Direct Booking Simplified Podcast – EP14 – Simplify repeat bookings using email campaigns with Lindsey Rodriguez

In this episode, Lindsey Rodriguez from Stay Booked breaks down why it’s crucial to invest in your own marketing and how to get more repeat bookings with effective email campaigns

Podcast Summary

We recently had an awesome chat with Lindsey Rodriguez on our podcast. Lindsey has been in marketing for over ten years, taking her skills to the short-term rental world. She shared some super helpful tips that anyone can deploy. Here’s what she had to say!

Why Direct Bookings Matter

Lindsey believes relying only on platforms like Airbnb isn’t the best idea. She says, “You don’t want to build your house on someone else’s land.” You don’t want to rely on one platform for all your revenues. Instead, you should be diversifying your revenues between the various OTA and direct bookings.

The Magic of Emails

Lindsey thinks the best way to get repeat guests is by collecting their emails. This way, you can keep in touch with them. If you keep popping up in their inbox, they’ll remember you and might book again.

Sharing Helpful Info

When you send emails, don’t just ask them to book again. Share cool stuff about your area, like fun events or secret spots. This shows you know your stuff and makes guests trust you.

Easy Tools for Collecting Emails

Lindsey uses a tool called StayFi to collect emails when guests log onto the WiFi. It’s super easy and doesn’t bother guests. Once you have their emails, you can set up automated messages that go out over the year. For example, two months after they leave, you can send an email saying, “Can you believe it’s been two months?”

Using Social Media

Social media is also important, but Lindsey says you don’t need to go viral. Just have a decent presence so when people look you up, they see you’re legit. Post some nice pictures and updates regularly.

Just Get Started

Lindsey’s biggest advice is to start now. You don’t need a perfect plan or system. Just begin collecting emails and posting on social media, and you can improve as you go.

In a Nutshell

Lindsey Rodriguez’s tips are simple but powerful. Collect guest emails, share helpful info, use tools like StayFi, and be present on social media. Most importantly, don’t wait to get started. These steps will help you get more direct bookings and build a stronger business.

For more awesome tips, listen to our full podcast with Lindsey Rodriguez!

Essential Highlights

Here are a few key takeaways from the podcast with Lindsey Rodriguez:

  • Building relationships and staying top-of-mind with past guests through automated email sequences is one of the most effective marketing tactics for driving direct bookings and increasing guest lifetime value.
  • The emails should focus on providing value (tips, photos, stories etc.) rather than just discounts to attract higher quality guests who will keep returning.
  • Collecting guest emails through tools like StayFi is critical for building your email list to enable these campaigns.
  • Social media doesn’t need to be overcomplicated – aim for 1 piece of content per week across channels to establish a brand presence. Don’t worry about follower counts.
  • Surround yourself with a supportive community and coaches to stay motivated and avoid isolation as an entrepreneur. Communities like STR Secrets provide invaluable guidance.
  • Just start somewhere with marketing. Don’t wait until you have everything perfectly figured out. Find experts who can help with areas you’re not skilled at.

The core message was to be intentional about building direct relationships with guests through valuable email content to increase their lifetime value, rather than over-relying on OTAs. But do it in a sustainable way that fits your strengths.


 It doesn’t need to be hard. Like it doesn’t, it doesn’t, it can, in fact, it can be automated. Like there’s a little bit of upfront work required, but this isn’t something you have to do and then do and then do. And then do it’s like, you kind of set it and forget it. I don’t want to oversimplify, but like, if you’re doing it, right.

It’s relatively low. 

Hey folks, welcome back to direct booking simplified. We break down the strategies and tactics to win in direct bookings on today’s show. We have Lindsey Rodriguez. She’s an SDR operator and it’s a digital marketer by trade. Today, she’s going to walk us through how she runs effective email marketing campaigns to bring in more repeat bookings.

So let’s bring her in.  Hey, Lindsey. 

Hey, how are you? 

I’m doing good. I’m not sick for once, uh, which is really good having two kids of my own. How are you? 

I’m good. I am a little sick, but, um, that’s just par for the course of the kid in daycare. So we’re going to get through it. 

Yeah. They, they’re like little Petri dishes.

Like they just bring home just about anything. And your job is done. Try not to catch it. 

Yeah. I’ve given up trying.  

You just embrace it.  

It is.  

Oh, well, it’s great to have you on the show. Uh, I really enjoyed, uh, you, your webinar last, uh, last week, it was like a couple of weeks back with Mike. Um, and I definitely wanted you to share some of the learnings and some of the things that you shared, um, On that  webinar.

So kind of before we get too deep into it, do you want to give a folks a brief intro on kind of who you are? Um, what you’ve done and kind of like your, even your W2 stuff, your, your, your day job. 

Yeah, of course. So my name is Lindsey Rodriguez. Um, I am a first and foremost, a wife and a mom. I live right outside of New York city.

Um, and my day job for the past 10, 15 years has been as a marketing executive. So I’ve worked for, I started my career with the Boston Bruins. Um, I’ve worked for a ton of big brands, uh, a ton of small brands. I most currently lead marketing for a company called Daily Harvest, um, frozen food company, you know, about a hundred million plus, so sort of middle market.

Um, and. We had been doing the W two thing for a really long time. My husband and I, we had a baby. Um,  our baby was about this now was I guess about a year and a half ago. Um, our baby was about four ish months old, got really sick, um, was in the ICU for a week and, I, my husband and I were like doing shifts in the ICU overnight and I was answering Slack messages in the ICU from my boss.

And I just had a moment of realization of like, what am I doing? And so that is what started us on our short term rental journey. Um, we had owned, we owned a long term rental at the time we were house hacking right outside of New York city. And, um, my husband and I were like, we need to build, we need to build our own thing.

We need to get out of the rat race. And so that’s when we decided to. Invest in our first short term rental in the Poconos. Um, we also joined a mastermind around the same time, short term rental secrets and to, to sort of help shortcut our learning journey. I was really, really new to all of this and really risk averse at the time.

Um, and. Fast forward, we’ve built, um, that house is absolutely crushing it. Um, we’ve built a co hosting business out there in the Poconos as well. Um, and a year or a week ago, my husband, Andrew actually just left his W2 job permanently to run our real estate. So, yeah, so really a fun, crazy, scary, terrifying whirlwind year and a half.

