Frozen Food Fiesta

Orlie Benjamin is the founder and CEO of Lasoh, a hospitality technology platform helping vacation rental and boutique lodging operators strengthen guest relationships through marketing automation, guest experience tools, and AI-powered workflows. After building her career with brands like American Airlines, NetJets, Disney, and Victoria’s Secret, she traded corporate life for entrepreneurship, launching both a vacation rental business and a hospitality tech startup. Susan and Orlie talk about guests, growth, and the great hospitality convergence.

Transcript

00:00 – Episode Intro

Narrator: This is Top Floor episode 249. You can find the show notes at topfloorpodcast.com/episode/249.

Narrator: Welcome to Top Floor with Susan Barry. This weekly podcast ride up to the top floor features tangible tips and excellent stories from the experts and characters who elevate hospitality. And now, your host and elevator operator, Susan Barry.

Susan Barry: Welcome to the show. Orlie Benjamin is the founder and CEO of Lasoh, a hospitality technology startup that helps vacation rental and boutique lodging operators market to their guests. Before becoming an entrepreneur, she built her career in marketing, pricing strategy, and guest experience with brands like American Airlines, NetJets, Disney, and Victoria’s Secret. Drawing from her experience in Fortune 500 companies, startups, and vacation rental ownership, Orlie is rethinking how hospitality businesses manage guest relationships by combining guest experience, marketing automation, and AI-powered tools into a single platform. Today, we’re going to talk about the convergence of hotels and vacation rentals and the future of hospitality technology. But before we jump in, we need to answer the call button.

01:38 – Emergency Call Button: Are Small Operators Still Profitable?

Susan Barry: The emergency call button is our hotline for hospitality professionals who have burning questions. If you’d like to submit a question, you can call or text me at (850) 404-9630. Today’s question comes from Ralph: “Is it still possible to make a profit with one or two short-term rental units, or has that ship sailed?” I think people are starting to sense that ever since private equity and the professionalization of property management, maybe the “onesies and twosies” aren’t worth it anymore. What do you think?

Orlie Benjamin: As an owner-operator of only one unit myself, I absolutely think it’s possible to make a profit — but I don’t think all units are equal, and I don’t think all business models are equal. Possible? Absolutely. I designed and built mine very intentionally, and I think your business model is only as good as your business strategy, your product, and your experience. There are a lot of variables to consider, but it’s definitely possible. It’s just harder — and not only because of private equity rolling things up. The pricing model around distribution channels has shifted, and a lot of changes happening right now to the overall environment are squeezing profit margins. So it’s definitely not as easy as it used to be, but it’s still a viable business model, for sure.

03:11 – From Corporate America to Building a Cabin

Susan Barry: You mentioned you have a single unit. What made that happen? What inspired you to leave the corporate world and build a vacation rental business from the ground up?

Orlie Benjamin: I followed the path my parents told me to follow, for the most part — go to law school, be a doctor or lawyer. I did all the things I was supposed to do, and then I started listening to myself. When I did, I recognized that being in corporate environments where I didn’t have the freedom to operate based on my own dreams wasn’t fulfilling me. So I created an exit plan: buying land and building a vacation rental business. I loved the whole process — the dreaming, the design of the property, and then operationalizing the business itself.

That’s actually how I ended up dreaming up Lasoh. I looked around the industry and thought, “There’s a lot of opportunity here, given how early-stage the tech environment is, and how much is missing compared to how I’ve seen things work at Fortune 500 companies. There’s a real business opportunity here.” I think it came down to a combination of being willing to bet on myself, after building enough confidence over my career, plus some specific experiences — I’d spent time in corporate venture capital at Scotts Miracle-Gro, and I was also head of marketing at a Silicon Valley-based startup. Those two experiences exposed me to the idea that I could actually be part of building something. When you spend your whole career as part of someone else’s machine, you don’t always realize you could build your own. So it was really that combination — exposure to building, and finally learning to listen to myself — that got it all started.

05:11 – Recognizing the Opportunity

Susan Barry: It’s interesting — a year before I started my company, I was having lunch with a woman who very offhandedly said, “Oh, you’ll probably start a business one day.” I’d genuinely never thought about that before that moment. It was like she gave me permission and unlocked a door. And here we are, seventeen or eighteen years later, and I actually did it. How far along were you with your vacation rental business when you realized the available technology wasn’t cutting it? Was that before you even started, or did you get down the road a bit first?

