free. Just copy it, dump it into your LLM of choice, ask for it to personalize it for your business and your brand and it will do it for you that you can then send out tomorrow. And who knows, you'll be able to get some direct bookings, which would be awesome. The link to that is in the Facebook group. Now, if you would like me to send you a template. If you would like me for down DM you1 of the templates and you haven't yet got it yet, just DM me the word template or put template in the comments or the chat and Karen's already jumped on saying downloaded one of the videos and it's ready to go for tomorrow, which is epic. Very, very, very, very cool. So if you're not in the group, go to facebook.com and then just type in boost your bookings virtual summit and you'll be able to find it. Come and join us. Very quick. Shout out to Mr. Sean Rakijis. If you don't know Sean, probably one of the biggest YouTube channels when it comes to short term rentals, I think I'm gonna guess here over 300,000 subs, which is insane. He's gone and created this product called the BNB Factory. He said, listen, post out about it today. Members can have discount. Absolutely on us. Very, very cost effective. I've even done a quick video earlier showing how easy it is to do. You're using some of our pictures. Go and give it a go. Go to the BNB Factory. Literally as easy as that. You can't say easier. And that's just for pin pilot's challenge. Sean saw what we were doing. He said, hey, can you go and do this? Send us out for the groups, which is great. All right, let's crack on, shall we? Let me just go and let Nico in. Hello, Nico. You're in the group. Right, let's go and crack on with today. So I'm going to share. Not share my screen. Let's come back to the main. We have got a very special guest with me, Reuben of guess Way co founder. The topic is one that when he sent over, I was like, brilliant. I'm really looking forward to this. Human first, AI second. So, Reuben, just very, very quickly, for the people that are tuning in, what, by the end of it, what will everybody learn by the end of this session? What's the main takeaway that you want for everybody to have?

Well, first of all, thank you for having me on. I think it's going to be an interesting one for everyone. Everybody's been talking about AI for the last year and maybe a bit tired already of the word. I think it's going to give you a better idea of where we're evolving towards and what you should see as to where AI should stop in your business, how to embrace it in the right way without replacing people. And I think that's going to be a really cool thing to talk about today and hear what people think.

Nice. And just give a little bit of background on yourself. How has Guestway come to be in a business that is doing really, really well? So how can you. What can you bring to the table today?

Yeah, yeah, love to. So, as you were kind enough to introduce me, my name is Ruben. I'm one of the founders of Guestway. We actually started Guestway because we were property managers ourselves, and I mean, still are. We managed about 700 properties, a proper mix of everything. Single apartments, multi units, hotels. And kind of were frustrated with what we're missing in the industry. Like a proper layer where everything gets combined into one on top of the pms. I couldn't find it. And then luckily my co founders are super, super good developers, so we started building it ourselves and then people came asking if they could use it and then we decided to give it a shot. And now we're here today, growing extremely fast and happy to talk here today to talk a bit about what we're doing.

Yeah, absolutely. And if you've been at any conference over the last, what, eight, 10 months, you will have seen Reuben and his team and the big blue banner at the event on the conference circuit. It's been amazing to see that. So I got to properly know him and learn about the product. So this is why I said, listen, let's get involved with this on a virtual summit so we can share this expertise. So let me go ahead and share the screen. And again, what I would love for you to do, everybody who's tuning in, whether you are live or on the replay, let us know where you are tuning in from around the world. Yesterday we had people in Australia, which is crazy because it's like four or five o' clock in the morning over there. So let us know where you are around the world. I'm sharing this screen now, and I'm gonna hit this little button here, this little button here to get Ruben's face back. We don't want double of me. I'm gonna do this. This is why you can tell we're live. All right, we're good. We're in. Now, just like yesterday with Frank, unfortunately, Reuben can't control, but I can. So at some random point, you're just gonna hear Ruben go, slide. And it'll be my cue to turn the slides over. But where would you like to start? Would you like to start on this slide or would you like to start on the. On the next one?

I mean, I think this one was basically discussed a second ago. So you can jump to the next one, please.

Nice. And we've got Jim joining us from Belgium. I think we know which gym that is.

Number one supporter.

Number one supporter. Uh, and where are you tuning in from, Ruben? We never. We never got that from you.

I'm actually. My wife is not so happy about it, but I'm on a skiing trip and I've been working today in Switzerland at the moment.

Yeah, well, we did get a nice picture in our group chat of Ruben on the slopes about to go skiing. So a thank you very much to Ruben's amazing and very, very thoughtful wife to let him steal him away for 30 minutes to come and. And do this today. Okay, so let's. Let's crack on. Where are we today? Where can we begin?

