Transcript
Introduction to Dina Belon
Hi, everyone. Welcome back to another Matt Talks hospitality. And this week in talking about hospitality, I thought I'd have Dina join me from Seattle. She is the president at Staypineapple. I immediately thought like, I know there's many fruit hotel brands, but I'd love to get to the story of Staypineapple specifically. But maybe do you wanna give us a short introduction to your background because you've been in hospitality for a while?
You can tell by the gray hair. Yes.
So thirty years almost.
And I really I started out in the built environment.
So I spent most of my career building, renovating, designing, developing hotels, and time share projects.
It was an amazing experience.
I love doing it. It was a great foundation, understanding that side of the business. When I started at Staypineapple, I indeed was brought in for real estate asset management. Basically, dispositions and acquisitions and making sure I always said that I was making sure that Max, Michelle's our owner's son, I was watching his inheritance. It really evolved, I think, and I brought together all of my different experiences in my career here at Staypineapple, which is really fun to kind of bring together different perspectives. So I've worked in really sustainability-focused positions, worked in the engineering department at a hotel.
I've worked in the built environment.
The one area that I've never worked is actually at the front desk and really checking guests in and checking guests out. So when I became vice president of operations, there was there were some questions around whether I could lead the operations team never having worked in operations.
And how did you fill that gap?
Yeah.
I think I was it was a very specific opportunity in an organization that I had been in for five years and had built a lot of trust already and had really great relationships with general managers in our hotels. Because as the asset manager, I spent a lot of time out in the hotels.
Yeah.
So I think that really was the key to how I was able to do it. If I had to come in from the outside, if I was hired as a new employee into that role, I think it would have been much more challenging. Not unable to be done, but would have been much more challenging. But so I've really been able
Chapter
What's at the core of Staypineapple Hotels
to bring it full circle, I think, and align the organization around what is the most important part of our business, which will surprise everybody because I came from the built environment.
It's not the building. It's the people. You know, as much as I spent most of my career building the stage for hospitality, I truly learned here at Staypineapple that the key factor, not even the key factor, ninety percent of the factor of a great hospitality experience is both the team and the guest and the co-created culture every day inside of the hotel, which changes and varies depending on who's there and the vibe evolves. And that's some of the things I think, the things that are great about boutique hotels versus big box hotels, is they have a life of their own.
Yeah. And that creative process is much more organic.
And if you describe Staypineapple, I often talk about brands that don't excite me because they're just so bland. But the moment I hit your website, I was like, oh, there's personality here.
But how would you describe Staypineapple to someone who's never heard of the hotel brand?
Yeah. We're quirky and different and, a little irreverent on occasion and fun. Most importantly, like, going to stay at a hotel, whether you're staying for business or pleasure, it should be fun. It should be enjoyable.
You should be engaged, and it should feel like a sense of community. You should feel welcome and, like you belong there. I'm sure you have had this experience. I've had it so many times where you walk into a hotel and you get checked in, but you feel like an outsider.
You feel like you're almost, like, in the way as the guest. You certainly don't have any sense of this is my living room, and that's my dining room. And I'm hanging out, and I feel welcome, and I feel like I belong here.
Chapter
Creating an inclusive culture
What do you do differently in your culture so that your team members include the guest into that?
It's actually very simple. We do the same thing with them. We encourage them to bring their whole self to work and be themselves, and we don't, our front of house team members aren't uniforms. We don't have rules about their hair or their earrings or their makeup.
We want them to be them, and we invite them to interact very authentically with our guests the way that they would. I have literally sat in the lobby of our hotels and cringed at the things I've heard our team members say to guests. I'm not lying.
What's the worst thing you've ever heard them say?
Oh my gosh. Just like, like, greeting a guest by "Yo!"
Oh my god. Did somebody just say that?
But it's so funny that, I mean, if I said that, it would not come across authentically because that's not me. But the person that did it, it was so authentic that by the time that guest and that team member were done talking, the guest literally slapped a person on the back and walked away laughing. That is a real interaction. And I think more than anything today, people want to feel like they're interacting with a human and not robot. We have so much automation and so much technology in our lives that when it comes to the position of the hotel business, we have a unique opportunity to fill a gap that the human race needs. Yeah. Which is really authentic connection and feeling like people care and that there are people out there who want to know who you are and believe it's important.
