From Overlooked To Overbookeds - The Power of Eye-Catching Photo

Podcast episode from the Boostly YouTube channel (Nov 4, 2024) interviewing Brian and Katie, co-founders of Overlooked to Overbooked. They describe the company's origins (they were long-term Airbnb 'super guests'), the evolution from a DIY video course to live 'done-with-you' and 'done-for-you' services, and practical photo advice for short-term rental hosts — especially using color strategically and sequencing photos to create a clear, emotional journey for potential guests. The episode closes with contact and website details.
Chapters
Hi, everybody. Welcome back to the Boostly podcast. This is the podcast that gives host the tools, the tactics and trainings so you can go out there and get yourself direct bookings. What we do on this podcast is we look at services, we look at great people out there who can help you with not only increasing your direct bookings, but increase your bookings in general. And part of increasing your bookings is making sure that you have really eye catching photos, which is the subject of today's podcast. We've got some special guests on here who are absolute experts. Looked at what they do and they have been, they're making a returning appearance on this podcast, but it's been a few years since they've been on, so we thought it'd be great to get them back on, get your attention refocused on this particular subject so you can go out there and you can increase your bookend. So let me introduce, we've got Brian and Katie. They're from a company called Overlooked to Overbooked and as I say, absolute experts with photography and ideas around what you can do as a host to improve your, your pitches. So welcome along Brian and welcome along Katie.
Thank you very much. Appreciate it.
Thank you.
Thanks for being here. So first question, can you just give an intro to your company? I know you're the co founders of Overlooked to Overbooked. Can you give us some, some kind of background and information on how you got started in this, in this sort of area?
It's very organically derived. We were what we call super guests for, you know, pretty close to three years between like 20, 15, 16 and 17. We were traveling and staying almost exclusively at Airbnbs for relatively long periods, like month, two months, three months. And the relevance of that is that it put extra pressure on the search process because you didn't want to pick a place that you're going to lock down for three months and then find out that it was a bad choice. And for anybody who was doing this back then, the listings were not very good in 20, 15, 16 and 17 compared to now. We'll talk about where they still could go. But I was head searcher and I was banging my head against the wall and pounding on desks. And Katie can talk about how frustrated I would get because such simple things were not being accomplished. It's like, why are there only 10 photos? How come only half the bedrooms have pictures? You know, why are they blurry and dark? And you know, what part of town is this, right? You just have question after question after question because they weren't being handled in the listing. And you know, the easy answer for that is the industry hadn't really matured that much. Probably most of those were being done by the host themselves. And not that that's a bad thing, but that host probably had other careers or at least one where they were a dentist or a lawyer or something. And this was like a sidelight. And um, so anyway, we, you know, Katie has, has a background that I'll have her tell you a little bit about. But it was a perfect fit that I started kind of coercing her into saying like, you know, you could help these hosts so much with the things that you've learned from your career. And the other thing that was really exciting about it is I thought the ROI should be massive. Like this should be the most no brainer opportunity for a host to upgrade their listing, upgrade their sales and revenue and nightly rates and occupancy. And it should be a win win all the way around. And so that was the impetus to start. What we originally built was a video course that was mostly DIY for somebody to be able to take their own pictures and edit their own pictures. And then we've since evolved and we'll talk about this later, where we now have a done with you and a done for you aspect where we can work with you live over the Internet on your phone, or we can send a couple of our people to your house and do the whole thing for you. So that's my version of it. I'm sure Katie has elements to add to it that I'm forgetting 100%.
Katie, let us know your side of how you got into things.
Yeah, that's essentially it. I mean, our backgrounds were kind of a perfect fit for this brand, kind of coming from sales and marketing. And I was an editor in Hollywood and I worked in a small post production company, but we worked for the big studios. And right now I spend a lot of time editing photos. And I kind of did the same thing even back then, but I would color correct moving images. But it's sort of the same thing and you have to apply the same logic to it, like how do you make this end product look as good as it can for the user? You know, I got to see what all of the viewers were going to see, like the final thing. And I really liked that aspect of it. And then of course, traveling, when we actually started traveling and looking at places, you can really feel the pressure as a guest, as a host. I know you have a thousand things going on, but as A guest. When you really are sometimes in a different country and you have to book a place and all you have is the listing, you don't get extra info, of course, you can message the host and ask a question, and then you hope that they respond in time. And you might have a bunch of browsers open, like Brian said, and trying to choose between a place. You really don't want to have to go back on that. I mean, you just want to get a good place. It's not something you can quickly like, oh, let me just cancel and change it like an outfit. You're putting your money me on this and people. We were working and traveling, but when people booked these places, they might be there one vacation a year to your place. So that's. That's a lot of pressure. So you're really feeling it. Like, just a lot of questions emerged that you might not even think as a host. And sometimes you don't see the forest for the trees. You might be burying your lead. You know, you have a really good amenity and you're not showing it enough, or, you know, there's a bit of a disconnect there. It's kind of, you know, bosses and employees, teachers and students. You're all kind of coming at it from an opposite perspective, but really you're in the same space. So sometimes it's kind of just good to swap roles. And I feel like that gave us a really strong start to kind of see things from the guest perspective and say, look, we as a, as a guest, I can see. I would want to see this. I would want to know this. If you just show me this, you don't have to give me a long explanation just to give me one photo of it. So we were kind of able to put together this guide from the guest perspective.
