Heads In Beds Show - Beyond E-commerce: How BuildUp Bookings Uses Mailchimp To Drive Direct Bookings

Episode Date: September 2, 2026

In this episode, Conrad O’Connell sits down with William Howard from Mailchimp to share how vacation rental managers can use email marketing to turn past guests and prospects into future bookings. We talk list building, segmentation, automations, abandoned booking campaigns, win-back strategies, email performance, and a lot MORE!Enjoy!⭐️ Links & Show NotesConrad O'ConnellConrad's Book: Mastering Vacation Rental MarketingConrad's Course: Mastering Vacation Rental Marketing 101William HowardMailchimpWebinar YouTube Link🔗 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.

Hey, everyone, Conrad here. Had a little bit of a different episode for you this week. This is a webinar recording that I did with MailChimp. And we talked a lot about email marketing at a high level. And we went down into some specifics about the MailChimp platform, how it works, how it can help you drive more direct bookings. And we just talked a little bit about the economics of email, which is a topic that Paul and I have covered in the past. But it's not something that we've done in a little while. And I've got some updated data and information and things like that that I was able to share in this webinar.

So there were slides on the screen, but being honest with you, they were mostly just there as visual reference. the meat of what we talked about with myself and William over at the MailChimp HQ was just kind of an audio discussion about all things email, all things marketing, all things, how MailChimp kind of plays into sending out great emails and the results of those emails. So if you want kind of a little bit of an email refresher, where you need to think a little bit about your email marketing strategy for your vacational company going forward, I think we'll get a lot of value out of this webinar audio recording. We're going to go ahead and roll that now.

And thank you so much for tuning in and listening. Go ahead and leave us a review when you're all done listening to the episode. leave five stars iTunes, Spotify, we get the most downloads there. We appreciate that. Thanks and enjoy. Appreciate it. Hey, everybody.

I'm excited to get started here with William today, talking all things, MailChimp and all things vacation rentals. William, thanks for inviting me to do this. Really appreciate it. We've been MailChimp users now. I've been a MailChimp user now for probably over 10 years between different roles and companies and organizations have been a part of. So this is a fun thing to kind of talk to someone at MailChimp HQ

and learn about all the stuff that we're doing every day. But basically the title of this kind of talk or presentation is beyond e-commerce. how build-up bookings, the agency that I own, a vacation rental marketing agency, use a mailchimp to drive direct bookings. So like I mentioned a few minutes ago, maybe a little bit of background filler context. I own an agency called Build Up Bookings. I started it back in 2016 and trimmed that entire time to help our clients get more direct bookings for the website.

So a vacation rental manager comes to us and they're looking to drive more direct bookings. Email and outbound SMS is one of the most key kind of pieces of our marketing process, along with paid ads and SEO work that we do. So as a result, building on the MailChimp platform has been great because we can do everything we need to in that system, and we can send awesome great outbound emails that get clicks, get opens, get bookings. And as a result, things work really well. I forget exactly when we connected, William, it's been a little while, but yeah, we're now an official partner agency. We're using the platform long before that, but now we're an official partner agency,

which has given us some new tools and systems and things like that to get the most on MailChimp for our clients. So again, excited to be here. Oh, yeah, thank you so much, Conrad. I think it's been a few years. I've started with MailChimp four years ago, and I think we met maybe a year or two after that. You've been super engaged, and I'm really excited to showcase your expertise along the way. And yeah, those that are listening, if you're interested in joining the partner program, learning a little bit more, just join us at melchimp.com slash encope. So really excited to dive in deeper today.

Yeah, absolutely. Awesome. Yeah, and we've used from now and probably it says 60 clients on that slide. It's probably a little bit higher than that at this point, to be honest with you. If you go back and we pull down months and months of data and going back many months, we're probably driven more than $50 million in bookings for our clients just through MailChimp emails. So again, super powerful tool. And I think the tool matters a lot when you're trying to get the job done the right way. And Mailchip has been a great tool for us. So I'm excited to share

what we know. I know. I think we're just doing an audit of your clients. And I'm like this is you have. Those we didn't even know about. So it's just really cool to kind of dive in to all the past and current work you're doing. Yeah. Yeah. Always more to sign though, isn't there really? Clients you have. Every agency wants more. I know. But now, yeah, I'm excited to dive in. Yeah. One, one like, like, maybe you've heard this before as well, William, I'm curious your thoughts on this, but I've heard this previously from people, oh, isn't that an e-commerce platform? And I'm like, well, I'm sure it's great for e-commerce. That's not a world that I spend a lot of time in. William could probably tell you all about how it integrates with Shopify and some of these other

e-comms systems. But yeah, for a vacational brand, it's like, first of all the e-commerce, we're very different kind of custom, unique form of e-commerce. But most vacational-material, of course, a fraction occur over the phone. But for the most part, people are using their email when they're getting emails from our clients to plan their next trip, to blend their next vacation. I feel like an email that they get from MailChimp, an email that they get in general, and newsletter-style email, kind of behaves very much like a top-of-funnel marketing traffic source. So I think some people misunderstand email,

and they think that it's more of a bottom-funal activity. It's really not. It's more getting people back into your website, back into your brand, and kind of back in that planning mode for a vacation. When you're booking a vacation rental, it's not really an impulse purchase. Maybe to go back to this e-commerce example,

like buying a T-shirt from your favorite company. Maybe that's more of an impulse thing. You just see you want to buy a vacation, especially a large vacation rental you might book very far in advance. could be something we have to talk to 10, 15 people, you know, before you actually make the reservation. So having email, having SMS be part of that journey is great. And I think MailChimp has all the tooling that you need in order to use, you know, all these systems, the platforms, etc., within there to get your message out to these people and kind of get that traffic back to the website.

