Discover the unexpected secret to skyrocketing your vacation rental bookings. Uncover the power of video reviews and the surprising impact they have on bookings. Find out how this simple strategy has increased bookings by up to 25%. 

Your biggest fans are the ones who’ve stayed there before. – Damian Sheridan

My special guest for this episode is Damian Sheridan.

Damian Sheridan, the mastermind behind the Book Direct Show and Scale, boasts an extensive background in the vacation rental realm, spanning over 20 years. His commitment to cultivating a sense of community within the industry has propelled property managers towards direct booking success, while his expertise in video reviews and guest relationship management has reshaped the way businesses approach their operations. With a genuine passion for sharing knowledge and facilitating partnerships, Damian’s influence continues to shape the vacation rental landscape, making him a pivotal figure for those seeking to elevate their direct booking strategies and enhance guest experiences.

In this episode, you will be able to:

Connect with Damian:



The key moments in this episode are:

00:00:00 – Getting Started in the Industry

00:07:17 – Importance of Community

00:09:40 – Scale Show Expansion

00:11:08 – Video Reviews Strategy

00:14:26 – Encouraging Reviews

00:14:51 – The Pressure of Five-Star Reviews

00:16:34 – Building Relationships with Guests

00:17:46 – Handling Negative Reviews

00:19:33 – Strategic Video Reviews

00:21:37 – Direct Booking Success

FREE GUIDE: 10 Ways to Drive Guests to your Website instead of Airbnb: https://directbookingsuccess.com/10-ways-to-drive-guests-to-your-website-instead-of-airbnb/

Show notes are available at: https://directbookingsuccess.com/podcast/

Follow Jenn on Instagram: https://www.instagram.com/directbookingsuccess

Join Jenn’s free Facebook group – the Marketing Hub: https://www.facebook.com/groups/strmarketinghub


00:00:00 - Jenn Boyles

Hello and welcome to another episode of the direct booking success podcast. I'm your host Jennn Boyles and today I have the luminous Damian Sheridan with me. Damian is the director of the book direct show and scale. Hello, Damian.

00:00:16 - Damian Sheridan

Hello, Jenn. Wow, what a welcome illuminist. That's very good, thank you.

00:00:21 - Jenn Boyles

I think because you're in Spain and the sun is shining, it's just, yes, that's exactly the feeling I'm getting today.

00:00:27 - Damian Sheridan

I thought it was about my personality. Right now it's just about fine, fine.

00:00:32 - Jenn Boyles

Of course, your personality. So I want to get started with how you got started in this industry. Can you take us back to the beginning?

00:00:40 - Damian Sheridan

Yeah, for sure. Well, much like I think most people are in our industry, it wasn't a goal of mine to get involved in. I guess what at the time was, was very different. We didn't really even have a name. You know, some people referred to this as about 20 years ago. Some people refer to it as vacation rentals, holiday lets, holiday rentals, short term rentals wasn't the phrase that really existed but it's a phrase I'm really glad does exist now because it does seem to be universally accepted and it's one that we can work with throughout the world. But I bought my first property in the south of Spain and I started renting it out and it was as simple as that. Pre Airbnb days. So less, less kind of reliance on digital marketing and more on business cards and print advertising and those very different days and just one thing just led to another. I started getting involved in websites with my work in business travel in London, quit my job in 2012, went all in on SEO, search engine optimization with property managers in their vacation rentals and yeah, and that led me to five years ago starting the idea for the book direct show which was really just an idea to bring people together because I was being asked by my clients, could I help with branding, social media, etcetera. And I said no, I can't, I have no idea. But I can put you in touch with people who can help you and who are very strong. That made me think, hey, maybe we should bring people together in some kind of community here whereby we can share knowledge. And so that led to the idea of the book direct show. Put some money down on a hotel in London in 20 without really thinking about it. In the next six months of worry, is anyone going to show up? Is anyone going to sponsor? But yeah, we had a nice event. 100 people came just before COVID literally weeks before COVID hit and added stress, could have done without, but yeah, so. And that was the first book direct show. We're moving on to the 6th in a couple of months. So it's been. Yeah, it's quite, quite the whirlwind. You know, we've all been through an awful lot over the last few years, so I hope we're all coming out of the good parts.