Orlie Benjamin: It was really early. While the house was still being built, I was already doing deep research into the available technology and setting up the infrastructure, so that by the time the house was ready, I was already pre-selling stays — before the property had even opened. You can set up your technology and future-sell, and future-selling requires marketing. So that was actually one of the very first things I did — starting my marketing journey before the place was even sleepable — and that’s when I realized there was a real gap.

Before I committed to doing anything about it, though, I went to several conferences, because just because I hadn’t found something on the internet didn’t mean it didn’t exist. I did a deep dive — I probably messaged over 800 people in Facebook groups.

Susan Barry: Good lord.

Orlie Benjamin: Literally. Real, thorough market research — not “is this a good idea,” but genuine customer discovery: where are your pain points, what do you wish were different? I spent about a year and a half building toward being ready to actually start the software business. First I had to get the vacation rental business operating. Second, I was still employed, and I needed to reach a point where I felt ready to leave a W-2 job to bet on myself — while also learning what it actually takes to be a startup founder before giving up reliable employment for a side hustle. I needed to really prepare myself for that transition.

07:41 – Corporate Career vs. Vacation Rental Ownership: The 60/40 Split

Susan Barry: Do you think what you’re building now has been more influenced by your vacation rental business or your corporate career?

Orlie Benjamin: That’s a great question — I’d say it’s close to 50/50, maybe 60% corporate and 40% vacation rental, mostly because of my history at publicly traded companies. But I’ve also immersed myself in this industry for the last three years — conferences, eating, breathing, thinking about nothing else, working something like 80 hours a week. I think those three years are probably equivalent to about six years of normal working time, so it’s genuinely close to even.

08:31 – Asset Management vs. Guest Experience: Lessons From NetJets

Susan Barry: Tell me about the distinction you make between managing property, managing an asset, and managing guests. I know you draw a real line here — I’m curious what that distinction is and why it matters.

Orlie Benjamin: This really comes from my time at NetJets. We had a team called Asset Management, whose job was managing the actual private jets — NetJets owns the aircraft. For anyone who doesn’t know, NetJets is a private jet fractional ownership model, owned by Berkshire Hathaway. It’s kind of like Uber, if Uber owned both the driver and the car, and you needed $5 million just to get in.

Susan Barry: NetJets is basically what taught everyone the word “fractional.”

Orlie Benjamin: Exactly — it was the original fractional ownership model, before timeshares even existed. It’s a 60-plus-year-old business. What I learned there is that Asset Management was one team, and I was part of a separate team called Guest Experience. There was also a Marketing team, and Guest Experience was really the bridge between Asset Management and Marketing. Marketing has a sales component — how do you actually sell the product? But once it’s sold, because the product is fundamentally an experience, everything after that becomes retention marketing: how do you keep someone who just spent $5 million on a jet share happy enough to stay?

So there’s an acquisition side and a retention side, and Asset Management was focused purely on the aircraft — what the seats look like, the plane’s product strategy, how many larger versus smaller jets, what amenities exist. That’s remarkably similar to property management, where the property itself is the asset. But the property is an asset within an experience — the actual product is the experience. The combination of guest experience and asset management is what people were really buying into. That’s exactly the framework I brought into thinking about this industry, because I think it’s fundamentally the same dynamic.

10:40 – Why Guest Experience and Marketing Get Separated

Susan Barry: Your software combines guest experience tools with marketing automation. Why have those traditionally lived in separate systems, and what do you think gets missed when they’re kept apart?

Orlie Benjamin: In every company I’ve worked for, there’s usually a marketing team and a separate operations or guest-experience team that handles customer touchpoints — reacting and responding to the customer’s engagement with the brand. Marketing, meanwhile, is usually driving behavior from more of a distance. I think great experiences make marketing easy. If the guest experience — and again, the product really is the experience, not just the physical asset — is incredible, marketing has the easiest job in the world, because when someone falls in love with something, it’s easy to resell to them, and it’s easy to sell to someone new through the social proof and loyalty that builds up.

I think a real disconnect in a lot of business models is the lack of connection between the people responsible for guest happiness throughout the journey, and the people responsible for turning that happiness into brand loyalty. That’s part of why the software is designed the way it is — again, something I learned directly at NetJets. NetJets has an 85% customer retention rate, which is pretty remarkable. Since the company wasn’t publicly traded, the CEO used to say, “If we had a stock ticker, it would be our net promoter score,” because customer satisfaction was directly predictive of how the company would perform. There are only so many billionaires and multi-millionaires out there — you have to work incredibly hard to acquire one of those customers, and then you have to keep them, because that relationship becomes a recurring revenue stream.