So maybe you hear the same stuff, William. But for me, it's been a little bit of education sometimes for a client who just doesn't really know what MailChimp is and how customizable it is for our vertical. Yeah, I think that's the biggest struggle right now is changing the perception of MailChimp. Right now, people think. McMillard was kind of old school, used to use it back in the day, but now it's a true omni-channel platform. So we've been able to incorporate, like you said, SMS, social media campaigns within it. And on top of that, so many automations where you can even span from e-commerce to just basic nurture campaigns. For example, I go, you go on vacation as many people do,

went to St. Bart, stayed at a really nice place, sign up for their newsletter, and now I'm getting Hey, thanks for staying with us. We'd love to have you back. I'm sure this is the kind of work that you're looking to accomplish with MailChimp, but that's just an example of me wanting to come back just because I'm seeing these emails and I'm seeing this beautiful picture of this room. I stayed in last month and it just really makes me want to just say, hey, engage with his email and stay top of mind for me. I think that's the thing too, right, is that email done well is that brand reminder that, let's be honest, right? People that, like, I'm sure you'd love to go back, but there's also

like life and commitments and things that sometimes get in the way. that awesome Caribbean vacation that you had. But the fact that you're getting the emails, the fact that you're remembering them, the fact that you're thinking of this resort, even though it's been a month since you stayed there, is the perfect proof of where, by the way, a lot of reservations come from for most of our clients is, quote unquote, direct traffic. People are just going to trade to the website and making a reservation. Who's to say exactly what it is that made them remember that brand? Could it be the email that they got? Absolutely. Could it be the SMS that got? Absolutely. Of course, other channels impacted as well. Seeing it out on Facebook repeatedly,

if you're in the retargeting audience, these things all matter. So to have mailchip in the background, being able to market to people. And we'll talk about metrics in a little bit. Open rates and click rates and things like that. But don't consider your email of failure. If William gets your email and then doesn't click and book right away, it doesn't mean that resort in St. Bart's that they stayed at did anything wrong. It sounds like they're actually doing everything right. They're creating this idea in his head of, I want to go back there. I want to stay again. And when you go back, you're probably going to seek out that particular brand and the email is helping him along the way. William might get 25 emails before he comes back and clicks book now again.

But it doesn't mean that those emails were a failure. In fact, it might have been a success, even if they don't result in a click or a booking right away. So again, we'll kind of cover that later, but you brought it up. So I think it's a really good example of kind of people misunderstanding the job of email or what it should do. I think some people think marketing in general is just like a click and book type thing in our vertical. And it's just very much not that way. It's very different. Oh, yeah, exactly.

It's definitely a long game. And I think as a consumer of the other end of it, definitely long game definitely works. For those listening, I think just stay engaged, open your emails and just take in the info that folks are sitting in you. Yeah, yeah, 100%. So this is just kind of a quick thing here. Anyone who's listened to stuff that I've done before, this will be very familiar to you. But these OTAs, like platforms like Airbnb and Verbo,

are great and they're awesome. And they give you a lot of bookings and we love them. They also take anywhere from kind of 15 to 20% of fees. And not only that, relevant to the MailChimp conversation today, you actually don't even get the guest contact information. So not only do you pay a very heavy marketing fee to get a booking from Airbnb, you get essentially a fake email that expires a few days after their checkout. So you don't actually have a way to reach out to that guest.

The email list that you have on MailChimp, the email list that you get of your actual clients, your actual customers, guests, whatever you want to call them, people that have stayed with you, and people that have transacted with you. That is one of those durable things that I think you have in your business as an asset. Your Airbnb account could get suspended and then your business is gone overnight, right? We all have heard these horror stories over the years of that happening to host and managers. But if you have an email list, and by the way, I don't think MailChimp is going anywhere. But if you have an email list, you could export that CSV and bring it to another platform provider if you want to.

I would recommend you do that. I recommend you stand MailChim, but it's something that you own is an asset. it's not tied to one specific vendor. So MailChimp is a phenomenal vendor. Again, you should work with them, but they don't own your guest relationship. You own your guest relationship. And Milchimp is just a conduit that gets you between your marketing

and what you want to say and the actual end consumer, the guest that's actually staying in your properties, who's going to receive that email, receive that SMS, and engage with it positively. So the way to think about this is that if I can send out emails and I can get even a fraction of people who stay with me before to book again, I'm saving that 15, that 25% in fees that maybe I would have to pay Airbnb if they just came back and made that booking again.

So your cost to run an email campaign, run an out by an SMS campaign on MailChimp is going to be a fraction. In some cases, like almost nothing compared to your actual cost of getting just five, six, seven bookings from Airbnb, where you might pay, if it's a $1,000 booking, you're paying them $150, plus every single time you get a reservation. When you could send out one MailChimp email and get four bookings and pay essentially very little. Maybe you're paying a MailChimp fee of $100 a month or something like that to host your list, that sort of things. Commissions eat margin. Your ability to go back and market out to your past guests helps your margin. much. We have clients that we've worked with who have massive lists on MailChimp. One of our largest clients has over 250,000 people on MailChimp. And when they send out an email, they're

consistently getting 10, 20, 30 bookings just in the window after sending it. And again, email is not even really a last click channel. So these are just people who book right away after they send the email. They get many more bookings from that email campaign in the following, let's say, 48, 72 hours, that sort of thing. And they pay no fees on that, right? Of course, they're paying MailChimp a fee to host the list and all that kind of stuff. But I promise you, it's a fraction, less than a fraction of what you pay for Airbnb. So it is something, too, that I would say in this kind of whole slide or this concept, where it compounds over time. When your list is really small and you're new, you're paying MailChimp maybe 10 or 20 bucks a month when you have a

brand new account, you don't see as much value out of it. I totally recognize that. So if you're a tiny host and you have a list of 14 past guests, sure, email is not really going to really move the needle for you. You should still be sending, by the way. But over time, once that list gets to be 100 people and 500 people. And William is probably one of 5,000 people or plus that are on that St. Bart's resort email list that they stayed at. That value of that email gets so much higher over time because it's one email that you write one time that you send one time, but it goes out to thousands of different people who are then thinking about it. So the value is so high. And I think it's again one of these channels that most people tend to underinvest in or don't put enough thought

into because they don't realize the benefit in their company of reducing their marketing costs drastically by getting someone who's book to just come back and book again through an email after an SMS campaign as opposed to having to reacquire new guests constantly from scratch on the OTAs, which is very expensive. Those are all good thoughts. A question that came to mind, Conrad, if you don't mind. In regards to your services and how you help these rental brands grow their business through email, how does that transition or how do you incorporate Airbnb listings within that?

Because I know a lot of folks do Airbnb, they have their own website, and they're trying to drive in both channels. What are your tips and tricks on that? And how do you incorporate that in your services? Yeah, so most of our clients are coming to us because they want to get those direct bookings in their own website. So they're setting up the infrastructure on their end to accept the direct booking, to do so securely, to do so in a way that's compliant with all the payment portals and processes, etc, that they have in their system. And they want to, although Airbnb is great, they don't want to take their email traffic and route it to Airbnb. You could do that, by the way.

