Heads In Beds Show - Rethinking Your Outbound Marketing Messaging

Episode Date: July 15, 2026

In this episode, Conrad and Paul discuss why most vacation rental managers overlook outbound marketing, how to reconnect with past guests and inquiries, and the best ways to use calls, texts, emails, and automation to increase bookings.Enjoy!⭐️ Links & Show NotesPaul Manzey Conrad O'ConnellConrad's Book: Mastering Vacation Rental MarketingConrad's Course: Mastering Vacation Rental Marketing 101🔗 Connect With BuildUp BookingsWebsiteBook A Call With Us🚀 About BuildUp BookingsBuildUp Bookings is a team of creative, problem solvers made to drive you more traffic, direct bookings and results for your accommodations brand. Reach out to us for help on search, social and email marketing for your vacation rental brand.

Welcome to the Heads and Bet Show where we teach you how to get more properties, earn more revenue per property, and increase your occupancy. I'm your co-host, Conrad. And I'm your co-host, Paul. All right, Paul, we're live. What is happening? What's going on? I'm prone, whether this five-second countdown is different than our usual three-second. I feel like I has deer in the headlights there a little bit.

I'm doing well. I told you already, this is my summer week off. My kids are down on the farm. Enjoying life for well-being. what I could ever give them in a week here. But yeah, it's been a good, effective power through. Let's get a lot done week. And my house even looks a little bit clean right now.

So how are you doing, sir? Yeah, all the trouble is still here at my house. But that's okay. That's all good. Who would know what to do without them after work? I'm saying. Just relax maybe for a minute. No, I'm joking.

It's all good there. And also, by the way, as Paul alluded to a second ago, we're trying new recording software. If you like the audio quality better or worse, let us know either way. Send us a note. We are curious how those things go. we're using it for some additional stuff.

So fun little admin out there. It's funny. Have you sent any texts or calls or messages to your folks that are watching your kids? Have you been doing that a little bit? I've gotten more inbound than outbound. Yes, we have been a little bit of we've definitely been texting back and forth. That's been something that has kept us in communication a little bit. Again, they're too busy for me right now.

Right, right. They're like, yeah, I'll get back to dad later. It's fine. Outbound. Some outbound, though, some stuff going out there. That brings us neatly into our topic today, which is rethinking a little bit at the outbound. So actually, I'll start with my kind of story here,

backstory here about people. Of course, every small business owner has an elevator pitch, right? Or they try to summarize what they do in a short period of time. At least one would hope good small business owners have that. So I used to, my elevator pitch that I worked on and refined over the years was something to the effect of we help vacation rental managers get more direct bookings through search, social, and email marketing. That was my one sentence description of what I did.

And I think that's still pretty accurate. But I've made a little bit of a tweak to it now. And I say more, we help vacation rental managers get more direct bookings through search social and outbound marketing. So a small little change. And that was because of SMS in particular, doing more text marketing and making that kind of a part of our core offering that we use for a lot of our clients, not all of them, but a lot of them. And it being very effective. But we thought today we'd expand even that further. So if we zero down into what we're talking about, we're talking about the idea of outbound, which I think could be both one to one, one to many, and it could be both voice,

it could be broadcast or it could be just plain text. So we're going to go through some those different concepts and stuff like that. And what I find is most of a casualty role managers that are serious about direct bookings are putting a lot of money into SEO. They're putting money into Google ads. They're putting money into their social content, et cetera, et cetera, et cetera. And sometimes, not always, but sometimes I find that they do very little actually around their past guest list. Or they do maybe, let's say, the bare minimum. They're doing something, but it's not really well thought out. And it's something that I think we need to probably sit down and review and revisit for everybody. I was in the call with someone this morning who has a list of roughly 500 people that

have stayed, the people that have booked. And then another 2,000 or so on a stafi email marketing list. And when he sends emails, he gets 40% open rates. And I'm like, often you send an email, he's every four months, not very often. So good timing for me to think about this a little bit more because you're going to pay money to acquire a guest through all those marketing channels, and it's much less expensive for you to keep the guests if they're willing to rebook or they're able to rebook

by sending them some of these outbound messages. So what's your experience in this realm? I know it's not maybe what you spent a ton of time on your career, but obviously something you're very familiar with. Yeah, I think it's funny to think about how we really focus on getting that, getting that direct booking, getting that initial booking, hopefully, but getting it to come direct. And then we do kind of let off on the gas pedal

when it comes to actually remarketing to those people. We remark it to people who have visited the site before, but it is. It's creating that true customer life cycle that's beyond just that first visit or hoping it's beyond that first visit here. This is something that I think I've got my first really peak behind the wheel at with track because we were trying to create all these automations

and triggers and everything. everything like that and it was everything was written in the very non-marketing way. So I think a lot of it was really just having someone else take a look at having someone from not the SaaS side of things, but the marketing side come in and take a look at things and say, well, we have to make this feel like a conversation, more of a communication. And I think that's a lot of what the outbound marketing is. It's more, it is more work. It's active marketing.