00:02:59 - Jenn Boyles

And I think, you know, I can see working with individual property managers and everyone, we always feel so isolated in this industry, don't we? We're working for ourselves and our own businesses and we don't have those offices, unless you guess you have how many properties you have. But most of us don't have big teams or offices that we even go to. We're working remotely. So there's a real importance on community, isn't there? With the book direct show?

00:03:30 - Damian Sheridan

There is. Joan. Yeah, as you say, you hit the nail on the head. This is a very lowly existence for a lot of people in our industry, whether you've got one 25-10 plus properties. We're so busy dealing with reservations, dealing with guests, dealing with cleaning. We have very little time to look up from our computers and actually meet other people and know that we're not alone here. So this is something that kind of come out of the shows that we do, the book direct show and scale more recently in that the kind of feeling of community within our shows is something that's very strong and that kind of collaborative networking that people get when they come to conferences or an online conferences such as your own, it's something that's important and that people really do treasure and they take back to their offices with them, and it really helps them with their ongoing strategies for their own mental mindset, I think, as well to know not alone, there are other people suffering the same problems and issues that we do. And there's, you know, there's a lot to take from that.

00:04:35 - Jenn Boyles

No, I completely agree. And it's really why I started the direct booking success summit online, because, you know, we were coming out of that pandemic and, you know, I could see that there were people everywhere that needed that sense of connecting with others, but we don't all have the money, the time, the resources to travel. So, you know, that's why I started that. So I totally, I totally. I understand it. And I think you talk to anybody who is putting on a conference. Community is such an important part of it, besides the education is.

00:05:10 - Damian Sheridan

Yeah. And it's something that I've been very aware of from day one, really. And, you know, you mentioned not everybody can go and travel to a conference. Not everybody. It's expensive. It's expensive, let alone the ticket. The price of travel, accommodations, subsistence for a few days, it is very expensive. I'm fully aware of that. People spend money when they come to one of our events, it's huge. But then if you can't, what are the options? We do have lots of kinds of communal, collaborative platforms out there. If it's an online event or if it's a Facebook group or if it's some kind of networking platform, they are out there. I think we need to explore that and know that we are. It sounds really corny, but we are kind of in this together, you know?

00:05:56 - Jenn Boyles


00:05:56 - Damian Sheridan

You might. You might be a bit more aware of somebody on the road who's a competitor, essentially, but really, you know, we are stronger bringing our ideas together and strategizing and just sharing that knowledge.

00:06:10 - Jenn Boyles

And I think we've really come into our own with this as well. I remember Heather Baer speaking about when she started and how, you know, people would really be secretive and guarded with their company secrets, you know, and now we're much more open and helping each other. I think we've really grown into the hospitality sense that we're wanting to help everyone in the community be successful in what they're doing. Do you see that as well?

00:06:40 - Damian Sheridan

I absolutely do. Yeah. If someone is successful in our town, then generally everybody's going to be successful. Your town, your area, your country, if it's known for being a thriving area for vacation rentals or short term rentals, it's only going to be good for you. So I think that kind of competitive streak that perhaps our American cousins are a little bit more fiery with, I think we need to get over that and we really need to see that if one of us is doing well, it's good for the industry as a whole.

00:07:13 - Jenn Boyles

So the book, direct show is obviously all about direct bookings. And then we have the scale shows that have really taken off. So when did they start?

