15. When is the best season to market your STR?

The best season to market your short-term rental is this season.

In this episode, Steve and Petar explain why STR marketing should continue during high season—not wait until occupancy slows. Busy periods are the best time to capture guest contact information, build direct relationships, seed repeat bookings, and turn today’s stays into shoulder- and low-season demand.

Key takeaways:
• Why marketing belongs in every season
• How high season helps build your guest database
• Why direct guest relationships outperform OTA-only relationships
• When delegating operational work creates a higher return than doing it yourself

Learn more at https://yada.ai/demo

Transcript

SPEAKER_01 0:02

Hello, everybody, and welcome to the fully booked STR podcast. My name is Steve Hasi. I'm a co-founder at Yada. I'm here with my colleague Peter Oydrovich. And today we're going to talk about when is the best season to do STR marketing.

SPEAKER_00 0:18

Peter, are you ready? I am so ready because this is a topic that's super interesting and it's a topic that a lot of folks have misconceptions around. And it's one that we have some pretty good insights actually from our careers in startups and around startups. And you know, there might be some some nuggets in there that that are pretty applicable and that that line up with, you know, when should people do marketing?

SPEAKER_01 0:44

Yeah. I mean, the the short answer if we just dive right into it is all the time. All the time. The best season is this season. Um, but let's let's get into the details because sometimes when I talk to people, they'll say, oh, it's the busy season right now, I don't have the bandwidth. Um, how do we help people get over? Like, I don't have the bandwidth. Like, why does that not make sense?

SPEAKER_00 1:05

So what's important to keep in mind is that marketing and and and driving go to market is the lifeblood of every business. Um, if we look at just businesses across the board, 90% of new businesses will fail within the first couple of years. And of those that fail, like it's almost entirely due to not making enough money and not making enough money consistently enough. Like business basics are very, very cut and dry and very, very straightforward in that regard. And the the the takeaway here is that making more money like is uh you know very, very directly correlated to how well you do marketing and how much marketing you do and how much you get yourself in front of your customers, past, present, and future. So, you know, when when somebody says, oh, it's like really high season right now, we don't have time to do marketing, or any sort of you know, growth activities, the reframe should be like, yes, it's gonna take a little bit more time to spin up a marketing engine, but that's gonna make sure that high season stays high season for longer and that low season and low occupancy seasons are not as bad as they usually are. So, you know, you don't want to wait for low season to start trying to fill low season because it takes a couple of weeks and months and cycles to get people to make their bookings and come back and things like that. Um, so you really want to be proactive about it and start doing it ahead of low season ahead of and ahead of the slower seasons.

SPEAKER_01 2:39

Yeah. The key really is to find a way to carve out the time now. And that is a mindset issue for you as a leader at your company, for you in terms of how you schedule your time. Because, yeah, when when people are knocking down your door and the you know room, you know, occupancy rate is high, it's gonna feel like the last thing on your priority list is to get more people in. Like the people are here. But what happens with STR marketing is you need a good database, you need a good system in place. And the high season is the best time to improve your database, to make sure you're capturing people's contact information so that you're ready to bring them back when it is the shoulder season, when you're prepping for next year's high season. If you don't start that while things are happening, if that's not in place during your high season, you're gonna have to work a lot harder to get that in place, you know, when those guests aren't flowing through.

SPEAKER_00 3:48

Yeah, yeah. So, you know, the moral of the story is if we start off this conversation with anything, is that you know, high season is great because you're super busy. High season is an is an indication of what peak demand looks like. So you know what your your limit is, and then the goal is to use high season not just to survive it, but use it as a way to set up repeat bookings and return bookings during low season and low season. So another uh point that I want to make is that high season is the best time, like while while people are traveling and visiting and making great memories and and um you know having a great time at your properties and and and uh you know doing their vacations, like high season is is is is the time to put the seed of a repeat booking uh into their minds and to get them started on the journey of interacting with your brand directly instead of interacting with your brand through an OTA or a marketplace, so that when you do reach out to them in six months or eight months, or even when you reach out to them in like two weeks or three weeks after they leave and start that direct relationship, that you're top of mind, front and center, every single time that you message with them and that they know who you are.

SPEAKER_01 5:03

You know what else is good? I guess this whole thing is kind of turning into a why should you carve out time for marketing during high season? If you're inviting people to come back to your properties and they look at the calendar and they see that it's really full, that's like that's the proverbial line outside the door and around the corner. That is only ever a good thing. When people know that you are popular, that you are premium, that people want to book with you, that is the ultimate social proof. And so even if you're even if those messages aren't going to drive bookings now, or even if some people might be um you know disappointed to lose out on their favorite property because someone else has booked there, that creates desire down the road. That creates exclusivity and um that social proof that will have them coming back to you rather than searching around for some other random place.