You talked about that a little bit as we're in the pre-show here. it's active marketing. Inbound is kind of passive marketing. You do, you still actively put the campaigns together, but you're not having to dial the phone. You're not having to, you're not physically sending the email, but you're sending those emails out there. So I do. I think that this is, it's one of the parts of marketing that gets shared, I think, maybe more than anything else. It feels, oh, this is part of sales. This is part of your operations. This is part of your, the whole guest stay within your PMS, but it is. It's bringing that type of communication, that type of marketing into what we do with more

of the newsletter, more with the SMS blasts. The one-to-many communications, as the PMS turns into a lot of the one-to-one communication. So that's certainly where I cut my teeth, but I think it is. I think email marketing is certainly, we've talked about it a lot. It's an effective way to get your message in front of people, and it stays in. front of people for a long period of time. One of my favorite parts of looking at the Attribution Path Resort report in Google Analytics is seeing a campaign from February that people use to book in June or July. That's the power of, when we talk about power of postcards, that's

the power of those emails is occasionally they do sit in people's inboxes. If they really, if you put some compelling messaging in there, if you put a great offer in there, there's something to that the shelf life of what email marketing and some more of these outbound marketing that our content-based kind of consist of there. So I do. I think that this is something that we probably don't focus nearly on enough because we do. We get to the direct side of things and let's drive more direct. Let's drive more direct. Let's optimize our rates. Let's do all this stuff. And let's, oh yeah, we've got to keep people coming back too. Yeah. There's a few things too that I think there's a lot thoughts I have in my head right now. There's a few levers that I think you can pull onto that

make a meaningful difference in how well this stuff works. Here's the obvious one that maybe doesn't need to be said, but maybe it does for some people, which is that if they didn't have a good experience the first time, let me let you in some good on some a little secret here. You could outbound SMS them, outbound email them one to one them, one to many them to death and they're not going to rebook. So what I noticed about working on this kind of piece of business with clients is that the list size is very much of vanity metric. It can mean almost nothing because if you have a list size of 100,000 people and it's people that have stayed with you, but you offered a very low quality experience of low quality stay, then they don't give a hoot about rebooking with you.

You're going to have pretty low response rates. You're going to have very low open rates, et cetera. I worked at the property manager for several years whose opening rates would tap out at about sub 10%. We're talking six, seven, eight, nine, ten percent type open rates. It was very low. And looking back on it, they had very poor Google reviews. They had, they cut a lot of corners. One of these property managers you hear about, oh, yeah, we're going to give you one roll of toilet paper for your week long stay. And it's not our job to give you the rest. A lot of of stuff going on. And yeah, like there, again, we could have made their past guest list, 500,000 people, a million people. It wouldn't have mattered because that people just booked it

because it was the cheapest. They were good at that. They were good at delivering the service very inexpensively. And that was part of their whole kind of ethos. And they were large. They did a lot of revenue. But it was, that was just their thing. They offered a really poor, I would argue, guest experience as a result of the past marketing is not going to work real well. Let's flip that with, as we've told now too many times in the show, my Kiowa trip that I did the spring with my wife. And I'm on their email list. And every time I get an email, I'm like, oh, I wonder what they're promoting. I wonder if there's a deal. I wonder if I could figure out a way to go back because I had such a great experience, right?

So it's all, that's maybe almost like step zero in part of this process that we're going to talk about today, which is that if the guests is not receptive or excited to receive a message from you, all these tactics we're going to talk about won't work about well. But let's go through the of those things that you mentioned there because I think they're worth going after. Maybe we'll start one to one and then go one to many. And then there's an automation layer between all that. So one to one, I would say this is the extreme minority.

So we can start with this one. Very few clients that work with do one to one outbound calling. But those that do always report these really strong. numbers from it, right? And one-to-one outbound doesn't mean necessarily that you're just cold-calling every single guest to stay with you before. That's not necessarily what I'm suggesting, although I don't think it's the worst idea. If you're desperate for bookings, then you need to figure out a way to go about it. There are dialers that will just dial your guests and you do voicemail drops. You could do a lot of things to potentially get someone to reach back out to you.

The more personal connection and relationship you have to that guess, the better I think that works, by the way. Though we have clients that we work with that are quite large that have teams, reservation department teams. Yes, they're smaller today than they were 10 years ago, but they're still there in these big companies. And they are doing a lot of outbound calling from people who by debate on the checkout flow. People that have stayed in years past but have not booked again this year. I have a client that has in a big market up in North Carolina. And he has what's called a VIP list.