I wouldn't recommend it, nor is it something that we really do very often. But in theory, there's nothing wrong with you building out of the email list of your past guest, by the way. Even if you weren't going to do everything I just described, focus on your OTA dependence or kind of build your own direct booking system. If that was something you didn't want to do, you could still build a MailChimp email. list and then just mark it out to your past guest and send them straight to your Airbnb booking link. You don't get the same financial maybe benefits of doing it through your own system because you're paying these commissions every time. But I'll tell you what, if you're trying to get more bookings in general, let's say maybe you're a very small property manager or a host of just a few listings.

I still think a MailChimp email list or SMS list is a huge asset to you because you can reach back out to the guest and you could say, hey, you booked on Airbnb before and you stay with me. We have an opening this weekend. We'd love to host you. And I know you're nearby. You're a short drive away or we are booking now for Christmas. We just open the calendar. Do you want to go ahead and make the reservation?

So there still be value in someone potentially using a service like Mention to market to their past guests and send them to Airbnb. They don't get this awesome sort of like fee reduction that we're talking about here. But it still would be in my opinion, again, somewhat of an asset to have that versus let's say you're an Airbnb host. You're sitting there. Your calendar's empty. You're making no money. And you look around and go, what can I do? The answer for most Airbnb hosts is just cut the price.

If I just cut the price low enough, someone will eventually take it, which is true. The joke that I usually make to client says, we'll get you 100% occupancy. We'll just make it a dollar a night. Everyone will make no money. You'll be in the poor house. but yeah, we can get all the booking. So anyways, the ability to get attention on your listing or the ability to get attention on your property, I should say it that way, whether it be on your direct booking site,

which would be my recommendation or even sending it to Airbnb is still a valuable tool in your tool belt to try to get the best rates you can for the property that you have available. Yeah, I was just, I was just curious. I again, stayed in an Airbnb and saw in the refrigerator. It was like, oh, scan the QR code to book directly with me on my website. It would save you tons of money, avoid the fees. All that stuff just comes to mind as I listen to your talk. Yeah, 100%.

And it's good to have your perspective today from kind of the other side of like not in our little bubble. I was call it like a little bubble that we're on the weird vacation rental stuff and just hear the perspective of the guest to be like, okay, you understand the benefit of it. And you have these examples of having some travel yourself personally and then noticing like art and getting these messages because a lot of that is what we talk about. And we know it works, but good to get to hear things back and up from there. Of course. Absolutely. Yeah. For my perspective, the reason that I think email does so well for vacation rental companies compared to maybe other verticals even, not that I know them as well.

but we have clients who have driven a million to three million dollars a year through their email campaigns. Most clients we work with will have like higher ticket booking. So they might get two to five thousand dollars might be like an average booking for some of the clients that we work with, which nowadays the rate the rates are going up for a lot of these listings. That's not even an egregious rate. We have a client whose average booking is over $10,000. A very small host we work with in the Bahamas has a booking rate or an average booking rate that's almost $20,000 per day. So one, literally one email that gets sent out and you get one booking out of it might pay for your mansion fees for two or three years.

Obviously, it's a great return on the investment like we talked about earlier. Demand is kind of seasonal, so you can customize your messaging, you can customize your graphics. You can customize everything inside your Mailchimp email that you're sending to go out to your past guests, to be seasonal. Hey, right now, maybe it's a Labor Day promotion that you're sending out as we record this kind of later in August before the beginning of September. That might be a reasonable promotion that you're doing. Or maybe you're all focused on fall. We have a client that we're chatting with another Mailchimp user who's based in the Smoky Mountains of Tennessee. And we're heavy now on fall.

Fall is our kind of focus for right now. They're already kind of full up, to be honest with you for Labor Day. so everything is just switched over to fall. So all of our emails is book now for fall. Here's when leaves are changing. It's going to be beautiful. The weather's cool. You're going to love it.

And that's all stuff that we do through the email campaigns and kind of build that awareness and that interest in someone making a reservation. And yeah, like this is a warm list. You're reaching out to people who opted out on your website. Maybe they stayed with you and they gave you their email address by their choice. They can't out-subscribe, of course. Mailcham has a compliant way to get someone down to subscribe if they want to. But they're on the list and they're opening because they're interested.

Like William St. Bart's example from earlier. So they love to stay. So in theory, like, it's quote unquote easier to get a booking from email than it is from other sources because we don't have to pay for every click. We don't to convince them, someone who's never stayed before, why they should come back and stay. We're kind of reaching out to someone that's like a friend. They're a past guest. They want to come back and book again. So as a result, it's easier for us to kind of see conversions from this traffic when they click over in our experience.

That's great. Yeah, actually, I'll go through this, William, and I'm curious your thoughts on it too once we kind of get through this block because I think a lot of our clients in the past have kind of done some, we've cleaned down. We've cleaned up a lot of Mailchimp accounts over the years, I would say, that we're just done, not really in the way that we typically would recommend them to be. So different ways to go about it. Our general approach might be that you would have a past guest list. You would have maybe like a prospect or a newsletter sign-up list, something to that effect, and a homeowner list.

Now, you can do this in different ways. You could have one list with different segments inside of it. You could use tags. You can use a lot of different functions there. Lately, what we've kind of trended towards is just having two lists. So we have a guest intent list. So it's kind of those first two blocks, past guests and prospects. And then we have a separate one, that bottom one for homeowners.

So these are the, maybe it's only 10, 20, 30 people in that list or hopefully you're a large company listing. And you've got 500 people on that list, your homeowners that actually own properties. That might be worthy of its own segment. What's cool about MailChimp is that you can actually build out to where you send the same message to all those different groups, or you could easily send a different message to each one of those groups within it. So, well, you miss someone who's very MailChimp knowledgeable.