There's a lot of people out there at the moment who have. They've got photos which they don't emote feelings from, which I think was what I picked up from you guys, especially from. I. I listened as a, as a fan of Bruce Lee podcast last time you guys were on this, and I picked up that it's about getting the emotiveness from the pitches. But also, how many people out there do you think are missing out on? I think you mentioned the journey before, taking people on the journey through the places. Do you think there's a huge amount of people out there who could. Could benefit from really looking at the order of their pictures? And I know this is something which Airbnb has just. They've Pressed a button and they've reordered everything for you, which is terrible for me for a lot of them. But, yeah. What's your thoughts on this?
For sure, there are a lot of people who could kind of take a moment and think about it again from the guest perspective, who could benefit from really thinking about the journey, which then it sounds very foofy, like, oh, the journey. And the emotional. Like, what does that mean in a photo? But it really means, like, does this make sense to a guest? And really, we think about it from a couple of ways, like, do I understand where I am in space? And then does it make me want to go there? And those are the kind of two things that we always try to marry. Does it still make sense, like, where you are in this location, location in the house, and does it make me want to go there? And not every space is equally sexy. You know, you get to take a photo of a bathroom, too, and they're not all that amazing. Or sometimes you just want to show that I have a bunch of kids stuff. You have a high chair and a pack and play and all that stuff. You just take a photo of them all and put it. But in terms of the journey, one of the things that people have now done. And of course, yes, you're right, Airbnb keeps throwing a monkey wrench at a beautifully crafted thing without asking anyone. I wonder who their consultants are. Again, we will just bleep that out or blur it. Just some ota. But. And I understand where they're coming from with the way they're now trying to organize the listings. They're trying to help host with the thing that I keep harping on when we do our, you know, calls and podcasts and all this is thinking about the sequencing. And they try to make it easy for you to understand where you are in space so that this place makes sense. Because sometimes what people then do is thinking, well, my house is kind of boring. You know, you don't have a lot of staged things or scenes or cute stuff. You'd be like, the way to mix it up is scramble the sequence. So we'll look at my kitchen, look at my pool, then look at the town. And then we're going to come back to a bedroom, and then we'll, like, go through the kitchen again, and then we come back to a different bedroom. I'm seeing this for the first time as a guest. I will be completely lost. Like, you've lost me once. You change spaces that many times. So it really is. And then about crafting like how do you take you. You still kind of want to take wide establishing shot, but not with a wide angle lens. But you want to give us a sense of space the way you would even like an old timey movie, they would always shoot it wide angle, medium shot, close up. Like that was kind of the structure because it makes sense for the brain. You want to tell people, where am I first? Did we just change room? This is the front yard or the backyard, where am I? And then you want to show me, oh, look at all this cute stuff. Like you would never in a million years take your friend to your house and just drag him by the hand over to like a little close up, like a little, you know, tchotchke or, or some clock or something. Look at this thing. And then kind of go back. Oh, and by the way, we're in the living room. Like you enter a room, like, go take a look at our living room. We just redid all the paint or whatever. And then you start kind of looking at the details. So that makes sense to us. And that kind of becomes the journey. When you think about like, oh, I experience stuff. Like what do I add in there? We'll just think about any space where a person's gonna sit down, hang out, spend time. And you're kind of creating a fantasy, right? Because in the fantasy, in the real estate world, the fantasy is that this is the house where I can build my life, right? Like I'm going to put my stuff in there. It's going to look like my home. Vacation rentals are not that you are providing ready made things. You can go a little crazy. You can have your neon signs and you can have your movie room and you can have your, you know, whatever, favorite sports team, house. That's what it is. You'll find your tribe. But then you kind of, you go through, you want it to make sense for people where you are. But then you kind of think like, wouldn't it be nice if you could just sit here, put your feet up and watch the game? Or wouldn't it be nice if you could just lay down in a hammock and read a book and like listen to the waves. That's then, then kind of becomes the experience. But you can think about it and it like, because it seems like such a mess when you're starting, like, where do I even begin? I just do whatever happened. You're just having a glass of orange juice, you enter a space and you think like, what would you do here? What would you want to do here? One of my favorite examples for hosts, if you can draw a bubble bath with that little tray on the bathtub and a book and a glass of wine, like, I'm in. I am never in a million years going to get to do that on vacation. As long as my kids are in school, that's not going to happen. But I enjoy the fantasy of it. I do it, we craft this, and it still works on me. Whenever I see it, I think, like, oh, my gosh, I've maybe had one bubble bath in my life, but it still works. Or just creating that, like you're all going to play a game together. We'll pretend screen time doesn't exist. Let's just play Monopoly. But it's the dream that you're kind of like, remember the fun times that you can have. And then kind of showing how they can have a good time at your place. How are you going to make this happen?
