
“I didn’t know there was a thing called direct bookings. I just knew I needed to do what I had to do—build my own brand and go after my own bookings.”
In our latest episode of Direct Bookings Simplified, we sat down with Jenn Boyles, a trailblazer in the world of direct bookings and marketing strategies for short-term rentals. Jenn has a wealth of experience as a host, marketer, and coach, and her journey from hosting an apartment in France to launching her marketing platform, BookDirectPro, is nothing short of inspiring. Jenn’s insights into building a successful direct booking strategy are invaluable. Here’s a snapshot of what we discussed—be sure to listen to the full episode for more tips on Simplifying your Direct Bookings
Summary & Highlights
Meet Jenn Boyles
Jenn Boyles is the founder and CEO of Direct Booking Success – the podcast | the summit | the program. Her mission is to help vacation/short-term rental property managers, owners and hosts increase their revenue and control with the power of direct bookings.
She started as a property manager and owner herself, managing her own award-winning properties from 2013 to 2024. Finding herself with a property in an over-saturated area was what initially led her down the path of building her own direct booking business.
She is the host of the weekly Direct Booking Success Podcast which is produced with a mix of educational solo episodes and interviews with Hospitality and Accommodation professionals along with fellow property managers and owners.
Jenn is also the founder of the annual Direct Booking Success Summit. This event is a FREE marketing and hospitality educational online summit for vacation/short-term rental property managers and owners who want to increase their revenue and control in their own business with direct bookings.
Her latest venture is founding Book Direct Pro, the all-in-one marketing platform built for vacation rental pros by a vacation rental pro. With Book Direct Pro, Jenn aims to simplify and streamline the entire marketing process, giving hosts more control over their bookings and profits. It’s designed to cut out the middleman, empower property managers, and make direct bookings a breeze.
1. The Power of Storytelling in Marketing
Jenn’s success in the UK stemmed from building a strong brand before launching her property. By documenting the construction and branding of her unique canal boat in Liverpool, she created a buzz and established trust with potential guests.
“People followed the journey and joined a waitlist, so when we launched, they were ready to book.”
Tip for Hosts: Share the story behind your property—whether it’s a renovation project, local attractions, or memorable guest experiences. Use social media, email newsletters, and even simple videos to bring your journey to life.
2. Start with One Property (and One Strategy)
Contrary to popular belief, direct bookings aren’t just for large portfolios. Jenn emphasized how smaller hosts can leverage their personal touch and storytelling to compete with big players.
“You don’t need 50 properties to make this worthwhile. Even with one or two, you can create a personal connection that larger operators can’t match.”
Actionable Idea: If you’re a remote host, batch-create content during visits. Showcase your property’s personality, local attractions, and unique amenities.
3. Focus on Guest Data Collection
Jenn highlighted the importance of owning your guest relationships through email marketing. Platforms like Airbnb won’t share guest data, so hosts need to find ways to capture it independently.
“Once you have their email, you can connect directly, nurture relationships, and bring them back for future stays.”
Practical Advice: Use tools like Wi-Fi sign-ups, digital registration forms, or automated guest surveys to collect guest emails.
4. Leverage Automation and Tools
For busy hosts balancing multiple responsibilities, Jenn stressed the value of automation. Her platform, BookDirectPro, simplifies marketing by combining email marketing, social media scheduling, landing pages, and more into one tool.
“Marketing doesn’t have to take over your life. Set up systems, automate what you can, and focus on what matters.”
Pro Tip: Use automation to schedule social media posts and email campaigns. Dedicate time monthly to batch-create content, then let technology do the heavy lifting.
5. Build Trust Through Personalization
Jenn shared how personalization drives direct booking conversions. Adding an “About Us” section, featuring reviews, and showcasing local attractions on your website can make all the difference.
“People want to know who’s behind the brand. Share your story—it builds trust and encourages bookings.”
Quick Win: Update your website with a personalized bio and real photos of your team or family to foster trust with potential guests.
Start Building Your Direct Booking Strategy Today
Jenn’s journey is a testament to the power of storytelling, relationship-building, and leveraging the right tools to grow your direct bookings. Whether you’re just starting or looking to scale, her advice is clear: take one step at a time and focus on strategies that align with your goals and resources.
If you’re ready to take control of your bookings, don’t miss the chance to try Jenn’s all-in-one marketing platform, BookDirectPro. Use code DIRECTSUCCESS for 50% off your first month, and schedule a free onboarding call to get started.
Follow Jenn Here ⤵️
Transcription
Gil: Welcome back to direct booking. Simplify where you break down the strategies and tactics to win in direct bookings on today’s show, I have Jenn Boyles, Jenn, welcome to the show.
Jenn: Aw, thanks Gil. Thanks for having me.
Gil: Yeah, it’s, it’s such a familiar voice. I’ve listened to your podcast on my car drives a lot. Um, so it’s really good to have you on, on this show as well.
Jenn: Aw, thanks so much. I hope I haven’t caused any accidents.
Gil: No, no, it’s a, it’s a, it’s a very calming conversation. So if anything, it helped me focus. Yeah, there’s not many shows in the direct booking space, um, that talks about direct booking. So I think there’s like the R2 shows and maybe a two or three others. And that’s pretty much it about direct bookings. Um, there’s a lot of more general, um, short term rental ones, but not many on marketing and direct bookings.
Jenn: Yeah, that’s very true. Airbnb has a lot to answer for.
Gil: Yeah. Yeah. But also like, I think even on our side, like you’re. You’re triple digits now and in terms of episodes, uh, episode count, right?
Jenn: Yeah, I think I’m at about 130 now. So, yeah. It’s a lot of work.
Gil: it’s a lot of work, but also like, just like any marketing, like there’s no shortage of like, not necessarily content, but knowledge that gets shared. So I, I, I bet you, like you can run five, 600 episodes and feel like you’re, you’re always giving something new back to the listeners as well, too.
Jenn: Definitely. Definitely. It’s such a big, you know, it’s niche in terms of Short term rentals, you know, the direct booking side of things and the marketing, but inside that topic, there’s just so much. There’s just so much nuances that we can just go into. So, yeah. Oh, there’s so much more to come.