What was, uh, what was it like? So I’ve, I’ve heard a lot from the STR secrets group and I know quite a bit of folks there. What’s your been, what’s in your experience with STR secrets? How’s that kind of like shaped, yeah, shaped. Yeah. 

Incredibly positive. I was, and I’ve said this to, uh, To Mike Sjogren, I was so skeptical at first.

I’m somebody who, like I said, is not necessarily of STR secrets, but just of like the concept of masterminds. It was new to me. I didn’t really understand it. I was like, you know, I’ve always been someone that’s like  kind of a penny pincher. Um, And it was just a new concept to me. And so I was like, why do we need this?

You know, and the more I learned from him, the more I learned from, from the group and the more I learned about short term rentals, I started to realize there was so much I didn’t know. And I didn’t even know what I didn’t know. And so I was. really, um, convinced at the aspect of the community. Um, entrepreneurship is incredibly lonely.

It’s something where I feel like during the day is, you know, more than anyone during the day at my W two, I’m like wearing this sort of like corporate Lindsey hat and then nights, weekends, you know, breaks in between. I’m like wearing this entrepreneur hat sort of like. Two personalities. And so it was really lonely.

It was really scary. Um, and so having that community, like extremely positive uplifting community, um, has, I think not only made the journey enjoyable, I’ve met some incredible friends, um, but also probably saved us a lot of costly mistakes over the year plus.  

Yeah. Yeah. So when did you join the mastermind?

Was it prior to even the acquisition or after it 

was before the acquisition, um, we use the mastermind as sort of like a gut check for a lot of our deal analysis. Um, because we originally joined and we’re like, we’re never going to co host. We don’t want to co host. We don’t want to deal with that. We were just going to buy.

And so we bought, um, we bought a six bedroom. We joined the mastermind in about October, November of 2022. We closed on the house in early February, 2023. So about three months or so after joining. So it was pretty quick. Um, and, uh, fully renovated. It was a dump beforehand, um, renovated it, designed it, launched it, and like three or four months.

Um, and. It was just super helpful to have like the backing of the community along the way. And then, uh, I’d say about August or so of last year, August, September, we were like, you know what, let’s try our hand at this co hosting thing. Um, and we had a couple of inbound leads. And so we, again, really leaned on the community to kind of shift our business.

And then, um, and our co hosting company stay booked. Essentially also evolved into a little bit of like a marketing consultancy because I had a lot of people just naturally coming to me asking for my support in developing marketing content for them and helping them remarket to past guests, which I know we’ll get into a lot today.

But, um, it’s really been this business that has sort of evolved over time. And STR secrets has always been there kind of like anchoring us and grounding us when things have gotten chaotic. 

Yeah, I’ve, I’ve always heard really good things from the folks from SDR secrets. Like there are some masterminds that are kind of like, you hear a little bit of positive, positive and negative, but like on the SDR secret side, I hear actually,  I actually very, hear very little negative anything of anything, but there’s an overwhelmingly like positive sentiment of just the community and kind of how you guys operate within, within that group.

Yeah. I mean, when we came up for renewal, I was like, this is a no brainer. Like this is an absolute no brainer. There’s no way. I would be where I am today, both mentally and just like with the business we’ve built without it. Like I would have quit a thousand percent. So 

you make up, you bring up an interesting point about like the, the mentally prepared side of things, or  I find that like Mike Strogan is actually pretty big on like mindset and kind of getting you in that zone.

Would you agree with that? 

Yeah, a hundred percent. I mean, he is, he really, we actually have a weekly call on Tuesdays as part of the mastermind where it’s just a mindset call. And I didn’t know what to expect at first. And it, that’s the reason we decided to launch our co hosting business. It unlocks. So many things for me and pointed out so many fears that I was grappling with.

And, um, it just challenged me in ways that I’d never been challenged in like a corporate environment where you’re sort of just like playing a game to climb the ladder politically. And like, you know, it’s not really about what you put into it and your mindset and all of that. And so it, I would say that Mike’s perspective around mindset and designing a business that fits into your life versus a business that just. 

Looks like a business you think you should be building. He’s really big on like your perfect week. Um, and what does that look like has really given us the almost like the, um, the path to the business to be really intentional and give ourselves permission to build a business intentionally rather than just like, we’re going to hustle as hard as we can and see where we get.

Yeah. He sounds, he sounds like a pretty like well balanced coach. 

Yeah. Yeah, definitely. 

How do you, how do you think that has applied towards like, Has that changed any way, like your, your aspect on W 2 or like, yeah, how does that play into it? 

I mean, I used to just get, I, I don’t know, I’m sure a lot of entrepreneurs would say this, especially ones who are balancing a W 2 and.

Um, and on a sort of entrepreneurial venture, and hopefully no one from my W two ever sees this, but it’s just made me care a lot less. Like I just, I, it’s easier to compartmentalize. Whereas in the past, I really struggled because I, I saw my W two is like my identity. It was my, it was the thing I was going to be doing for 30 plus years.

So I was like, I better, I better figure this out. I better like it. And, and when it went wrong, It really, or, you know, when something happened that was hard or some layoffs happened, it felt like my world was crumbling. And now that I’ve built a business that intentionally serves my family versus a venture fund or, you know, shareholders that I’ve never met, it’s like, wow, this, this feels so right.

It just feels like what I should have been doing all along. And so now it’s so much easier for me to sort of like,  You know, especially a lot of the mindset work we’ve done to, to sort of like put work in its place and to prioritize the things like family, which are the reason that I’m doing this all in the first place.


yeah, I, I kind of felt the same way when I first got into my, my SDR, like experience there, like in SDR yet full. Power both on the positive and negative side. Like if things don’t go well, it’s on you. 


And if you want to accelerate and scale your business, it’s on you. 

Yeah. But 

then you turn back on your W2 job and you reflect back and you’re like, wait a minute, like I’m asked to do these things and I’ll still get the paycheck no matter like how much I put into it at the end of the day.

I think that like, it almost like forces good managers in the workplace to really extract out and really, you know, like, Give you that sense of purpose in the workplace and if you don’t have that sense of purpose and you’re really there to exchange time for money, like it’s really hard to get that same attachment that you would on something that you are pouring your whole energy into and you’re, you’re seeing your baby, um, like grow over time.