How would you recommend someone maybe consider splitting these three things out as far as doing segmentation or kind of simple groups within MailChimp? What's kind of your recommendation? Yeah, I'll start with the high level. I think you have an unslide the one MailChimp audience. And then a lot of people get a bit confused when it comes to audiences. And audience in MailChimp just means everyone in your list. And we always recommend just having one of those so that you're operating under one main audience

and all the analytics are the same. You can really track analytics over time within that one audience and then break it down again into those segments. And those segments could be past guests, people that are currently staying in our property, own the property, so many different ways to segment it. But then if you dive in deeper, you can tag those folks based off of certain actions they do within your mail-chimp campaigns. Let's say that those homeowners are wanting to learn more about taxes or different aspects of promoting their rental properties. And like you would tag them accordingly. And then that really gives you an idea of like what your audience is up to, what they're interested in.

And then that just kind of had that catered messaging. And like Conrad said, giving like the full, hey, this is what I want to send out to everyone or maybe break it off in the two segments or really dive deeper and really hone in on like what maybe those two one or two people are really interested in sending an email to them and then they would just flourish from there and really get becoming an engaged member in your campaigns and again boost your analytics and open the click rates over time especially if you're sending to people sending information that's relevant to those people and what most of our clients I think need to do is actually tell their homeowners that they are marketing their listing sometimes they don't know that they're not aware of that maybe they're not

on the list. So we've had clients that have gone in and added their homeowners to their guest marketing list. And they're like, hey, we're sending out emails regularly. We have stuff going out maybe one, two times a month in a broadcast format, to bigger chunks of audiences. We'll talk about segmentation in a second within that audience. But maybe we have one or two a month that's going out to the broader audience. And then we have a lot of automations in the backside where, hey, it's been 90 days since you've checked out. So we're going to send you this email. It's been 120 days. We're going to send you this email and so on and so forth. So all those things definitely add up. And if people aren't on the list and they don't see it. So I think adding them in there from a

homeowner perspective, lets them know that you're doing potentially a lot of creative work to get their property booked. And on top of everything you might be doing on the OTA platform. So definitely a good thing there. And then, yeah, most people under communicate to their homeowners. It's just an epidemic, I would say, in our industry. And this is something I learned from Rob when I worked with them on some project work in the past. Rob Holderness, he's up in Torre right now, which is in the absence of information, people assume the worst. And I love that quote because it's a great way to think about what happens when you are emailing people, are communicating with them, not letting them know what's going on. They're just going to assume, hey, this manager is over there sitting on my home.

home doing nothing and that's why I have no bookings, but if they see emails going out, they see activity in their text inbox on their phone and they see you doing a lot of this marketing stuff, it's very visible, isn't it? And as a result, I think there's some upside in that. A lost homeowner is a terrible thing. So if we can do something to mitigate that or not churn a homeowner and let them know what we're doing, that's another small little value you can get from your email marketing as well with MailChimp. I love that. Awesome. So yeah, this is something that we're continuing to work on. I would say right now it's a little bit more early days for us, but I think we're seeing more and more capability for us to build bridges between

your kind of PMS or your property management system and the list in MailChimp, the audience in MailChems. We've worked on some of these platforms already. We're going to have more to announce soon where you can actually have a system that's actually picking up new emails as they come into a system like track, Host Away, Guestie owner. These are like these PMS or kind of niche specific tools that help manage calendars and all that kind of stuff and getting the data over there. Some of these actually have native Mailchimp integrations. I think Guesti is one that actually has a native Mailchimp integration that works pretty well. There's probably some things that we could do

a little bit more robustly there in the future. But yeah, just be aware that like the ability to kind of so-called vibe code or build your own little solution to get your email data from your PMS or your SMS information from your PMS over to MailChimp is getting better by the day. So if that's something that you're worried about right now,

oh, how can I possibly keep the list up to date? Just know there's a lot of tech that you can build yourself that will kind of make this stuff work really well out of the box. And some of these platforms like SDI actually already have a native integration with MailChimp and it's only going to get better over time. So I'm a big blue

that defaults are really powerful. So if you have the ability to just click on, flip in an API key one time, click a button, and then once a day, things are just syncing over there. When you go to marketing MailChimp or send an email in MailChimp, you're going to have this rich source of information coming in from your PMS system, your platform system. And as a result, it's going to make your life a lot better. And it's going to make your emails land a lot better if you have a little bit more context about that user, what dates they stayed, whether they were pet-friendly or not when they made a booking. Maybe how far in advance they book, maybe where they live, might be a good day to have because you might want to send different messages to people who live more

in a smaller drive-to-r radius versus like the example that we gave earlier with William where he's all the way in Denver, Colorado. He was doing a stay over in St. Bart's like that's not really a quick weekend getaway, right? That's pretty far away. So he's probably going to book that closer to 90, 120 days in advance plus more so than booking at last minute, whereas our clients that we have that are based in kind of these drive-to beach markets, we could tell someone, hey, the weather's awesome. Recording this on a Wednesday, come on down tomorrow and they will. They'll come down for the weekend and just drive down a few hours. So anyways, having that data come from your PMS and management is super valuable. I think that's going to get better and better over time. But it's

something that we're kind of leading into and trying to figure out more and more kind of infrastructure to make this easier and more seamless for our clients. So we're excited to build on this and improve it for sure. Oh, yeah, I love that aspect of targeting the right audience so they can come in a decent amount of time, especially if you want to drive bookings quickly. And I think in the next slide, I'm really interested to dive deeper into those channels with you and understand. One thing, one thing, William. I'd love for you to go down. is the API. So Mailchimp is a very robust API and that's where we're doing some of this stuff. But any kind of thoughts you have on that or experience, because we've worked with other systems

that are not MailChimp and their APIs, frankly, are usually pretty terrible, whereas Melchimp's works really well. So I don't know if anything wasn't in our notes, but just anything you want to, you know, tie into that. Yeah, in regards to integrations, like with other like other PMS, like other CRMs, basically. Yeah, exactly. So these PMS is kind of acted in a way where it's holding all the reservation data. So when you go make a booking, it's held in these systems. But then it's when we go to the markets of them, we need to get that data from this PMS system over to Miltcham. We're doing that through the Maltim API, which is quite robust. So just any kind of knowledge of background on the API stuff or just, I'll just say it

this way. Mavium's API is better than almost any other system that I've worked with where it actually works and it's reliable and all these things. And then plus we have a really smart team of support agents that can help build that or help you build it basically to say, hey, this is what you're doing wrong, this is what you're doing right. And that way you can know, code it appropriately. And then, again, we have an open API.

so you can really just build anything through us. If it's something that isn't possible, we have other connectors like Sapier that can really just be that middle ground between the DAPs you use and Milchimp. And then again, the 300 plus that we have as natively built on Milchimp's platform that you get a divot into as well.

