The Game-Changing App Every Host Needs in 2025

Welcome to another episode of the Boostly Podcast, the ultimate resource for short-term rental hosts looking to level up their business with direct bookings. In today’s episode, we shine the Boostly Spotlight on Happy Guest, an innovative guest management system designed to simplify and enhance the guest journey.

Our special guest, Mike-O’Connell, the founder of Happy Guest, shares how this groundbreaking platform is helping hosts deliver seamless guest experiences, boost direct bookings, and streamline operations—all while keeping hospitality at the heart of their business.

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Boostly Spotlight: Transforming Guest Experiences

[00:00:00] Liam: Welcome to the Boostly podcast. This is the podcast that gives hosts the tools, the tactics, the training, most of all the confidence for you to go out there and get yourselves more direct bookends. Why do we love direct bookends? Because it usually means more money for your pocket as a host, but also in general, it is just the best thing to do in a competitive market.

[00:00:18] Liam: We've got the Boostly spotlight today where we shine the Boostly spotlight on a service or an app or something which will help you within your hosting business. And today I'm super excited because this is something which. I'm always passionate about the guest journey, the guest experience. And today we're going to be speaking with Mike.

[00:00:36] Liam: He's the founder of Happy Guest. And if you haven't heard of Happy Guest, do stick around. This is going to be so worthwhile because this is really exciting. They're doing something a bit different and it's something that you need to be aware of, especially when we're bringing it to you right now. This is fairly new.

[00:00:52] Liam: So I'm really excited to be sharing this with you as our guest and our listener. So welcome along, Mike. Thank you for joining me. 

[00:00:59] Mike: Thanks for having me, Liam. Appreciate being on. I've been friends with Mark for a long time, and the whole Boostly team. So it's a pleasure to actually be on this. Long time coming.

[00:01:08] Mike: So, yeah, thanks for having me. 

Introducing Mike and the Vision Behind Happy Guest

[00:01:10] Liam: First of all, before we dive into, like, what it is, what it does, what do you want people to get out of the next 20, 25 minutes that they're listening to this episode? 

[00:01:18] Mike: Yeah, just like a basic understanding of, You know, no matter how large you are, how small you are, we're all professional operators, right?

[00:01:25] Mike: We're all, for the most part, entrepreneurs, and you don't really need to be limited by the technology that's out there. You can operate your business just like that big, you know, 1000 property and property enterprise business does. And. Anyone can operate like an enterprise business from a technical side.

[00:01:43] Mike: And that's kind of why we, we created the platform just to show people that it is possible to run their business like this, these large enterprise companies, you don't need to be bullied by OTAs into, you know, booking through them and only being able to book through them. I think. You know, not to jump ahead, but there's this sentiment in the space that, you know, you need to book through an O.T. A.

[00:02:05] Mike: They're going to protect me. Um, and that's not the case. So we're here to try to, you know, both educate and provide solutions, you know, to help people be able to book directly and be able to sleep at night knowing that, you know, they're going to be safe with those guests that arrive. 

[00:02:19] Liam: Let's dive in. What is Happy Guest? 

[00:02:22] Mike: Yeah, I just want to touch on that because they were here before. I remember my first VRMA conference years ago And I was working at a company called Turno and I said to this, you know member of VRMA Yeah, no, we help you find cleaners for your Airbnb and this guy went absolutely nuts And it was just like every time I hear someone refer, you know to a short ladder or to a short term rental as an Airbnb As a noun, it always brings me back to that moment.

[00:02:49] Mike: It was very humbling. And since then, I never, ever did that again. What gets Happy Guest is, it's called a guest management system. So you have your property management system. Now we've coined this term. I like to think so. Um, it's really a guest journey or guest experience tool that. Is everything post booking?

[00:03:07] Mike: So you guys did a great job. You got that direct booking. You got the booking through the O. T. A. Now I have that guest coming to stay with me. So from that point on, we need to deliver an exciting guest journey, right? Something that's seamless and take care of these guests. Because we've got to remember, we're always were hospitality professionals, right?