Right, right. Totally. Yeah. I, Could not agree more. So it’s been, it’s been very positive both for my entrepreneurial life as well as for my w two, because now it has sort of forced me to think critically about where I’m spending my time. And are these, is this worth my emotional energy? And you know, all the things that I was not thinking about a year and a half ago, 

you’re, you’re absolutely right.

Right. On like the emotional energy side of things. Like when you are someone in w two, you.  You can easily try to get everything done that you should get done. But when you have the perspective of like an entrepreneur, you start to look at your list and you’re like, you know what? Like this person asked me to do it, but like, it’s a real big waste of my time.

Like you have a lot more strength to push back and say, no, I’m not saying no because you’re lazy or you don’t want to do it, but you now have a different perspective on like how much time is actually worth in your life. 

I could not agree more. I was just thinking about that as you were saying that. One thing that Mike and the STR secrets group is really big on is the book, my one thing, or, um, the one thing.

And so now I’m always reflecting on what’s my one thing today. And what’s, and essentially like what’s, you know, the whole framework is what’s the one thing I could do today that will make everything else unnecessary or easier. And so. That has really changed the way I approach every single day because now I realize the time I was filling my days with nine hours, 10 hours plus at my W two.

I’m like, what was I even doing? I’m getting the work done in three hours and it’s probably done better because I’m focused on higher value activities. So it’s been really a big eye opener for me. 

Yeah. So what’s, uh, what’s next for you? Are you next on the list to, uh, leave the W2?  

It was originally going to be me.

And then we decided for, you know, family reasons that it made more sense for Andrew. My husband is, was in sales. And so he was heavily commissioned. And so he was like, you know, I’m not doing the work I need to do to see this, to see the, see the commission. And so it made more sense for me. To stay, but I will be next.

Um, we have some big goals by end of 2024. And so hopefully, um, you know, my time will come next year. Um, and yeah, we’re just going to continue growing. We’re we’d love to acquire one or two more properties this year. Um, and then we’d also love to continue growing our co hosting business. My husband’s actually out the Poconos at a photo shoot today.

So, um, just rapidly scale. 

Yeah. So right now, what does your portfolio look like? How many, how many. It’s properties that have you acquired versus how many co hosting? 

Yep, two acquired. Um, and we co host four. Um, and yeah, and so, um, so we’ve been sort of stagnant I’d say for the past, like four months ish while my husband and I were both working and Like we were just barely, it felt like we were sort of just like staying afloat, like the duck sort of sailing on the water, but like the legs underneath are like paddling furiously.

That’s how it felt for the past few months. And now that he left as of a week ago, it feels like there’s just so much more, um, the pressure valve has been released and now he can focus on things like prospecting, which we just did not, we had no bandwidth for before. And so, um, so we’re really excited.

Nice. Very nice. Um, I wanted to kind of get into like the meat of like what I wanted to introduce you into the show for is like, you seem to  have like really nailed on how to like drive more repeat bookings. And you, I won’t spoil it, but you have one particular thing that you try to coach others into really doing and doing well, and which will kind of kickstart the whole direct booking, um, engine there.

Um, I kind of, I’ll kick it off to you and like,  first off, like, why does this even matter in the 

first place? Yeah. I think that’s a great place to start direct bookings and marketing and all the buzzwords that come with it are a very hot topic in the STR space right now. Chances are you’ve seen it.

You’ve seen some of the influencers in the space tell you, you have to be doing this. If you’re not doing this, you’re going to fail. And it’s like, okay, great. Well, like. Why do I need to be doing this? And so if you’re having those questions, or if you’re like, Oh my gosh, another thing I have to do, like, I get it.

I was there a year ago. I was like, wait, I have to build a custom website. Like what it made me so terrified. And I’m here to say that it does not have to be scary. It does not have to be, you know, the main thing you’re focusing on, but.  It is important and there’s a couple of reasons why the first is purely financial This one is sort of obvious, but you have you can increase your profit margin.

So it’s a win win for you It’s a win win for the guest because when you’re circumventing fees on the OTAs You can either charge the guests more or you You know save on the host fees that they’re charging you  and the guests End up saving as well. They’re happier to book with you. They feel like they got a great deal.

Um, and so, so, you know, win, win there. The, the other one that I think is talked about a little bit less, um, is that it’s a great avenue for brand building and loyalty. So what I mean by this is like,  it essentially deepens your connection, the, your connection and your brand’s connection with the guest. So if you think about like the brands that you’re loyal to there.

Or, you know, brands you shop at, you know, every couple months or brands you’re constantly thinking about are brands you follow on Instagram. Like you end up spending more money with them over time because they’re top of mind for you. And so. You’re essentially higher lifetime value, meaning over the life, over your lifetime, you’re going to spend more with them than you would with a competitor.

And so the goal of all of this is to just increase the lifetime value of your guests. If someone’s going to stay with you one time, you’re going to say, you know, it’s 2, 000 booking. That’s great. But if they stay with you three more times, then all of a sudden that’s an 8, 000 guest. And so when you can build a one to one connection with a guest and they can really experience your brand and build loyalty with you, and they’re going to do so because they know they’re going to save money and they trust you and they trust and love your hospitality, then that’s a really great investment on your time.

And then lastly, And this one is also sort of obvious diversification. So like just protect your downside. So we all fear the dreaded party that a guest unauthorized party that a guest has, and then we get the email that our account’s been suspended. Like the, the truly the things that keep us up at night. 

There’s the saying like, don’t build your house on someone else’s land. Like that’s essentially what we’re doing on, on OTAs. Now it’s not to, what I’m not saying is like, you know, 70 percent of your booking should be direct. What I am saying is that you should think about how you can create a diversified stream so that you are.

Marketing to guests who have a desire to book direct and say, so Airbnb will always spend more money on advertising than you. They will always have billion dollar ad budgets are always going to show up top of Google search results. There will always be guests that go to Airbnb directly. So it’s not saying abandon that, but it’s just saying consider diversification so that you have a healthier mix of that, um, in of inbound requests.

Should you lose one of them? 



Yeah, that’s a good point. You mentioned the second point. Um, being like  having your repeat guests and then thinking of them, not just as first booking. I actually never considered that term LTV. We talk a lot about an e commerce of like LTV and repeat purchases and like,  but not in the short term rental industry.

We all think of it as like, Oh, I got my booking and I got that 1, 600 from that guest for this weekend. And that’s it. But what you’re saying is actually the LTV of that one guest could actually not be 1600. It can be on average. It could be a couple grand more because they’re actually going to book with you several times over the lifetime of, of them.

