12. Bold Hospitality: Building a More Profitable STR Business

In hospitality, playing it safe can feel responsible — but it can also keep your business stuck.

In this episode of STR Sovereignty, we explore the entrepreneurial mindset required to build a stronger, more profitable short-term rental business. That means being willing to take thoughtful risks, test new ideas, partner with other innovative companies, and move faster than operators who are waiting for the market to get easier.

We’ll talk about why the best hospitality entrepreneurs don’t try to do everything alone, how strategic partnerships can create better guest experiences and more direct revenue, and why the willingness to experiment may be one of the biggest advantages an STR operator can have right now.

This episode is for owners, operators, and hospitality leaders who want to build with more courage, more leverage, and more upside.

Transcript

SPEAKER_00 0:02

Welcome to the STR Sovereignty Podcast. My name is Steve Hasi from Yada. I'm here with my co-founder and CEO, Peter Oydrovich. And today we're going to talk about bold hospitality, building a more profitable STR business. Now, in hospitality, it feels like you should play it safe. You want to make sure that the guests are taken care of. But the fact is, playing it too safe can have your business stuck. We're going to talk about the entrepreneurial mindset that will help you build a stronger, more profitable short-term rental business. We're entrepreneurs over here at Yada, and the best operators that we work with share certain things in terms of how we're building the company. And we just want to share some of those secrets with you in hopes that you can be more bold with your hospitality and build a better STR business.

SPEAKER_01 0:52

Yeah. And, you know, I just want to add here that every business at the end of the day is an entrepreneurial journey, whether you're Hilton or whether you're, you know, a two or three-door operator, it's all a really, really, really engaging, dynamic entrepreneurial journey. And having that energy and that willing to make bold bets and willing to take risks and willing to try new things and look to the future is one of those things that every successful operator shares and every successful company shares. I mean, even enormous brands that have global portfolios like Marriott and Starwood and Accor make bold bets. They try new things, they look at new channels, they attempt different brands and products, like Moxie is a new product that was that was created to target inner city, uh, city travelers and business travelers. So if the largest hospitality brands on the planet have the guts and have the desire to take big risks and make big bets on what the future is going to look like and how they can improve their business and continue on this entrepreneurial journey, even after being around for 120 years, uh, operators that have been around, you know, less than five years should also have that same and like a tenfold increase on that desire for growth and that desire to try new things and that desire to make big bets.

SPEAKER_00 2:17

That's powerful stuff, man. And what it brings to mind is if someone is selling you the playbook for how to do this, they probably don't actually have it, right? They're probably making it up to try to get paid. Um, because this is about you and your business and what bets have not been taken yet. If someone's saying, I know the bet you need to take, don't listen. You know, that's that's why the process of thinking about this, the process of really sitting with what's unique about my operation, what's what hasn't been tried in hospitality yet, where can we go? Those are the directions to start looking for your own bold bets.

SPEAKER_01 3:00

Yeah. Why do you think it is, Steve, that that you know, sometimes we'll talk to folks who've been running uh a property management like a PMC for you know four or five years. What is it that that that sometimes slows folks down from continuing on that entrepreneurial journey and you know being as nimble and agile and driven in years five or six as they were in years one and two?

SPEAKER_00 3:23

Well, success has its own downside, right? If things are working, the temptation to rock the boat goes down, down, down. Yeah. And you know, that's why it takes a level of discipline and a level of um just kind of forcing the issue in terms of trying new things, especially if you're successful, because you're like, but it's already working, you know, trying new things is hard, trying new things might fail. But that is the only way to ensure that the brand will continue and that you can have those growth levers.