But I'm sure a lot of you probably have something that's outside of that list in which our support team is really here to help. As Conrad said, it's top tier. And a lot of folks really build incredible connections through it. One of your competitors, William, has that rate limit.

So you can only put a certain amount of emails into the system. And MailChimp, if they have a rate limit, it's very generous because we tried that same thing with MailChimp recently. We were putting thousands of calls into the system. Everything was syncing over instantly. Whereas one of the competitors out there to MailChimp was like, oh, yeah, we only accept a certain number of emails on this API in a given minute. And it was just choking it on our whole system we were trying to build.

So, yeah, having the right tech in the back end, when you need it, it's like MailChimp is a robust solution for that. And some of the competition out there just doesn't have the same tooling that MailChimp does. So it may have a little. That's very interesting. I'm glad to hear that. Yeah, I can talk about this a lot, right? Which is I'll tell you one thing to make your MailChimp a lot more exciting and a lot more profitable for you.

Make your list a lot bigger. So get more emails, get more SMS. Get more SMS phone numbers out into your system. Three kind of concepts that we talk about a lot. Or like, this is some of the main ways you're going to get a lot more email addresses into your MailChimp database, which is on site. So a pop-up modal or something like that. On the site that collects email, have an offer there, by the way. What a lot of our clients we have, the offer on the pop-up itself, let's say it's something to the effect of, say, $50 off your next

reservation, sign up to get in our list and we'll send you the promo code through MailChimp. That's a very effective way to grow your list a lot. If you're getting meaningful website website, website coming into your drug booking website, very reasonable to expect you're going to get 1 to 2% of people who come in off that website to actually make a reservation. Or excuse me, not make a reservation. That'd be awesome. So to sign up for the email list and sign up for that discount offer.

So if you're getting thousands of people a month, you should be adding 50, 75, 100 people, two, three, four people a day to your website just by having something on the site that connects to your in MailChimp Automation and then fires back a promo code or an offer code to them. So huge fan of that. That's probably like the most standard thing that we do with pretty much everybody. It's if we sign a new client and they're a MailChimp client and they're an email marketing scope, we're getting that on-site pop up on there as soon as we can so we can start to get more inbound. So that list grows bigger. In property is super valuable. There's some systems out there like stay-fi, for example, that integrate natively with MailChimp where you can actually gate to the

Wi-Fi. So you get a log on the Wi-Fi and it says, welcome. We're excited to have you. Enter your email address here and your name and we'll connect you over to our Wi-Fi. And then you can use that for marketing with their consent, of course. So big fan of Wi-Fi's, welcome gates, things like that. So if they're actually in the property, they're looking around. They're on vacation, but they want to connect to the Wi-Fi, right? So having a little bit of a bridge or a gap there to automatically pop that email and put it in the MailChimp is excellent. Again, we use Stafi for that for that's a great system for that. And then social. Giveaways are, I'm doing giveaways now for 10 plus years and they work really well. I think the key with a giveaway, though, is to basically

have it hosted in a really easy to use landing page. So the landing page on there, ask for their email or their phone or something like that, and then automatically pops it over to MailChimp. And then target relevant people with the giveaways. You know, one thing you don't want to have. I mentioned earlier how MailChimp has a very fair pricing, and I do agree with that, but you don't want a bunch people on your list that are never going to buy from you or never going to be a good customer for you. So you want to clutter up your list with people that are not actually realistic guests. So if you're doing a giveaway campaign, when you're mostly a drive-to market and you're in South Carolina, don't target people who are in Washington State or Texas or California if they're never going to

come to your destination. When you're doing these giveaways, they are great ways to guard your list, but focus, obviously, on audience relevance. Don't focus on just making a list really big. It's really easy to get a big list. It's harder to get a list that's actually engaged. That should be your goal. I'll take every day of the week a 50,000 list that's engaged, that people will open the emails over 200,000 list that's basically dead. And unfortunately, in my career, I've seen that happen quite a few times. People that have these large lists, but they just over email to them. They're maybe too aggressive. They kind of quote-a-quote burden the list. Or they run giveaways and they target it too broadly or they target stuff that's not really relevant. Hey, you get an iPad. I've signed up for my

email list and they just don't get their highest quality audience on there. So I want the email list to grow, but I want to grow in the right way. And giveaways are a great way of doing that. but they're a double-edged sword. You can kind of cut it good and cut it bad depending on how you use them. But all that should flow into MailChimp. MailChimp has phenomenal automations for when some of these sort of inflows occur, like the on-site pop-up sign-up or the in-property stay or the giveaway.

You can quickly trigger out emails from MailChimp that let them know, hey, you're on the list, here's what to do next. Here's our company. Here's our website. All that kind of stuff. The automations are excellent, and we use them literally every day. There's probably been five automations that are fired since we started this webinar on various client sites that we work with through MailChimp that are welcoming people to the list.

so super valuable. That's awesome. And a question, how would you convince someone or maybe show the value of using these different core channels if someone's using like a guest book in their property to collect some of that stuff manually and then typing it in later? How would you convince them to kind of switch their method to conform to this? I think obviously adding like tech in the process can be again good or bad thing. When the tech works and everything is functioning, oh, look at all this time savings we're having and our life is easier and there's all these pros, right? But the tech can fail. can screw up and not work. And then it's, why should I just go back to doing this the old way?

I feel like we've had clients that have gone that way before. I think it really just depends on how good your coverage is. And is that a constraint in your business? That's kind of my two questions I would ask. So if you're, let's say you have a guest book and they're going and signing and they're putting their email in there. They're writing it down somewhere. Are you going every time and taking it out of that book and putting it into your

management audience manually? If you are in like, that's not a constraint on your time and you can do it, then like, you're probably fine. But I suspect what's going to happen once you get to two listings and 10 listings and 20 listings is that's going to fail. And it's going to fail kind of quietly. Oh, yeah, we used to do that, but we weren't doing that anymore. And I'll tell you what, I've had some kind of like almost awkward or strange calls in the past where I kind of go to someone who's maybe been a business for five or ten years.