Yeah. A hundred percent. And yeah, I hate to use acronyms, but so I’m glad you picked up on that because at daily harvest where I lead marketing currently, we’re a subscription business and so we are totally only focused on LTV. We’re not ever just looking at. First box purchase. We’re looking at the value of the customer over the lifetime.

And so it’s hard for me to divorce myself from that. And I don’t think a lot of people think about that. You know, I’m the same way. Like I get my booking on Airbnb and I’m like, Oh my God, my booking. But like.  You’re leaving money on the table and ensure not everybody is going to book again. In fact, most people will not.

A lot of people are just traveling to that area for one time, but like, there are guests that will, that are looking to book every single year and they want to know what to expect because plenty of guests have showed up at an Airbnb that looks nothing like the photos and they’re terrified of that. So yeah, there’s a real case to be made that we should be talking more about LTV.

Yeah. That reminds me back. So I was Product director at a company called Narvar that does like the best purchase experience. And one of the metrics that we looked at, so the product was you would, anytime you purchase like something from like Sephora, Home Depot, um, sacks, like they use Narvar as the email mechanism tool to let you know when your package is coming.

And the whole reason why these big hun like top 100 IR companies were investing into Narvar. For these post purchase emails was to drive repeat purchases. And that was the one metric that we will look at all the time is like  when someone prior to sending out emails,  the repeat purchase rate might be, might be two. 

But when you start to engage your customer. After they, after they purchase and you, until when they actually unbox the product and whatever, um, you nurture them through that whole entire journey. The repeat purchases were phenomenal. Like it’s like a 1. 5 X difference, which is a significant difference on something that you’re, all you’re doing is just lighting the guests or letting the customer know.

When the package is arriving, like something so, so simple that  you’re bringing me back to like my e commerce logistics days. And  yeah.  

When I worked at a small company called the inside that actually sold to a larger company, um, I was on the founding team there. We use Narbar, um, and we were very focused on repeat purchases.

So that’s no surprise there.  Um, yeah. And I mean, that’s a great point because and we’ll get into this, but like, it doesn’t need to be hard. Like, it doesn’t, it doesn’t, it can, in fact, it can be automated. Like, there’s a little bit of upfront work required, but this isn’t something you have to do and then do and then do and then do.

It’s like, you kind of set it and forget it. I don’t want to oversimplify, but like, if you’re doing it right,  it’s relatively low lift. So we can get more into that in a bit. 

Yeah. So why don’t you spoil a little bit? Like what is the, the, the one thing that you can do that it, that can be automated? What do you, what do you, yeah.

So I think the thing that if you’re going to do anything marketing related and when you hear marketing, you know, it’s,  it could be, it means, it means something different to everybody. To some people it means like, I want to go viral on Instagram, spoiler alert, you won’t.  Most, most likely you won’t. Um, it could mean I want to work with an influencer.

It could mean I want to do, you know, um, social media. I want to, it could be a million things. What I think your best investment on your time is, and what can be automated is generating a rebooking sequence in some sort of CRM. So it doesn’t need to be, you know, anyone specifically most CRMs. Um, where you essentially nurture a guest from the time they check out at your property, it could be the next 200 days.

It could be the next year and you essentially add value to their inbox every, you know, say two weeks to 30 days,  essentially directing them back to your direct booking site and giving them a reason to rebook with you. And the reason you do this is because. You never know when someone’s in the mindset to book a vacation.

Like,  you know, if you’re like my mom, who’s the most type a lady I’ve ever met, we’re not even checked out of our Airbnb before she’s thinking about like next year, I’ve got all the kids together. We need to plan our vacation for next year. And she’s rebooking the next day. Some people won’t be booking until, you know, It’s nine months later.

And so you never know when they’re going to be in that mindset. And so  your job as your, you know, brands marketer is to just stay top of mind for them so that when they are in the right mindset, you give them a reason to push them over the edge to come back to you. And so this could look like a lot of different things and I’m happy.

You know, people can DM me or. Email me and I’m happy to just give examples of what this looks like. And I’m happy, you know, just give away my own content. Um, but what this typically looks like is like, you know, somebody checks out, Hey, so and so thank you so much for staying with us. Reach out if you have any other questions, we can help you at any time.

Super simple. And then maybe the next day you send an, or, you know, a couple of days later, you send an email. Hey, um, we wanted to offer you 10 percent off. If you book with us directly in the next 14 days for your trip next year, something along those lines, I’m oversimplifying, but like,  That’s sort of like your discount driver. 

And then from there, if they don’t take you up on that, your job is just to add value. You’re just dripping them value in their inbox that feels personal and authentic and reminds them why they fell in love with your property or that market. So for example, like one of my clients actually got engaged at In one of the markets that he co hosts in.

And so one of our emails has a picture of his wedding and explains how, why this place is so important to him, why it’s so special. It builds a connection. It’s not like marketing brain surgery. It’s like really straightforward stuff. Like what would, what would you resonate with? And so then, you know, one of our emails just to use that market as an example.

Another one of those emails,  um, talks about like the five things you probably missed or the five things that like you can’t find on TripAdvisor, like the locals sort of tips. Um, and so we’re just adding value and then we’re including a link to our direct booking site and explaining that you can, you know, skip the OTA fees, which essentially maps out to be about 10 to 15%.

Um, if you book with us directly and in our first two months live, he had, I think four or five people. End up past guests that probably would have booked somewhere else. Um, end up rebooking with him directly for the following year. He actually had one of the guests that we were emailing that was like, Hey, this is so, this is actually interesting.

Like, would you be open to, um, To, uh, recommending a realtor in the area. It turns out, you know, my client’s wife is a realtor. They got some commission on the deal. So like, there’s other things that end up manifesting when you build these relationships that aren’t even planned for. So that would be my number one piece of advice is create something that is automated, that, you know, a guest checks out, they’re automatically entered into this workflow and they receive.

Emails that go direct to a direct booking site that again, does not have to be over complicated. There are, you could certainly go down the rabbit hole of hiring a developer to build a custom site for you. Tens of thousands of dollars later with, you know, if, and if that’s not your jam, then I would not recommend that at all.

Um, there are plenty of incredible solutions out there that can do this very simply for you and will get the job done. And. Allow you to continue focusing on the things that are highest value and most enjoyable for you. 