Gil: Yeah, and I haven’t done this series yet, but I’ve always wanted to bring other folks from other industries into our conversations. I don’t know if you’ve thought about this or you’ve done this already, but I find that a lot of the things that we put into practice is not unique to short term rentals. In many cases, that’s actually a lot of marketing fundamentals.
Jenn: Definitely. Definitely.
Gil: Yeah. Have you?
Jenn: Because, you know, I’m learning from others. You know, all the time and no, they’re not all in the short term rental space. Um, they’re in marketing and other spaces, you know, that deal with, you know, the fundamentals of marketing. Yeah. They’re the same all around the globe.
Gil: Yeah, and one thing I find interesting is that, like, even folks that have no marketing background and there’s a few conversations that I can remember very vividly where we bring on guests onto our show and they don’t come from a marketing background, but they got into short term rentals and because they didn’t come from a marketing background, they almost approach it with Very open ended like mind.
Gil: Um, and they’re thinking about how to actually promote their, their short term rental and most effectively. And I’m seeing people done really well and just really being very personable on Facebook groups, like very niche Facebook groups and be successful in that. And I like, that’s not like Traditional marketing.
Gil: Um, if you think like, Oh, what? My one channel is going to be Facebook groups, and I’m personally posting on there. Like who would have thought that they can get 40 60 percent direct bookings with just some of those basic tactics.
Jenn: Yeah, no, it is. Marketing’s changed, you know, um, we want to see behind the brand. We want to see behind the curtain, you know, the Wizard of Oz. We want to see who that voice belongs to and people buy from people. It sounds like a cliche.
Gil: Yeah.
Jenn: so, so true, and, but it’s so easy to hide behind that brand, it’s so easy to just keep putting, you know, I, uh, I used to say, I lived in England for a long time, and I used to say, we don’t want a we all over the place.
Jenn: And it used to get a huge chuckle, right? Um, but the idea is that instead of using we all the time, use I. Because that’s just so much, much more personable and much more relatable.
Gil: Yeah, yeah. Um, before we get too deep into it for folks that haven’t listened to your show or listen to it on a drive. Do you mind giving yourself an introduction? Yeah.
Jenn: at all. Not at all. Um, who doesn’t love to talk about themselves, right? Um, so I started hosting way back in, what was it, uh, 2012 ish. Um, and we had an apartment in France and thought we’d put it on Airbnb, put it on one morning and that afternoon I was on the ski slopes, doesn’t, it’s, it wasn’t as glamorous as it sounds, but I was on the bunny slope, okay?
Jenn: I was on the bunny slope and my phone is pinging away with bookings. And I was like, Oh, this is interesting. And so we had great success with Airbnb, Superhost, all, all of it. Third property rolls around and the bookings aren’t coming in. They’re just not coming in. And we had, we had bought with our, our hearts, not our heads.
Jenn: So real estate people can wrap me in the knuckles. I know we did wrong. Um, but. It was a saturated market, and I think it set me up well for what’s been happening post pandemic, because I was in this saturated market where everyone was vying for bookings on the big platforms, and even though our place was amazing, it didn’t stand out against the others because, you know, it was a chalet and there was all these chalets, right?
Jenn: So, people were looking at price, um, and that was a hard lesson to learn and I started going after my own bookings and building my own brand because I had to, it was a necessity. I didn’t know there was a thing called direct bookings, I didn’t know about any of it. I just knew that I needed to do what I needed to do and that was to get my own bookings. forward to the next brand, New Country, I took what I’d learnt and I launched with 80 percent direct bookings. Yeah. And it was amazing. It was absolutely amazing. The pandemic hit. We all know what happened there. Airbnb was canceling bookings, just left, right, and center. No communication. People were freaking out because there was their income just tanking.
Jenn: And it wasn’t just that their income was being taken away. It was that they had no control. They had no control. And I was looking around going, hang on a second. You weren’t doing what I’m doing. I was 80 percent direct bookings. I didn’t understand why people weren’t doing the same thing I was doing.
Jenn: Well, that’s when my eyes opened and I realized I had lived a different experience. Um, and so I started helping others. So the pandemic was really, I think it was a pivotal moment for a lot of us. But it really made me think, you know, if, if you’re beholden to a platform, that’s just going to wipe out your business with a click of a button, then you need to be doing something different.
Jenn: And I can, I can help there. So that’s what sort of segued me into helping others doing what I’m, what I’m, what I was doing. And that’s almost, Oh my goodness, it’s almost five years ago now. And so things have grown from there. I started creating websites. Um, then I leaned more into the marketing side of things. Um, I’ve got the podcast, the annual summit, um, and now my, my new venture, BookDirectPro. So it’s been a wild, a wild ride.
Gil: Yeah. Yeah. And are you still doing some of the other stuff as you kind of move and progress? Um, so I know you’re still doing your annual summit. You’re not focusing on book direct. Do you also do continue to do your mentorship and your coaching program as well, too?
Jenn: Definitely. Definitely. Definitely. What I learned was when I first started doing websites out there, and I do not do them anymore, I think I’ve got a couple left on the books. That I, I maintain for people, but it’s not something that I put effort in because I was giving people these amazing websites and they were great, but then they were coming back to me going, well, hello , where are the bookings?
Jenn: And I realized that nobody knew what to do once you had that booking. So that’s or what the website. So that’s why I segued into more of the marketing side of things.
Gil: Yeah. It sounds like also. Also, now you’re, you’re focusing on the technology side to enable folks to take control of themselves as well to, um,
Jenn: Definitely, definitely. Yeah.
Gil: kind of kind of rewinding back just a little bit. You mentioned, uh, you went into a new country. I believe that’s Canada. Is that right?
Jenn: No, it was, uh, it was the UK. Um, yeah. So my properties have all been in, they’ve been in France. the Netherlands and the UK.
Gil: Okay. Okay. And now you’re now you’re in Canada, right?
Jenn: Yes, I’m in Canada now.
Gil: Um, when you launched in the UK and you got 80 percent direct bookings, what was some of the fundamentals there that helped you really get that high rate?
Jenn: Well, I, I built the brand first. So we were building a boat, um, uh, a wide beam canal boat. So a 60 by 10 boat as a unique stay in the center of Liverpool. So Liverpool is an amazing city. I’m sure you’ve heard of the Beatles. Um, a lot of things have, a lot of things have happened there, but the Beatles, I’m sure.