I think we understand obviously the reasons really why we need to be all. Considering our folks photos and, and the kind of journey and the emotiveness without giving away the secret sauce, what are some of the things that the audience can do which are either I say quick wins. I mean, there's anything that's worth doing is worth putting some effort in, but what are the things that, that people can do to really move the needle forward for them? And of course, I know there is a course which you guys do, which we'll talk about in, in a moment. Without giving away the secret sauce, what is, what is a couple of tips?
Well, first I'm going to say we give away the secret sauce. We tried to decide whether there was stuff that we should be holding back. And we've kind of gone all in on telling everything for a couple of reasons. One, because there's a certain kind of person that is going to just suck that up and use it. And that's great. And that doesn't cost us anything. We got plenty of business. But it also ends up being a way of generating business because certain people are going to hear it and say, that makes a lot of sense, but I don't have the time or the inclination to do that. So how much would it be for you guys to do it? So it kind of, you know, I'll expose our ulterior motive as well, but, but we really do want everybody to be able to benefit one, one way or another. I mean, I'll rattle off a couple of them and we've got probably 10 or more. So Katie will fill in some gaps. Color is a big one. Because if you. And this comes back to you, even if you don't stay at short term rentals yourself currently, you should pretend like you're going to like go and pick a town and pretend you're going to go to Denver for a weekend or something like that and say, how many guests are we going to have? How many bedrooms do we need? What part of town do we want to be on and, and look at what your options are and look at how good is the competition. You know, do they all blend together? Fortunately for us, like to this day still, there's a lot of listings that are kind of average. You know, they're not bad, but they're average. Right. So they're not standing out from each other. There's a lot of. And I don't know if that's because of Williams and Sonoma. And Crafton. What are those? A pottery bar and all? They're all grays and tans and browns and doesn't mean that those are bad things to have in your house. But you're back to square one when you're next to 50 other people who went to those same shops. Right. So we, we like to strategically use color to grab like kind of the lizard brain part of people when they're seeing something just to get them in the door. Right. So that's one for sure. We talked a little bit about research. The kind of research you can do is your own listings. If you don't have a lot of listings, you can look up the reviews of your competition. What kind of people are coming to stay with them and what are they saying they enjoyed. Maybe you can take on some of that stuff. Maybe you have some stuff that your competition doesn't.
So thank you so much to you both for spending your time with us on this. I've certainly learned a lot and it's been fun. I say catch up as if I was here last time. That was Mark interviewing your last time. But it's just great to have you both on the podcast. And I advise everybody listening to this, if there's any, any sort of listings and you want some advice, go and check it out. Go to the website. The website's in the show notes but if you just want that again, it is overlooked to overbooked. And if you just put that into.
Google, the number two not to in the middle.
Ah yes, good point for, for this numerical too. And yeah, you'll come up high on.
Google if you do end up signing up for an assessment and you don't See a time that's convenient for you. I'm Brian B R I a n@overlooktooverbook.com. katie is K a T I at overlook to over. And we often have relatively sparse options on the calendar because we only book so far in advance, because we never know where I'm going to be and, you know, which weeks I can take a lot and which ones I can't. But usually I can. I can fit in more than will actually show up on the calendar. So if you say, hey, you know, these are all inconvenient for where I live in the world, or something like that, I will find a time that works for you, no problem.
That's cool. And, you know, the great thing is about that is because you're actually walking the walk as opposed to just, you know, you're out there doing this, which is. Which is cool. Which is, you know, why there's limited availability is like, you say you're out and seeing these real places. So if you're listening to this on the podcast or watching this on YouTube and there's somebody else who can get value, please do share it with a friend or with a fellow host or on your social media. That's it for this episode. Thank you, Brian. Thank you, Katie. And we'll see you again on the Boost Lee podcast. Having a blast. Gonna get it on the Boost Lee podcast. Bruce Lee. Like Bruce Lee, because it's so hard and the T is loosely making up those rhymes. Don't write it, just do it loosely.
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