Yeah. You, you mentioned something very interesting. I, I, I want to pick up on it because you mentioned it several times, um, through that you mentioned value.

Um, you want to be, you mentioned that  you want to be sending emails that are valuable to people’s inboxes.  Why do you think value rather than saying, here’s a discount, here’s a discount every, every couple of months? Like why  is that so important for you? 

Yeah.  The same reason that you, you know, I’m a firm believer that  oftentimes there’s exceptions to every rule, but the guests, first of all, that are going to ask you for discounts, even on the OTAs or tend not to be your best guests.

They’re guests that are looking for some sort of like very quick fix. They’re maybe last minute travelers. They’re usually the guests that are kind of. Going to make the most mess. Um, at least in my experience. And so  the first piece being that you want to attract the type of guests that you want to keep coming back to your property.

And so if you’re just marketing to discount driven guests, chances are those are not going to be your highest lifetime value guests. It’s the same principles we apply in e commerce marketing, where we, if we’re constantly, I think there’s a good case study on this. Of, um, J crew actually, where J crew used to be this, like, when I was in high school, this like super premium, expensive brand that was like, kind of like, you know, my mom never let me shop there because it was too expensive.

And now they are consistently 50 percent off, like. They cannot, they found that they started discounting and then they couldn’t stop. And so now the customers they’re attracting are customers that expect J crew at 50 percent off. And so I think it’s really important to make sure that you’re putting out the energy and the, the sort of, um, signals that you’re attracting the guests that you want.

And then I’d say even more importantly, like  think about the emails you get in your inbox. We all get what a thousand emails a day, like across my seven inboxes, probably. Close to a thousand emails a day. And I’d say like three quarters of them are transactional discount driven or spam. And so immediate delete, immediate delete, immediate filtering.

If I see 10 percent off, okay, I don’t, you know, delete. It also cheapens the, the thing for me, right? Like it makes it feel like. Why is this on sale? It’s sort of like cheapens the experience. Now, if you’re going to come into my inbox and you’re going to not ask me for something, and you’re going to just say like, here’s some value I want to add.

And I also want to talk to you and like trigger a memory from this like incredible experience you probably had with your closest family and friends or your spouse or whatever it is, your kids, like when you can pull on that heartstring and do it well, like, People will do anything for you. And so that’s really what you’re trying to evoke is like that emotional connection.

Yeah, I couldn’t agree. I couldn’t agree more. Like I find that like when we send out our emails, we, we almost focus solely on, on, on value. We probably sent out one or two discount code emails, but on average, we probably send out four or five emails of value before we even ask for even a sale. Like a lot of times we’ll send out emails and there’s probably not even a link.

To, to our direct bookings. Yeah. We just trying to keep them top of mind and like, maybe there’s a link on it, but it’s not like a big call to action button. Right. But like, it’s really about like,  really them thinking about you as the place that they wanna stay at. Yeah. Um, so like that’s what we focus our most of our campaigns around.

Yeah. And so I couldn’t agree more 

on, on the value side of things. 

Yeah. And a lot of what we do too is like, so, so that’s like the automation. There’s a lot of.  Jargon for it. But what I’m referring to, and when we keep saying this automated flow, this automated flow, you’ll hear them called flows. You’ll hear them called workflows, automations, email sequences.

It’s essentially like. A trigger happens, a guest enters into it because that trigger happens. So it could be that in this case they checked out and then every you choose the trigger, but every every set amount of time they are filtered through this workflow. So you’re not manually sending any emails, you’re setting them up and forgetting it.

Now we also do campaigns, which you just touched on. Those I think are great for moment in time events. So for example, um,  in the Poconos, there’s a NASCAR race. And so, you know, we’ll look at what our lead times are for booking. Say it’s like 30 days out. So like 30, 45 days out, we’ll send an email to our whole email file.

That’s like, Hey, did you know, um, NASCAR race? Are you traveling for this? Um, a lot of our guests are, are fairly like driving distance in the Poconos region. So, um, you know, those sort of like shorter lead time bookings are very possible. And so we’ll say like, Hey, if you are XYZ property still has an opening, like we’d love to, we’d love to help you out here.

And if, if you’re interested reply, and if you’re not reply to us and we’ll give you some other recommendations of other rentals. We love it.  Like. We’re not pressure like, obviously we want you to book with us, right? But like, I, I want to help you and when you can show that authentically and like actually mean it,  people can, consumers today are very savvy.

So they, they see right through it.  

Yeah. I never thought about like reaching out with the reply for us. Most of our emails have, has like a call to action on it, but 


I like the warmth of the reply and also like the more human element of it. There’s a lot of times like.  It’s my wife and I, it’s like, it’s like a couple that’s hosting it.

So there’s like a real human connection. Like when we message, we always sign it to our, ourselves, my, my wife and I’s name. 

So like, 

I, I think that like that, that reply is actually,  that’s a neat trick. 

Yeah, we do. We get a lot of replies, especially, and it all depends on your avatar, right? Like if your avatar is people who are maybe millennials and maybe care less about like talking to a person, that’s one thing I love talking to a person, but like, If you’re dealing with like a boomer generation in your market who tends to be your buyer, like  Maybe they’re not trusting of this direct booking website, or maybe they’re just not as savvy And so having that reply function like that We get a lot of people for my clients that will reply to us and say like, Oh, I’m actually looking for, you know, the week of blah, blah, blah.

What do you have available? Cause they don’t feel like searching. They just don’t want to do the work. And so having the reply function also shows that like, we also keep all of our emails totally plain text. Sometimes we’ll add an image and be like, you know, but we don’t have a logo. We don’t have a header.

We don’t have any sort of anything coded. It’s just plain text. It looks like I sat here and I typed you an email and I hit send, which is intentional. That’s how we want it to look. 

Yeah, yeah, yeah. We use, um, Oh, we used to use the email tool like Clavio and I’ve learned about Clavio because I come from the e commerce space and it’s such an easy tool that like, You can build out those sequences.

You can build out those campaigns. And I think they even started to put in SMS into Clavio as well, too. Actually, that kind of leads me to one of the questions I want to ask you. How important is SMS as part of your campaigns? 


Well, actually, your sequences. 

It’s a great question. We don’t do that currently because I was not.

So, so I’ll start by saying this. I, coming from the e com marketing world, am triggered by SMS because it is a highly litigious space. Unlike email, you need to make sure before you start sending anyone anything promotional via text, you need to make sure that they have explicitly opted in to receive.

