How to be proactive rather than reactive in getting more bookings! the easy way to increase bookings

Do you want more
Direct Bookings?

This is one of my favourite episodes of this year and will provide you with a ton of information on how to improve your profitability. Marketing your business can feel like an uphill battle, but it all comes down to making your target audience care about what you’re selling.

I had an amazing time talking with an industry expert Andrew McConnell, Co-Founder and CEO of Rented Inc. Andrew joined me on’s The Accommodation  Show to discuss how to create a coherent demand generation strategy that works. Andrew shares his best practices for setting up a solid marketing campaign that generates demand and acquires more heads on your beds. 

We talk about some creative marketing strategies to convert and create more customer loyalty and help you in identifying where you are in your own sales process and how your marketing efforts can help support you in growing and maximizing those opportunities so that you can get more guests.

In this episode, we will guide you on how to get the guests to understand not just what you do, but what problems you solve. We discuss how to help guests recognise that they need what you offer, which in turn helps to create demand for your business.

 If you do it well, demand generation can create awareness with your desired audience, deliver more qualified leads to your sales funnel, and help link your marketing efforts to revenue. An ideal strategy will help optimize the number of bookings you generate, while at the same time building brand awareness and managing your reputation.

Andrew McConnell is the Co-Founder and CEO of Rented, Inc., the pricing engine for professional short-term rental managers, and The Wall Street Journal bestselling author of Get Out of My Head: Creating Modern Clarity with Stoic Wisdom. 

Art, Rented’s Automated Rate Tool, is the only dynamic pricing software built for and by professional short-term rental revenue managers. With Art, your in-house specialists are empowered to set the right price for every property, with intelligent rate recommendations and easy custom adjustments.

For companies that need hands-on support, Rented’s Revenue Management Service provides a dedicated revenue manager that specializes in handling every detail: setting prices, monitoring performance, and making custom adjustments.

Have a listen to these tried-and-tested ways to help you create more demand for your business. Keep grinding, and keep working on your demand generation efforts. Here’s to growing your business to infinity and beyond!!

Topics covered in this episode:

The basics that every marketing plan should include.
How to measure the success of your demand gen strategy.
How to deliver targeted and personalized advertising, promotions, email, and web communications, along with an optimized booking experience that will convert.
The basics of a good content strategy.
How to use display ads to raise brand awareness.

📣   Listen to the episode here
👓   Watch the episode here


Bart: Hello and welcome back to The Accommodation Show. We help accommodation owners like you get the knowledge and skills to grow your business, improve your guest’s experience and increase your profitability.

Andrew: Thinking we’d get five or 6% revenue left and it would make sense for us economically at that scale. And what we saw really shocked us. Within a month, for every single property we took ourselves on, we hit a minimum we’re lifting the revenue by 30% And it’s sometimes we’re more than doubling it. And this was the same manager. This was the same property was on the same listing sites. We were just managing appraisers. Wow. This is a really, really big opportunity. And so that’s really where Rented in its current form was born and 2020. We spun it out, we built out the technology that our team was using, and made that available for other companies, and any professional manager to be able to access we integrate directly with their property. management software. So our automated rate tool gives everybody the best in class technology to go manage their pricing and revenue management.

Bart: What an incredible story and what I like about your Andrew is you’re the embodiment of my understanding of short-term rentals. And you were there at the very beginning before probably even property managers even existed as a concept. You know, it was always just rent out a bedroom and that sort of thing and then the professionalization of the industry, and then you were the forefront of that side of it. And then the one part that you were ahead of the curve on was data analytics, revenue management, and really understanding some of these key principles that kind of this particular part is kind of come out of the hotel industry. Because they had bigger budgets, and they were able to look at this sort of data but the one thing that is incredible is that we work with data scientists in our business to drive more direct bookings. I mean, it’s the bread and butter of what we do. But so few businesses are doing it and maybe and I’d love your opinion, maybe a lot of people don’t understand the value of actually getting this right and how monumental getting this right can be.

Andrew: Yeah, I mean, it’s there are a couple of points here. I mean, is It is ironic that this industry would be behind hotels or even behind airlines, right? We’re all used to searching for a flight and then coming back an hour later and the flight price has changed. And yet, for decades people would separate in November the year prior, like, oh, no, this is my summary. Oh, this is my off-peak rate. And why even though the hedge fund was around longer than airplanes existed, right, people were renting out spare homes and spare rooms before we had air travel. And yet, airlines because they got to a scale and hotels because they were at a scale to build these in-house capabilities. They had more sophisticated technology, they had better collection and data. 