And I go to them and say, cool, tell me about your email list. Where's that at? Where is it? Where are you managing it? Where are you sending marketing messages out from? And they say the words that I hate to hear, which is, oh, we don't have it. Or we don't really, we've never really focused on that before. We just kind of focused on our next booking or our next guest.

We don't really go back and collect emails. and I'm like, oh my gosh, you've just been sort of slowly throwing away the value of the brand and the value of this contact information over 10 years. And there's no going back and getting it, right? Like, it's just gone. So I think you want a system that works without you really thinking about it. And these things like Wi-Fi gates and things like that are set it and forget it for the most part. Of course, check in on it every once while.

I'll make sure it's working properly. But we have clients who set up the Stafi gates and their property don't really think about it for a year. And then I go and tell them, hey, we've got 4,000 new emails from Stafin, you know, in the last 12 months that are now on our Mailchum Bliss that we can market to. that's an audience. If I put 4,000 people in front of you right now, you'd be like, that's a ton of people. But when we see it in a spreadsheet or we see it in a web interface, it's like we forget how many people that is, but these are all people that have stayed in your property before. So if we get them and they're in there and it's flowing automatically, it's just humming along in the background, you don't really notice it until like time elapses.

And then you're like, holy crap, I have a lot of people on this list now that are going really engaged with my marketing. So that kind of be what would be my argument, people who are like, oh, just do it the old way. It's like, can you sustain that? And the answer for most as they scale their business is definitely not. Yeah, yeah. No, I get it. I agree. Thank you so much. Yeah, absolutely. Yeah, absolutely. So we've danced around it for a minute now, haven't we here?

But segmentation, right? So what I was thinking about with segmentation is that we want to work with meaningful segmentation. And I mean, you can do in MailChimp any sort of segmentation that you want to buy travel dates. Hey, they booked in the fall of last year. So we could pitch them in the fall of next year. Let's say you had different markets or even just buildings. We just signed on a client recently who's in the Panama City Beach market and people actually book there based on the building they go to. So maybe they prefer to go to building ABC versus building XYZ. So you could tag that and maunch him. You could have that and say, hey, this is, excuse me, a guest who typically books this type of building.

And then you could only send them feature to units from that building. One thing that William and I were talking about before record is pet friendly. People who brought a pet on vacation and its drive-to market tend to want to keep bringing their pet on vacation. So highlighting pet-friendly properties in that email is a meaningful form of segmentation. I think you can, unfortunately, create non-meaningful segmentation. So the example I usually give is someone who booked a three-bedroom versus a two-bedroom. It probably doesn't matter. They probably would book one or the other.

their small differences in their group, maybe when they're coming one time it's with this family member, then that family member is not going the next time. It's a different family member, and things are a little bit bigger and smaller. But I think you can do not meaningful segmentation or try to get things a little bit too small. I think you want to focus on building a handful of segments and really marketing to those things, unless you have unlimited time and unlimited budget, which if you do, please reach out to me. I'd love to talk to you. But most people have a limit on their time and how much they can actually spend on these email campaigns. As easy as much it makes it, it still takes time to put together different segments, different messaging, different copy.

all these types of things. Even with the advent of using AI to kind of create some of the content, it's still going to take time. So I think you want to build segmentations that matter. And again, that could be location, that could be behavior-based, that could be seasons,

that could be pet-friendly, all these things that kind of come into play. But again, Mouchon makes this super easy. But I'm curious your thoughts on this because you probably have a lot more knowledge of all the tooling in the back end of how segmentation, tags, all that kind of stuff work as well.

No, I think you say everything pretty accurately. I have to just echo that make, keeping it smart. And knowing the audience, the more you know your audience, the better your emails will be. And again, I've said the example before of if they're interested in beachfront or head-friendly, adult-only, things like that, just really help you send the right messages, especially as

you're pushing out your property. This is great. Yeah. Yeah, absolutely. Awesome. Yeah, awesome. Quick note here on automation. And basically, like we've talked about before, you can add a field of MailChimp and you

can fire automations off that field. So for example, someone's check-in date, you could send a pre-arrival email through MailChimp. You can also do this through your PMS, so it's just kind of depends on where you want that to live. A lot of our clients do choose to put it through the PMS, but just know that you can do a lot of this stuff through MailChimp, where you can at least have connected emails that fire based on a date, like a check-in date or something like that. That is a field, a custom field that you can add into MailChimp list. We've done it many times before. So a pre-verrival, a post day, a review and a reviewer, is what we call it. Hey, you have this awesome stay in St. Barts.

I hope William left a five-star review for that awesome place to stay in St. Barts. And then they want you to come back and book again. If you book right now for summer of next year, we'd be willing to offer your small discount. Winback. Maybe someone has stayed three times in a row. we have a client that we work with where we call those VIPs. MailChimp actually has that function as well, VIPs. Hey, this person has booked three times in the past, but then they haven't booked in 16 months. What's up with that? So we might actually send a message out to those folks and say, you're not engaging

with us. What's going on? We'd love to welcome me back. Maybe we offer them a special deal or a special value for their next day. Maybe it is a discount. Maybe it's just you get something for free. Maybe you get a check-in for free. Maybe we can offer you a tour and activity, that sort of thing. So win back and work well. Abandoned bookin, big fan of this, something that we've been working on a lot lately. So if someone goes to a checkout page does not actually finish the process, you could route their email over to MailChimp and then send them an automation from there. Hey, William started to book this St. Bart's trip. You're going to come back and then you stopped. You put in dates.

You got rates. And then you stopped. Oh, no. Could we get you back? Mailcham has that functionality where you can do an abandoned booking campaign super valuable there. And then, yeah, a homeowner nurture, a great way to most people who are reaching out to for property management services will not sign right. I don't care how good you are at sales. You're going to lose more than you're going to win, right?

You're not going to have 100% close rate when it comes to homeowners. But what you don't want to do is say, oh, Okay, William has an awesome second home, vacation home in Steamboat Springs. He says no to me. I'm a Steamboat Springs property manager. I don't just want to ignore William and never reach out to him again. I want to be like, maybe something changed. Maybe he went with another manager and then he ends up not liking that manager.

Maybe he ended up doing himself. And then he goes, gosh, this sucks. Why am I doing this myself? I need a property manager. So if we have something going on a regular basis to him, you could easily build a homeowner nurture sequence automation inside of MailChimp and say, these are all people that said no to me. Let me just drip something out to them.