Promotional message via text from you. There are a lot of people out there looking to Sue who receive unwarranted, you know, marketing messages via text, um, unlike email. And so you have to explicitly have somebody consent to that. So like if you’re using stay five, for example, like you can check, like, I want people to have to consent to this.

Um, and if you’re just collecting email, like we were collecting phone numbers, but like just through Airbnb, we weren’t having them like opt into marketing. And so I intentionally don’t use this because I was not collecting it properly. I don’t want to get sued. Um, that said, uh, when you think about like an average email open rate, it’s like sub 50%.

When you think about an average text open rate, it’s like 98%. I mean, I don’t have any texts that I haven’t read on my phone. So it is, it cuts through the clutter, but it’s a very fine line because like if you send me more than two marketing texts and I didn’t agree to it, like I’m pissed, you know? So it’s a fine line.

Yeah. You’re absolutely right. Like for SMS, you have to be a lot more aware, a lot more careful about that double opt in like, or even the opt in, like you want to make sure that whoever is opting in for that text that they actually agree to it. I think a lot of, even a lot of tools now, like. Like  they will have you in email marketing tool will have whoever’s receiver is actually type back.

Yes. I want to receive this. And if you don’t type back, yes, you won’t get any of the sequence moving forward. 

Yep.  Totally. Yeah. That’s why I always warn people. I’m like, if you aren’t a lawyer and if you aren’t, you know, a marketer.  Who’s dealt with this before I’ve worked at companies that have gotten sued for tens of thousands of dollars.

Um, then, you know, it’s just not worth it unless you know, and you are working with a company who is collecting those opt ins for you where there is a paper trail. Um, so that would be my only advice, but I think like.  You know, I don’t say that to scare anyone, but rather to say like,  SMS is great. But like, if you’re just going to start, like, just start somewhere.

Like, don’t, you don’t need to have the whole email strategy figure. You don’t need to have the whole marketing strategy figured out. Like I always like to say, marketing’s like an elephant. How do you eat an elephant one bite at a time? Like just start. Yeah. Somewhere like just take a bite, like,  and I, and I will back up even to say like, all this email stuff is great.

And I’ve talked to clients who were like, awesome. I’m sold. Like, help me create email content. When can we start? Can we start today? And I’m like, okay, awesome. Like how many emails have you collected? And they’re like, none. And I’m like, okay, well let’s back up for a second. First and foremost, just make sure That you are, if you have zero properties, if you have one property, if you have 50 properties and you’ve never collected a single email, like just put the pipes in place to start building your email list for you on your SMS, if you’re, if, if you have the capability for that.

So that would be my first piece of advice. You could do this manually. So you could do this. through like your VA collecting emails, or you could do it yourself. Like we were doing that in the beginning. That’s one thing I wish I did differently. And like one learning, which I like kick myself for, because I’m a marketer and I should have known better, but I didn’t get stay fi right out of the gate and I have a property that is six bedrooms that can sleep up to 12 people.

And so I was collecting one email per reservation. I probably could have been collecting 10 emails per reservation. And so that’s one learning that I had that I was like, God, like that’s embarrassing that me, the marketer didn’t think of that. But like, you know how it is in the beginning, you’re just trying to stay alive.

You’re just trying to not quit. So, um, so that’s one thing I would have done differently. 

I, I a hundred percent agree with you. We started with stay five pretty early on, uh, in our bigger cabin and we just started to roll it out into our smaller cabins as well because we saw pretty, pretty good traction with it.

So like, I a hundred percent agree.  Even before you start with your email campaigns, like you really need to start collecting those emails because you can have that pretty much on autopilot. And while you’re collecting those emails over the period of time, you can start to think about how you want to, to write out your sequences.

Yeah, yeah, totally. So it’s not to say it’s either or, but just make sure you have the foundational elements in place. And then once you start building your email sequences,  It’s fairly, you know, spend a, spend a couple hours, get them uploaded the right way. Um, and then, you know, it kind of does its work and you watch, watch the magic happen.

You can certainly optimize them as time goes along, meaning like, you know, test different things. That’s a little bit more sophisticated, but. Um, but yeah, I would say like, don’t, don’t trip. It’s like the question that I always hear is like from people getting started, like which, which, um, PMS should I choose?

Should I go with guests to your hospital or owner? And we spent weeks making this decision. I mean, I, I’ve, I was there at that, you know, not too long ago. And I say the same thing to people getting started in marketing. I’m like, just start somewhere like  somewhere. So that would be my biggest piece of advice. 

Yeah, I completely agree. So I think kind of like recapping, like for emails, there’s really two different types of emails that you want to be thinking about. There’s one that sequence space where someone is added to your email list and over a period of 200, 300, whatever, whatever period you’re, you’re in. 

with emails every month or so. And that’s really to stay kind of top of mind. And then you have your campaigns, campaign based emails, which is really focused on really driving  traffic back into your site specifically for moments in time events, whether or not that’s fall foliage things to do and in Christmas. 

I’ve had. Many hosts that try to like blend the two together and they get so tripped up because they’re trying to match their sequences with holiday stays. And like, how do I match that up? It was like, no, you can’t, that’s not, that’s not the most effective way to do it because in every, every quarter, even you might have to like change out your sequences, rather draw your sequences and those stay pretty much static and then start building out your campaigns throughout the year.

And have those as two separate pipelines almost. Yeah. 

Totally. Um, and you can schedule the campaigns in advance too. Like you can, you can, I could schedule a campaign today for a client that says 2025 calendar now open and schedule that for January 2nd. Like I could do that today. Um, but the ever, the camp, the sequence emails, the automated ones should be evergreen.

Like they should not be tied to a moment in time. If you’re going to tie them to a moment in time, have it tied to the moment in time relative to when they left, when they left your property. And by that, I mean, we have one of our emails that says, can you believe it’s been two months? That’s the subject line.

And it’s like, can you believe it’s been two months since you last stayed with us, but we’re not referencing seasonality. Cause we don’t know when they checked out.  We’re not saying like, it’s going to be through two months until Christmas. We’re just saying like ref, we’re only referencing the time that they checked out of our property.

Um, yeah. 

Yeah. That’s a, that’s a good way to scale it without having to put like too much nitty gritty into each email and have to feel like, Oh,  it’s been like two months since Christmas. Like that would be kind of hard to actually build out in a sequence. 