Jenn: big one. It’s a, it’s a port city. It’s got a rich history. It’s an amazing place. Um, and they have a long dock area there and we thought it would be really different to build a boat. So we created a brand and I showed the behind the scenes. Of what we were creating so the actual physical renovation the building of the boat and talking about what there was to do in Liverpool and it was mainly through social media that that I did that.
Jenn: But I knew the power of data, and so I was getting people on a waitlist, a waitlist for when our website and the boat would be ready for bookings, um, then I could open it up to this waitlist, and that’s what made all the difference, because I had people who were following the journey. And they could see what was, what was happening and then they could get excited about when they could actually book that stay.
Jenn: And that’s really what drove the, the initial success of that, of that launch.
Gil: Yeah, I’ve heard a similar story now a few times over. And in contrast, I also hear folks with just one or two different properties. And they’re like, there’s no way that I can drive enough marketing myself. And I just see two different perspectives where one People are documenting their entire build out and really telling that story and people love following stories.
Gil: People love it. Um, and just seeing that build out over time. That’s like fresh, fresh content that they’re looking for entertainment that they’re looking for. Um, so I can totally understand from a, from a entertainment perspective, it can draw people in there. And on the flip side, I have folks that Have a few properties, and they have no idea how to drive traffic, and they don’t really understand.
Gil: But I think, like, if you have a small, small portfolio, you’re very hands on, and you’re actually in the build process, you can actually use that to your advantage. You don’t need to be a large property manager to be able to drive drive bookings. And it sounds like in your case, that’s the approach you took.
Gil: You really documented your process, and you saw attraction. You continue to do so. And You end up creating funnels at the very end of it to help convert when you actually went live there.
Jenn: That’s exactly it. That’s exactly it. And I get the, I got the question yesterday. How many properties do I need to have to make this worthwhile? And I go back and I say one. And they look at me so shocked. You know, they’re like, I’ve got two or three and I’m like, well, then hello, you should be doing this because it’s, it’s about scale.
Jenn: Um, one property, two properties, how many bookings do you need? That’s you know, you know, you need to drive enough traffic to bring those bookings in. If you’ve got a portfolio of 50. Properties, you need a heck of a lot more traffic, and there’s different tactics and strategies to use to bring in those higher numbers, but a host with one or two properties. You actually have an advantage. You have an advantage over the big guys, but you also have an advantage over Airbnb, Booking. com, Verbal, you know, the big three there, because you can make it personal. You can bring people into your story. You can build that, that community of, of. Potential guests that really are invested into your story and want to, to stay with you.
Jenn: And it wasn’t just me. I have gone on to work with a few clients where we’ve done the same thing. And I’ve had clients who have come to me and said, I don’t want to be on any platform, none. I just want to do direct. And of course, my first thought is, are you sure? Because it will be a bit more work. And it is nice to diversify and have those other channels bringing you, bringing you business.
Jenn: And they’ve said, yes, I want to do this. And we’ve done it, you know, launched 100%. There’s still 100 percent book direct because they’ve brought people in to their story. And they’re great hosts, they really are. And they’re not looking at it like, I want to have 50, 60, 70 properties, I don’t want to manage for other people. I want my small portfolio. And this is the majority of people out there, right? The majority of people in our industry around the world are people who have a couple of properties, maybe on their own actual property, or in a place that they would like to, they like to visit. And they don’t realize that the gold they’re sitting on and it’s their story, it’s showing their face, it’s showing what they’re doing and creating that, um, that community around it.
Gil: Yeah, slight slight tangent just for a little bit, and I’ll come back to it. But do you find this tactic and strategy also applicable if you’re remote as well, too? Because a lot of hosts, at least here in the States, these are often vacation homes, which is a lengthy drive away or sometimes even a flight away.
Gil: Do you feel like that? That personal brand is still replicable if you’re a remote host.
Jenn: Definitely. Definitely. The, the issue that you’ll run into is that you’re not there every day. So you can’t be going to the property or filming yourself or getting the, getting the assets, the, the photos, the videos that you need, but you will go there. And you can batch create right let’s do things smarter you actually probably have an advantage over those that live right there because they’re doing it all the time you go for a weekend and you take a whole bunch of footage and then you take it away and you can cut it up and drip it into your into your marketing um I’ve always been sort of a remote host I think the closest I ever was to a property was, you know, It’s a 45 minute drive, so I wasn’t hanging around there all the time, um, but I have been a 10 hour drive away, you know, or a flight away.
Jenn: So it’s the same thing where you’re taking that, those photos and the videos you’ve taken and then save them for later.
Gil: yeah, yeah. And there’s two people that I have in mind that have actually done this really well, where I thought on the other end, they actually were there live in person, because they’re actually on a weekly basis, publishing content, as if the build out was happening. And I end up asking them like, How are you doing this?
Gil: I haven’t like I thought you were still living in Arkansas and and and trying to do your build out. They’re like, No, I actually I hired a drone photographer and every two weeks they come and they circle the property with the drone and they pay him a couple 100 a month and have content that they are still to this day.
Gil: They’re still dripping and it’s the property is already live.
Jenn: Yeah, that’s amazing. If you’ve got someone that you can hire or somebody that’s on site to do that for you, that’s even better because you’re getting that, that up to date, up to date footage.
Gil: Yeah, and I’ve seen folks even with just one property and they have their contractors, the inspection videos that they take, they ask their inspectors, like, I want you to walk the property. I want you to show me the new tiles that we just put in. Just fill me a 10 second, 10 second video, and they’ll use that for their reels and they’ll do their own voice over it.
Gil: And I had thought that they actually were at the property, but they were just having their contractors Film on their phones. It’s
Jenn: Yeah, and with technology now, we can do so much more. Um, but it doesn’t have to be just somebody who’s doing a build out, you know, or renovation or, or starting a new property. You know, the footage that you’re taking, whatever your story is, whatever your, um, area is. You can use it. So I don’t want anyone listening to this thinking, well, but I’m not starting from scratch.
Jenn: And it’s, you don’t have to, you don’t have to, you can start today by taking some footage or, or planning a trip to your, to your property where you can then put some footage together. Um, and it doesn’t have to be. It doesn’t have to be, you know, the tiles or what amenities you’re putting in. It can be, uh, the view, it can be your local area, it can be, you know, a dog coming to stay.