Once a month, once every six weeks, it doesn't have to be annoying or overwhelming. it's just to check in with them and run so on and be like, hey, here's what's going on. Hey, here's a tip for this. Hey, here's this. And the majority of our clients that we work with to do a lot of homeowner marketing, get many deals on a regular basis from someone that they might have first had contact with 12 months ago, 24 months ago. But no one's going to remember in their brain like 25 different homeowners they talk to and all the various stages. We can remember MailChimp.

You could just have a sequence there, tag people in or manually add them when they fit this criteria of said no to my managing their property. And then you can get them back that way. So if there's an idea you have, if I should be keeping in touch with this group of people for this reason, you can basically build a Mailchimp automation and then add people to it and just a little bit of against it and forget it, which I think is what we're all after with marketing. It said something at one time, let the automation in the back end do that job. And these opportunities present themselves back to you because of this automation you might have set up six months ago a year ago, that sort of thing. So big fans of that.

Yeah, I love to double click on the windback because I think, and I think it was this week I learned loyalty programs, reward programs, and you can scale it down to really talk about this for the local homeowners that are renting their properties. I was having a segment of these are folks that are routinely staying with me. I want to treat them well. I want to get them in a special series where they're like, like you said, give them a tour, give them an weekend activity or discounts and then they maybe build up some points or whatever. And get a free stay in a month or two. And they just like, that would also boost your analytics as well.

These are the most engaged audience you'll have because they know that they're going to be treated special and have that VIP feelings. Yeah, I just wanted to double click on that. And then second, you did mention Steamboat. If you know anyone in Steamboat has a great property, I love to pick your brain because I was down for a nice weekend trip. There you go. There's going to be a small portion of this audience, William, listening, who are a

vacational manager. So if you're a, if you're Steamboat Springs based property manager, you need to be sending William a message here. Exactly. You get your next guest right here, given that he's based in Denver. Yeah. Yeah, I'm curious your thoughts on this one, too. This is just a quick slide I wanted to put in here towards the end, which is people always

ask this question to me when we start to send the email out. We send, let's say the first one out. They get a 32% open rate. The next thing out of their mouth is, is that good? And the answer is yes, that's good. Most of our list that we work on. We're in this 25 to 40% range. Honestly, the bigger list, the lower, it tends to be on average.

But again, I'll take an email list with 100,000 getting a 20% open rate over an email list of 1,000, getting a 40% open rate. Or you can do the math on that if you remember your algebra. So these are just kind of averages that we see 25, 40% open rates, 3% to 5% click rate, so people that open the email. Again, you may be above this, below this, that sort of thing. I will say if you have very low open rates, like sub 5%, sub 10%, you've got very low click rates under 1%,

MailChimp's probably doing its job fine. Your email is probably not good enough. You probably need to think a lot about your audience. You need to think a lot about your design of your email, your subject line, you're targeting. There's probably some things that you can improve quite a bit there. But that's just kind of what good looks like and just an average, based on a bunch of different accounts we've worked on over the years.

Yeah, I agree. And, yeah, if you see anything lower on this, he said, make improvements to your campaigns. There are certain words that work in your subject lines, certain words that don't. I know Gmail, AOL, Yahoo, they will omit emails and put them into different folders based off of what. what you put into the subject line.

So just always keep it in mind of, if you're saying, oh, brand new deal right now, they're probably going to put that into a promo folder, and it's not going to go into their inbox. And it's just going to be something they probably don't make, they might miss, which will decline your open rates, maybe making things a little bit more intimate. Again, circling back to the segments,

it's like, oh, thanks for your stay. Here, let's chat again or come stay again. Things like that would make it more intimate and less gimmickie through the subject lines. But again, you always also want to incorporate a little bit of kind of a hook. So just different tactics. It comes to subject lines.

And then the call to action within each email can drive, increase or decrease your click through rates, of course. Click here button maybe in a different spot that the user may not like or maybe a different color that they're not really too keen on, just different things that you can really improve. And I know Conrad has so many different strategies to develop those emails and those campaigns and make them the best for your business and your brand. One thing that's a recurring theme I see over and over again in the past, I feel like

this has gone away a little bit, but everyone must. wanted to clean emails. We want it to be clean and simple and that kind of stuff. But it would be so clean, there'd be no obvious button. So it'd be like, oh, our email click rate sucks. And I'm like, well, there's nothing here that actually indicates it's a button. There's nothing telling me what to do next, which is search properties now, big button that I can see. Especially if you're on phone, you want that button to be at least the size of your thumb, if not a little bit bigger. So you don't want these little subtle white ghost buttons. You don't want text-only stuff. People just don't click on that as much. So yeah, it sounds simple, but you'd be surprised

sometimes I ought to an email campaign. Maybe that's someone else sent out. And I'm like, it looks nice. Whereas the, what's called action? What's the buttons? We need to go back and just think marketing 101 was the next action we want them to take and why should they take it right now and yeah email emails a great way to drive urgency but it's got to be something that actually makes sense and sometimes you'd be surprised how often we could just take an existing template tweak it a little bit and get way better click through rates by just making small changes to things like buttons i know it sounds simple but it makes a meaningful difference i love that the big you the thumb that's neat yeah exactly so you can't miss it exactly but yeah just a bunch

of mistakes we see over and over again so good segue there batch and blast which is just we're going to keep sending batch after batch i talked about this person a few minutes ago who had a 5%, 4% open rate. I was sending twice a week. It was just not getting the hint of like people you're over sending. Yes, Mailchip can handle that. I guess that's a good news from an infrastructure standpoint, but you're just burning the list.

People don't want to get that many emails from you. Their unsubscribe rates were very high. People have stayed in the list. Their active engagement was low. They'd stay for a little while and just kind of dump off of it. So don't over send. No one wants 10 emails a day. It's just not there, especially for vacationals.