SPEAKER_00 6:00

Yeah. I also want to add something like I, you know, of course, we focus a lot on like what tactically short-term rental operators can do to grow. Um, but I want to take a step back a little bit and really uh, you know, this is sort of like a direct conversation with the folks that are listening and that are watching. Um, and that is that, you know, at some point or another, there has to be a very clear distinction and a choice between what kind of business you want to build. Uh, if something is gonna be a side hustle, then your high season is gonna be busy, your low season is gonna be slow, and and you just treat it as a side hustle, and that's great. Um, in which case you probably don't even want to bother with marketing, or you, you know, it's just not something that's really gonna make a big difference for you uh if you're not willing to put in the cycles and put in the effort. Um but if you really treat your short-term rental business as a business and you have the goals of driving uh significant growth, you know, whether it's portfolio expansion, whether it's uh increased occupancy, average daily rate, things like that, these are these are things that require time and effort, and they're not super easy. Like you need to invest the time to spin up a platform like Yada, even though it is super easy to aggregate your contact lists and get all of your CSVs and Excel sheets and things like that. Uh, but the point that I'm trying to make is that the effort is extremely worth it when you zoom out and look at it over the span of like six months or a year. And this adage that I always go by in business building is that if it's easy or if it's if you're having a good deal of success, then you're not working enough and you're not doing enough. So when you look at high season and you're like, oh, this is amazing. Like I'm getting 95 or 100% occupancy, and people are paying quite a bit to stay with me, and I'm getting five-star reviews left and right and all over the place. It seems like things are going really well, and they are for that movement moment. But every single one of those moments where you're thinking to yourself, hey, things are going really great, high season is really good. It's like 10, 15, 20% better than last year's high season. Zoom out on the calendar and then zoom in on low season, like take two or three weeks during low season when it's at like 10% occupancy or 20% occupancy or 30% occupancy, and put yourself in the shoes and in the mindset of looking six months or eight months in advance to see what you can do to improve that uh that cash flow six or eight months from now. So, in pretty much every business, whether it's a software startup or a construction company or an HVAC company or a short-term rental business or an airline, you know, you can't only look at what your cash flow looks like and what you're doing for your cash flow like in the immediate present. You have to look down the road and you have to be very intelligent about what you're gonna do down the road and very decisive about what you're gonna do right now, so that those moments down the road where occupancy is low are not as bad as they could be. And that's really the name of the game. It's like low season is always gonna be slow, but it doesn't have to be that slow. And it's always gonna be slower than high season, but it doesn't have to be that much slower than it usually is.

SPEAKER_01 9:15

I love that. Uh honestly, that's one of the reasons I love working with you, Peter, is that fighting spirit where you just don't accept your fate. Like I'm gonna fight my, you know, what what the world says is my fate, and I'm gonna make this thing work. And and that is what everyone needs as a founder, as a business leader. You need to say, no, the low season will be lower, but it doesn't have to be bad. We don't have to suffer during the low season, and what can we do to change our fate? And so um what that's one of the reasons that we launched marketing, or not marketing, uh loyalty uh with Yada, so that when people are earning loyalty points during the high season, during their stays in summer or winter, whenever's the great place to come visit you, uh they can redeem them and get extra bonus for those points during the shoulder season, during the low season. So then you are as a STR owner and leader um creating that demand for those times when otherwise you just have to shrug your shoulders and say, well, I guess this business sucks this time of year. Uh there are tools out there that can help you improve those uh those dips.

SPEAKER_00 10:26

Absolutely. And you know, it's it's on it's the onus is on you to use those tools to again do everything that you can during your high season so that you're set up for low season for it to be better than it was last year. So if we kind of go back to what we started this conversation with, which is you know, it's high season, is this really the right time to do marketing? The answer is that high season is the best time to do marketing because the high season will take care of itself. Shoulder season, off season, and low season that need that need help.

SPEAKER_01 10:59

Yeah, and it's an interesting business question in terms of ROI. Like if you take some of your time and resources away from the normal stuff that you're doing during high season, maybe you're helping with the cleaning, you're doing some turnovers, maybe you're helping with ops, you're managing personnel, whatever is taking your time when things are crazy, and you put somebody else on that. Maybe it's a virtual assistant, maybe you increase headcount during the high season. So you're you're kind of adding expense. But with that time that you just bought yourself, you put marketing into play to bump up the shoulder and bump up your low season, the ROI on that is going to be much higher than the cost of replacing yourself for that kind of headless chicken work that you'd otherwise be doing when things are really busy.