Jenn: It can be so many things. Whatever works for your, your property, your brand. And whoever your ideal guest is, that’s the stuff that you want to create to encourage more people that identify with your ideal guest to come and stay.
Gil: Do you have, uh, a mental list of some of the story arcs. So we have like the renovation story are kind of the visiting one visiting. Like, are there certain categories of content that you find that works extremely well for for social media?
Jenn: Um, I, I do, I think that there’s something about, about your, your property, your properties, you know, the actual, um, uh, footage that Sorry.
Gil: The character of it.
Jenn: Yeah, the character of it, um, I hesitate to say amenities, but, you know, showing what’s unique about it. But I wouldn’t stop there. You know, it’s the local area people.
Jenn: There’s very few places that people are coming to just stay at your property. They’re coming for a reason, right? So they’re coming for, um, an event in your area. They’re coming to go somewhere. They’re coming for a reunion, a wedding, whatever it is, they need a place to stay. And then your secondary. So what are those things that your ideal guest is doing when they stay with you? Are they going to, uh, a train ride or to this farm or, um, uh, to this pub or to this restaurant? Like, where are they going? And those are the things that you can be highlighting and saying, look, our area has these things. Come and stay.
Gil: Yeah. Yeah. I’ve I’ve heard many times now that it’s really about capturing the moments that people are having. And that happens in your pictures as well, too. Like you want to capture what it feels like when you’re actually staying either at the property or staying in that region as well, too. So it seems like really capturing whatever those moments are that people will remember if they’re looking back on their trip.
Jenn: Yeah. Yeah. And you know, we want to see people.
Gil: Yep.
Jenn: just want to see empty, empty places. We want to be able to, uh, you know, think of ourselves there, picture ourselves there, but it’s nice to see how the property is being used, what people are doing. Now, I’m not talking about listing photos. That’s completely different, right?
Jenn: We don’t really want to see people there. We want to see the actual. Bedroom and the dining room in the kitchen, but for marketing, it’s almost creating like a vignette, you know, a little story of showing people how they are using it. And I’ve got a client who does it really well. She’s brought in friends and family.
Jenn: Put them together to create like a multi generational family kind of look and then spent the day taking photos They just had a great time. They were playing board games. They were having a drink So she would take little groups of them, you know and take photos graphs and take videos of them having a good time You know, even the dog was there so You know, it’s thinking a bit outside because you can’t, you’re not going to go and film your own guests.
Jenn: Don’t ever do that. That’s a whole different show, isn’t it? But, you know, bringing in people who could be your models. You know, give them a, if they’re friends and family, give them a free night. Go and have some fun. Most people in your friends and family network are gonna want to support you.
Gil: Yeah.
Jenn: You know, they’re not gonna want anything in return.
Jenn: They’re gonna come and have a good, a good time. Feed them, give them drinks, you know. And, uh, let them play some board games and they’re gonna, they’ll, they’ll be happy to help out.
Gil: Yeah. Yeah. It’s more likely if, if, if your guests, they’re probably going to be creating UGC, their own content for themselves and they’ll share it with you. And
Jenn: That’s a whole other Other way to use social media. Definitely.
Gil: yeah. Um, kind of like dialing back just a little bit on, on some of the things that you’ve seen over the years were some of the, the mistakes I would say, like people make when they start getting to direct bookings.
Jenn: I think the first mistake, and I think I, I talked about this, uh, how I sort of went from websites into, into more marketing is that, uh, people look at it and go, okay, um, I’ve got a website done. And that is so, that’s just the start. Your website is never finished. You need to keep tweaking things. But nobody’s going to know about it until you start telling them about it.
Jenn: And that is marketing. That’s really what marketing is about. You telling people that it, that you exist, that your business exists, that your properties exist. And it’s, it’s, do you remember that movie? Um, you know, field of dreams. Where, you know, okay, Kevin Costner, maybe it’s before your time, you’re so young, so you never know.
Jenn: Um, Field of Dreams, Kevin Costner builds a, uh, baseball diamond in a corn, I think a cornfield.
Gil: Okay.
Jenn: And he says, if you build it, they will come. Okay. It’s not true in marketing. It’s not true. You know, so you’ve got, you build it and then you have to tell people about it. You just have to keep telling them until you’re, you think, Oh, people are sick and tired of, of listening to me and hearing about it.
Jenn: No social media, hardly anybody sees anything. You have to keep talking about it. So that is probably number one. I think even before that though, it’s. It’s the fear of the unknown, it’s, oh I hear about these direct bookings, how much is it gonna cost me, is it really worth it, I only have one property, you know, it’s It’s the, it’s the fear of, of starting. And the thing is, is it doesn’t have to be done all in one foul swoop. You don’t have to create a website and start your marketing plan and everything in a day. It’s a process. We’re very lucky in our industry to have the likes of Airbnb and Booking. com and Verbo, even though I love to bash them, you know, just like the next guy.
Jenn: We are lucky that we’ve got them as a acquisition source, bookings. We just can’t put all our eggs in one basket and think that they are the be all end all. So that’s where I think is a big mistake of people just afraid to take that action. Um, one more if, if I may. Another one is, um, once they’ve taken that action and they’ve got the website and that is Not doing anything to personalize it.
Jenn: I know we’ve been talking about this, about videos and showing people and people buy for people, but it’s so true. And, but it’s so easy to hide behind that brand and not talk about you and your story and why you’re there and why guests love you guys, like why they come to stay. It’s not about becoming a celebrity or, or anything like that, or sharing things you’re uncomfortable with.
Jenn: It’s just getting out there to make the actual connection with others so that they can say, Hey, I want to come and stay. And not only will they come and stay, they’ll treat your place like their own, they’ll treat it with respect because there’s a connection. You know, we hear the horror stories, Airbnb.
Jenn: Somebody’s trashed my place. Somebody’s left this gross stuff or whatever it is. They’ve broken this. They’ve done this. Well, to them, they’re just booking a place on Airbnb. There’s no face. There’s no responsibility. There’s no, there’s nothing. It’s just, you know, it’s, it’s, it’s even worse than a hotel room.
Jenn: Because a hotel room, at least you’re in the building, aren’t you, of the hotel. you’re in someone’s property, somebody’s house. You know, you’ve got the whole place. There’s no accountability there, really. There’s reviews, of course, but, you know, people don’t feel that same responsibility.