They were using it better. They are further along in that progression. And I think the same in general when you’re talking about looking at the data informing a lot of these companies are not at the scale where they are right. They’re not Delta Airlines. They don’t have 30,000 employees and billions a year in revenue to invest in what they need to do. And so what it really takes a lot of times is third parties who can service hundreds, if not 1000s of smaller companies and say, Hey, we’re going to build this scale as a service. And then we’re going to let you just buy the pieces you use. It’s not that different than what Amazon does with Amazon Web. Services. They said look, we are buying and managing and using so many servers for our business. Why don’t we just build that as a capability and let others buy that from us? It’s probably I’m dating myself but you know, in the 90s and even early 2000s If you wanted to go start a technology company, you had to buy a server, you had to have somebody who knew how to manage a server and deal with that on premises. And so it costs more than a million dollars out of the gate. Now you can spin up an AWS instance and you get best-in-class server access for pennies on the dollar. And that’s really what it requires when you’re talking about data analytics or some of these more sophisticated capabilities that really make a big difference in your business that hey if you get a 30% revenue lift that on a million dollar business that’s $300,000 you didn’t have before, but if to build that you have to hire somebody who’s at $250,000 a year data scientist by the data that’s going to cost you $25,000 month and go through all these other pieces. That doesn’t pay for itself. So you have to be able to buy just what’s right for your size of business. And I think that that is where this industry is a bit different from airlines, right airlines because airplanes are so expensive. They have kind of a minimum size they have to operate in.

Bart: Look, I mean, I think these kinds of principles apply to hospitality in many different ways. You know, even if you’re in a restaurant as well, you want to understand what’s going with your pricing and you want to be changing things dynamically like even the new prices it should be done on a daily if not a weekly basis rather than you know, setting it for the quarter or whatever based on what you think a potato is going to cost. But I’m not going to digress too much into that but it’s such an important thing and I always try to the way that I kind of managed to visualize it for people is if you can get that at 1% extra revenue across the year then it means you’re working three days less a year. So you know what would three days extra holiday mean to you? So you’re great three more days holiday call, do something. And then and then you go well if I can get 10% more then all of a sudden you’ve got 35 more days to do whatever you like, how does that work? Right? And that’s all cool and you can equate it to something which is tangible rather than just a number that is 10% or $1,000 or $100,000. 

Let’s jump into our topic for today. And that’s what I really like is that we run our businesses, right so you’re looking after this particular part. And you know, we’re doing direct bookings, but there’s also these opportunities right and that’s what we’re gonna talk about today is opportunities that many folks will not be taking advantage of because when we’re looking at our portfolio and this is hotels as well, by the way, this isn’t just short term rentals, this topic. We look at our pricing and we’re quite reactive a lot of the time to what’s coming in, right? So we’ve got bookings coming in from all the different channels, and then we set our pricing and then we optimize our pricing, but what can we do proactively to guarantee more bookings or to get more bookings? And that’s what we’re talking about today. Have I summarised it correctly?

Andrew: You have. It really is working back from the funnel, right? So the price is almost the last thing that people are seeing. They have to get far enough along to look at the price for it to be relevant. Before that, you have to attract the eyeball far enough in and even their most the time. It’s being reactive, whether you’re on a third-party listing site, and so it’s reactive to somebody going to that site or using an app and then searching to end up in front of your property. Or it’s a direct booking on your site that somehow through a marketing campaign. They have come in. But there’s this entirely separate category of opportunity to incept the movie Inception incept the idea of travel and set up the idea of a vacation, of visiting your property, visiting one of your properties in your location. 