People have stayed three times or more. And those people get an outbound call if they have not booked. So by springtime, if they've not booked for a summer stay, you bet you're going to have an out call in a voicemail drop to be like, hey, Paul, you've stayed with us three last four years. You didn't book your state this year. What's going on? That's a better script than that. But that's just of what they're actually reaching out to.

And they can generate tens of thousands of dollars of revenue on a weekly basis from these types of campaigns because, oh, I just haven't got around to it. oh, life is busy. Oh, my, my mom was sick, but she's okay now. And I just didn't book it. And it's, we'll get you booked right now. What are you looking for, Mr. Manzi? We're happy to help, right? So I think that is a super underutilized channel. And I think it takes the right, and I think the right personality on the outbound call themselves. And we all know what kind of person would do well there, the gift of gab, whoever's got that gift of gap is going to do really well there. And it's a sales environment, right? And I think back to content I've seen from people like Doug Kennedy in our space where it's get to the end of that call and then ask for

the booking, can I go ahead and book it for you? Can we go ahead and reserve it right now? Can we save the dates, can I get your credit card, all this kind of closed things that make a big difference. But yeah, it's the highest effort, let's be honest. So I think you'd want to focus and bias your time towards people that have raised their hand and indicated interest, check out abandons. They've been on that website recently. They've booked many times before, et cetera, et cetera. But if you're ever in that mode of, I don't know what to do, I've got no bookings coming in.

You've got to feel like that's a tool in your tool belt you could pull out. So maybe I'll stop there and then we can build on that. I think that role, that position, that person, that was a non-negotiable for the hospitality space 10, 15 years ago to not have someone who was doing some type of phone, outbound phone, whether it be for maybe some support, maybe some operations, maybe straight sales. The reservation is, was that job. Now, again, direct bookings, all these other things. Well, I would actually, I'd say online bookings there was the divergent, the path

of the woods that occurred there, which was both a mix of direct and OTA, but yeah, I keep going. Correct. Yeah, no, online bookings, that is the key there. But now it feels like more of a luxury, like devoting one person just to doing that, not even saying that they're not good at their job. But that does. It takes a very specific person. And there's going to be days that person does not sort of sell it to the reservation.

It's the high awareness play. It's the, I think if you've got, again, the right systems in place, this is going to become a bit of a systems thing. But I think the people who are using their CISN, I think, the people who are using their CRM effectively. You talked about some good ones there, the anniversary, they haven't booked yet, the VIP, all those things that someone could be tagged for, be noted for in the CRM to be able to come back and say, hey, we've got this event coming up, this is what you should be doing. I think that's where around specific campaigns, the one-to-one makes a lot of sense.

It is going the 60-number dial-off every day and hoping for the best. It's just, it's not even most effective use of your time. So I think that's where doing that one to many, because it is, at that point, if you're just smiling and dialing, that isn't one to one. You are giving the same pitch. You are not giving 60, even if you talk to 60 people, you're not going to give people 60 conversations of value there. So you're just repurposing one to many with a one-to-one face on it. And it's, it's, I think that is where it's not effective. That's where you've taken away the high effort, the high intimacy, and it just feels, oh, I'm getting pitched and this isn't for me. And maybe that's why some people have gotten away from it as well.

So that's something where maybe more the impersonal, talking more to the younger generations of that one-to-one with the SMS. You've had a lot of success with that. You can dive into that a little more. Yeah, 100%. That same client that I'm talking about North Carolina that I work with, does the outbound phone calls one-to-one, also does the same thing through SMS. So it kind of happens simultaneously, almost to some degree.

I actually wonder, this is one thing. we've talked about this before. I don't really know where we landed data-wise on it, but it's just more food for thought. You might make sense. I'm someone who doesn't pick up a phone call that I don't recognize. I say this as someone who's, I think this is a good idea you should test.

I'm not the target customer for this as a marketing technique or tactic. But if you gave me a little bit of context, your chance of me of picking up the call are a million percent better. So if I got a call, if I got a text at 1 p.m. And it said, Paul here from the Kiwa Resort's booking department, was going to give you call at 3 or 4 o'clock today

and see if there was something that we could help you reserve for a trip this fall. We got some special rates that I could share with you. And then you called me in four. And I read that message, obviously, between the time that you sent the message, the text message and the time the phone rang, my chances of picking up are way better because I'm like, oh, this is Paul calling from Kiowa Island. And maybe I want to pick that up if it's something that I'm more interested in. Have you just called me from a number that I don't recognize that's just going to go straight to voicemail, right? But I think that just because we're not the customer, we always have to remember this as marketers. And I think every marketer, young marketer at some point

goes through this process of like they put themselves in every situation. I wouldn't do that. I wouldn't pick up. I wouldn't respond to that. But it doesn't mean that someone else wouldn't. And I've had to go through that lesson for sure in my career around things that I personally have been like, this doesn't make sense. Then I come around on it and test it and try it. And I'm like, oh gosh, direct mail is really powerful. Like what an amazing thing to get in front of you getting someone's attention in such a specific way. Direct mail is awesome in the right context for the right setting for the right situation. Same thing I would put into this bucket with out button SMS, outbound phone calls. They are for the right person. The best thing that you could do to reach back out to them and get them