00:07:22 - Damian Sheridan

So really? Yeah. So the book, to make sure we hosted a few of them, and as you say, they're just primarily, much like your own, all about direct booking strategies, how we can reduce that reliance on otas and bring a level of control into our own business. The scale show really came from some feedback that I had with professional property managers. And by that I mean companies and operators who have 20 plus properties when it's very much a full time gig for them. And, you know, they may have several members of staff involved and multiple units. We found that speaking to them at conferences, that their experiences at these events just weren't up to scratch up to what they expected. Levels of expectations were very different. For example, somebody who was managing 50 units didn't necessarily want to be sitting beside somebody who was renting out a room on Airbnb and be with them for, you know, for a day or whatever, or to be sharing the same knowledge on stage. So the educational process was different. So I kind of thought of myself and Gian Paulo, a co-founder, scale show, we thought, we felt that there was something lacking and that there was a niche here for the professionals in our industry. So we again just put some money down on a venue and before we thought about it, before we knew it, it was coming up in a month and put all of our effort into curating great content without any sales pitches. We don't guarantee any sponsors, speaking slots or anything like that. We very much just curate it around our attendees requirements, which they tell us at the point of booking a ticket. And it just worked. The first one just worked. Amazing feedback, especially in terms of the community, communal kind of networking element as part of the couple of days. And, yeah, it's just snowballed since then. We have eight conferences this year in different countries and I probably won't remember them all. Two in the UK, one is specifically green related. We've got one in Italy, one in Dubai, Cape Town in two weeks, two in Spain and France. So, yeah, very exciting.

00:09:30 - Jenn Boyles

Yeah, I love it because they're very local and so the issues that you can address and the speakers can come from the latin community.

00:09:40 - Damian Sheridan

So our french and italian events are explicitly in those languages, in French and Italian. People like that, they don't necessarily want to have to come to Barcelona to hear something in English which is not their mother tongue. Yes, we find, and all of the content is driven for that market. So the data, all the insights are brought by those industry experts and it just is that more, more meaningful for those professionals. So, yeah, we do that now, as I said, in Cape Town, in Dubai as well. And it's true. Yeah, it's exciting. It's exciting to see it grow and it's exciting to see the property managers get a lot of it too, and start to form partnerships themselves as well. Outside of our conference time. It's great to see those relationships.

00:10:28 - Jenn Boyles

You and Asiel, Spain recently, and you did a talk there about direct bookings and was there something that came out of that talk that really resonated with the audience?

00:10:39 - Damian Sheridan

So, yeah, I did a talk with Daniela Doreen, who was my partner in crime for doing talks at some of our events. So one thing that did kind of come out of it, when I say come out of it, it's something that a few attendees now have come up to after this show just to say, hey, I never thought about that, that's great. And twice have fed back to me a couple of months afterwards to say, this really worked in our business. And that is video reviews. So we all know the power of reviews for our reputation, be it on a platform or be it on Google or on our website, we need reviews. We need people to see how credible our properties and our business is. But one thing that really takes it to the next level for me and for clients that I've worked with over the years is video reviews. And this might sound at first to be a bit difficult and something that might not be actionable, but it's really, really simple in that we, I think all businesses I think have for the most part, are Pete bookers. We know people, there'll be some people who will stay once or twice a year or will come back year upon year. These people are really low hanging fruit in terms of the gold that they can provide you with a video review when they're in situ in your, in your home or in your property. If you ask them, they will do it as well. And it's very simple. Ask them for a 2030 2nd video of them in your property, telling you in front of the camera, on their phone what a great time they're having, and just give us a little bit of insight into, and as I said, it needs to be really short. Just needs to be really short, not professional at all. This is the thing actually. If anything, the worst kind of production it is, the more real it actually will look and the more genuine it will look as well. So I know we can't play videos. I'd love to though, because I had two of one, a woman, a man in apartments in Spain, just talking about what a pleasure their experience was. One woman was holding the camera, looking down at the beach from her balcony. And these are just have been embedded, put onto YouTube, sorry, and then embedded into a website, onto listing pages and onto a homepage of the website. And these people come back to me to say that they have noticed a significant difference in the conversions on those pages, because, you know, people are dreaming always when they, when they come to your website, there's a reason they're there. And if they can feel and really get a flavor of your property and see themselves in there in a better way than a simple text review can provide. This is gold, and I do this with my clients. Also, as a result of these talks, I've seen and heard of property managers who've increased their booking by to 25%. It's staggering, the influence of video review. That's just one little tidbit for me. It's something I think is perhaps a little bit different. Something maybe, maybe your previous guests haven't shared or something many people see or hear on conferences or online. It's something I think should be explored by any property manager and I can share more information.