Susan Barry: Right — there’s no infinite pool you can just fish in and replace people from. It’s a finite group. We’ve talked before about how the period between booking and arrival really matters. Can you talk about that, and how your software plays into that window of time?

13:15 – The Underserved Window Between Booking and Arrival

Orlie Benjamin: I read somewhere — we’ll have to track down the source after this — that 50% of the joy of a vacation comes from anticipating it. If a great experience makes for great marketing, and you’re essentially ignoring half of that joy between the point of booking and arrival, that’s a serious untapped opportunity. If you can build excitement and goodwill before someone even shows up, you’ve already secured half the experience before they ever get a door code.

That’s why I think this part of the journey is so underserved — most operators think deeply about the period from arrival to departure, but that’s genuinely only half the journey. Combine both halves well, and it’s a pretty unstoppable combination.

Susan Barry: What are some specific things you communicate to guests between booking and arrival?

14:08 – What Great Pre-Arrival Communication Looks Like

Orlie Benjamin: It’s about communicating the right thing, at the right time. Great hospitality anticipates needs. We give operators tools to build things like local recommendations into our guest portal — we have a section called “Our Favorites,” built more like an e-commerce page than a wall of text: it’s filterable, sortable, and interactive, almost like browsing product pages while shopping for clothes online. Each recommendation includes a personal note from the operator or host, which gives the stay a real “local” feel.

Our research has shown guests really value local recommendations specifically — anyone can go to Google or Yelp, but people also don’t want to feel like they’re imposing by asking the host for a fully curated itinerary. If that’s simply offered to them, unprompted, they can plan ahead and make the most of their trip, because a vacation is really about buying time to make memories. Using pre-arrival time well means more output from the actual trip.

That’s probably the most impactful thing we’ve built. We also have a concierge-generated trip itinerary that pulls from those same recommendations but personalizes them heavily based on guest inputs. That matters because you can only deliver as good a stay as the context you actually have about the guest — the more you know about who they are and why they’re coming, the more you can act on it. In fact, one of the biggest mistakes operators make is having information about a guest and doing nothing with it — that’s almost worse than knowing nothing at all, because at least knowing nothing is forgivable. If you know a guest is coming for an anniversary or a special occasion, you don’t need to physically show up with a cake, but simply acknowledging it goes a really long way. So much of this is emotional — just being seen matters enormously.

17:02 – Underutilized Guest Data

Susan Barry: We like listeners to walk away from every episode with something practical they can try. You mentioned underutilized data — beyond the obvious, like date of birth or phone number, what guest data do you think operators already have that they’re not taking advantage of?

Orlie Benjamin: ZIP code is a really good one. Knowing whether someone is a drive-to versus a fly-to guest changes how you should communicate with them, especially around last-minute getaway offers. If someone’s within driving distance — or you know them well enough to think they’d hop on a plane — you can craft a message that’s actually meaningful to them, rather than generic. Proximity to the property is genuinely important context.

There’s also behavioral data you can extrapolate — do they typically come on weekdays or weekends? That tells you whether to remarket around workcations, weekend getaways, or multi-generational family gatherings. There are so many layers here, because it really comes down to how much context you have and what you can unlock from it. A lot of operators are sitting on data they could act on, but unlocking real value from data is its own challenge — and many aren’t even gathering it in a way that’s usable, because you need somewhere to put it and a real strategy for piping it in. There are plenty of easy use cases just around understanding the type of stay someone had and building campaigns off of it.

19:08 – The Ski Trip Example: Credit Card Data and Personas

Susan Barry: I always think about anonymized credit-card data matching that you can pay for. If you’re a property or any business, you could build trip personas by connecting that credit card data to behavior — say, if someone spends a lot at outlet malls, and there’s an outlet mall near your property, they fit a “shopper” persona, and you tailor messaging around that. I just don’t know if individual short-term rental owners have the resources to execute a strategy like that, whereas hotels do — they just often don’t.

Orlie Benjamin: We’re actually working on that, and I’ve done it myself in prior roles. You can go to Experian, which has around 10,000 data points, and here’s a simple example: I ski. It’s a pretty clear cohort. Vail Resorts is already emailing me constantly, and I’m also getting ads through pay-per-click and Meta as an identified skier. That’s such a clean use case, because skiing is expensive, involves an overnight stay — usually more than two nights — and knowing someone has a ski propensity lets a ski destination prospect an entire audience of similar customers. I’m sure hotels do this well, since they have the infrastructure — maybe some choose not to over privacy concerns, but retail absolutely nails this kind of targeting.