Gil: Yep. Yeah. Yep. Yeah. I totally agree with you, especially on the kind of the personalization and the trust part of it. And we found as we’re building out our sites and really testing out and seeing what works and seeing what drives conversion is people do want to see that, especially if you’re a smaller host.
Gil: Who the person is kind of behind the scenes, who’s actually hosting the who’s actually because that’s that’s actually part of the service there that they’re, they’re not just staying for the property, but also the service that comes along with it. And we’ve now gotten to a point where, as part of our templates, we actually include in there a section about us and we make it not necessarily a mandatory section, but almost a default section there.
Gil: So everybody that’s using those types of templates. They’re going to be encouraged to put their bio and a picture of of them or their family. And we found that the folks that do lean in on that they actually have a much higher conversion rate because of that. Um, so I, from a data perspective, I 100 percent agree with you on that one.
Jenn: Yeah, I would make it default if I were you. I, you know, I would. Or not default, but, you know, um, that they have to use it because it makes such a big difference. And I see that mistake not just for people with small portfolios, but people with larger portfolios. You know, they think, well, I’ve got a few hundred properties.
Jenn: Why aren’t people coming to stay? Well, it’s your reputation. Who are you as a company? You know, at least with Airbnb, I have an idea of who runs the company. If I go on a website that’s got all these properties, I’m like, well, who is this? You know, where’s the trust? And we need that. We need that trust to be able to, to book.
Jenn: And so I really find that that’s a huge mistake. I see is people hiding behind their. Their brand and their, their logo. And it’s, it’s an easy fix.
Gil: Yep.
Jenn: It really is. It’s an easy fix.
Gil: Yeah. And I think there’s a there’s a few things that goes into like the trust side of the thing. And we kind of, you know, For our side of our craft to stays, we actually embed that back into our product and we found like that one trust comes from one being personalized and really knowing that there’s someone on the other end that they’re not going to get scammed when they booked on this to kind of along the same lines is you want to make sure your site works really well and it feels trustworthy because you’ve been, I’m sure you’ve been to many direct booking sites that feels a little bit clunky, the calendar feels a little bit off.
Gil: It’s not connected. Um, and those small little things starts to break trust. Especially if you say, call me to book like that. That is that’s going to erode trust like almost right away. And I’ve seen that many, many times where folks don’t aren’t integrated back into a PMS. And they’re just asking for a phone call to book and those conversion rates are very, very low.
Jenn: Mm hmm. Mm hmm.
Gil: And the last thing is really around kind of the reviews. There is like if you have reviews, you have it on the O. T. A. S. Pull that back into your website and really showcase those and you don’t have to showcase all of them. And we actually encourage our guests not to show especially the one liners, but the ones that actually talk us about the stay what they’ve enjoyed in there.
Gil: I like those on your home page and really talk about that and put that on your property page as well, too, because you’re gonna have to build that trust over time. And you probably know this. It People aren’t going to book very likely on the first time they visit your site. They’re probably going to visit your site several different times before they end up booking with you.
Gil: Um, so you want to make sure that you’re building that trust with every single engagement.
Jenn: Yeah. And it’s not just your website. It’s in your marketing too, right? If there’s so many ways to build that trust and in all of your marketing, social media, email, you’ve got to keep showing yourself and showing up, um, to build, to build that trust. Um, and you know, using a third party provider for, for vetting, for damage deposits.
Jenn: You know, gone are the days of, hey, just send me a check, I’ll give it back to you when you’re finished with the place. You know, we don’t want that anymore, guests don’t want that anymore. So using the technology that is out there, um, embrace it. You know, it can be scary and there’s lots of things out there, but, you know, have a call with a company and say, Hey, I’m, I’m interested.
Jenn: How can I, how can I use this? Um, but yeah, embrace that technology and look at other ways that you can build that trust.
Gil: Yeah. On. For folks, a lot of folks that get into this, they also still have their W two job, they’re working their nine to fives and they’re doing this over time to hopefully build not necessarily passive at this point, but income on the side there. Do you find it that those that are still like they’re not 100 percent into short term rentals, they either have other responsibilities, they have a job.
Gil: Can they still run an effective marketing campaign to drive enough direct bookings?
Jenn: Yeah, I did it. I’m living proof. I wasn’t full time into this until the pandemic, you know, that’s where I made, made my shift. And even then. My properties were only a very small part of what I was, what I was doing. Um, it doesn’t have to be, you know, it doesn’t have to be your full time job. It really doesn’t.
Jenn: You know, it depends on the portfolio. You’ll have to spend more time the more properties you’ve got and running that, running that team and depending on where you’re, where you’re located and how far away you are, all those kind of things. But it doesn’t have to be, you know, as a host, as a property manager that you wear so many hats. It’s not, and it, it’s the same as any other small business owner, you know, it’s not just. Um, the, the advantage we have is that we have some, some booking platforms that we can, we can leverage. Um, but if you look at that Baker down the street, what do they have that they can leverage? They have to do their own marketing.
Jenn: They have to do their own accounting. They’ve got to actually create the product. You know, you’ve got to wear all these different hats. And I know a lot of people, I was talking to somebody yesterday and I said, I know that you did not become a host. To do marketing, you know, but the reality is, is that you’ve got to do it unless you’re getting to a stage that you want to pay someone else to do it, but a lot of the smaller portfolios, you’ve got to do it yourself.
Jenn: And it can be done and again, use the technology out there. it’s also one of the reasons why I created Book Direct Pro, um, to help people so that their marketing doesn’t have to take over their whole life. You know, you can have strategies that work, put them into place, and some of them you can set them in and forget them. But there’s nothing passive about this industry. Unless somebody else is doing all the work for you and you’re just sitting back as an investor. Fine. But the host’s job is not passive. Lauren Madewell said the best phrase ever. Passive my assive. And I stand by that. I really do. Because it can’t, it can’t be.
Jenn: And if you look at the people out when we came out of the pandemic. Hey, when we had that sort of gold rush boom town in this, in this space, there were people in this space saying, oh, you can drink margaritas on the beach and everything’s done for you and it’s all passive and it’s so easy. The ones that have made it to, you know, today are not saying that anymore.