What Is Happy Guest and How It Works

[00:03:24] Mike: You know, we're not Internet professionals, we're hospitality professionals. Um, so What Happy Guest does is it consolidates, um, that post booking guest journey. So, the guest is going to be sent a link. That's a static link that's assigned to each property. From there, they're going to go through their house rules.

[00:03:42] Mike: They can sign a rental agreement. They can purchase a damage waiver, upload their IDs. And, once they complete all those steps, That's when they're given their check in instructions. I can't tell you how many times I'll talk to a host or a PM that has rental agreements, but maybe 10 20 percent of them get signed because they're going out via email, and then it's the day they're there asking for the door code, and that person could be in the house without signing a rental agreement.

[00:04:06] Mike: You might not have their ID on file because you're scrambling to get them the door code. You're scrambling to check them in, right? So this is a clean, easy way, um, to guide them through that guest journey. And once they're in, Right now we have directions on how to get to the property, personalized videos, um, upsells.

[00:04:25] Mike: We have guidebooks all in one place. So it'll replace some of the other tech that you're using. It'll work alongside your PMS. Um, if you're not using a PMS, that's okay. We can, we can still help you there. Um, but that's basically Happy Guest in a nutshell. 

[00:04:41] Liam: I'm sitting in a lot of, um, masterminds and groups of people at the moment who go, Hey, We've got a lot of tech at the moment.

[00:04:48] Liam: So what makes Happy Guest different and having a look at how to look at it and seeing it, I know this, but I want you to, what, what makes it different? 

[00:04:59] Mike: Yeah, I mean, there's a lot of things that make it different. Um, it's a little bit wild, a little bit out there, and that's why we love it. One thing to remember is, uh, depending on who you are operating, most of us are, you know, facilitating vacations.

[00:05:11] Mike: These are fun and exciting trips for families. And someone even said, Wow, your app shits rainbows. I don't know if we can swear on here, but that's not an insult to me. It's exciting. Right? So we have a loading page. That's a satisfaction video, um, where they're going through these steps. It's all curated.

[00:05:31] Mike: It's almost a gamified check-in process. And from there, you're capturing their phone number, you're capturing their email, which is very important for retargeting, um, all in a fun way. It's not like I'm going to an email and signing a rental agreement. I'm, I'm skipping out on, you know, a lot of these really awful tasks that people just skip because guests don't want to do it.

[00:05:51] Mike: And guests barely realize they're signing a rental agreement. And, um, then they're checking in and they're having a great, great experience from there. 

Unique Features That Make Happy Guest Stand Out

[00:06:00] Liam: If you could just talk us through how it helps a host. First of all, how easy is it to get the information about this? Cause it's one of the pain points, right?

[00:06:09] Liam: I don't want to spend a lot of time doing it. 

[00:06:11] Mike: No, I mean, super easy. we're integrated with, you know, a handful of PMS is that you guys are probably using, um, when we built this, we built it originally to run pretty agnostically on an ICAL integration. Um, so if you have a calendar. We can, we can run this for you.

[00:06:28] Mike: One thing that we're really good at and what we like doing. Um, and I'm not dissing anybody, but when we have people self onboard, sometimes they just don't know if I gave someone the keys to a Ferrari, they might not drive it well, and I think we've built a Ferrari. Um, but we're going to help you along the way.

[00:06:44] Mike: We're going to help build out the guidebooks. There's a lot of psychology when it comes to the process and the colors and you know, how everything's laid out. Where we wanted to make sense to that guest. I could give you, you know, a guidebook and you could put 10,000 lines of text in there. Um, and the people might be confused.

[00:07:00] Mike: One thing we implemented, which is really special is you can embed personalized videos that are property specific. So if you have a weird coffee maker at one place, do a 10 second video on how to, how to use it. We have a host that just onboarded and she did this on her own where she's got this tree house up a half mile hike and it's up this weird trail.

[00:07:18] Mike: She has a time lapse that she filmed of herself walking up there and that's a heck of a lot easier than you reading. Okay. Walk up this hill, take a right down this path. Like there's just these little things that we can do to really, really, um, you know, boost that guest experience in, in small, meaningful ways.