Susan Barry: Right — a ski vacation versus a garden-variety “in town for a family reunion” trip represents very different spend, so your cost of acquisition for that lead can be higher, and you can retarget aggressively. I think part of the issue is the “three-legged stool” in hotels — the brand, the ownership group, and the management company are usually three separate entities, and nobody wants to pay for anything. It’s like the Scarecrow in The Wizard of Oz pointing in two directions at once. That’s probably why these strategies don’t get executed well in hotels, whereas Vail Resorts is vertically integrated — they own, manage, operate, and brand everything themselves. They have the data; they just can’t agree on who should pay for using it.

Orlie Benjamin: In vacation rentals, you have the owner as the asset, but the management group also manages the brand — so at least you’re down to two legs of that stool instead of three.

22:13 – Where AI Will Actually Matter in Hospitality

Susan Barry: What role do you think AI will realistically play in hospitality over the next five years? Where’s it making a real impact, and where’s it being overhyped?

Orlie Benjamin: That’s a tough one. I had a really interesting trip in May — I went to the VRMA Executive Summit in LA, and then flew directly to San Francisco for SaaStr, the world’s largest gathering of software companies. The conversations happening at VRMA versus in Silicon Valley were so split-screen that it genuinely felt like I’d traveled years into the future between the two.

I don’t know exactly where adoption will land, because technology can exist without adoption. But I think, broadly, anything repeatable is heading toward agents — building agents is going to become extremely common, even at a high-school level. The next layer of sophistication is orchestrating a whole set of agents so they communicate meaningfully with each other. And beyond that is the ecosystem those agents live in needing to talk to other software ecosystems. It’s a lot like building a team of people: you hire someone, train them, hire more, train them, and eventually they’re working with people outside your business too — before you know it, there’s a whole network of intelligence. I think people will lean heavily on agentic intelligence for rote tasks, and the future skill will really be teaching and training agents — anyone who’s a natural teacher has a real superpower right now.

For this specific industry, the real question is when AI becomes guest-facing versus staying backend. I think there’ll be much faster adoption on the operational backend, because there’s essentially no downside risk to the business — only upside. It lets operators do more with less and keep operating costs down, growing the business without proportionally adding headcount. That’s going to be a genuine tailwind for the industry, the same as in others.

What I’m less certain about is adoption for AI directly engaging with guests, and how good that will actually be. I’m personally not comfortable with pure chat interfaces yet — I think it still needs heavy human supervision. Even in how we’ve built Lasoh, we don’t have a chat feature. We have a lot of agentic capability, but it’s designed to help operators do more with less, not to interact directly with guests. I think there’s still a long way to go there, though you have to start somewhere, and right now it’s a very early-adopter stage for brands that genuinely care about guest experience. But I think we’ll all get used to talking to AI agents the way we talk to people, and I think that shift happens within the next four or five years — and it’ll happen fast.

25:51 – Agents Talking to Agents

Susan Barry: What I keep hearing isn’t so much that we’ll get used to talking to agents ourselves, but that our agents will be talking to each other’s agents.

Orlie Benjamin: Websites are already being designed JSON-first. We don’t read raw code, but if you’re searching for something through an AI tool and it needs to quickly pull information from a website, it doesn’t care about imagery — imagery is actually hard for it to process — it cares about code it can grab fast. So completely agreed, Susan — that whole world of agents talking to agents is the later stage of this. It all feels a little Black Mirror, honestly, but I think it’s coming fast.

26:32 – Reducing Dependence on OTAs

Susan Barry: How can hospitality operators, in the meantime, reduce their dependence on third-party distribution channels like Airbnb and Vrbo?

Orlie Benjamin: I think it starts with being a brand, in the most basic sense — forget the technology for a second. Create a great experience, be memorable, and don’t let Airbnb or other distribution channels effectively become your brand. Think about how guests describe their trip — they say “we’re going to an Airbnb,” not “we’re going to a [specific boutique brand] property,” unless that brand makes sure it’s evident throughout the stay that they’re somewhere with a real point of view and identity. That can happen through every physical touchpoint during the stay, and just as much before and after it.

Being known — physically and digitally — is a genuinely simple place to start. And just gathering whatever guest contact information you can, and actually doing something with it, even something as simple as “How’d you hear about us?” or “How was your stay?” — those are easy, low-lift steps. At the end of the day, it’s called customer relationship marketing because there’s an actual relationship. If they know who you are and you know who they are, that’s a real advantage.

28:00 – Predicting the Future of Lodging

Susan Barry: We’ve reached the fortune-telling portion of the show — you have to predict the future, and we’ll see if you got it right. Here’s the next one: as the lines between hotels, vacation rentals, and residential communities keep blurring, what’s your prediction about the future of lodging as a whole?