And that to me is, I think the most exciting opportunity of the next decade of this industry of “hey, we’ve done so much to build category awareness where people are willing to stay and so when they’re searching we’re now part of that conversation. What’s that next step, to inspire people to take trips they weren’t thinking about before?” And what really kind of highlighted it for me was working with our clients through COVID, where Florida, and different locations. That you were in Australia’s closed borders and made it much more difficult. You couldn’t just depend on reactive travel, and booking Airbnb, all these pulled back billions and ad spend. So you had fewer eyeballs coming in what could you do to generate new demand and the clients that we had that were the most successful that we’re working with her once it rethought what they were selling, how they were selling it, what they were providing? And so working with insurance companies on relocations and say, Hey, I have this home like how was going to be used or, Hey, I have these people that I know come every year in July in June right for the summer, but free now they could get an entire month for what they spent for that one week. They’re not going to the office. Their kids aren’t in school. I wonder if I could get them excited about coming out here. And these companies almost doubled their occupancy over the course of the year in some cases, we’re more than doubling revenue over the course of the year in what should have been a terrible year because they were able to generate new bookings people were sitting at home, they weren’t searching travel. It wasn’t on their mind that we turned COVID and go travel and then they said Wait, you’re right. I’m not going to the office. You know, they get an email, they get a phone call, they get a text message. They get whatever it is they get a push ad display. I said that that seems really good. I want to go do that thing. And I think figuring that out is there’s just infinite opportunity there.

Bart: Great topic. And I have to say I’m in love with these sorts of ideas. And you’re absolutely right during the pandemic, during COVID Especially for companies that were doing things a certain way, they had to sort of start to think a bit more laterally about their business and how to reach their audiences and how to think about their businesses differently to survive, right? That was a survival thing, right? And we got through this thing. Now it’s like okay, we’ve gone through there and it was actually better the survival was a boon for this particular segment, but then you go Alright, so how can we inspire people to want to take that extra trip to want to visit us to create those opportunities with what we have and in my mind, Andrew, there’s kind of two sides to this equation. 

One side is what do I have on offer? What is my portfolio look like? Are we talking about and this is where it’s important especially? So hotels can be easier. For some property managers, it can be easier or harder. For example, you might have a portfolio of 10 houses and you go okay, so I’ve got this penthouse experience that I can deliver. You might have something which is location-based, which is by the beach, he puts a beach holiday and then you’re off-season so what can we do to inspire people you have to look at what you’re offering. And one of the things that I suggest with this particular part and I’ll go over your thoughts on this. If you’ve got a property management company, they’ve got 50 properties all over the place, right? And then it trying to create some sort of cohesive messaging to go out there and be proactive. Hey, come and stay at our properties. It can be difficult because those properties are targeting different advertising and different guests, and that’s the second part of the equation. So one is who are the people that are traveling and the other one is What do you have to offer them? So one of the questions that I have is what are your thoughts on property management companies with a disparate range of properties and being proactive?

Andrew: Yeah, I think you have to narrow the focus, right? You can, even if you’re scattershot with the properties, bucketing on what is it that you’re providing. So you talked about who it is and what you have. I think there’s a third piece of why people are traveling and can you create the why that would inspire that who to your specific one, and just one illustration of this. So there’s an area in the north of Georgia you know, I’m originally from Atlanta, and called Blue Ridge. And they noticed that there was one weekend year on year, there was always the least booked for all the managers there everybody who had a cabin. It was very slow for business for restaurants, everything and it was right in mid-September, it was kids going back to school, people were at work, they weren’t taking summer vacations, the fall breaks hadn’t calm, they weren’t taking a summer vacation. So it was just nobody was traveling. And, you know, the natural thing is saying, Okay, well let’s just write that off. 

Let’s focus on these other areas. The other way we say hey, people aren’t coming because we don’t have a good why for them to come. What if we created a great why for them to come to our area? And so they started working with the local Chamber of Commerce, a whole group got together and said, Let’s create a blues and barbecue festival that we’re gonna hold this weekend every year and now it’s the number one revenue generating weekend of the entire year and went from dead last to number one because they generated a reason to come. And so I think this is one of the things we were talking about with packages and other things. We have the opportunity to do short-term rentals with our own portfolios is can you create a unique why, an exciting why that you’re what uniquely fills for that who and really tying those pieces together and what that story is, is what’s going to help you generate new demand that was not there before. Nobody wanted to go there the year prior but now that there was that event, people are knocking down the doors.

Bart: I love it. And I think that this why can be super varied. Okay, so one of those things of setting up a festival setting up an event is one really effective way in that that works really well because you’ve got scale of the local community supporting it. Social media engagement, hundreds of people talking about rather than just using one single operator in a particular area. But you can also I mean, the ideas and this episode for folks is just about trying to unlock some of these proactive ideas of things that you could potentially do with your portfolio. 