Happy to talk about. So, yeah, where are we today? I mean, I touched upon it briefly just a second ago. I think if you attended any of the conferences in 2025 last year, you saw AI everywhere. Everybody was screaming about first AI this, first AI that autopilot. And I can imagine it was a bit scary for a lot of people who were walking around, but we've been running this industry for quite a while. This is a people's business, and there's a lot of unclarity about what's going to happen. You hear things like, AI is going to automate everything, it's going to replace your team. The whole hospitality industry is going to be running on autopilot and it kind of poses the question like we should use AI, but like where should it stop? How can we use this in our day to day lives to help us but not replace us? And I think that can bring us to the next slide.

I like it.

So to continue on that, I think it's becoming more clear that there's a clear split happening in the industry of two kind of lanes of thought, what people are thinking. You have some companies and some people going like, hey, for me this is going to change the whole thing and we're going to replace everyone. There's going to be no human interaction anymore. My AI is going to be talking to all the guests. It's to going, going to solve everything. And basically I set it up at the start and it's going to be doing everything on autopilot. That's for me is AI first. And then you have a second part of it where people are saying, I feel like AI is a great tool, I want to use it in my day to day business. It's helping me to, to make, to make life easier and to be able to work better on my relationship with the guests and stuff. But you know, solve some of the tedious repetitive tasks for me and that, that's what we call UI first slash human first. You can jump onto the next slide, please.

Nice.

Why is that important? I mean, I'm not saying that the first path that people are talking about, where you talk about using an autopilot to replace everything, is per se for everyone, a bad thing. I think for some people it makes a lot of sense. If you are doing property management as a side business, which are a lot of people that do that and you don't have time to be answering messages at 2am in the morning or to be constantly available during the day. I think it makes sense to have it help you, but it will start hallucinating at some point. We are sadly not in the AGI era yet and there is still a lot of mistakes happening, especially in a sector like ours where so many variables are at place. So making these mistakes is inevitable. And when you're managing five units, it's an annoying thing. It can happen, but like I said, it's probably your side business, so you don't care that much. At 50 it's very annoying. You don't know really who to blame, who to blame if something goes wrong. And if you're Running a business even larger than that. This is something that can ruin your reputation. If for me, myself, if I pick up, I'm in a hotel right now, and if I pick up the phone and try to call the reception and there's an AI picking up, it kind of ruins my experience if that AI is hallucinating. So I think scale changes everything with this aspect. That's, that's kind of the point where I'm trying to go to with this. It's like for some people it makes sense and some it really doesn't. Next slide, please. All right. And the reason that is because there are quite a few hidden risks behind AI. You know, it's. It's all very sexy and very cool to talk about, but, you know, there's some things behind that that, that can scare you and should maybe in some point it allows you to lose control. The system is acting for you, which is great if it's working well, but if it's not working well, then the accountability kind of blurs. You know, who am I blaming for this? Like, who is responsible for what went wrong? And that trust between the guest and the property manager kind of erodes. It's hard to complain to an algorithm and it's even harder to fire them, which I think is something that a lot of people are going to run into these issues in the next few years, if you haven't already. So I think that can take us to the next slide. Mark, if you don't mind, before we.

Do jump on, I would love to get everybody's temperature check who is watching. So we've got a lot of people tuning in live and this would be an awesome opportunity. Even if you're on the replay. Drop this in the comments so we can look at it afterwards.

But what.

Where are you with the world of AI? Are you. Are you all going all in? Are you using it on a daily or like Ruben is laid out here? Are you sort of like a bit hesitant because of this hidden risk that a lot of people aren't really talking about on, you know, Instagram or conferences etc. So let us know where your temperature check is. Reuben won't be able to see the chat, but he will on when he goes back and look at it later, once he's apologized to his wife for. For missing a vacation to speak to us. But what he will do when he comes back on later. So just let us know what your temperature check is as we go to the next slide.

Okay? So please be kind in the comments, but let's pick this up from here. So that brings us to kind of like reframing AI. Like I said before, AI is definitely not a bad thing. And it has amazing qualities such as pattern detection, summarizing information, flagging risks. And those are things that it's super good at, and you want to use it for those things. But on the other side, humans are a lot better and very good at, you know, judgment, what's happening, what's going wrong, showing empathy to people, taking responsibility for things that go wrong. And I feel like there's a healthy mix in between there. And you should be able to, you know, put that 50% of boring stuff onto the AI, but then let people really focus on the meaningful 50%, you know, what they're good at, what they're used to do, and what they thrive in. Yeah. Next one, please.

Mark slide coming up.