SPEAKER_00 11:48

Because again, you know, as a business leader, your your goal is growth. And you you really have to delegate out the things that take up a lot of time, but that are linear, right? Like every hour that you spend managing cleaners has linear returns, right? Like you spend an hour managing cleaner, cleaners, you get one more hour of of work out of them. But during high season, like every hour that you spend running marketing has exponential returns as it layers in the messaging that you're sending out, the loyalty reminders, the rewards, the points, everything like that. So yes, like building the database, um, you know, finding those those avenues to get contact info and to build those direct direct relationships with the guest, that has a compounding uh effect over time. So the logistical stuff that that seems really tempting to do in the moment is really important and it has to be done. But let's be honest, like a lot of it is busy work that compounds linearly. Like growth and marketing compounds way more than linearly over time. So it's so it's it's you know, if if I was, you know, Steve, we both mentor startups as well. We we we mentor other founders and and builders, and and I think that the biggest piece of advice that we would give them is to focus on the stuff that is gonna have the biggest outsize impact on your growth trajectory and on your your uh your ramp. So yeah, you're hitting those ramp moments faster and and and easier and better.

SPEAKER_01 13:28

Yeah. And so if I were to offer any mindset um reframes for the high season, for the busy season, it's that basically taking what you said and turn that into your own kind of uh principle. Like my time is best spent on things that will help us compound our returns, on things that will help us grow exponentially rather than just staying busy because I'm a body on deck. Um when you see yourself as a leader and as a builder of your business rather than just a body who's available for work, then you will be able to find the time to do the marketing and to set up the systems and to you know take things to the next level, regardless of the season, because hopefully your business is going to be here many more seasons in the future. And by making those low seasons stronger, it's gonna make it much easier for future you as well.

SPEAKER_00 14:28

Totally. Very, very critical stuff. Focus on growth, do the marketing during high season, build the relationships with your guests so they understand your brand while they're already there, reach out to them right after they leave to get them enrolled in loyalty, to get them aware of you as a brand, and keep that momentum high on last year's guests this year during high season so that they come back during children low season.

SPEAKER_01 14:57

Yeah.

SPEAKER_00 14:57

And if it's low season for you while you're listening to this, also do marketing.

SPEAKER_01 15:02

Yeah. I mean, this is when you tend to have a little more time on your hands. You're kind of taking some time to set up those systems. Um now in low season, cash might be a little tighter, right? Uh STR businesses often have you know big uh capital expenditures, maybe for remodels or for uh taking on uh acquisitions or whatever it might be. So maybe cash is a little tighter. Um, it's still the sort of thing where when you look at how marketing compounds over time, you got to put on your business leader hat and decide how best to invest for the ROI that you're looking for.

SPEAKER_00 15:42

Yeah. So I guess to make it even simpler, what's the best time to do marketing? All the time. Every single day, every single season, every single week.

SPEAKER_01 15:51

Yeah, some of my favorite stories are from companies who during economic downturns, recessions, even market crashes, take those opportunities, like they're ready for them. They've got money in the bank. Because as soon as those things happen, their competitors will shrink back, they'll do less marketing, they'll do less advertising, they'll cut headcount. Yeah. The great stories are the people that lean into that. When other people are afraid, they jump in and act aggressively because they know that everyone else is getting quiet.

SPEAKER_00 16:24

I'm trying to think of the statistic, but I distinctly remember that like I think it was called The Innovator's Dilemma or Outliers, or one of these books that I read. But like the vast majority of companies that have been around for more than 50 years and that have been very successful for a long period of time are companies that built their culture during recessions, during depressions, like during moments where they took the opportunity when things were not like when things were slow to move faster and like move better, and then took the opportunity while things were hot to build out like business multiple years in the future so that they avoided like really hurting and having to downsize and uh and not be able to move as quickly during those slower moments. So it's like all the time, like slow moments, they use slow moments to get ready for fast moments, and then they used fast moments to minimize the impact of slow moments and and um kind of weather them as best as possible and make them as as beneficial as possible.

SPEAKER_01 17:27

And so I think the um the mindset to have as a business leader around marketing, but like growth in general, is to be the captain of your ship. Yeah, to not be a victim of now it's high and I don't have time, now it's low and I don't have money. Like figure out how to make it work regardless of these challenges. That is the that's the challenge of business, that's also the fun of business. Like that, like you were saying, Peter, if it's all just easy, you're not you're not uh you're not digging in enough. So uh realizing that the difficult times, whether it's you're too busy or you know things are too lean, that's what defined the business that you're creating and you as a leader.

SPEAKER_00 18:13

Yeah, agreed. That's uh that's all there really is to it, you know. Just keep growing, stay fast, don't slow down and use the moments when it's busiest and when it seems most hectic to really double down and show yourself and show your team what you can do and how you can do it.

SPEAKER_01 18:34

There we go. All right. Well, thanks for listening. We'll talk to you next time.

SPEAKER_00 18:39

Until next week.