Okay, so what have I got and how do I create that y the y is going to be associated with an avatar with the person that you’re kind of targeting so what is the why it’s targeting families? It’s one thing if we’re gonna go romance kind of packages or romance type ideas, and we can do all sorts of different things. And I love the example that you gave before of, you know, you can stay for way longer. You know, you paid X amount at this particular point, you can stay with us now and it’s gonna cost him a quarter of the amount of half of the amount, and not only that, we will create an extra few add-ons to make the experience extra special for you. And then provide every single year right so the work that you’ve done the one year you can then roll it out.

Andrew: And I think that last part is really important in the what doesn’t have to be static to what is more than the physical structure, and the what is the whole package that you’ve pulled together and the what is the experience that they are going to be able to have and that is something that not only can you but you should be looking at, you know what, what is it that’s getting the best reviews is getting repeat guests. What is it that gets the hook for the right who and continues to hone that messaging to hone that delivery and stay in front of those people? is definitely how you take somebody who used to come once now comes every single year and now comes twice a year for two totally different reasons. But just rethinking what the what is and can be.

Bart: Yeah, great. Okay. So, so in terms of different things that we could do, right? So what is work with the community we can do to put together events, and we can create packages, which are kind of time-based. So some sort of a deal right or some sort of extra value based on the time of the year. Do you have any other kind of examples in terms of proactive things that people can do to create more of that why to travel?

Andrew: Yeah, I mean, this is we’re really getting down to the data to better understand your past guests. And their profiles. So the white of knowing the different school districts within a two-and-a-half hour drive of your homes, and being able to have specific marketing campaigns around their school schedules. And when their breaks are saying, hey, you know, the airports can get super crowded, wouldn’t you love to be able to just drive and be here. The same day later the same morning, after School’s out. You know, you could have dinner here, just thinking about the story you can tell and who that would be compelling to and just play with it. Who would enjoy what you have any given day of the week because there is somebody that’s going to be excited by that and just playing with it?

Bart: For sure. And then so hopefully, if I have folks that are listening or that are watching, this is starting to get the creative juices flowing. Okay, cool. These are the different things that I could do now, if we talk about being proactive in terms of so if we’ve figured out and here’s what I would suggest is brainstorm, brainstorm on your own, go to a cafe go to go to a field and sit down on the grass with a pen and paper and just think about it.

Andrew: And talk to your guests. Talk to the guests. Why did they come? What did they like most talk to your guest?

Bart: And like so it’s a great exercise regardless because a lot of this proactive demand generation it doesn’t have to be off-season as well can be on the season and you’re still making more money right from what you’ve already got. But what we’re trying to tap into and I think I’ve got this right, is trying to get someone that wouldn’t consider booking you at that particular moment and try to get the juices flowing. I actually shouldn’t make this booking and I shouldn’t make it those should make it now. So we’ve got that part nailed. And then we want to go to market with it right? We were like okay, cool. We’ve got these ideas. Thanks, guys. Ideas are amazing. What do I do now that I’ve got these proactive ideas to reach out to people how do I find them?

Andrew: Yeah, I mean, there are a few different flavors of that one. Probably the easiest is if you’re keeping a past guest list if you’re keeping an email list at all, not just for past guests, but maybe you have splash pages and you’re capturing the emails of everybody who stays at your property and so you can mark it not just the people who booked, but anybody who’s ever stayed in the property and expand that email certainly one piece there’s then there’s the proactive display. So again, knowing what are the areas around you, especially like that the easiest kind of last-minute booking are people who live within an X hours drive x miles of where your homes are. 

And so with how targeted advertising works, whether it displays or it’s social, wherever it is pushing ads to geofencing at the right times for those people when you’re doing a promotion you could do on a Tuesday. Hey, guess what, we have a special three-day weekend package for anybody who books in the next 24 hours. Right? You just have gap inventory that you’re able to get in front of the right people because you pushing that ad to someone who lives three flights and 2000 miles away is irrelevant. But if you can push it to people that they are the ones that are like, Yeah, I actually can book this and start getting in my car and the next hour. 