That and so as you build that culture, and you've been there for ten years, I think. So you've had a long road to getting to that culture today, but what were some of the things you did to build a team that feels like they can authentically be themselves?
Yeah. It really started with Michelle Barnett, our owner. Michelle went to UNLV for hospitality management and worked for ten years in the brands.
Her mom and dad asked her to come back and help run their real estate business, and she said, that's great. I'm happy to do it, but I wanna buy hotels. And they were like, okay. We can do that.
It started out small, but Michelle had had a core belief, which was there's always a better way to do it. And she didn't believe that the way that the brands were systematizing everything was the way to accomplish true hospitality. She went to Europe a lot and traveled and experienced wonderful boutique hotels over in Europe and saw there was an opportunity and potential in the United States to bring what is much more rare here, a really innkeeper mentality into the hotel business. And it not be a, and both thought processes are valid, but our philosophy is very different than the brands.
The brands want to create consistency and common experience, and they want you, if you check-in at a Courtyard here or a Courtyard in, you know, the middle of Alabama, it feels the same and consistent. What we're really after is you feeling each market and its unique character and unique nature. And the consistency comes from just great customer service. The building doesn't need to be the same.
Culture, the community doesn't need to be the same. The core element that you're gonna feel at every Staypineapple is that same sense of welcome and belonging and relationship building. We talk about, we use technology to remove the transactions so that we can build relationships. So Michelle really believed in that.
And, originally, she bought a couple hotels and had other people running them and just couldn't like, she wasn't happy with the way they were being operated. And then she bought a Ramada Inn and couldn't find the value that the brand was bringing from an owner perspective.
Yeah.
She was like, I can do this better. I know I can. So she started her own management company and took the three hotels that she had. The fourth was just finishing up, the Maxwell, which she built.
Started with three people and grew from there, but the corporate office really didn't intend to grow a brand in the beginning. But because she was doing things that were so different and so unique here in the United States, it became an external conversation that wouldn't Staypineapple be a cool brand to grow.
Did it exist from day one, the brand, or was it added then at a later stage as the company started growing?
Yeah. It was very evolutionary. So the first four hotels, were just managed as independents. They were all just unique, our own unique hotels.
Yeah. And then when the fifth hotel was added, in Portland, there started to become conversation that, well, we've got we have unique boutique hotels, but now we're starting to build something that's bigger and maybe a overarching brand just for our buildings would make sense. And so Staypineapple was created. That was three or four years into the company's existence.
And then the fifth and the sixth hotel was added. And then Staypineapple, really five years in, Staypineapple really became something that was different and unique and well defined.
I think any brand is evolutionary, but particularly because it really came from a real estate company into a management company and into a brand, and it grew very organic. It allowed us to not put too many fences or boxes around the brand. Yeah. And let it kind of grow naturally from the bottom. The brand was created by the people inside the organization.
Michelle created the framework, but the people inside the hotels and here at the home office innately created the brand. And then we started to figure out how to really define it. We defined it after we already knew what it was. Does that make sense?
Yeah.
We wrote the sentence after
Chapter
How to build an authentic hotel brand
we knew what it meant.
Because you probably instinctively knew what you were doing. And it's only when you put it on paper after, it's like, yeah. This is absolutely what we were doing, but we didn't think about that.
We were just running yeah.
Yeah. I think it's the difference between creating a mission statement yourself or having an external, you know, brand company do it for you. You know? And, like, when you allow it to grow inside first, I think it's more successful.
It's certainly more authentic. Everything inside our organization is very authentic. Dash, the little pineapple pup, the stuffed dog that sits on the bed is actually Michelle's dog named Dash. Like, it's a real dog.
He runs around the office. Right? The reason that the name Staypineapple was created was because Michelle's dad used to call her his little pineapple because she wore her hair up on her head and looked like a pineapple. You know, I just, like, everything comes from there was no marketing agency creating any of this.
As you scale, how do you ensure that you still bring in like, you hire probably for personality rather than skill sets. And, like, every skill, you can teach them, but how do you ensure that they don't become scripted at scale? Like, that you want to retain the originality of when you were smaller, but now you're ten hotels. And how do you retain that?
Yeah. It is, and we wanna
Chapter
Is trust scalable?
grow further. Right? We would like to become fifty hotels. How do you do it at that scale?