back into the fold. So yeah, but out by an SMS, the scripts can be almost the same, right? It's like the same BIP script from earlier. Hey, Paul, we've loved hosting you three the last four years. I see you haven't made a booking quite yet. Do you have travel dates already planned? Do you have different travel already planned for this year? You could test different hooks or whatever the case may be. But the client that I'm referencing that does that. Does there a CRM that's not vacation rental specific, by the way? They use a CRM called Close to do that. And so it's more of a true sales CRM. You could use it for any kind of business, to be honest with you. They got that set up years ago. And as a result, they have all these numbers and dialers and everything configured in a certain way.

And they get a lot of, they have a lot of success from that. So yeah, absolutely that's like very, And we could argue there's some level of automation you can slip in. Let's say if a block of 40 people that are all kind of part of this IP group, you can send 40 people the same message with a little Phil Field, hey Paul, or hey Conrad, hey John Doe, whatever the case may be. But that's kind of quasi automated, but it is based on like a specific criteria. So yeah, very bullish on like outbound SMS. It could also be, hey, you hang the phone up with someone.

There was an inbound call. And oh, I do have to talk to my 1,000 objections you're going to get, right? Of course, the most common one. I've got to talk to the people that are booking this trip with me before I go and give you my credit card. Oh, it's no problem. But I'm going to go ahead and send you a message right now with a link to the website, photos, reviews, everything that's there available to you so you know exactly what you need to do in order to make that reservation.

So I think there's a lot of like little outbound SMS things you can do that just tie that into it. And yeah, most vacational managers I talk to do very little around the outbound SMS. They do very little around the outbound phone calls. But those that do, I think, see a left from it. There's almost like this, again, we talked about this divide before with respect to those that came up during COVID and this post-COVID, where they got all their bookings from Airbnb. They find the idea of doing this kind of stuff very odd and quirky. and oh, that's weird.

And yeah, I guess maybe I could try it, but it's strange. Any client I've talked to that's been around for obviously kind of this pre, let's call it more like 2017, 16, like that cut off in before. Let's go someone that's been around for 15 years. They're like, yeah, we used to do that. Maybe we just fell off a little bit. We come back on it. They see it as like getting back on the old bike marketing wise.

Whereas I think that new manager feels like, this is really strange and odd. And I'm not really set up for this. So it's a funny kind of line that I've noticed in the sand. But yeah, sometimes this is almost like another Dan Kennedy thing he talks about. You probably should study a company that's been around for 50 years or 60 years or 40 years. And of course, in this industry, we love to demonize those companies and say, oh, they're going to go the way the dodo bird and a big national manager is going to take them over. And we've seen those companies fail a lot more often than some of these companies that have

been around for a long time. So maybe you should look at what they're doing. I'm not saying emulate everything, but maybe you should look at a company that's been renting properties for 45 years, unless you figure out a thing or two that works. No one can lose money 45 years in a row and stay in business. So good little lesson for us there. When you think about the people, think about the people we know that have been running their vacation rental businesses for 45. Like truly more often than not, the most specific and the single piece of advice they give is pick up the phone.

That's kind of those things, especially on that was always the discussion on the owner's side of things. It's just pick up the phone. That's it. Like, we know that maybe not on the own, maybe, and that's where on the guest side of things, it does feel like a little extra effort, maybe not to get the return. I think you feel more comfortable investing it on the owner's side when that home potentially brings in gross booking revenues behind.

all your wildestream's there. But I do think that is just one of those kind of areas there where we fall into this. Okay, maybe we shouldn't or no, the people who consistently perform. It is about a lot of the communications. It's because they have refined some of these communication pathways that we're talking about. But certainly on the calling and texting side of things, it is. It's just a matter of being responsive. and people who have only been managing the business for four or five years,

I hope they have the mechanisms in place to have that communication, outbound, inbound, all of that. But sometimes it does. It takes that time. It takes the effort. It takes having been wrong a few times and having to do those communications again to really get to where you're being more effective with that messaging and you can spread it to more of a diverse hate, not just one-to-one,

but then one-to-many and making sure that you are taking, greater advantage of all the other digital marketing efforts, all the other marketing efforts that you're doing to get that contact information there. That's what maybe go on this for one second, then we can flip over to one to many a little bit more. But this idea of, I think this is why having offers is so important because if we have an, like I just did a Labor Day offer for a client yesterday. We worked on and we kind of came up with the concepts and messaging around it. And it's not even like the best offer in the world, if I can be honest with you. But you know what it is? It's a reason to reach out, right? And I call this and I've done this ad nauseum on the show, but I call this mattress store

marketing. There's no reason to buy a mattress. Like it just happens randomly almost to you, right? Oh, it's eventually old enough. You might do that every, what, X number of years, that sort of thing. And I'm not talking vacational managers that are buying mattresses for furnishing vacation homes. That's its own thing. I'm talking like your personal mattress that you sleep on at night. Like you do it so irregularly, what, every five, seven years, something like that. But yet when you go to the mattress store, there's always, oh, you came out at a great time, Mr. Manzi. We've got the, we've got the Fourth of July sale going on right now. They're the end of Friday. We're going to hook you up with something awesome. It's going to be great.