We want them on that list a long time. If you have good segments and you're not using them, it's a bit of a gap. I think no segmentation is a mistake if you have the time and budget to fix it. I will say no, segmentation is not the end of the world if you have a pretty defined past guest list audience that you're marketing to and they have somewhat similar interests. But if you can segment, you have time budget and you can do it, then do it, kind of go from there. Ignoring past guests, again, more often than you might think. And these kind of bottom two, I could tie together. People actually will come to us and they say, oh, got a millionchimp account. Yeah, I've got a 10,000 people on that past guess. And I go, awesome people, yeah, I've got to go in there, cadence. And they go, yeah, I sent one a year. Or I sent one a year. Or they sent one in August. And they're like, oh, I haven't sent one since. So people forget about you. So Mailcham's not going to send the emails for you, right? Like you got to go in there, log in. And you. And you got to go in and actually design something and click send. And if you have a big list that you're not using, then you're just leaving a Ferrari in the garage, man.

You got to get out and drive that thing. So if you have a past guest list and you're not marketing to it, huge gap. And I just see this all the time where people get busy. It's not number one priority. Again, they send an email. They don't get that instant dopamine rush of a lot of bookings right away. So they just kind of put it off at this side.

They don't realize the brand building that they're doing. And they can work for a long time. And then they think they can just turn it back on later. And the truth is you can. If you ignore your email list for a year or 18 months, the first email you send is going to have a really high unsubscribe rate. Because people are like, who is this? They forget. If you ignored your list for a year and you didn't send something for a year, they probably have seen 50,000, not an exaggeration, maybe even 100,000

marketing messages since your last email. So in their brain, they just file it away. They're like, I don't remember what this is. Maybe I say, I don't know, click, unsubscribe, spam, whatever, they just don't care. You got to keep top of mind. And that is being not overly top of mind, not annoying, but you got be consistent. You got to be present. You got to be there. And as a result, you're going to get much better results from it. If you let these, another analogy I do sometimes is like, your past gas list is like milk. It will go bad. You can't leave it out forever. You got to out ways to market to in a way that's appropriate. But I see a lot of, I see more understanding than over-sending, but I see a bit of both in my career. I love that. I love that.

Sure. Yeah, and just a random example, a client that we worked with in Colorado, they're very OTA dependent. We got mountchimp in place, different list, segmentation, full automation. They're getting 12 bookings every month down, $40,000 a month in revenue they were not getting before. Run that over a year, run that over a few years, and those numbers will only go up as they get more inventory. And you can see how they're literally getting hundreds of thousands dollars of additional revenue every year just by sending a few emails a month. So it's not really rocket science here folks. Sometimes it's pretty simple. And as a result, it can work really well. So I'm a big fan of it. And I think it'll get a lot of value out of it if you do the same as well.

Yeah, that's a great segue to some other real world examples. I just love the numbers here, 12 bookings per month and average 40K per month in revenue. That's quite a big increase, which is really great. But yeah, and we have so many different options, so many different case studies and news cases for MailChimp. But I'll just go over two today that kind of just kind of stick out to me and also that are relevant to the audience here. First, that's Stash Hotel Rewards. And then I know I mentioned the reward program before, but this is a loyalty program that connects travelers with, you know, over 300 independent boutiques and hotels across America. And they have about 729,000 people in their audience. And they're using MailChimp to use it as their main

channel. And a lot of for those small hotels, it's like the number of way, number one way they're getting discovered. And this is like this meant they've been able to use two totally different audiences, there's travelers and partner hotels and transfer that to just one channel and one on a design that works for them. They leaned then to MailChimp's AI insights and instead of going off like building their own analytics and that's like something I want to really double click on the Mailchimp's analytics are super super robust. And the more I guess as you go up and plan, the more you can do with the analytics and the more it you can you can get out of MailChimp. For example, A-B testing, AB-test subject lines. They can segment members by location and then resend to those

that didn't open the first time. And it's really a great way to kind of say test what works, test what see what doesn't work, and then increase that open-click rate over time. And then with those results, they got 69 bookings from a single five-day flash sale, which resulted in 76%, which was over 76% of similar campaigns that they did, plus a 19% bump and increase in click-through rates on partner campaigns and then the 30%, 38% open rate. So again, over those benchmarks we mentioned before, all through MailChimp's tools and analytics to decide what works and what doesn't. Excellent results for sure. Yeah. And this one is travel online. So next, another example in the travel industry. This is actually an Australian travel agency out of Brisbane. They do flights

and accommodation tours, holiday packages and all that stuff. And then they have a list of about $315,000. So this one is basically, they used something pretty old. They were doing more generic blast, you know, sending it to everyone, those things we watch out for. And it was really killing their engagement. And this is the exact model we are trying to push everyone away from, especially when Conrad's just really trying to say,

there are so many different tools and strategies out there that can increase your revenue over time. And this is just another great. example of that. With MailChimp, they drove real segmentation and personalization and tailoring how they, how often they emailed and also what they exactly sent, which brought their unsubscribes way down. They cleaned up their deliverability with a domain warm up by sending out a couple of emails here and there to say, hey, I'm still here. Are you so interested? And that way that increases open rate over time. And then circling back to Mailchip's API, they're able to use that to

build out a contact list. And then an opt-in source, they can connect travel online. to MailChimp. So once they opt-in a job online, automatically MailChimp, and then just go from there. So the payoff, they had 66% of an increase in open rate. They decreased their unsubscribeers by 38% and then increased the return on investment by 13% despite using email marketing. It was a really great, really cool quote here from Shari. Email continues to be one of our most valuable channels, especially when it comes to balancing efficiency, was personalization. One of the ways you tackle this is through smart segmentation. And then that's actually an exact quote from Conrad as well. That smart segmentation truly helps build out your success over time. And then it's kind of like

that one thread that connects everything. It's stop blasting emails, making more tailored, start segmenting. Let these tools do the heavy lifting. Milchimp has your back and so does Conrad and build up bookings. I love it. Yeah, I'll, I guess quick plug here at the end as we tend to do in these sorts of things. So we'd love to help you build your list. We've got to help you get everything in there, build segmentations, do any automations you require and build some measurement in the back end. Just go to buildup bookings.com, click the book a free call button right on the homepage there. It brings you to getting started. And you can chat with some of our team and we'd love to help you.

Yeah, sign up from MailChimp for sure as well. Of course. I know. Yeah. If you have any questions, you reach out to me in this, in the video, in the bio, you'll see our contact info, my email, Conrad's email, which will contact form. And that way you can get in contact with us and learn a little bit more about the platform, how we use it.

And yeah, really would love to chat with you and set up some time. So again, thanks for watching and share the news, share this video, and happy sending. Yeah. Thanks, Bill. I appreciate it. This was fun. Thanks.