It's trust. Again, I think the really amazing thing about our organization is we're very good at boiling things down to what really matters and letting the stuff go that isn't core. So trust is the foundation of everything inside of our company, and that includes all of our team members at the hotel. That's how this really relationship-based innkeeper mentality is able to be fostered.
Put in your head an actual experience in an inn. Right? It's a husband and wife. It's seven rooms in a house.
Everybody comes down in the morning and has breakfast together. That is a very personal relationship based yeah feeling. How do you reproduce that feeling in a hundred and fifty room boutique hotel?
Well, you do that by allowing the team members ownership and trusting their instincts and their creativity.
So we create the framework or the end result that we're after. We say, okay. The end result that we want is this hotel to have a community and be part of the community where it's located. Most of our hotels well, all of our hotels are in city centers, but most of them are also within, lot of residential, high-rise, or mid-rise residential.
And so there's a lot of density, and so being part of that community is really important. And then creating a sense of community for the guests, so they feel like they're interacting with locals, and they're getting a real sense of what that area is. That's really critical to how we've developed Staypineapple and how we deliver on that promise is that trust element. It's something very few hoteliers, in my career, before I came to Stayineapple, I'd never experienced it. Yeah.
Everybody always talks about it, and everybody handed me a manual and told me how to do my job at every job I ever had. Right? And we don't do that. We don't have manuals.
We don't, I mean, we have SOPs that are technical.
Right?
Like, the Mews SOPs. Yeah.
Or how you learn how to use the PMS system. We have things with training, but we don't have SOPs around how to greet somebody, how to, you know, do the soft skills, how at the bar do you interact with somebody and get them to talk? Or a really cool thing I learned the other day from one of our bartenders, the secret of getting guests to talk to each other at a bar. So you're at a busy bar, and you're the bartender.
And in normal circumstances, it's your job to engage with people. Right? Yeah. In a really busy bar, you don't have time.
You're, you know, slinging drinks. So the skill to get guests talking to each other so they're entertained and sling drinks at the same time. That's a skill.
How do I teach that? I don't teach that. We might show it. We might say, you know, we might learn that from somebody and say, here's a best practice, and the team member that does that really well can explain it to others.
But people have to figure out how to do that. Yeah. Their own authentic way. Right? Again, you can give the kind of framework, but not the end result, but not how to get there.
Yeah. And it's, like, it's EQ or, like, the ability to communicate really effectively with different people that have different styles and very quickly reading the style and then jumping into it. But that is something that is very hard to teach people, I think.
Yeah. So it's about hiring. Right? Hiring the right people and hanging on to them, retaining them.
Give an example maybe of a person that really impressed you through their empathy and how they built a relationship with one of your guests.
Chapter
The power of empathy
I have so many. I have so many examples.
One recently that just blew me away. We had a guest check-in at our San Francisco hotel, and they were of a specific ethnicity.
And, they were in town to eat at a restaurant that they were really excited. They were in town for work, but she was really excited about eating at this restaurant, and it was closed. I guess it was closed for a special event or something, and so she wasn't able to go. It was the food of her culture. Right?
And so the front desk agent was also of the same culture. She went home and made the dish for the guest and brought it the next day and set up a, like, formal dining experience in our lobby bar area, that's true. With candles and everything for the guests the next night. Like, I can't teach that. Yeah. That is just innate empathy for and caring for other people.
And that doesn't happen at any major big brand that no one would think to go that extra mile. But because, I guess, the culture you cultivate, people take the initiative. Does it ever go wrong where you're like, they've taken initiative and you're like, right. That was maybe too much initiative?
Absolutely. It happened. It doesn't, shockingly, it doesn't happen very often. I honestly, I'm surprised we don't get more of it. Because, you know, like, we had an experience, here's one, and nothing went wrong, but I was like, risk management, risk management, risk management.
We had a team member that was really into those scooters, electric scooters. And he took a group out on an electric scooter tour around town, and I was like, oh my great idea.
Did we get any waivers signed? Did we like, it's like, I like the idea. I love your initiative, but maybe not scooters. We do something like a walking tour. I think a much slower walking tour would be a good idea.
Chapter
How changing hotel tech affects staff
I love that. So it's a bit of a pivot from talking about empathy and culture, but, like, a very big important part of running a hotel is obviously the technology that you use in the background. And preferably, it shouldn't be intrusive to how your team members communicate. But how did you go about rethinking your technology stack in the last couple of years?
Yeah.