So I'm not gonna make this into a sales pitch at all, but I kind of felt like would be easy to give a couple of examples of, like, how do we look at this? Like what I'm trying to say here. And on the right hand side there, you see a, you know, quick snapshot of our inbox and a couple of things that are in there that, that will make this make a lot more sense. Like what? We use AI for message type detection, you know, kind of analyzing what kind of message am I receiving here? Is this an issue? Is there an emergency? Is there a specific request? Because AI is very good at detecting these kind of things, you know, and being fast at it, which makes you able to filter on those kind of things. Then second thing which is super helpful is sentiment tracking. You have a lot of guests passing by each day and you kind of want to avoid, of course, that they are unhappy and leave the property, leaving you a bad review. So being able to have someone look over your shoulder and check, like, how happy is this? Guest filtering on that and being able to offer them something or help them out before they leave and leave. A bad review. Super helpful. Summarizing conversations. Let's say you work in two shifts, like people doing the night shift, answering messages. If something goes wrong there, it's quite a tedious task to be scrolling up through the whole conversation seeing what went wrong. So it's very helpful if then you can get a quick chronological summary of the most important things that happened in the chat before you dive in and take over. Reservation risk score. Super cool. You kind of want to know who is coming to your properties. Maybe there are your properties, maybe there's someone else's but it takes some time to go through all of the reviews of these people and analyze. Is this a big group of guys coming? Did they make the reservation recently? Is there a kid coming? This is something that the AI in there will do for us. You know, kind of look over those reviews and give it a score out of five if you want. You can then, for example, automatically pre approve a booking if it's a very good score. Suggested replies, pre write a message for you to answer, and then urgency scores, you know, seeing if there's a fire somewhere. You kind of want that to be booted up to the top of your inbox and not get lost inside the other messages. Kind of. The point that I'm trying to make here is you really want to move towards a future where, like, you have faster understanding of what's happening, can reply better and get better, you know, a better feeling of the context with losing less time in that sense and being able to be more efficient in how you're working during your day.

So here's a question. How does guestaway pull this information in? I assume it's coming from a PMS or Airbnb. How is it sort of pulling it into this dashboard that you can then do your skills?

Exactly. So, yeah, we integrate with most of the large PMSs, like a guesty host to a mobile whatever. Even if it's not there on our site, we can always set that integration up if the PMS does not provide that info. We do, for example, have a direct integration with Airbnb. It's something that we worked quite a while on and are happy to talk about. So that allows us to get a lot of that information. Of course, sometimes you're going to be limited if your PMS does not have that information by itself, that can limit maybe the amount of data that the reservation that can be fed into the reservation risk score, for example.

And then obviously, once it's in your dashboard, this is what we're talking about with the guest sentiment, because you'll have all the formulas created to be able to go, oh, this is actually starting to escalate, or this is on the way down. And I guess that's a massive thing. And, you know, how, how does the tool then go, okay, there's messages come in, the guests asking for WI fi. How does it then analyze these messages to go? This is something that you need to take care of. How does that sort of formula work behind the scene? Scenes?

Yeah, it will kind of like assess how urgent is this message. Like if someone asked for a WI Fi that could be easily answered. You probably have a guidebook in guest way for that apartment. So it's going to be suggested directly and. Or you can turn on our mini autopilot inside the platform that answers messages like WI Fi code and stuff. Not the important stuff. But yeah, we assess based on that and there's a lot of things of how people like to run their business. We, for example, love to filter on those sentiment scores. We love to filter on people that are currently being hosted. We have automations that we recently launched in the platform which make life a lot easier. For example, automatically prompting people with a satisfaction score of 5 out of 5 for a review because those are the people you want to ask and you don't want to forget. So there's a lot of things happening. It's super cool. You can basically tailor it to your specific business.

Lovely. Well, this is good. Let's go to the next slide.

Yes. So this is kind of like a quick recap of what we were saying earlier that. I'm not saying that this is a bad thing to per se have AI First. I think there's definitely the kind of business that would benefit from that. I can see on the left the AI first companies, smaller portfolios where maybe this is a side business and you don't have that much time to be able to allocate towards it and you do have a higher risk tolerance then I think for sure this is something that can help you out. But then the other side, what we see is, you know, human first businesses where it's professionalized operators that have a reputation to uphold that have teams working there that knows how their business work and you want to make them more efficient. And I think that in that sense control is not something that's optional, but it's something you kind of want to keep.

Yeah, nice. Very, very nice. Right, next slide.

So this is, yeah, to come back to that, this is why we build guestway for those professional teams and not in the sense where we want to see AI as something to replace people. I think people have got up a lot of experience over those last years and got where they are today. And we want to empower them and make them more efficient, to be able to do more with less. And that's how we built our platform ourselves. We know how things work. We've been through the trenches ourselves. And I can kind of feel like you see that in every feature that's in the platform. We talk about AI as an assistant and humans are the ones that decide.