00:14:08 - Jenn Boyles

Yeah, well, this is definitely a topic that we have not spoken about here on the podcast. And do give me those links. I'll put them in the show notes so that people can click through and have a look. But I'm curious. Okay, so I guess what you're saying is to start with the people that are already your biggest fans, they're the return guests. Because when, you know, a lot of times people come to me and they say, well, how can I get people to make it? To give reviews? Because we're not on Airbnb. There's not this tit for tat, is there, for the review process. And so when there isn't that sort of incentive to get your review done for those that are booking direct, you know, do you have any tips on how we can get people to actually do the reviews like written? You know, yes, we want videos, but do you even start with the written ones?

00:14:56 - Damian Sheridan

I have very strong views about reviews, Jenn.

00:14:59 - Jenn Boyles


00:15:00 - Damian Sheridan

And I think the pressure upon hosts to get a five star review has turned farcical over the last couple of years. The need to be at a 4.8 or a 4.9 to achieve a certain kind of status is, I think, has brought reviews to like, into a situation whereby they're not anymore where hosts are being forced to. To contact or to just ask if there's any problems, for example, during the stay, it's like an utter disaster if someone has seen get like a four, a four or lower review. So I think, look, if you've got a problem with a guest during this day, of course you, somebody said in Marbe, you own the relationship. Be there upfront straight away. So an actual back to what could have been an utter disaster can be mitigated. And actually, you could end up with your five star review anyway because you've had a great relationship and rapport and how you've dealt with them. But that aside, to actually try and get a review from your client, be it outside of the platforms or on the platform, I think just the best way is to provide just a great experience. I think it's as simple as. And to have had a good rapport as well. I think sometimes with the advent of automation in our industry, we tend to be a bit faceless. A lot of hosts and managers out there, we don't see our guests. We have no relationship with them before, during and after their stay. People don't know who we are. It's a statistic that 80% do not remember who they stayed with two months after their stay. But they'll remember they stayed at an Airbnb. We don't want that. No, we love Airbnb. We love what the large otas have done for our business, but we want them to know who we are, what our brand is. You know, the brand could be you or I. You know, that's how I did quite well with my short term rentals. I was the brand and it was just the relationship that I had with my guests, that was the reason they came. So I think having a relationship makes a big difference with your guests providing a great stay, because you're never going to get a great review, let alone booking a repeat booking, unless you've achieved that. So I think we've come back to basics. A great stay, great experience, great relationship as well.

00:17:35 - Jenn Boyles

Yeah, no, I completely agree with you. And you just need to go into any Facebook group and there's somebody complaining about a four star review and wanting to get it, you know, taken off of there. And it's just like, oh, you're missing the point. You're missing the point. But, yeah, no, it's become. It's become a huge thing, hasn't it?

00:17:55 - Damian Sheridan

That's it. I saw something, actually, you might be talking about the same. I saw something on a Facebook group I think just last week, somebody got a one star review and they thought it was unfair, but there was a problem. They wanted to take their property off, off one of the platforms because of this review and start all over again. There were a whole load of people saying, yeah, that's what you should do. You should delist and list your property again because of that one story. The mindset has changed very much since perhaps you or I started in this industry, but for me to have negative reviews, a sprinkling of negative reviews, or real reviews in there is essentially. That's it. Yeah, it's a different way of thinking about it. As to how I might.

00:18:41 - Jenn Boyles

No, we can curate the reviews on our websites and have, you know, let just show the best ones and, and that, but I had someone the other day who was glowing in the review but only gave four out of five stars, you know, and it's like, oh well why didn't you do that? Well it doesn't really matter because it just shows that it is real, you know, not just somebody creating fake reviews and five stars all the time. I think you're right. Back to basics. Give them the best experience possible. If there's a problem, get in there and fix it. Because you know what could have been a two star review can be a five star review just from your actions, can't it?

00:19:20 - Damian Sheridan

Absolutely, yeah. Back to basics. I couldn't.

00:19:24 - Jenn Boyles

Yeah. And I love your idea of video reviews. I really can see them. Cause it's. And seeing is believing.