And then you go next week and it's the, oh, you're in the, you're in the Sultan of the summer sale going on right now. And you go the next week and it's all, we're doing our pre-back to school sale. Then the next week, it's a back-to-school sale. Then it's the end of summer bash. Then it's, they just come up with stuff all the time. And I laugh about it. I'll laugh about it.

But you know what? Again, it works, right? So I think always having some kind of offer sale that's there that's omnipresent is a great reason to reach out, both one-on, one-to-many, having something to ref out. Hey, if you do this by this day, I can do this for you. We can give you a late check-in. We are late. I check out. We can give you an early check-in. We can give you. We can weigh this one fee. We can do this. We can do that. People kind of want to feel like they get a deal a lot of the time. Or again, going back to those, I've gotten, I've gotten, or again, going back to those. I've gotten, I've got, I go, that's okay. It's a, there's an additional experience. If you book this, you get this extra thing that you wouldn't have gotten otherwise that you would have normally pay for. So it's not a discount. It's added value. So I think there's a lot of ways around that makes sense. But this is why I think it's very few clients I work with. I can't think of any really from being honest with you overdo their offers. There's. There's a lot. one that kind of comes to my better. The other 100 companies I've seen and worked with over the years,

they're just like, I have to beat an offer out of them. Whereas like I think, and maybe it's because they have dynamic pricing and they think, if I have dynamic pricing, then in theory, I'm trying to put my best foot forward to maximize my yield and maximize my pricing. But when you're direct marketing, I just think you've got to come up with reasons to reach out. It can't just be like book my place. It has to be like a little bit of a hook in there and kind of something to play with. So yeah, those are just some thoughts I have. Maybe you can take that and dovetail it into one to many, which kind of is my how you get, get the word out about that kind of stuff. As someone who was in the furniture store this weekend, I can tell you. That's funny. There was a new

deal. There was a new Fourth of July Independence Day Freedom, something. I don't know what it was. 17. They were going to throw something at you. Oh, yeah. It's just as effective as it was when it was the winter sale on this. It is. I do think that in the deals and packs, that offer is important. It's not, I got a deal package special. It doesn't have to be that. It's the perceived value. I think that's something that people are willing to pay more for perceived value. Again, whether they were going to get it or not, whatever it is, if you're throwing it in, that's great.

But I do think that without that something to spice the pie, I know, spice things up to sweeten the pot. It's very difficult. I think it's more difficult to do it in the vacation rental space because, we do you have so many different homeowners you have different units it's not just some condo complexes sure you're going to have all the same condos everything looks the same maybe ish then you can feel like you're discount but you can't because again we have the strings to pull behind the scenes but having that again a welcome package something that you can do to enhance the stay i think that's where especially in the luxury side of things when you are trying to give people that

ultimate experience or that high level experience, that truly branded experience, if you want to take it in that direction. That's the way you do that there. And it begins with, again, some of these communications when you have an offer, when you have some more of these interesting things that you can talk about, you can put together more of a one-to-many communication. Email newsletters, we talked about this. I've seen these go a lot of different ways, whether you're talking about deals, newsletters,

a property highlight newsletter, company updates, what's happening in the neighborhood, all these reasons to book your properties, or reasons to learn more about your business, or reasons to learn more about your area. I think there's a lot of different ways to kind of take these communications, but a lot of it is thinking about it, it's a conversation. This is something you're trying to continue the conversation. You don't want to just lead people to a point where it just feels salesy and salesy, and they're not seeing anything new, they're not hearing anything new,

and all of a sudden you have lost that ability to market to that person. Because again, the only reason to do this outbound marketing is to continue to do the outbound marketing so that you can keep them in the sales funnel and kind of drive them further down there. But like, where have you found the most, you know, as you're looking at segmenting and putting into different areas, how have you found the best results on the email marketing side of things? I'll refer back to what we started a few minutes ago, which is this idea of the

quality of your list matters the most. Two things came up this week that kind of triggered this for me. One was a client that we had talked about doing another giveaway on. And giveaway's work and then grow your list a lot. But the quality of the average email address on a giveaway is obviously much lower than an email address who might have sourced as a past guest and that sort of things. If we're doing segmentation, we also needed not just do segmentation in theory based on what they booked. So they booked a one-bedroom condo versus a 10-bedroom home. Let's say you had both, for example. That's an important level of segmentation if you're looking to do more specific offers. You also have to look at what's the source that email. How the heck they get