That’s an entirely different prospect. So just thinking about what the timeline you’re selling and who you’re targeting to, allows you to think about where are those people. And how do I get in front of them whether it’s email marketing, whether it’s text messaging, whether it’s display ads, this is really where partnering with someone and look, I don’t make any money from this? This isn’t what we do, right like we set the price I’m saying that’s for in the funnel, you need to do something for the back and get more people to come to see the price in the first place. So I don’t have a dog in the fight and hiring a third party to do it. But depending on the size of your business, you’re just going to be better served by having some really does this eats breeze lives it day to day.

Bart: Okay, cool. So, I love some of those ideas and so email, obviously right text message is a really interesting one. You can reach out to people through text messages if it is done well. And with text messages, I would really recommend it if you’re ever going to put together a deal or an offer. Try to make sure that it doesn’t feel like an advert because the more it feels like an advert, the more people are going to be frustrated because they’re just getting people getting that many text messages nowadays, but if you personalize it Hey, I was thinking of you. I was thinking of you when blah you came here six months ago. Come here again those are super high-converting messages and it has to be super genuine so you can still automate a lot of that but you have to get it right if you don’t bother with SMS messages will just do more harm than good.

Then we’ve got the sort of paid funnels as well. And the geofencing is brilliant, because you can choose the areas but also don’t forget, you’ve gone back and you’ve looked at your avatar you looked at the people that you’re targeting, you’re thinking about their demographic you’re thinking about a targeting high wealth individuals. Are you targeting families are you targeting people with pets at home targeting people that are newly married and that kind of stuff? And many platforms such as Facebook, and Google, they can get into quite good demographic targeting. 

So not only understanding where someone lives, but also what their makeup is of their age, and profession and that sort of thing as well. So you can really drive home that message to those particular people. And the other one is you can also do quite a fair bit for free. And it’s a free means to jump into Facebook groups and community groups and say, Hey, I’m a local business owner. We’re doing this because we want to give back to the community because they’ve worked so hard for X, Y, and Z reason so you go in there, find different communities and come up with some ideas and give all the different ideas away but it’s not hard to do. Are we missing anything on that side of the funnel, any thoughts and feedback?

Andrew: I mean, the only thing I can say is yes, we’re missing a bunch because I think we are in Day Zero of the opportunity on this. Right, so it was new to even get online 20 years ago when VRBOs started putting listings online to get to Instant Booking, to get to dynamic pricing. This is all a relatively recent history. And so to open that funnel in the US if we rewind to 2007 only 7% of travelers had stayed on a vacation as of 2021 81% of millennials had stayed in a vacation home. Right? Were 10 axing the pool of people looking at this category, how and where and why do we get them to look at it more frequently, and what the use cases are with? Could they be a digital nomad? Could they work remotely? Take a week or two off, and play with that kind of thing? The only thing I’d say is these are all great ideas. And there are going to be more new great ideas and great opportunities that just keep coming our way. And so just staying on top of it is the most important thing.

Bart: And you’re absolutely right and to me, it equates to this is that a lot of people think oh, that sounds like a lot of effort sounds like a lot of work. Am I going to make a positive return on investment on it? And the reality is this. You don’t have to do this. You can sit there and be reactive and get your bookings and that sort of thing. But the issue you’re going to have is someone else will do this stuff. And they will do it well and they will blow you out of the water and then numbers will double yours because they’re doing it well. They’re doing it effectively and they put it into their plans, or how do we create this how to create this demand? How do we build to the future and not be over-reliant on one channel or an OTA or being reactive, and then finding that your business is at the mercy of a, you know, a change in the algorithm on a particular platform and that sort of thing? So my feeling on this is you don’t have to do it, but if you do it and you get it right, you’ve got a huge opportunity, would you agree with that?

Andrew: Yeah, absolutely. Absolutely. You know, my I wrote a book literally called Get Out of My Head about taking control of what you can control and releasing what you can’t. And the more you can bring into your control, the more you’re the hero of your own life of your own journey of your own business. And exactly what you’re saying, being at the mercy of someone else on they’re going to write my story. No one’s going to write a great story for you. You have to write that story yourself. And so taking that ownership of the demand generation of the demand driving is the most powerful thing I think you’re going to be able to do in your business going forward. As we progress as an industry

Bart: Yeah, you are like a natural at this Andrew as we come to the end of the episode, the book, and that was probably one of the main reasons why I reached out is because I’m a huge believer in you know, it’s all great to get marketing knowledge and knowledge about making wealth and all this kind of stuff. But I also have a deep inherent belief that my health is beyond just this kind of pseudo success that I’m creating and that sort of thing, that where my head is at and when my mind is that is incredibly important. And so keep that in check. Tell us a little bit about the book and also tell us why people should buy it.