And as you well know, we did a massive change out in 2024. So we changed our PMS to Mews. We changed our POS system to Toast. We changed our CRM to Thynk. We changed our housekeeping tool to Optii, and we changed our guest communication tool to Akia.
It was a herculean effort, and I say all the time that I burned a lot of goodwill in 2024. 2025 is the year of Dina rebuilding goodwill inside the organization. No, actually, the team handled it really well, but they were tired.
How did you culturally prepare them for the change?
It was a huge part of what we went through. So this is also just months after I took over as president. So it was a new leader, new technology, all this change happening all at once. So it was a lot of why and including everybody in the decision.
And working up to the actual changeover was the most important part. I think we talked to you all about the fact that there are two primary reasons why we ended up picking Mews. And one was at the corporate level, and one was in the field. The one at the corporate level was a culture connection.
Like, our cultures are very aligned. We're a very innovative company.
We were looking for a PMS partner that would innovate along with us and continue to grow and find new ways to be special.
I think the most important part was that the end user had the loudest voice in the room. So I could have loved Mews or the marketing team could have loved Mews or the IT group was in love with Mews. All of that didn't matter if the ops team, and when I say ops, I mean operations in the field, the front desk managers, the general managers, and our everything people didn't find it a better tool for them than what they were already using, and they weren't excited about it. They had the loudest voice in the room.
And I said that as we were going through the selection process over and over and over again, every time everybody would be like, oh, yeah. Let's do this. I'd be like, okay. Wait a minute.
We have to make sure that operations feels like this is the right decision because it's their tool.
Yeah.
It's not marketing's tool. It's not the accounting department's tool. Although everything feeds off the PMS in our organization. Right?
All of our financial. Yeah.
Start at the PMS. You know? Our guests, our guest information is all in the PMS along with CRM. That's a whole another conversation.
But the end user, the people that use it every day in and out, are the ops people in the hotels, the actual hoteliers in our organization. I say this all the time. People in the home office, in our company, and in other companies call themselves hoteliers. And I'm like, if you don't work at a hotel, you are not a hotelier.
Yeah. And how, was there a moment of disagree and commit? Because it's hard to get a hundred percent of employees on board with the decisions that are being made. Did you at some point say, right, we need to put a stake in the ground, and at this point, this is what we're doing going forward?
Yeah. Absolutely. I mean, not everybody was excited about, there were voices that didn't want to make a change.
Yeah.
It really wasn't so much, not liking this application or that application. It was more, do we really need to change at all? Is this the right time to do it? Yeah. And I believed I knew, and I was right, I would like to point out, that the hyper-personalization that we were doing as a company and a culture for the last fifteen years was going to become the trend in the industry. And the way we had been doing it, very nontechnical without technology.
The open pen or, like, Excel sheets or what were they?
Not even that. I mean, it was just organic. Right? It was cultural.
Yeah.
It was literally a team member overhearing somebody in the lobby saying something or a bartender talking to a guest and them telling them something. It was all first party conversational.
So how many guests were we actually able to touch? We were able to do amazing things, but it was a small amount of our guests.
Yeah.
And so I knew that we had an edge because we already had the culture. We had the edge to do this and do it quickly and well and be able to impact many, many more guests than we did, the old-fashioned way. Right? And so that's what Mews has really been able to do for us is create a tool that allows us to have guest data at our team's fingertips all the time.
It's important information. It's pertinent to what they're doing, and it's across our portfolio. So, previously, if a team member had heard something about a guest at the Maxwell, Staypineapple in New York didn't know about it. Right?
Now they do. We record it. We not only record what we hear first party from our guests, we then record what we do. So in the profile?
Or where do you put that information?
Yeah. We put it in the guest profile. So I hear that you're really, really into cycling, and I send you over to my buddy at the cycling shop, and he lent you, like, the bike that's the one this year. I don't know.
I don't know if that happens. I'm not good with bikes.
Right? So I put that in there. I sent them to the cycling shop, and this is what they rode. This is the bike they rode, you know, blah blah blah.
So that one, either we don't repeat the same thing, or two, we can jump off a bit and add something, like, what's the next thing that we could do related?
So I think it's super important piece that it's not only we need to know things about the guest, but we also need to know what we're doing for them.
Chapter
How to best collect guest data
But that culture of asking open questions and listening and then documenting, I think the documenting bit is the thing that we struggle with. How do you how do you make sure that people put it back into the system? How do you incentivize it in the right way?