our list in the first place? Do they come off our website? Did they come from a giveaway? Did they come from being a past guest? Did they sign up through some kind of guest book or stay fi or something like that? Probably more engaged than those that come in off those other sources. So yeah, not all email addresses being equal leads me to your core question there around one too many working really well. I think consistency matters quite a bit. And our team is pretty adamant about this. And that's one thing I feel matters. So everyone always wants to have that question, right? What's the best time to send. And I'm just like, I don't know. I think just being consistent with it, because we can point to plenty of examples where we seem to get a better open rate when we send at 5 p.m. localish time for

that most of those guests versus we send at 10 a.m. or noon or whatever the case may be. So I don't even know if it matters as much as people think it might, as long as they know, hey, I get these at the beginning of every month around this time. And I look at them and I consider. And people may click on 10 emails in a row and not book. That does not mean your email is not working. I rarely actually believe one to many newsletter style email communication functions much more like a top of funnel than like a bottom funnel or a middle funnel type of campaign. So what I mean by that is people see the email. They click through when your analytics is going to say very few of them booked and you might go, ah, it's not that effective. And I'm like, no, you just

planted that seed in someone's brain that they, and they're on your list because they stay with you before most likely or they've signed up before, et cetera. You just put that seed in their brain that and then click through their property and looked around for two minutes. That is a great top of funnel starting journey to kind of get them. That person is going to go down, middle funnel, bottom funnel, much quicker than someone who's just like randomly scrolling Instagram and then sees an ad. They may or may not even click on. That's often referred to as the best top of funnel advertising that we can do. So yeah, once the guest becomes aware of the fact you're there, you have a property, they're interested in it. You've got them two or three kind of steps down this slide or this

whatever, whatever you want to call it, process or funnel that you've got in place. And I think that's what good one to many style newsletters do is they get you in that mode very quickly. So those are kind of be my thought processes around around that. And honestly, email versus SMS, if we're going to kind of cover both here. The problem with SMS is you've got so little space to work with. I know it's not an awesome insight, but it is true. So I think with SMS, you've got to make something really short, really punchy. You've got your link, and then you've got 140-ish characters or 155 or something like that. You just don't really have a lot of space to work with them.

So as a result, it's can you write one sentence that gets people to click over when are you giving them values? I don't really have a lot to say other than you should be doing SMS if you can, because we have a client, the large client that I was referring to earlier here in the Myrtle Beach area. And they now have many properties they manage that are getting more results every month that I can attribute bookings to in their analytics data from their SMS list, which is like a few years old, maybe it's your three years old for most these properties, then an email list that's 20 years old. And the size difference is sometimes five or 10x more. So I'm saying it would be more valuable to have 1,000 people on an SMS list than potentially five to 7,000 people on an email

list, depending on their level of engagement and activities. So that is a very compelling thing to think of. Now, I do think this, the SMS unsubscribe trigger is a little quicker than the email unsubscribe trigger. And I'm this way as well. If you, if I do sign up for any sort of SMS based offer, which I do sometimes, and you start hitting me too often, you're out of there because I don't like my phone dinging nonstop. So if you have that attention, you've got to respect it. But if you keep that trust and you keep that attention in people's SMS inbox or messages inbox and you use it well, it can outperform email by a very wide margin if done well in my experience. That was exactly what I was going to talk about there. It is the unsubscribe territory.

It feels like you have to tiptoe around that in a much more careful level on that SMS side of things. It is. I think the, and maybe you confirm, deny whatever it is, but like it feels more intimate. Like you give the phone number, you're getting a text or a call, like to talk to someone or to feel like they're in your phone. That feels like a more intimate conversation. Even though you're opening your email the same way, maybe on your phone, that text message just feels a little deeper.

It's next to a thread from my mom, my dad, and my wife, right? So it's like when a marketing message gets popped in the middle of that, it's, ah, Like that's, it feels, you're right, it feels different. Yeah. So that is, I think that's one of those things that, and I think now, it's from the same standpoint on the email marketing side of things, the last thing you want to do is overdo it. And I think that there's something of, you do have to find a way other than your homes

to provide value. I think it is. I think it's travel tips to the market. I think it's, however you're doing it, you have to find a way to sprinkle some other things in. And I don't think you can do, I don't think you have that same luxury with SMS, even when you're doing, like you have to be, it has to be more branded, it has to be more personalized. Like, you can. If you're in the Smokies, you can have a travel guide or travel blog or something that's a highlight in two of your four emails in the month. And you can still