Andrew: Yeah, I mean, the book, Getting Out of my head Creating modern clarity was stoic wisdom and it could build on this concept of there’s only one asset there’s only one piece of real estate any of us ever can or will own and that’s our mind. Our body can be infected by a virus, we can get sick, we can get hurt, but our minds we, can control. Any physical possession that can be confiscated by a government can be broken, but our mind is the one thing we can control. And yet our default state as humans is to give it away for free. 

We give it away to social media, we give it away to Netflix, we give it away to 24/7 news cycle we give it away to what someone said it was mean to us last week or what we’re worried is going to happen at work next week. And we don’t exercise ownership over that one precious asset that we have. And so the book is really getting into “look you’re not alone. Feeling like this. Everybody says “man, I just need to get out of my own head or man, I have these tenants living rent-free in my mind. 

Look that that is almost universal. It is universal and you’re blessed. You’re basically Buddha. And so the book gets into why is that you know, what is the science behind why your brain works this way and then uses stoicism as a framework to come out with 13 core tenants of how to address it from How do I stop running to other people? How do I stop running to events and circumstances outside of my control? How do I stop running to different imagined versions of myself and then illustrate with examples from entrepreneurs founders and DocuSign social activists like Dr. Martin Luther King’s daughter, Navy SEALs, Olympians, and artists, all over the spectrum of people who’ve taken these principles and really implemented them to incredible effect in modern day society? And then your chapter closes with exercises to take it off the page and start to put it in your life and really implemented it because words are NP paid. written words are spoken words, don’t do anything. It’s only when you act, that change can occur and that’s really why the book is, is written how it is. And the reason I wrote it is to learn from his passion, but it’s also an incredibly selfish act unless you do something purposeful with it to benefit others and I really wanted to help others.

Bart: What I love about people that write books is they’re taking their time and their effort to really go a bit deeper and have a think about you know, because like you said, you kind of passively taking all of the knowledge in and then you start to practice it in your own life. It’s like well, how do I convey summarise everything that I’ve learned and then and give it back to other people? So look, I have not read the book, but it’s something that I will definitely be looking forward to reading because it aligns with a lot of my thoughts and I’d love to see where your take is on all of this. 

And for those of you that have never read a book that’s like this, do it. Just do it. Pick up Andrew’s book, pick up any book, because you will learn an awful lot from people that have experience. Then you can put it apply to your life and you’ll find that there’s a certain sense of calmness that will come with it, which is it’s really liberating. Andrew, we’ve come to the end of the episode. Thank you so much for coming on and sharing some of those and those ideas on being proactive rather than reactive. If anyone would like to engage with rented or then there’s a link in the show notes and they’ve also been kind enough to offer a free 30 days is it?

Andrew: Yes 30 days free to no commitment, just try it out and see how much more money we can make you.

Bart: Yeah, and you quote, The Accommodation Show. Generally, it’s sort of 20, 30, 50 properties and above, which is where this solution becomes most effective. But also feel free to reach out as well because they do have different products for smaller property managers as well but they’re now and they’re coming. For the book. We will put the link in the show notes as well. So you can download that and get yourself a copy. And then of course you can reach Andrew on the socials as well and follow him and give him some love. Andrew, thank you once again. I really appreciate your time. It’s been wonderful 

Andrew: Yeah Bart: It’s back to connecting on socials. I feel like we’ve done that for a while. So it’s been great catching up live.

Bart: Appreciate it, and I’ll catch you hopefully over in the US in a couple of months’ time So until then, take care, and folks if you are listening if you enjoy the episode. We really appreciate it. And to help with the episodes and help us keep doing what we’re doing and getting awesome guests from all over the world from all sorts of industries within the accommodation space sharing their tips and insights. 

Thank you so much for listening to the show. You can find us at where you can find all the show notes. links to resources we have talked about in transcripts from the show. I really do appreciate you listening. And if you’d like to support the show, and please subscribe, leave a comment and share it with others.

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