Gil: Mm-hmm
Jenn: And I see the direct booking message creeping in. I’ve listened to podcast episodes and they’ve gone, well, why do I want direct bookings like a real, um, negative. Thought I’ve got Airbnb, it does everything for me. You listen to their podcast now. Oh, they’re talking to people about direct bookings and building their brand because it’s essential if you want to have success, but you’ve got to do it in a way that works for you.
Jenn: Your business is not the same as the person’s down the street. Your life’s not the same. You’re not in the same stage of life as someone else. You’ve got different responsibilities. So marketing can be fit around. What you, what you want, what you can do and what’s going on in your life. And that’s why I really love it.
Jenn: There’s different strategies. You don’t have to do them all, but you can do what works, what works for you and your business to bring in those bookings.
Gil: Yeah. Yeah. I, I a hundred percent agree with that. What are you, what are some of the, for folks that are, they already have a full plate and you mentioned some, some said, and forget it. Like there are a lot of things that you can do that you invest that time upfront and maybe you invest that time upfront every six months or every period.
Gil: Um. But it starts to pay off over a period of time. What are some of the things that you you advise folks? Like if they’re getting into it, what is the fundamentals or the must have things that they should be doing?
Jenn: Well, there’s a lot there, there can be a lot and it really does depend on your business and what you’re, what you’re wanting to do. But one of the easiest things to do is to start scheduling social media posts. Don’t sit there on your phone every day going, what am I going to post? Oh, I’ve got some video or I’ve got a photo.
Jenn: I’ll post that now. What hashtag should I use? Sit down and batch it. Batch create it. Give yourself an hour, two hours a month, you know, create it all, schedule it, be done with it. Come back into the platforms when you have time to do your engagement and whatnot, but don’t be around it all day. Don’t be around it.
Jenn: I have people that will, uh, text me on LinkedIn thinking that I’m there, message me on LinkedIn thinking I’m there all the time. I’m not. I’ve got other things to be doing than be sitting on, on social media all the time. So you can limit that. You can really limit the amount of, of time needed to do your marketing, but also the time suck, right, of social media.
Jenn: Mm
Gil: Yeah, I think like doubling down down now and it’s like, it’s actually the switching of context that you have to get into the right frame of mind. And if you’re Thinking about every single post as a thing that you must do on a regular basis, you’re going to fall short of that very, very soon. It’s very hard to sustain being able to post every day, a couple of times a week, whatever the amount is.
Gil: And if you look at even large companies, they also don’t produce content like that either. They also batch post as well, too, and they’ll batch create, um, and they’ll have different lengths and periods and they’ll have promotions, but they usually have So, yeah. Some some type of marketing calendar that they have behind the scenes, and they schedule things out because in a business, there’s many things that you have to do.
Gil: Even within dedicated marketing, marketing teams, there’s many things that you have to consider. Um, so the only like really sustainable way if you’re looking to nurture your social media over a long period of time is really to batch and schedule.
Jenn: And look ahead, exactly what you were saying, is look at your, your calendar. But not just the calendar of, of annual events and things going on, look at where you need the bookings. So if you’re doing all your content about the summer and the beach, and you know, you’ve got this beach side place, and the thing is, you’re fully booked all the time anyways.
Jenn: But it’s September, October, November, whenever it is that you need those bookings in, then do the content for those shoulder season, you know, those shoulder months. Where do you need the bookings? You know, and create the content for that.
Gil: Yeah.
Jenn: Christmas is always booked out, and you don’t need to do any marketing for it, then don’t.
Jenn: Because, excuse me, you will get to the point where you’ll be doing, you’ll be promoting something like summer, or sea, you know, come to the beach, or Christmas, and then people go onto your website, and you’re booked.
Gil: yeah,
Jenn: You know, that’s not a great feeling to go. Oh, I’ve got so excited about potentially coming here and is already already booked out.
Jenn: So look at where you need those bookings and then create content around that time of year and and push those through.
Gil: yeah, that’s true. Um, what are some of the other like fundamentals or things that people should be doing with limited time or just getting started on this? So we talked about social media and batch posting.
Jenn: Yeah, we’ve talked a lot about social media on on this episode for sure. Um, but we need to be getting people’s data. And that’s even more important. And when I say data, I just mean their email address. You know, you don’t need all their stats. You don’t need to know how old they are and if they’re bringing their dog at this stage.
Jenn: We just need first name and email. That is really what we want to get. Because once we have their data, then we can email them. And that’s way more personable. It’s way more personal and People will actually open it. You’re going right into their inbox. It’s not like social media where you’re shouting out there, hoping somebody catches it as they scroll past.
Gil: Mm hmm.
Jenn: This is targeted. It goes right into their, into their inbox and you can create that relationship with them, which It’s what we’ve been talking about, right? Being personal, creating that relationship, nurturing that relationship, um, and showing that you offer what they need and for them to come in and book the stay.
Jenn: So that’s something that needs to be done. And I do hear from people saying, okay, well, how do I do that? You know, how am I going to do that? Airbnb doesn’t give me, that’s the thing I always hear. Airbnb doesn’t give me their email address. Well, think about it. Why would they? It’s their guest. It’s not your guest.
Jenn: It’s their guest. They’ve booked with Airbnb. Airbnb has taken their, their payment. You are a supplier of accommodation for that Airbnb guest. Sorry, it’s, it’s not a business, it’s not a sustainable business, is it? Um, but you need to get that data to turn it into a more sustainable business and to stop relying so heavily on the platforms and there’s a few ways of doing that. One is to actually ask them, you know, if you’re face to face with them or you’re in a text with them I’m not saying to do anything You know against Airbnb rules or to get yourself, you know blacklisted But you know, you can ask them you can put in things in your business that need that data You know, you can do a Wi Fi sign up so that, um, they have to give you their data before they can get on the free Wi Fi.
Jenn: You can put in a digital registration form that they have to give their email in. You can do, uh, guest vetting that they have to give their, their data for. So you think about things in your business, how can I run this as a more sustainable business? And get those, get that data from people that I can reuse later.
Gil: Yeah, yeah. And I think on on that one way we have another episode on on some of this as well, too. But when you’re getting that data, you want to make sure that you’re using the right tools to actually market them. You don’t want to be just using your Gmail and starting to email folks and blasting that out on a quarterly basis.
Gil: You want to be using some email service provider because I think things What people have to realize is that people may or may not want to hear from you, or they may want to hear from you now, but they may not want to hear from you later. And you want to give and respect people, and give them the ability to opt out of those things.