get some people who are interested. It is, you might get more people who are more interested in that than the blog posts than they are in the actual homes. But eventually, that's, the road and this is why we love the power of these one to many email or one to many outbound communications is that we do have an opportunity to continue marketing to them and we're not going to burn our whole list because we're going to do it in a smart and thoughtful way that's going to lead people down that booking path again hopefully yeah exactly and that is also the way to go all right so all right so let's recap our we've been so doing outbound calls to the right types of people is a moneymaker. Actually, one thing I meant to say earlier, I didn't, so I'll insert it now. You should be anchoring all these costs against, I guess, kind of two things, right? In theory, in action. So if I just don't set a message, I'm probably going to get very few people who are just going to on their own, come back and book with me again. So that's like what you should anchor it against. But honestly, just let's just keep coming back to 15.5 percent. Right. Let's come back to the Airbnb fee. Why not? Right. So if you're getting someone to do an app on a call or an app on SMS, you're paying an agency, a service, etc. Someone on your team to do it. And they're getting you three, four, five, six, ten, twelve bookings a week, whatever it is.

just go sum up that revenue and say if I was going to get those same bookings from Airbnb, it would have cost me 15%. So if you have one person smiling and dialing over the course of four days on a week or five days on a week and they're driving $20,000, $40,000 of gross revenue, you would have paid from Airbnb. Let's pick a number, $25,000. You would have paid 15.5% of that in commission. It would have been a lot of money, right?

You would have been paying significantly more $3,800, you know, $3875 in commission from that person. So if you're paying that person, presumably, less than a week of wages, probably a lot less than $3,800, one would imagine, then yeah, like your arbitrage there is incredible. Now, people always say this. So email is the highest ROI channel, which is true. Well, let's email and SMS and these types of past guests marketing. Things do have a high return on investment. That is true. I guess the reason I just don't say that or use that in a lot of my own messaging or marketing is like that's it indicates almost that it's something that you can just pull a lever on hard and continually see a row ass.

What happens as we just alluded to a few minutes ago with SMS is that you can exhaust your list. very quickly. So if you overmarket, you burn a list, I'll tell you what, there's no ROI there at all, right? So that's one thing I wanted to say. But anyways, sorry, we're on like tangents today, but it's all coming back to the same topic, I think. So one-to-one outbound phone, one-to-one out-bound SMS, like broadcast style and then one-to-many email newsletter style or even like, in my mind, segmentation is still one-to-many. It's just I'm sending this offer to all the pet-friendly gifts, but it's still one-to-many in my mind. So it's the same pieces. Let's go automated. Let's talk about that. Let's head in that direction before we come to a close here. So this is stuff

where in theory, it's more of like a set it up once and don't fiddle with it a lot type of marketing. We like that. I'm sure a lot of people listening like that instead of paying some consultant like Paul or some agency like mine, I got to pay the fees every month to keep doing this stuff. In theory, this is stuff you might set up one time and not fiddle with it. I love what you're saying earlier with respect to the developer set up the booking confirmation email. I actually saw this reminded me early in my career when I saw a booking confirmation email from a programmer

who was just like, let me just get it working and they'll make it pretty later. And it was like four lines of text or it was like, hey, Paul, your booking is confirmed. Your city dates, date, amount paid, this. Thanks. It was like all plain text, no logo on it. And there anything. And I'm just like, okay, we can do a little bit better job at that, right? But the developers, yeah, I'll make it pretty later.

It just works. So anyways, yeah, but just think of how many automated messages go out. And by the way, this is worthy of an audit, your automated kind of messaging flow. You should book one of your own properties every once in a while. And you should look at every single message you get from point eight to point check in or whatever, even check out honestly, of all those things work. And you'll be surprised by what's missing or not firing. How many doubles you get. That's happened to me multiple.

times when I've stayed with the client, I got a guidebook over here from this system. Then it was confirming my information or give me some kind of information in this format. Then the PMS sends me that same confirmation email, but it's formatted differently. And then I'm confused and the door code in one is not the same to the door code and the other. I'm like, what's going on here? So you should absolutely be auditing all those kind of things because every single one of those automated touch points, even on the booking flow. And certainly in the marketing flag we're going to talk about here in a minute, the more high quality they are, the more polished they are, the more likely your marketing is to work 30, 60, 200 days, three years down the road when it's automated. So, yeah,

we could do it in a whole hour in automation spa, but what's your experience with what types of sequences, what type of automation the manager should be probably starting when they're diving into. And I think the easiest one, again, thinking about that cut, that life cycle, is thinking about an annual booking cycle. Thinking about it from the perspective of they're probably going to take one trip every year, approximately the same time. So put those guardrails into place up, start warming that communication up at the, hit the holiday markers. Whenever you can, I think holidays are a fun thing to do, but hit the six months. Mark. We're excited to have you back in six months and we're starting to think about the activities