Nice, very nice. I like the route that you're going with this.

Thank you. Yeah. So how do we see the future and maybe some of you do now as well? We'll see. We see it as assisted, not autonomous. And I don't think that AI will replace and should replace professionals, but it will separate the amateurs from the professionals. You should embrace it. You should use AI in your day to day life. I think everybody knows that by now. If you don't, you'll probably get left behind. But it's important to think about how you want to use it, how far should it go and where can it help you and where should it not help you?

Yeah, I mean at the end of the day if, if you're not using AI in a business capacity, you are going to get left behind. It's the most easiest, quick win that you could have in 2026. Doesn't matter whether you've got a thousand properties or you've got one, it can massively, massively help. I still think you can't go 100. You've got to use it to get your 80 of the way there and then use 20 of your own intuition with a lot of things. Don't just blindly copy paste and, and send it. You do have to have some form of mental capacity to do that. But it is so super powerful and you know, we've been talking about it now for what seems like the last, well, forever, but it is still very new. And even if you're thinking, oh, I've not, I've not cracked into this, I don't know what I'm doing, just that literally, just start because you will be ahead of probably 90 of your local area just by starting now. I still believe the only people that are truly using this is business owners and geeks. I've been saying this for the last two years and you know, it will come to a point and I've seen it, I've started to see it like, you know, normal Joe blogs, public are starting to use it. My friends who aren't entrepreneurs, I met up with them that, that they're, they're not online, they hate social media. I've known them since the age of four, they're all employed. We went to the pub a few weeks ago and I showed him something on Google Gemini with very, very simple and I felt like I've just blown their mind. So like you say, it's, it's still very, very new. But again, I love this. AI won't replace professionals, it will separate them from the amateurs. Lovely little Phrase that I will definitely talk about and still and move and take it with me this year. I love that. Ruben, thank you very much for this presentation. Now I'm quickly going to move you away from this QR code. Now, if anybody has liked anything that we've been talking about today when it comes to AI, especially guest away and Reuben, please go and scan that QR code. I assume it will take people to a calendar booking link. In fact, let me go and test it, test it with you. Now it'll take you to a calendar booking link where you can go and book some time with with Ruben and the team. There is no demo spots available this week, so you've got to be quick if you want to get on board of it next week. There's spots available on Monday, Wednesday, Thursday, Friday. So even if you're on the replay, go and scan that code. Go and book in some slots and see how they can potentially help you. Really, really fascinating. Thank you very much. Now, Ruben, anything, any words of wisdom that you would like to leave us with today?

Well, I think that this is something that it should be an open question, right? It should be something you think for your think about for yourself. Like, what do you want? How do you see your future? Where do you want to go? How do you want to help your team? It is relevant. It's like you said, some people are still so behind on it. So I can imagine it gets very stressful for people as well, like seeing all of this around them and you always feel like you're behind but you really shouldn't. Like if you talk to the right people and you know, jump on a call sometime, let people help you, it will make sense. And I think there's a very nice way of handling things where you can really work in the sense of like being hand in hand, you and AI and your team. And that's where we should go to in the future.

Love it. Really like it. Right, Ruben, thank you very much. I'm gonna, I'm gonna let you go again. Please do say thank you to Ruben in the chat. Go and scan that QR code and if for whatever reason you miss it, just leave some messages and I'm sure he'll come and find it and reach out to you. Reuben, what's your favorite social media. Where can people go and follow you to get more insights from you? Where's your favorite social media choice?

I think for now LinkedIn is, is our favorite social media of choice.

Social media choice. Fantastic. Go in and check him out. Thank you very much. I'll let you go get back to your vacation and. Yeah, and say please say thank you to your wife and, and I'll see you at one of these up and coming conferences.

This was great. No worries. Thank you so much for having me on. Good luck tomorrow as well.