Yeah. Well, the incentive is, they want to have that kind of data from their other team members. And so everybody has figured that out. Like, this collaborative team environment that we have between our hotels too, not just within individual hotels, has really created this culture of we have chats, you know, internal chats and. Right.
Hey, you know, this about you know, we just did a really cool thing. They record it on Mews, but then they also like to get on the chat and say, hey. We just did this really cool thing. Here's a really neat idea if anybody else wants to use it.
That collaboration and sharing, yeah, is the way that we incentivized it. We didn't need to, like, put a bonus on it or, because it's a culture. Yeah.
When it when it's your core belief pattern as an organization, people want to do it because they want their other team members at other hotels to do it so they can use the information.
They started to see how valuable the information was to them to do their job every day, and it that was the incentive to put more information in the system.
And earlier, you talked about, you know, you went through this complete transformation. Not only did you change the PMS, but you also changed the event system, the housekeeping system, the restaurant point of sale. You had a CRM installed, a chat, application.
Which of that stack has been the most impactful to your business?
That's a great question. Depends on which department you talk to, probably. If you talk to housekeeping, I bet they'd say Optii. But, I would say overall, because it's at the heart of all of that.
Mews and I think, one of the things I love to say now is a few years ago, we always used to talk about, the single source of truth. Yeah. We needed a technology that was the single source of truth. And we created, we decided that would be Salesforce.
And so our CRM was a single source of truth, mostly because our current PMS system didn't work for us.
So when we implemented Thynk and Mews almost simultaneously, we were able to create an integrated source of truth instead. And that integration has been critical. So I don't know if it's actually, I take back my answer. Mews is super important. But I think the integration is the most important part.
Yeah.
It's the most important, it's not a technology.
It's the data flows between all of them that has to just mesh.
Data flow between. So the fact that the data can be in Mews and Thynk and Optii and Akia, like, we can share information among all those tools. The connective tissue is probably the most important.
Chapter
Advice for women in hospitality
My last question, and it's probably the most important one for me, is, like, recently, you were named one of the leading female voices of our industry, and I love that. I love seeing women like you thrive. What's the advice you'd give to a younger version of you as a woman coming up in our industry that they should do to thrive like you in your career?
The same advice that I give our team members, to be honest.
Find your strengths. What are the things that you're great at? Don't worry about what your weaknesses are. Every young woman that I talk to and I have a few mentees, and they're always like, oh, I need to work on this, this, and this.
And I'm like, do you? Do you want a career in accounting? Why do you need to be an accounting expert? You don't.
Like, you know how to do math. You graduated from high school. Like right? Instead, focus on the things that you're great at and grow those.
Yeah. Make those your focus. That will get you farther and faster than you can imagine. I am dyslexic.
I learned that, I think, through having a learning disability. Don't worry about the disability.
Focus on how you can learn. And I had an instructor when I was young teach me to learn differently than the public institutions teach. That's the problem.
Yeah.
It's not, you're not the problem. So you just need to figure out how you learn and then use that to gain the knowledge that you need. And I was able to make my way through college that way when, you know, I think many people with dyslexia give up and decide that they don't want to fight that fight. Yeah.
Because they don't get that information because they feel like I can't ever do it because I don't have the tools that the learning institutions require me to have, instead of going and finding and set a set of tools that work for them. That is correct. The same exact thing I tell all of our team members. It's the authenticity piece at the hotels.
Right? Figure out the tool set that works for you. Greeting somebody at the front desk with yo is the way to do it, then, you know, lean in and be yourself.
And you'll be shocked at how people respond positively because you are being you and people feel that inside. They feel it instead of just seeing it.
Yeah.
They feel it.
I wish I were a younger me, so that I could apply for a job with you because, actually, I think I would love working for a manager that thinks so deeply about the person underneath it all.
And it's very rare, like, to find people like that in hospitality that are in leadership roles that deeply care about emotional intelligence. So I really want to thank you for spending time with me and sharing this also with the audience. But I just love that we get to work together and that I get to watch some of the exciting things that you do. And, hopefully, we get to work many, many years together. But thank you so much for being here today.
Thank you so much, Matt. This has been great. I love talking with you guys.
The culture fit between our organizations is clear and broad and long lived. I'm sure.
I hope so. Thank you.