Orlie Benjamin: I think the future belongs to experiential places — that could be boutique hotels or vacation rental operators. A giant hotel property that can’t easily be repurposed for anything other than hotel use is a much bigger underwriting risk than a boutique hotel that could later become an apartment complex, or a vacation rental that could later become a home. There’s a real financial argument there.

From a guest perspective, we’re all so immersed in technology that it’s desensitizing us, and I think people are craving real, human experiences. Surveys I’ve read show Gen Z and older millennials increasingly prioritizing spending on experiences over things — we’re craving human connection because technology is making life lonelier. Being experiential as a core business strategy is a genuinely strong path forward. And for the first time, I think smaller operators with something truly unique have a lower barrier to entry than ever, because the underwriting is easier, and they can differentiate in ways that are genuinely hard to replicate at scale. So going back to how we started this conversation — I think smaller operators actually have real opportunity to come in and build something special. Scaling is where things get genuinely hard, and that’s where operational professionalism at bigger companies really shines — but those first few steps really favor people offering a real experience.

30:19 – Luxury in Friction

Susan Barry: I wonder if there’s actually a kind of luxury in friction — the inability to scale an experience is part of what makes it feel luxurious. The lodging brand landscape right now feels so undifferentiated, and I keep hoping someone somewhere will draw a real line in the sand and take a genuine point of view about what they are and aren’t. Those are the people who’ll win.

Orlie Benjamin: I think there’s room for both. Starbucks is crushing it because it’s consistent, reliable, and known — but so is a solid boutique coffee shop that roasts its own beans and has real character. There’s space for both, and they serve different use cases. Starbucks is the place you know you can stop on the road for a predictable $7 sandwich, a $3 coffee, and a clean bathroom, when you don’t want to gamble on a mom-and-pop spot mid-trip. But if you’re settling in and want something specialty and distinctive, that’s when you seek out the local coffee shop instead. Hotels work the same way — sometimes people want something elevated and special, sometimes they want something dependable and trustworthy. It’s the same customer, just different occasions.

31:52 – The Magic Wand Question

Susan Barry: If you could wave a magic wand and change one thing about how hospitality companies think about guests and marketing, what would it be?

Orlie Benjamin: I’d want them to think about the guest as an asset, exactly the same way they think about the property as an asset. When the property asset and the guest asset are both properly balanced, that combination is genuinely a superpower — one plus one equals three. The businesses that get that right will build a real moat around their business.

32:23 – Loading Dock Story

Susan Barry: Okay, folks, before we say goodbye to Orlie, we’re heading down to the loading dock, where all the best stories get told.

Susan Barry: Orlie, what’s a story you’d only tell me on the loading dock?

Orlie Benjamin: One of my first bookings at the property was a last-minute reservation — maybe booking number ten. It was a rainy weekday evening, and the guest booked the two-night minimum. I thought, “Oh, this is great.” Then the cleaners came afterward and told me none of the beds had been slept in. I thought that was interesting — and it turned out there had definitely been an OnlyFans shoot at the house. It took me a while to piece it together — I went down a whole rabbit hole figuring out who this person was through her Instagram, and eventually found paywall buttons linking back to her content.

What was left behind in the house was a lot of random frozen food, Doritos, and Gatorade scattered everywhere — almost like a very “collegiate-level” stay at a fairly nice property. The whole thing was entertaining, since I was still brand new to hosting, and the whole detective process of figuring out what actually happened was quite the experience.

Susan Barry: That’s amazing. Has she been back?

Orlie Benjamin: She has not, and I haven’t exactly nurtured her to come back either.

Susan Barry: Well, that’s a shame. Orlie Benjamin, thank you so much for being here. I know our listeners are intrigued and excited, and I really appreciate you riding with us to the top floor.

Orlie Benjamin: Thank you, Susan, for having me. This has been a blast.

34:18 – Outro

Susan Barry: Thank you for listening. You can find the show notes at topfloorpodcast.com/episode/249. Jonathan Albano is our editor, producer, and all-around genius — he even wrote and performed our theme song, with vocals by Cameron Albano. You can subscribe to Top Floor on Apple Podcasts, Spotify, or wherever you like to listen, and a rating or review goes a long way in helping us bring you more of what you like.

Narrator: Thanks for listening to the Top Floor podcast at www.topfloorpodcast.com. Have a hospitality marketing question? Reach us at 850-404-9630 to be featured in a future episode.