Yeah, yeah, it’ll just overcomplicate. And again, like the goal is here is to stay top of mind.

You don’t need to be the most sophisticated, you know, there’s, there’s, there’s people I work with in my day job who make a lot of money whose whole job is marketing automation. Like they do this at a very complex scale and create personalized journeys. But like, this is the one Oh one, one Oh two stuff.

And, and you can do this, anyone can do this. And so it’s just a matter of like, Deciding to do it, getting the pipes in place and either creating the content yourself, having someone create the content for you, and, and then you’re on your way, you’re now a marketer. 

Yeah. Yeah.  There’s one other topic that you, that we talked about in the past, which is, uh, social and how you leverage social effectively.

I wanted to, you kind of dive a little bit deeper into that, um, and talk about kind of  how much should you be investing into social? How much should you be really thinking about your followership? Um, and kind of like, how would you think about social when you have multiple properties as well? Yeah. 

Yeah, it’s a great question.

I think so. This is actually, you know, especially in the mastermind, a lot of folks know that I do marketing my day job. And so I get a lot of random questions like, you know, Hey, what do you think about this? Should I be doing that? When a lot of people think about marketing, this is the first thing they think of.

And that’s just because us as consumers, like we’re so online these days. Um, and for many brands, social media is a discovery tool, meaning it’s the place that you hear about the brand first. Like how many of us have made an impulse buy on Instagram or Tik TOK? Like there’s the whole hashtag, like Tik TOK, maybe buy it.

And so there certainly is a whole marketing strategy to be dedicated to that for certain brands. That being said, those tend to be impulse buys  and those brands tend to spend millions of dollars. I spend millions of dollars a month on these things, you know, in my day job, like that is not STRs. And so  you are not going to be.

The place on Instagram where someone discovers you for the first time, chances are. Now, there are certainly exceptions as there are to any rule, but if you are a new entrepreneur, if you are new to STRs, or if you are extremely busy, which I’m sure everyone listening is, and you have a fixed amount of time and you’re not passionate about social media and content influencer in the space. 

If you are great, if you’re not, then like social can play a very fixed role for you. And so this is what I tend, like 90 percent of the people who asked me this question, I tend to guide them in this direction. I say that  the goal of social media for you is essentially social proofing. It is validation.

It is that. When you see that little Instagram icon on somebody’s direct booking website and you click it and you see that these people posted on social media this week and you see that their Instagram is full and it looks good and it doesn’t look scary like some, you know, fake sort of like scam. And it just, it just is like a notch in your belt and it’s just a reason for them to trust you.

And so, that, and that’s the case for, you know, for myself. I know the way I shop. If I, I was getting my hair done, I was gonna get my hair done the other day and I found a, I found a hairdresser. And I had never heard of her before, found her on Yelp or something, which is like her equivalent probably of us on Airbnb.

And I was like, let me go search, let me go learn more. I went to her Instagram and she had an awesome Instagram feed and she like posted every, every week and she had great content. And I was like, Oh, I trust this. If I had gone to her Instagram feed and I saw that this one had not posted a piece of content in two years.

I would have probably thought twice. I probably been like, is this lady out of business? Or like what’s going on here? And so it’s not to say I definitely wouldn’t have bought or, or shopped, but it’s just to say that like, I didn’t have as much, I wouldn’t have had as much confidence in the experience I was buying.

And so, especially an experience like that, that tends to be very personal, just like vacations. And so I think all to say that you’re not going to, you know, your goal should not be to like, Create 10 pieces of hi fi content, meaning like highly produced content on Tik TOK or Instagram or whatever, every week, it should be what I like to say is one piece of content a week for six months, do that at a, like, aim for that and cross post the content to Instagram and Facebook.

If you do have a Facebook page and hire somebody or do it yourself. To build this in bulk and then use a social media scheduling tool. Some CRMs have them, you can find free ones online, um, and just schedule it out all in advance. So block your calendar for a couple hours, knock it out, and then never think about social media for the next six months.

So that’s my advice. Don’t worry about your followers. Don’t worry about just build a brand presence that you feel like is reflective of what you’re offering and don’t try and overcomplicate 

it. Yeah. And I think that’s exactly what we did with our social campaign. And I actually forgot that our sequences ran out at a period of time.

I scheduled it  four months in advance. So I, I spent like Yeah. And I completely forgot about it. And I was like, Oh wait,  I haven’t posted in like two, three weeks or I, I haven’t posted in two or three weeks. I had to go back and refresh it all again. But it doesn’t, it doesn’t take a whole lot of time to do that.

And especially if you’re aiming for like one, two, maybe even three a week, like it doesn’t take that much. Yeah. 

Yeah. And it doesn’t need, you don’t need over complicated either. Like we all have the beauty of our business is like the challenge for other businesses is they don’t have enough content. We all pay professional photographers to take photos for us every time we launch a listing.

And if you don’t, then that should be marketing. Step one is go get a professional photographer. Well, we all have these repositories of hundreds of photos. Use them, just use them. If you have photos that guests have tagged you in, obviously get their permission first. But if you have photos that your cleaners can send you, like it does, especially if you don’t co host in a market near your house.

But like my husband’s out there today doing a photo shoot. Like, and I was like, get behind the scenes content. Like it doesn’t need to be, you don’t need to overthink it. Like we had, we hosted friends at our cabin two weeks ago, um, for the first time, since we launched it, which was really fun. But while we were there, I was getting content of my friends going in the river and all that stuff in the hot tub.

Um, and I’m, I’m posting that. So all to say that, like, don’t overcomplicate it. Um, the other thing you had asked was what if I had, and I get this question, this is my, probably the question I get most frequently, like, Um, what if I have, you know, what if I own four properties in four different markets?

Should I make four different Instagram pages or should I make one Instagram page for my brand? My answer to that is always like, what are you going to, what are you going to stick to updating? Like, are you going to create? Content for four Instagram pages. The answer is almost always no. And so my answer to that is like, just do something, do something that you’re going to be consistent at.

And if, if after a few months or a year or whatever, you realize that like, you know what, I really think this property is so standout and deserves its own spotlight, and I’m going to build a page just around this property or whatever. Great. Do that. But like, just don’t.  Overcomplicated at the beginning, or it’s going to become so daunting that you’re going to be like, this is not the right use of my time.