that the people can do. I think that's thinking about it from a life cycle standpoint really does, and everybody should be thinking about emails in that standpoint is that it's not just a, every email, even a blast, even something like that is, has to be taken into the full kind of customer experience there. And I think we do when we think about, okay, we've got this sequence for someone who book property here. We've got this sequence for someone who booked golf over here. We've got this sequence for someone who's in the newsletter. We've got this over here. Okay, now we've got these people enrolled in 12 different workflows and they're receiving, I think that's where it's very easy to get over automated and over workload and things like that. And I think that's where

you start to what you hit the nail on the head. Book your own property so you understand how many workflows and sequences you actually have going because in some cases you may have additional things that you don't want to be constantly barraging people again they're gonna they're going to after they've seen your marketing email and your sales email and then your operational email and your booking email and your book back your rebook email okay that first sequence would have been fine the second sequence okay but now we're potentially missing vital guest communications of once they get on site or on property now maybe they didn't get their door

code or they didn't get their Wi-Fi password or now we're impinging upon their ultimate experience with the site and we know that cycle the thank you review rebook might have just stopped a thank you because we didn't get the review or we didn't get the right review and certainly we're not going to rebooking this time so i think as we get into the automated side of things that was always my again it's making sure the content looks good but then look at all the ways they're being enrolled into our communications. Please, please, let's make sure that if they are enrolled here, make sure you're putting exceptions and rules-based is so important on some of these automated emails and SMS is because practically in a single instance, in a linear path, that workflow looks amazing.

But we know that the likelihood of them interweaving with some other workflows and communications and marketing just with our business is probably pretty high. So make sure that you're not inundating them with everything and just kind of again keeping as many of those communications again combining some of those communications if you can putting them multi-channel if it helps clear up that communication path email to SMS and pushing them for specific things over here while giving them more of a long-tail experience for talking about that on the email side of things so I that was always my concern is that we've now over-communicated with them

And that doesn't always seem possible, but in this case, it is. So we almost have to be careful at that. Yeah, it's something, again, I think people are always worried about, oh, I don't want to be seen as a spammer or overdoing it. So sometimes they just never put their foot on the gas pedal at all. I think you're absolutely describing an edge case, which is people that overdo it. And we all know. There's brands that areatories for this.

So you've got to find your level. And for you, it might be a little bit of a more comfortable spot. But it's, in my experience, generally, it's probably more than you're doing right now. There's probably a higher volume of messaging. you could be doing, especially if you're splitting it across email and SMS and do a lot more. So yeah, tying it all together. Like I don't see these. These are all like kind of discrete tactics. But if I go back to where I started the episode with, it's this idea of broader outbound messaging, automated manual, one to one, one to many. There's all a bunch categories within that for the most part.

That's kind of how I think about it. But it's all your audience. And people talk about this a lot in the email marketing world. We don't talk about it in theory as much in the direct booking world. But it's the one thing they really can't take away from you. If your email marketing tool of choice goes out of business, HubSpot goes out of business. That seems impossible. you dump your list out to a CSE file, you upload it to MailChimp, and then you're back in business or vice versa, right? So it's like, this is one thing that's very much an asset. And if you're looking to sell your business down the road too,

this is a heck of a selling point. Hey, I have an email list of all the people that have stayed with me before. They're responsive. They're getting all these messages. They're booking from it. Here's my system. Here's my flow I've built up. And you're building this idea that I believe of OTA non-dependence

and something that Madlando has talked about many years ago. He doesn't talk about as much anymore. But this idea of a table, there's four legs of a table. I kind of want 25% of my bookings to be OTA-driven. maybe an Airbnb of Arbo, booking.com. That's totally fine with me. New people are going to come in through that. Some people only search on those platforms. Great. Love it. And then I want those other legs of the table to be new guests finding me direct, past guests coming back, and then maybe other channels can kind of be part of that fourth mix. And then I've got a really

healthy business. And I'm using the platforms to my advantage. And I'm getting benefit from that. And I've got stuff coming in from other places. No one's in control other than me. I think that's a good way to go about it. That brings us to a close here. I think Paul, as far as time goes, any other odds and ends before we put a bow in this one. I think this recording went pretty smooth in our new tool hopefully. Outbound's worth of work. I think it is. I think it is work.

It does take a little extra effort, but it's 100% worth it. And I think find some quick wins, find some ways to get yourself reacquainted with it if you're not doing it or you haven't done it and keep doing it consistently. Yeah, I couldn't agree more. You know, it's not a lot of work. It's an outbound thing. You're going to open your app of choice. You're going to click an outbound link to leave us a review.

Go to your podcast, Apple, Apple, Spotify. We get the most downloads. Click five stars. Leave us your review. Be super. appreciate that, keeps the downloads coming, keeps us smile on her face, and keeps us going on, and more shows coming here down the pike. Thank you. Appreciate it. Have an awesome rest of your day.