Stop Chasing Tactics: Grow Your Direct Bookings with Chantell Hammond
The Short Term Show
October 21, 2026
On this week's episode, Avery is joined by Chantell Hammond, founder of Strategy Square, to discuss how short-term rental owners and property managers can grow their businesses through smarter marketing and direct booking strategies.
Speakers Chantell Hammond, Avery Carl
TopicsInvestingBusinessEducationHow To
Chantell Hammond (0:00)
If you are 100% reliant on those OTAs, you don't really own a business. The OTA owns your business, right? Like you might own a property or a contract with a property owner, but you don't actually own the business if you're completely reliant on them. And that can be scary for property owners and managers to recognize that they're completely reliant on these OTAs. And if something happens there, their business could be gone the next day.
And you don't have to live that way. You don't have to live in that fear. There are clues in your business that can help us build something out so that you can have a little bit more security in what you're doing.
Avery Carl (0:45)
Hey, y'all, welcome back to an episode of The Short Term Show. As always, I'm your host, Avery Carl. And today we have a very cool guest named Chantell Hammond. She is the founder of Strategy Square, which is a marketing company that helps small businesses, particularly interesting to you guys, short-term rental hosts who might want to do some marketing for your direct booking website. So we're going to have a conversation with her today. How's it going, Chantell?
Chantell Hammond (1:10)
It's going good. It's great to be here. Thanks for having me.
Avery Carl (1:13)
Yeah, thanks so much for coming on. Let's start by just telling our audience a little bit about you, how you got into this and what you do.
Chantell Hammond (1:22)
Yeah. So like you said, I'm the founder of Strategy Square and I help short-term rental owners and property managers strategically grow their businesses. So I get to help them uncover the strategy that's already hiding in their business so that they can build towards their goals.
I do that by helping them read the clues that are already there and helping them see those things that I think are really easy for us to overlook, because those tell them exactly what they need to be doing next to grow.
Avery Carl (1:56)
Awesome. Love that. So how does that translate over to maybe a short-term rental owner, host, or property management company?
Chantell Hammond (2:05)
Yeah. I think it really translates by showing people that success leaves clues. And even if you've gotten started on an OTA, and you're having some success over there, as long as you're having any kind of success with your properties, with your portfolio, there's clues there that can help you build outside of those OTAs and help you understand what you can be doing so that you're not completely reliant on the OTAs for your business, which is really important because if you are 100% reliant on those OTAs, you don't really own a business. The OTA owns your business, right? Like you might own a property or a contract with a property owner, but you don't actually own the business if you're completely reliant on them. And that can be scary for property owners and managers to recognize that they're completely reliant on these OTAs. And if something happens there, your business could be gone the next day.
And you don't have to live that way. You don't have to live in that fear. There are clues in your business that can help us build something out so that you can have a little bit more security in what you're doing.
Avery Carl (3:17)
Awesome. Love that. I think we all, all the listeners understand for sure the value of having a direct booking website and being able to get clients, customers to come directly to them.
So what are some ways that you, your company can help with getting some marketing done, driving some leads to those direct booking websites?
Chantell Hammond (3:40)
Yeah. There's a lot of ways, there's a lot of tactics that we can leverage. I like to talk about pulling different levers and helping people understand that there's hundreds of levers out there that we can pull. But in terms of which ones are the right ones for people to get more direct bookings, again, that's going to depend on the success clues that are already in your business, which is going to be different from one property owner to another, depending on the type of property, the market, the different locations, and the type of guests that are staying at your property and what they're looking for.
I don't struggle. I always struggle knowing which ones to start with. When people ask me, well, what can we do that's a blanket statement? I'm going to, if it's okay, give you an example. Yeah. This is very specific for one specific direction.
What I'm seeing is a lot of owners are seeing one property, for example, maybe somebody's got a property that they've set up that is getting 60 percent direct bookings. One of the levers that they're pulling is maybe social media marketing. What happens frequently is I see a lot of property owners are thinking, well, I have to get into social media. Social media is the secret to increasing my direct booking. What happens in that case is we see a lot of property managers, property owners that are chasing the success that they're seeing other people achieve. When they're doing that, they're actually just chasing one tactic to another, and they're not even paying attention to their own business. What we need to do is take a look at your own business.
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