Thank you. Thank you. All right, so he, he dropped in some cool little preview of tomorrow. So tomorrow is Book Direct Day. I'll come back. But before we do that, please do go and say thank you again to Reuben and the Guess Way team. They were part of the companies that I've mentioned that without them we couldn't be putting this on. It's taken a lot to put on this week. We put a lot of money into it. And you know the team at Guess hostfully, obviously with Boris and I've got another company to show you tomorrow. Two companies with flat away and scale. They've massively helped put this all together. So again, please do go and book a demo. Go and say thank you to them. Even if you just go to LinkedIn and just say, hey, thanks for that really nice different way of talking about AI. And I feel like I'm probably guilty more than anyone the way we've been banging on about it on this channel and these lives and these summits and these boot camps for the last couple of years. But, but a real nice perspective to have it. And again, that quote is going to stick with me, is I won't replace professionals. It will separate them from amateurs. And I love that. And I am for sure going to steal that phrase moving forward. Okay, so we've got some really nice comments in the, in the chat, from what I can see. We are live streaming right now on YouTube. We are live streaming right now over on LinkedIn, over on Facebook, over on everywhere. And I guarantee there's going to be one question that comes in, which is, where's the replay? The replay is going to be right in the YouTube. Wherever you are watching it, just hit refresh later on and you can go back on anything we've talked about. Now, this is coming towards the end of Tuesday, the 3rd of February. Tomorrow, when we come back, it is obviously going to be the big one. Tomorrow is Book Direct Day. Book Direct Day is something that was started a long time ago by somebody in America. I can't remember who, but I've sort of carried the torch a wee bit in my own little way. Last year I put a big billboard up in Nashville. The year before, I put billboards outside the Airbnb offices talking about direct bookings. We've done loads of cool things over the year and tomorrow what I wanted to do is. Oh, he's still here. Hello, Reuben. What we're going to do tomorrow is we're going to do a huge live stream. We're going to start at 6pm and we have got, I think there's 10 people joining me. Mark Lumpkin, Simon Lehman, Brittany Magsig, Raj and Chida. Madison Rifkin, Rose Tipka, Natasha Hirschman, Danny Roostein, Damien Sheridan. And we're going to kick things off with Boris from Flat Away AI, who is going to talk about websites and AI, which is pretty cool. Loads of topics we're going to discuss. I've asked everybody just some quick bullet points and everything that they've said is going to be epic. Brittany is. If you don't know who a mountain mama's cabin is on Instagram, my gosh, you're in for a treat tomorrow. Over, I think I want to say over 400,000 followers on TikTok and Instagram combined. Could be more going to talk about how she did it. Then we're going to bring in Rajan Chida. If you don't know who he is, he is a phenomenon on social media. Over 500,000 followers just from documented his story. He only opened his property. He's got one property. He only opened his property in December. Fully booked, 100% on, 97% on direct 0 or 1 or 2% on Airbnb. This is a guy. But if I try and get him in a year's time, we wouldn't. He's already elevating to massive stardom and it's very lucky to be able to get him on tomorrow. Maddie Rifkin has got some breaking news for us. Rose Tipka is talking about how she's got over 60 repeat bookings direct and how she does it and so much more. Danny Roostein, Optimizer BNB's Come and Talk about pricing. Damien Sheridan. Come and talk about website. Simon Lehman, talking about the. Is this the end of the hobbyist host, which is a bit of a spicy topic, but yeah. Loads and loads and loads kicks off tomorrow, 6pm 6pm UK, 1pm Eastern. If you haven't done so already, go and add it to your calendar. If you don't know how to add it to your calendar, come into the group. Click into here. All of the links that you need from the WhatsApp group to the calendar to everything is in is in here. All of this week is absolutely free. No sales pitches, no Big reveals, big launches or ever. It's just free for you. All I ask in return, just my one massive favor is just come into here, tap on this, click on this and just go and invite as many friends of yours on Facebook who are hosting to the group. If we can get that to 3,000 by the end of the week. Look, it's so easy. I just literally tap here, tap it up, tap, tap, tap, tap, tap in and then they get invited in and then as we can get this group to 3,000 but yet before the end of the week. Amazing. Don't forget the free templates, don't forget all the cool things tomorrow. The question is how many hours to block? It's hard to say. I'm preparing for three hours. So from six till nine, realistically it could go to 10 o' clock UK. So three or four hours. You don't have to be here for every single bit of it. I totally get it. But you can jump on, jump off, jump on, jump off, we'll be there. And again, all the replays will be stored and, and all that good stuff. But if you do join us live, you know, there could be some prizes to be won. You know I like to give prizes away, but yeah, I've got a, a big, big old long night tomorrow with everybody. All right, with that being said, want to end on this cool little comment that I've seen come in, Reuben. I like the idea of using AI, but humans decide as this is the real down to earth touch, which at the end of the day, which is what hospitality is, one on one, it's always going to be human base, it's always going to be human led. And with that I'm going to leave you. Have a fantastic night, have a fantastic afternoon. To our friends who are tuning in from Australia and New Zealand, have a fantastic morning. Join us tomorrow as we finish our book direct virtual Summit and we have a very big and a very good book direct day. Have a good one everybody and I'll see you all tomorrow. Ta.