I should be, my time should be spent prospecting or training my team or whatever. So that’s always what I say. 

Yeah. That’s a good tip. I never realized like.  What did you really need to do is make sure that you’re consistent on doing it for a very long period of time, because very likely you’re going to rent, you’re going to own that rental for many, many, many years.

And if you’re going to try to maintain even two or three different social accounts,  You’re going to stop doing it six months down the road and that’s not going to do you any good. Like then you’re going to have stale content across three different channels that you don’t want to update anymore.  

It’s also a great way to just cross promote.

Like if you own rentals, if you own, you know, one in the Poconos and one in the Catskills, like that buyer, there’s a lot of overlap for the person who might stay in the Poconos and the Catskills. And so like, it’s a great way to introduce across your different properties as well. 

Yeah.  Awesome. Lindsey, you dropped a lot of nuggets of information here that I, I got a lot of value out out of, um, I’m sure our, our, our listeners did as well too.

Uh, is there anything else that you want to share before we kind of go into  my last two questions?  

I would just say like the thing to keep in mind and I think the mistake a lot of people make is they aren’t, they, they aren’t mindful of where they like to spend their time or what their genius zone is meaning like what are they good at and what do they love.

And so they try to, they try to You know,  build a ton of content and they realize they hate it. And then the content ends up not really being great or it’s sort of off the shelf. And then their marketing doesn’t work. And they’re like, why doesn’t my marketing work? And so just remember, you’re only as good as your content.

So like there are plenty of resources out there that can help you create great content. There’s people who can do that for you. Um, I’ve helped a bunch of people with that. Um, Or, you know, just know that like, it’s, it, you are only going to be as effective as your content is valuable. So just keep that in mind.

Like you just can’t shortcut that. 

Yeah. You call it the genius zone, right? 

Yeah. Yep. 

Awesome. Awesome. All right. To, to round us out, I usually end with two questions. One is a mindset question and the other one is kind of a overall recap of it. Um, first one, what is one piece of mindset advice that you would give to anyone that is starting something completely new? 

Oh gosh. Oh my God. How much time do you have? Just kidding. Um,  mindset advice. I would say like the biggest thing that has transformed my journey as an entrepreneur has been just  Surrounding myself with people who like raise my floor, meaning like they hold me accountable and they  challenge me to be a better version of myself.

And so, um, you know, it helps you. I have found stay what I, a lot of people in STR secrets will say, like, stay in the content, meaning like when, when things start to get to. Get really hard, which they will, it can be really lonesome. And you could sort of do like the ostrich, like stick your head in the sand and like isolate, but that’s like the worst thing you can do.

Cause then you’re just like coming up with reasons why it was so much easier when you just worked a W2 job and didn’t like try and do all this entrepreneur stuff. And so my advice is  stay in the content, meaning like. You know, read, read the books that are going to challenge you to be better. I’m currently reading psycho cybernetics, which is like changing my life.

Um, say, you know, listen to the podcast and most importantly, listen to your coaches. Listen, I, I formed an accountability group. We meet every Monday. Um, we laugh together, we cry together. It’s like the, having that community is going to be the difference between you feeling like, what was me? Why did I do this?

I’m going to quit. This is too hard. And like, okay, this is hard, but like, I get to do this and I’m excited about this. And I see all these people around me who are doing it and coming out the other end. And like, I have faith that that too will be me. And so, um, my biggest piece of advice is like, surround yourself with community.

I love that. I love that. 


Awesome. The last question. What’s the.  One thing that you want all of our listeners to be able to take away from today’s show.  

My biggest thing that I would want you to take away is just to start somewhere when it comes to marketing. Like, don’t let it be the thing that you’re like, when I figure out X I’ll do marketing.

Like, because you never know when, you know,  You could get kicked off Airbnb not to be a fear monger, but like, you just never know. You never know when, um, you know, you could be leaving money on the table by not doing this. Um, and also you never know what’s going to come up down the line. Like there’s always going to be, there never is a, Uh, like a moment as an entrepreneur, at least in my short year and a half stint as an entrepreneur, there has yet to be a moment where I’m like, huh, I have all this free time today.

Maybe I’ll do some marketing. Like you have to be hyper intentional about it. And so my advice would be just start somewhere. Block a weekend, block a day, make it your one thing for the week that you’re just going to get your marketing system set up and, um, and figure out the other thing I’d say is like,  um, you know, one thing I’ve taken away from the mastermind is the book, who not how, like figure out who has the answers.

You don’t need to know how to do this yourself. You don’t need to know how to build a website or how to, you know, Create all this content or how to use a CRM, like find the people that know how to do it and pay them to do it for you. Like your time is worth more than that. So, um, that’s what I would want people to take away.

That’s awesome.  All right. 


Where, where can folks find out more about you? Stay in touch with you. 

Yeah. Um, so you can, um, Find out more about us on our website, stay booked.com, at stay booked.com. Um, you can email meLindsey@staybooked.com. Lindsey is with an ey ’cause people always, always get that wrong.

Um, and you could follow us on Instagram too. We have two Instagram handles for our own properties and for our property management business. Um, your stay booked or Cozy Mountain Rentals. Mountain. MNTN. So, um, we’ll drop all that down there, but, um, but yeah. Lots of places you can DM me on Facebook, whatever.

I’m happy to help however I can. If you’re like, Hey, this was great. But like, I still don’t know where to, where to start. Like I am more than happy to just walk you through that. 

That’s one of the things I really appreciate about you is that like, even within the few interactions that we’ve had already, You aren’t  trying to hold information back and you really want to see the people around you to be successful.

So, and I definitely like genuinely see that, like you’re sharing content without asking for anything in return. So definitely I’m, I’m really happy to have you on the show and I’m. Definitely folks. If you need help, reach out to Lindsey. So 

love it. Well, yeah, I mean, that’s the whole spirit of your show as well.

Like you’re sharing and giving all this away for your listeners. And I love that abundance mindset. Like, you know, we don’t need to gatekeep anything. And so, like I said, I’d be happy to share the, the, um, rebooking blueprint that I designed for my own clients and for my business. And you could just like.

You know, delete stuff and make it your own. Um, so just reach out to me in one of the 75 ways I just listed.  I’ll get that over to you, but thank you so much for having me. This was a lot of fun. 

Thank you, Lindsey. 

Awesome. Bye. 


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