00:19:32 - Damian Sheridan

Yeah, absolutely. I mean as you say, we can post all of the best reviews that we've had on there. You know, for the most part it's on our own websites. We can copy and paste or we can use an aggregator for reviews. I mean anybody can do that. It's not necessarily authentic or real. If you're just saying, hey, yeah, Jenn had a great state. Five stars. It was brilliant. The beach was so close, etcetera. But if you have somebody actually saying, hey, I'm in the property now check this out. That is worth so much more in terms of incentives, incentivizing. Somebody actually click, click on booking.

00:20:12 - Jenn Boyles

And you're not saying to just ask everyone to give a video review but to be really strategic about it.

00:20:18 - Damian Sheridan

Absolutely strategic. Yeah. I mean you look, you can incentivize people to do this and that could very much work with an early check in, late check for example, or gift card, free coffee at your local cafe, something like that. Things that cost you next to nothing. There are very easy ways to incentivize people to do it. But for me, your biggest fans are the ones who've stayed there before they come back. So use them and ask. For the most part, you will not need to incentivize them with any, with any carrot. They will do it and they will be glad to do it and use that and keep them on YouTube as well because that in itself is a search engine. Monstrous. People can find you.

00:21:02 - Jenn Boyles

Yeah. A good way to start a YouTube channel. Yeah. Oh brilliant. Brilliant. Well now as the head of the book direct show and how many have you done now?

00:21:16 - Damian Sheridan


00:21:17 - Jenn Boyles

Okay, so the 6th one is coming up. There's a lot of pressure on the answer to this question because you were like the godfather of direct bookings. Okay, so I've got to ask you, what does direct booking success mean to you?

00:21:31 - Damian Sheridan

Can I use two words?

00:21:32 - Jenn Boyles


00:21:33 - Damian Sheridan

Control and independence. Simple as that. Bringing control back into your business, because it is your business. After all, you're not working for another major Ota. You're working for yourself. Bringing control back and being independent.

00:21:50 - Jenn Boyles

Yeah. Short and sweet. Love it. So I'm going to put links for the direct book show and scale rentals shows in the show notes. So everyone listening, go and check them out and see when the next show is coming up because I can hardly wait till you bring scale or the book direct show over to my side of the world. I think that would be absolutely amazing. I'm putting you on the spot now, but I would absolutely love that. But thank you, Damian, so much for coming on.

00:22:19 - Damian Sheridan

Before we sign off, can I put you on the spot, Jenn?

00:22:22 - Jenn Boyles

Uh oh. What?

00:22:23 - Damian Sheridan

Yes. Well, you. You, in their very modesty, have not said how you're going to be involved in the next book direct show in May. Come on. I think you need to tell me.

00:22:32 - Jenn Boyles

Well, I've been, I guess, shortlisted one of three for the best educator award at the book direct show, which will be happening in. In Barcelona in May. And so, yeah, I'm traveling over from Canada to it and I can't wait. I really can't wait.

00:22:50 - Damian Sheridan

Very modest. You should be mentioning this from the very beginning. Oh, now, well done. Alongside some fun names there. And, yeah, we look forward to seeing you on stage and.

00:23:01 - Jenn Boyles

Yeah, and not winning, but that's okay.

00:23:05 - Damian Sheridan

Oh, who knows?

00:23:07 - Jenn Boyles

Who knows? That is right. No, I am. I'm very flattered and humbled by being shortlisted for it. And no, I wasn't going to mention it because this isn't all about me, but it's what I'm passionate about is direct bookings. You know, I don't talk. I had someone come to me the other day and say, would you promote my course? You know, I know you don't do stuff with the OTAs. Could you promote my course? And I just went, no, no, because it's not in my. It's not what I do. You know, direct bookings marketing, that's what I'm interested in and that's what I help people with. So it's a real big pat on the back. So it's wonderful.

00:23:45 - Damian Sheridan


00:23:46 - Jenn Boyles

Thanks, Damian, and thanks for coming on today.

00:23:48 - Damian Sheridan

No problem. Thank you for having me, Jenn. Appreciate it.

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