SPEAKER_01 3:56

Do you sometimes feel like um you know, in software, we we have to be, I don't want to say paranoid, but we have to stay on our toes 24-7 because things can move pretty quickly. And, you know, at Yada, one of our big um obsessions is to continue innovating day and night, year after year, month after month, like never really step off the gas. Do you think that in in hospitality businesses, sometimes the pace of of change uh leads to some like a significant degradation of the entrepreneurial mindset because uh it's not as obvious the need to innovate and the need to drive forward? Um do you think this is something that that hinders operators or it's something that helps them kind of stay relevant or or kind of not make the mistakes that could damage their business? Like how how do you how do you think about that? How do you feel about that?

SPEAKER_00 4:54

Yeah, it is interesting because there's definitely differences. If you're working in software and you mess something up, you just roll it back. Yep. You've got little areas that you can experiment with and it's not gonna hurt anything. You just kind of test it with a test account and see how it goes. If you're working with a building, if a property and guests, like there's a lot more at stake than, you know, do I need to roll these lines of code back? It's like, did I just wreck this relationship? So I think it feels like there's more at stake. But really, that same principle that we use for building a great software company can be used for building a great hospitality business. You don't roll it out to everything on day one just because you had an idea. Yeah. But you want to find out what is that minimum viable product? You know, whether it's a guest experience that you're rolling out, a new marketing channel that you're rolling out, start with something small, start with something kind of over on the edge to see how it works, how do people respond to it? And once you get more data, then grow it from there. So there's ways to innovate quickly without risking relationships.

SPEAKER_01 6:06

Well, I also think like the risks that a lot of folks think about are not really as risky as um one might think they are. So we talked to a lot of operators uh who are willing to kind of rock the boat. I wouldn't even say rock the boat, but like willing to grow uh their marketing operations at scale. And then we talked to some operators for whom the potential of like overstepping and overreaching uh overrides their desire to grow. And I think this is frankly, uh, you know, it's kind of like um at odds with being an entrepreneur uh and and and continuing to grow a business. I think if you're, you know, if there's more of a concern with overstepping and overreaching than there is with doing everything that you can possibly do to grow direct bookings, to grow repeat bookings and all of these things. I think entrepreneur, like it's not gonna be something that you're gonna be able to sustain for five, 10, or 15 years, just because there's always gonna be a competitor. There's gonna be someone in your market, someone in your area, someone who has a portfolio similar to yours who's willing to make those plays and willing to move quickly and willing to move at scale and in a large way that can then come in and overtake you. And um this, you know, I would I would just kind of put together a word of caution for for all of our listeners here, you know, uh primarily around um having this hesitation of overreaching and over-messaging and over-marketing. Uh I think that's a very false um fear, and it's a really unfounded fear that is it really is at odds with growth. You know, if if if Marriott, which has probably some of the biggest brand recognition on the planet, can send me like five or six emails a week about offers and rewards and things like that. I don't think anyone should, in the short-term rental space, should feel an ounce of hesitation about messaging around availability, like messaging around offers, messaging around portfolio performance, like where to go, things like that. I just don't think I I really like I will die on this on this hill. I don't think that there's any downside what's you know, to being, yeah, I'll try not to, but there's like no downside to being very, very, very um like volume driven around this, to be honest.

SPEAKER_00 8:43

Yeah. And we had a conversation recently where where the concern was, well, but we have kind of a once-in-a-lifetime uh bucket list location, right? People don't come back to our location. Like there's always a reason why you may not want to do marketing. Like, oh, uh our properties are very high-end luxury, the the touches need to be very uh personal and very bespoke. We shouldn't do marketing around that. Um, our properties are very low end and kind of budget. Like, why would we market our you know, micro tel versus uh something else? Yeah, so many operators have this uh mental block around why they shouldn't be marketing. And that is something to pay attention to. Yeah, those hesitations to building your brand come up, then that is work that you need to do kind of on your own mindset and like what is the purpose of your business? Because you will not be growing as strongly as someone that does not have those same mental blocks. If you just think about the amount of money that a big brand will spend just on name recognition, it's absolutely astonishing.

SPEAKER_01 9:55

Yeah, many orders of magnitude.