Jenn: Definitely.
Gil: I always encourage folks, make sure you get a domain and tie that domain to an email address and use an email service provider to send out those emails. Don’t send it. Maybe you can send out personalized emails within your your own personal inbox. But if you’re doing any type of marketing, you need to make sure that you’re compliant against regulations.
Gil: And also that you respect the guests that have stayed with you as well, too.
Jenn: Definitely. And it’s trackable. You want to be able to track these things. With email marketing, it’s amazing because you can see who’s received it, who’s opened it, who’s clicked. And on the flip side, who hasn’t opened it, who hasn’t clicked. Um, so these are really good stats for your business to find out what you’re doing.
Jenn: Um, and it’s so much easier. It’s so much easier. People that are using a Gmail or Outlook or whatever it is and just grabbing all these email addresses and putting them in like, oh, the time, the effort. I had someone yesterday, or was it yesterday, a few days ago saying about Um, they’d created a, a newsletter in word and they were taking it from word into their email program, you know, like outlook or whatever, and it wasn’t working and I just have to say to them, look, it’s never going to work, you know,
Gil: It won’t scale.
Jenn: sorry,
Gil: It also won’t scale.
Jenn: it won’t, it won’t scale.
Jenn: No, this is not a, and it’s not a sustainable business practice, is it? It really isn’t. And they reverted to, resorted to having a PDF and then, you know, who’s going to open a PDF that’s sent to you by someone that you don’t really know. Like. No, use the email, uh, program and, um, yeah, just. Let the, the, the programs, you know, do the platforms, do the heavy lifting for you.
Jenn: That’s what I like to say with BookDirectPro is, you know, I’ve created a tool that I’ve always wanted for my business and I’m creating it so that others can, can use it, but let it do the heavy lifting. That’s what it’s there for.
Gil: Yeah. Yeah. Maybe kind of like on the, closeout of this, I would love for you to kind of talk a little bit about why first off you created that direct book, direct pro in the first place. And maybe a few of the things that you or your customers really leveraged the platform for.
Jenn: Sure. Sure. Well, BookDirectPro it’s, um, I launched it summer 2024. Um, still fairly new, but it came out, it took me, uh, quite a few months there to put it sort of together because I was tired of telling clients that they had to go get a scheduling tool, and an email tool, and something for landing pages. And people would just look at me and go, More money?
Jenn: I have to do another subscription, another login, another, you know, it was just too much. And I thought, well, it was actually a business coach of mine who said, Well, why don’t you just create your own?
Gil: Hmm.
Jenn: hadn’t even thought of that, and I thought, well, this is what I have always wanted in my business. I wanted to make it easier for myself.
Jenn: So, um, yeah, so I’ve created this, BookDirect Pro, and you can do all of your marketing inside it. Um, you need a PMS, which I’m sure you’ve talked about a lot on your show, a property management software, because that runs the operational side of things. But something like BookDirect Pro, which is an all in one marketing platform.
Jenn: It is where you’re gathering those potential guests together, where you’re welcoming, um, return guests in. So you’re gathering people together to talk about how they can come and stay with you and what that looks like. So logistically, email marketing, um, very important as we’re talking about social media, the scheduling, you know, sit down, batch it, schedule it for a year in advance if you want.
Jenn: Um, that’s, uh, very easy to do. Uh, landing pages, um, what else, QR codes, brand boards, quizzes, um, it just goes on and on. It’s all these things inside, countdown timers. Who doesn’t like an email with a countdown timer if you’re doing a big promotion? Um, but all of these things, the, the, the, the basic, the basis of it is the email marketing, the social media.
Jenn: It’s a CRM. your notes of your guests in there so you know what their preferences are, when they’ve stayed, so that you can target them. Automations, you know, I know we’re getting heavy into the weeds here with all the, um, things that are included, but Automations, you know, um, when they signed up for something, uh, that they can, your emails are going out automated.
Jenn: So you don’t have to be doing it, um, live. There’s a communications hub where all your communications from all the social media and your email can come together in one place.
Gil: Yeah, I think that that’s the big point is like around automation, like we all have busy lives and marketing. It’s not the only thing that we do. So the more that we can not necessarily set and forget it, but spend a little bit of time to set up the system, set up the content and trickle that over time and create that automation in there.
Gil: It allows us to more sustainably and scalably roll out the marketing Strategies that we want to do, because it’s not just doing it that first time, but how do you do it in a consistent manner that drives enough traffic and also be able to monitor that over time to see which tactics are actually driving those bookings in there?
Jenn: Yeah, it’s using the stats. It’s using that, those stats so that you can see what’s working and then double down on it. Use that more.
Gil: What?
Jenn: that aren’t working, look at it. Why isn’t that quite working? Let’s tweak it here, tweak it there. That’s what marketing is about. It’s making small tweaks that make big, give big results.
Gil: That’s that’s 100 percent right, like you need to know what marketing tactics are going to work and some marketing tactics will take a lot longer like SEO and organic that takes time for it to to move the needle, but nonetheless, you should be monitoring where your traffic is coming from. And which campaigns you’re running that is driving the most traffic or even what emails that you’ve sent out.
Gil: That’s driving the click through rates. That’s bringing people back onto your web page, because then you can analyze and say, Oh, yeah, actually, that’s valuable content that my audience really appreciates. I should be creating more content like that, because if you’re consistently doing the same content over and over again, you’re not looking and you’re not looking at your funnels.
Gil: You’re not looking at your click through rates, not looking at that data. You could be spending a lot of time on things just that just is. Waste energy.
Jenn: Yeah it definitely and you know very few people got into this business to work in marketing and so i’m hoping that by creating this platform and bringing it to others with vacation rentals is to help them understand. That they don’t have to be doing all the things that they can leverage the same way that we’re leveraging, you know, Airbnb and the others, let’s leverage a marketing platform that was built for our space.
Jenn: That’s got automations built out in it, and I’m creating more. I created last week. I created a, um, a wifi signup funnel.
Gil: Mm.
Jenn: So with your own landing pages, and you can give out the, so people can give their details for your, for your wifi. So. Building these things out so that you can leverage them and that you don’t have to start from scratch.
Jenn: You don’t have to reinvent the wheel.
