November 10, 2026
Staypineapple’s Plan to Cut OTAs Out of Hotel Bookings
When online travel agencies gained control of hotel bookings, the industry gave up more than commissions. Now AI presents another major change in how travelers discover hotels, and independent operators face some important decisions.
At The Hospitality Show, Glenn Haussman speaks with Dina Belon, President of Staypineapple Hotels, about her plans to connect the company’s booking system directly to AI platforms and bypass online travel agencies.
Dina explains why AI search offers independent hotels a different way to compete with major brands and what she wants hotel operators to understand about direct bookings. She also raises an important issue that often gets lost in discussions about distribution costs: the guest information hotels surrender when travelers reserve through third parties.
Hear how Staypineapple Hotels plans to approach AI booking, what that means for the guest relationship, and why Dina urges independent hoteliers to prepare now.
Thanks so much to Entegra for supporting this podcast. EntegraPS.com, your GPO partner in hospitality.
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Transcript
Glenn: [00:00:00] Hey, everybody. It’s your hospitality friend Glenn here on the show floor at the hospitality show. I got our friend Dina Bolen over here. You know her as president of pineapple. Say, pineapple, what am I? I’m having a hard time this morning, but that’s okay, because we are sponsored by our friends over at Entegra. Check them out at Entegraps.com, your GPO partner for hospitality. Yeah, I got that right. How are you thinking about things these days when it comes to artificial intelligence?
Dina: [00:00:26] It’s all anybody is talking about.
Glenn: [00:00:27] I know I’m actually I’m actually required by law to only talk about that now.
Dina: [00:00:32] Oh, yeah. So we are really excited about AI distribution in particular, right?
Glenn: [00:00:39] Because my hunch is it kind of puts you on that level playing field. And for a brand that doesn’t have widespread distribution of some of those names, you know, out there, that’s pretty important stuff.
Dina: [00:00:50] It is. And you know why? One particular reason, because guests that are using an AI are not, are not asking room night where I’m staying, right. They are asking I want something unique and different and quirky and I want a great bar experience. Right?
Glenn: [00:01:07] Oh, I like that. Did you just take that ChatGPT thing from me? Because I do want everybody to know I’m staying at an independent hotel here, and I did that sort of thing. Exactly. My parameters were a little bit different, but I was like, I wanted a balcony. I wanted to make sure it had a sense of quality to it and all of that kind of stuff, and boom, boom, boom. It made me consider things I never would have before. Right.
Dina: [00:01:27] 100%. Because it’s not a giant list that has prioritized every Hilton and Marriott in the area in it because they pay the higher right marketing rates. Right?
Glenn: [00:01:37] Yeah. And you can’t necessarily do that because you’re a smaller upstart company, but you’re nimble.
Dina: [00:01:43] We’re nimble.
Glenn: [00:01:43] And you can you could use technology to, like I said, equal that playing field. So how do you think that’s actually going to work for you and start to get more in that customer zeitgeist and get more share stays from them?
Dina: [00:01:54] So I’ll tell you what we’re doing. By the end of the year, we will have our brand new website launched, which is AI native with our own MCP that will connect directly to the ChatGPT of the world and all of the other ones. And you’ll be able to book directly to us and not through an OTA on an AI, which is really important to our sector. And I am talking to all the independents out there. Please, please do the work. It’s a lot of work. It’s a heavy lift, I get it, but it’s super important for you to compete.
Glenn: [00:02:30] Right.
Dina: [00:02:31] And not get lost in the noise.
Glenn: [00:02:33] This no hyperbole is a once in a generation opportunity. All right. I’ve said this before, so I’m sorry if you have to hear it again. But we lost that opportunity in the dark days after nine over 11 when the internet was really surging. The major hotel brands, they didn’t know what to do, so they ceded a lot of the booking opportunity to third party providers. And the industry has been paying a cost for that ever since. They’re not bad. They’re great for strategy, but we’re talking about ultimate control over your product. This gives us an opportunity to get that back.
Dina: [00:03:04] And the guests to be your guests, not their guests. Right? That’s a whole nother piece of the independent boutique space. Like what is so important to us is the pre-arrival process. Like our guest experience starts well before you show up at the hotel. And I can’t do that with OTAs because they won’t give me the information. And so when you book direct with us, the experience is completely different than when you book with an OTA.
Glenn: [00:03:30] So that must be just frustrating. Very frustrating, right? Because you can’t create that impression that you normally would be able to. And you’re almost like, got that one hand tied behind the back.
Dina: [00:03:39] Exactly, exactly. Instead, you show up as a, a black box to me at the front desk. And I’m trying to then then we’re back on our heels right where in our direct booking guess which? We’re very lucky. We worked really, really hard at it. About 55% of our bookings are direct. Wow. And so more than half of our guests walking in the door we know a lot about. I know your psychographics. I like know what you’re passionate about, and I can formulate an experience that’s unique to you. But I can’t do that if I don’t know.
Glenn: [00:04:10] I know, I think I’m gonna be staying with you guys in January, so I can’t wait to find out what that’s going to be like. All right, before we wrap up, we’re talking about technology and stuff like that, and we’re hanging out with our friends over at Integra. How are you thinking about procurement and stuff like that when it comes to this new level of technology?
Dina: [00:04:23] It’s a huge part, right? So we need to be able to if I’m going to personalize your experience and I know so much about you. First of all, I’ve built an expectation, right? Right. Now you expect me to do that?
Glenn: [00:04:35] That’s a really good point.
Dina: [00:04:36] It is. And I need all of the partners that we work with to be able to help me in that workflow, including procurement. Right? Yeah. If I need something specific for you, I need to be able to get it. And again, if I have that information a week or two in advance, I can reach out to Integra and go, I need this thing that’s special for this gas and I need it by this date. If I don’t have that information until you show up, I can’t do that. I can’t help me, and I can’t do what I want to do.
Glenn: [00:05:05] All right. So I want you guys to tune back in in January. We’re going to find out whether I’m not if I’m the most difficult guest that state pineapple has ever had. All right. Does that look good. Sound like a good plan? That’s fair. Anything else you want to say before we wrap up?
Dina: [00:05:18] Really enjoy the show. I think Ala has done a great job. We’re really excited about the boutique committee is getting ready to start. So if you’re an independent boutique and you’re not already part of the committee join.
Glenn: [00:05:31] Awesome. Well, I want to thank you so much for being here. Really appreciate it. Like share, subscribe. So for Dina and myself, Glenn, thanks for watching. We’ll see you next time.
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