SPEAKER_00 9:57

Yeah, and so as a smaller operator, the fact that we have these direct channels that you can send a WhatsApp, you can send an email, you can send an SMS, and you can personalize it to that individual. And the very worst thing that will happen is your brand will be more present in their mind next time they think about a trip. That is a lever that you need to pull if you are going to be a bold operator who grows in the future.

SPEAKER_01 10:23

Yeah. You know, I think what we're touching on some pretty, pretty important things here, Steve. And um, you know, I just want to bring this point home that entrepreneurship is not like being timid and being an entrepreneur are two things that cannot coexist in the same space at the same time. Being timid and being an entrepreneur is a guaranteed way to get lapped by competitors, to get lapped by um by anyone else who's competing in your market for the same eyeballs and for the same space. If you are a luxury rental entrepreneur and your client list is on the call list at four seasons, believe you me that they will have an army of reps sending notes, calling in, sending texts, making sure that you stay with the four seasons instead of staying uh at one of your luxury properties. Being timid about reaching out to those people and building that relationship essentially guarantees that that one interesting idea they had to stay at an Airbnb and stay at a big luxury villa instead of booking four or five rooms at the four seasons. If you don't keep them wanting that and build that relationship, they're gonna they're gonna go back to the brand they know and and they'll they'll step back into their comfort zone just because you step back into your comfort zone.

SPEAKER_00 11:51

Yep. So so entrepreneurship is about that kind of anti-timid reflex, like running towards the danger. Um it's also about creativity, right? Because sometimes folks will say, Oh, I don't know how to um, I don't know how to uh uh reach out. Like, what am I supposed to say? The machines can help you, you know, feed some ideas into the AI. The AI will give you some ideas on what to say, but also like you know your business better than anyone. Some of the best ideas I've seen have come from operators who are just thinking, they're just cranking on like what would be interesting? How can I engage people? So, as an entrepreneur, bold hospitality means you're on that wheel of creativity, of sparking ideas that say, what do I want to talk to people about today? Because there's always something that you can share that will engage people with your brand instead of the others that are out there as options.

SPEAKER_01 12:46

Yeah, you know, I think uh short-term rentals, building a portfolio, building a great company is an entrepreneurial journey. It never ends. There's no such thing as the finality to an entrepreneurial journey. Um, you have to stay smart, you have to continue innovating, you have to stay hungry, you have to stay with the times. You can't, you know, what worked five years ago doesn't necessarily work today. Um, and you can't be timid about it. You it's yeah, yeah.

SPEAKER_00 13:16

So to that end, we actually created something new and awesome to help people do exactly this. We're now doing a weekly marketing mastermind, and this is this is sort of like an advanced preview. Right now it's only open to Yada customers. Um, it's free with your Yada subscription, so we don't charge extra for it, but it is a space uh guided by us, you know, me and Peter, and uh attended by some amazingly competent and creative and successful entrepreneurs who are building their STR businesses with some remarkable marketing. Uh so that is a space for people to trade notes and kind of pump up that entrepreneurial spirit, give other folks confidence that they can do it, um, trade ideas about what's working. So we are super pumped about that, and and so are our customers. So if uh if that's something you're looking looking for, you can become a Yada customer and join us there. At some point, we might open it to the broader public because it is something that seems like it needs to be there. We're not gonna say that we have the answers. We do have great technology, but ultimately we build based on what people are trying and what people are getting results from. Uh, and so yeah, it's it's very much uh a dialogue in how do we create the next iteration of a hospitality business in short-term.

SPEAKER_01 14:37

Absolutely. What a great session! You know, really looking forward to seeing as many of you as possible on that masterminds next week and listening into what we have to say. And good luck on that entrepreneurial journey. Take the bets, be bold, be strong, move quickly. It will pay off every single time.

SPEAKER_00 14:55

Thanks for listening, everybody.

SPEAKER_01 14:57

Thanks for listening.