Gil: Yep. Yeah. Awesome. Well, Jenn, I usually end with two questions. One’s a mindset question. One’s kind of a take away action oriented question. So the mindset question first. What’s the one piece of mindset advice that you would give to someone that’s starting something completely new?
Jenn: Well, in the terms of, you know, in the, in the relation to direct booking marketing, um, I would say that the mindset of advice would be to try it. Don’t get too freaked out because there’s a lot of nuances there. There’s a lot of things that you can be doing, but it’s, you know, you don’t have to do it all at once.
Jenn: You don’t have to do everything at once. So it’s one step at a time. Don’t make a to do list like, you know, build this, build that, like break it down into smaller steps so that it doesn’t feel so overwhelming because it will. Marketing’s huge. You know, look to a, uh, look to somebody to help you guide, guide you through it. Not saying me. I’m not, you know, it doesn’t have to be me. It can be anybody in this space. But look at somebody, find yourself a mentor that can help you with this because it is, there’s a lot of, it’s a lot. We’re working mostly by ourselves for ourselves. We’re isolated and it is hard. It is hard. It’s, it’s, there’s, I know there’s nothing passive about running your business and doing all the things that you, that you need to do.
Jenn: So I probably don’t have the best mindset advice. I think just keep at it, try to take some time for yourself, and know that you’re building towards something.
Gil: Yep. Yep. And I’ve always found that for direct bookings. It’s. a compounding effort. It’s not something that you’ll do one thing and you’ll have to do it again and over and over again. No, it’s things that you do that build up over time, you grow your list over time, you build your templates and your sequences over time, and you invest that energy early on.
Gil: But you do enough of those things, you start to drive massive momentum, maybe the second year or the third year, But that first year you’re putting a lot of like structure in place there, and we’ve I’ve seen a lot of people basic become successful even within the first year. But what I feel like happens is that people put in a little bit of energy in the first year, and they didn’t see what the results that they had, and then they didn’t realize that they’re actually investing into a longer term future, and it does take some nurturing to do.
Gil: Yeah,
Jenn: it’s not a quick win, it really isn’t. It’s not a quick win, it is a long term thing, and don’t get discouraged.
Gil: yeah,
Jenn: things need to be tweaked.
Gil: yeah. And that that’s probably the biggest difference between building your direct bookings and relying on the O. T. A. S. The O. T. A. S. Is a great transactional source. If you’re looking for that next immediate booking, there’s no better way than the O. T. A. S. Um, but if you’re looking to build a marketing engine over time, you need to nurture that.
Gil: Um, and you don’t have to, like you said, you don’t have to do everything all at once. But you should be nurturing that over a longer period of time and start something that maybe you’re comfortable with, or that you can put into practice on the day one. Um, and just slowly build on that. Um, on the second question, what’s the, what’s one piece of tactical advice that you want people to walk away with?
Gil: What do you want them to put into practice? Maybe even today?
Jenn: Getting your, your guest data,
Gil: Hmm.
Jenn: figuring out a way, if you’re not already doing this to get their data so that you can talk to them afterwards, um, figuring out a way that makes sense for your, for your business and if, and when you do this, or if you’re already doing this. I would say the second thing is to use the information you’ve got.
Jenn: Start emailing them. Don’t this, the idea of an email list is not to collect it, to see how big you can get it. No one’s gonna give you an award when you’ve got 250 years, 500 or whatever it is. You’ve got keep, you’ve gotta email them. You’ve got to, uh, keep that up and just start, be personal,
Gil: Yeah. Yeah. And
Jenn: personal.
Jenn: Don’t hide behind that brand. And it’ll be okay. It’ll be okay.
Gil: yeah. And email is one of those things that. Does have a little bit of an expiration date there if you collect emails and you sit on it for too long, if you email them, maybe a year after you collected, they’ll be like, Who is this person? Why are they messaging me? Um, but even if you send them out 11 message a quarter, um, they’ll keep you top of mind.
Gil: They’ll know kind of the content that you’re producing for them. And they’re more likely not unsubscribe where if you sit on that email for too long, Okay. It’s, it’s going to be less valuable than, than you acting on it.
Jenn: Exactly. Exactly. And done is better than perfect. You know, I’m not saying to go out there and make a hash of it. I’m saying done is better than perfect. So even if you’ve sent an email and you’re like, Oh, maybe I should have said this, or maybe I should have worded that better. Eh, it’s done. You don’t have to think about it anymore.
Jenn: Move on to the next thing that you can look at.
Gil: Awesome. Jenn, where can folks find out more about you? How can they learn more about direct pro? Um, yeah, where can, when can people reach out to you?
Jenn: Uh, Instagram’s probably the best place. Uh, direct booking success. Um, yeah, I’m active on both of those, um, and the websites as well, directbookingsuccess. com and bookdirectpro. com if you’re interested in seeing more about that all in one marketing platform.
Gil: Awesome. And is there, if someone wants to get, try out book direct pro, are you running any promotions, are you doing anything right now on that?
Jenn: I would love to give your audience Uh, 50 percent off on their first month and they can come and I can give you that, we’ll give you, put that discount code in your, in your show notes, I guess. And um, uh, yeah, come in and try it out, uh, 50 percent off for your first month and I’ll have a call with you and.
Jenn: You know, get you on the right, the right foot. We have onboarding, free onboarding for everyone. Once you’ve signed up, you book an onboarding call. And, um, I will do a call with you as well to make sure that you’re ready to go. And you figure out what is going to move the needle the most for your business to start with.
Gil: Yeah, awesome. I’ll be sure to include that also for our customers as well to, um, if they don’t already have a tools in place, if you don’t have those structures in the place and they’re looking, um, to automate some of that and to simplify some of that, I’ll, I think that’s a great value for even our craft to say users as well, too.
Jenn: Definitely. They’ve got what the best website out there in our space. So we want more people to see it.
Gil: Yes, yes, absolutely. Thank you, Jenn. It was really good having you on the show and really. Just really diving into kind of your experiences over hosting for so long and really more recently or over the last five, six years, have you’ve coached others and some of the lesson learns there and how we can actually for folks kind of limited on bandwidth, how can they start to move the needle almost, almost soon ish.
Gil: Yeah.
Jenn: no, that’s great. Thanks Gil so much for having me.
Gil: Thank you, Dan. Right.
Yeah. Yeah.