[00:07:36] Mike: Um, one thing that I'll say too, is it's like, I'm an operator as well, so we have a boutique hotel in Florida, and we have this rule, if two guests message about the same thing, we're, we're doing wrong. We're doing something wrong. So if I have two people message me, how do I find the Wi Fi? Or, you know, where do I park?

[00:07:53] Mike: Then something's wrong in our guest journey, and we're going to kind of help you identify that. 

[00:07:57] Liam: One of the things which definitely, for me as a host, I, Struggle with, I don't want to charge guests out of their security deposit. If it's something a bit, you know, uh, replaceable, you know, sometimes there's, there's some linens which marks on and stuff like actually this entire waiver thing gets rid of that worry, right?

[00:08:14] Liam: If they've paid that waiver, you never have to worry about it because they are, um, you know, they're, they're effectively covered. And because you're as a host, I mean, let's face it, most people are going to. Markup on that on that waiver and they're going to be making some income that's going to help you to You know cover these costs when when you need to which is which is 

Simplifying Onboarding and Enhancing Guest Communication

[00:08:35] Mike: So yeah And then there's some methodology there too with the price that you set that I always give the option if it’s you want to put a hold down i'm never going to make someone forcefully buy a waiver, not my style.

[00:08:46] Mike: Um, so you can have the option, right? And you, you pit them against each other. So say it's 1, 000 versus that 40, um, non refundable waiver. Um, odds are a lot of guests are going to, you know, pick the waiver, which is nice because you have that protection and you're not dealing with chargebacks and all that kind of fun stuff.

[00:09:03] Mike: There's not many complaints about it. They understand, you know, when you're going to check into, uh, You're gonna see a security hold. You're gonna be asked for your I. D. It's not something that's, that's wildly different. Um, especially with these traditional, you know, vacation rental brands.

[00:09:20] Mike: They've been doing this for years and years, but since before you and I have been in the business, you know, you're going to the office, you're putting your I. D. Down and you're sometimes giving a cash deposit, right? There's companies that still do it that way.

[00:09:33] Mike: So that's kind of where that comes from.

[00:09:34] Liam: And lastly, and I love  ending with this sort of question, which is, is there a motto or a mantra, which is kind of. Helped you on your journey or something which comes to mind as being like, you know what that has always run true for me. There's something which I perceive as true

Mike’s Motto: Listen to Your Guests

[00:09:53] Mike: Yeah, just don't be afraid to do something that's, uh, unexpected, right?

[00:09:58] Mike: Something, uh, that's not ordinary, right? So like when we started this business, like it's a bit wild. It's a bit out there. Um, we were showing it to, you know, some early stage hosts that are like, you guys are crazy. Um, and you know, we're now at a point where we just crossed 30, 000 reservations on the platform.

[00:10:16] Mike: Um, so guests seem to like it and that's what matters, right? Listen to your guests. Please listen to your guests. That's, that's the one thing, um, that I would say, and, and your branding is great. Like everything's great, but like your guests are ultimately the ones that are, you know, putting money in our pockets, right?

[00:10:33] Mike: 100%. 

[00:10:34] Liam: Thank you so much. And I couldn't agree more. Uh, so is there anything else you want to say before we bring it to a close, Mike? 

[00:10:41] Mike: No, thank you for having me on Liam. And it's always a pleasure working with the Boostly guys. Um, and yeah, we'll go from there and hopefully I talk to some of these hosts soon.

[00:10:51] Mike: I'll be around. 

[00:10:52] Liam: And if you're listening to this podcast and you're going to know what, this has been really handy for my business. I'm going to go and check out happyguestofficial.com/boostly Share it with somebody you know, share the love, right? There's other hosts out there.

[00:11:05] Liam: Maybe not somebody in the same patch as you. Share it with another host in another city, because ultimately this is going to be giving you the advantage, but ultimately do share it with somebody, because this is a very collaborative industry and community, and I look forward to seeing happy guests grow and to seeing you as a host succeed.

[00:11:23] Liam: So thank you very much for listening to the Boostly podcast. That's it from us. We'll see you on the next one. Bye for now.