Rewriting the Rules: Orlie Benjamin on Building Lasoh for a Better Guest Experience

Send us a message! In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered.

Transcript

00:00 – Cold Open

Orlie Benjamin: Hotels kind of woke up and said, “All right, we’re going to create loyalty programs, digital apps, value-adds. We’re going to own our guest, we’re going to know who they are, and we’re going to own the relationship.” Vacation rentals aren’t brands if they come in through Airbnb and the operator never establishes themselves as an actual business. Airbnb is a $90 billion software company, and those operators have one or two units. So what can the little guy do?

I think it’s actually very much a legal question, and I’d love to see the FTC, the DOJ, or an attorney general come together and ask: is this anti-competitive? Because it feels like a restriction of trade. AI is going to change the game — I think it can make marketing really easy for people who don’t know anything about marketing, because it can suggest the right things. It turns marketing into a push system instead of a pull system. As much as I see risk, I see reward. But AI trained poOrlie can be more harmful than nothing at all.

00:51 – Welcome, Orlie Benjamin

Alex: Welcome to Alex and Annie, the Real Women of Vacation Rentals. I’m Alex.

Annie: And I’m Annie. And we are joined today by Orlie Benjamin, founder and CEO of Lasoh. Orlie, it’s so good to have you on the show.

Orlie Benjamin: Thank you both for having me — I’m really excited to be here.

Alex: We’re so glad to finally have you on. We talked to you at the recent VRMA Nation conference, which I think was one of your first industry conferences. We were keen to get your take on the space, and it’s clear you’ve embraced it and it’s embraced you right back. For listeners who don’t know you yet, tell us a bit about your hospitality journey and what brought you to Lasoh.

Orlie Benjamin: Sure. I’m the founder and CEO of a software company building marketing technology specifically for the vacation rental industry. The goal of the software is to help operators drive bigger profits through deeper relationships with each guest — essentially relationship marketing, with a lot of words in front of it.

I got here after a fairly robust career in corporate America at brands people would recognize — American Airlines, Victoria’s Secret, NetJets. Throughout those experiences, I was always at the intersection of marketing and digital. From there I moved into a startup, and also decided to build my own vacation rental business. That’s when the idea for Lasoh really crystallized, because I realized a lot of the marketing technology I expected to exist for this industry simply didn’t — not compared to what I’d seen at larger companies. In the spirit of solving my own problem, I cobbled together a mediocre tech stack from what was available, and eventually decided to build something better: software that would give operators a real edge in owning their book of business and driving more direct revenue.

I’ve spent most of my career at vertically integrated businesses that own their customer relationships, and I believe it’s essential for an operator to know who their customer is and build the business backward from that customer’s pains and needs. Retaining customers is one of the smartest strategies any business can have — it’s practically an annuity. Someone who comes back and tells their friends is a flywheel you don’t have to pay for. Those are some of the philosophies behind Lasoh, and the goal is to empower other operators to own their book of business through good marketing technology.

Annie: You actually had properties yourself, right? You had rental properties, so this was a real pain point in your own situation.

Orlie Benjamin: That’s right — I operate a vacation rental business out of Hocking Hills, Ohio, called The Acres.

03:29 – How Lasoh Works in Practice

Annie: Explain exactly what it does. Take us through how someone actually uses Lasoh in a real-life situation.

Orlie Benjamin: Sure. It’s essentially a digital portal — think of it as comparable to a Disney experience, or what you’d get as a Marriott guest. The portal lets the operator elevate the guest experience by giving them a digital companion for whatever they need, whenever they need it. It’s much more than a guidebook — it’s a full interface with everything from stay fundamentals to recommendations, and we’re currently building out experiences, similar to what Airbnb just launched, where the operator can drive incremental revenue directly through that interface. It blends e-commerce and experience strategy, the way Disney does.

The other important piece is the CRM component. Everything captured through the digital portal is stored in a CRM, from which direct marketing can happen. We gather guest data at the point of booking — not at the point of arrival, which is how some other guest apps handle it. I strongly believe starting the relationship at the point of booking is critical, because that’s your window to drive incremental revenue before the guest even arrives.

Annie: How are guests actually presented with Lasoh?

Orlie Benjamin: It’s all through automations and API integrations. Say, Alex, you’re coming to stay at my property in Hocking Hills and you booked through Airbnb. The PMS integration flags the new booking, and an automated message goes out — in this case a text to the phone number Airbnb gave me — saying something like, “Hey Alex, we can’t wait to host you at The Acres from June 3rd to June 7th. We have a digital portal that helps you plan your trip, with key info as well as experiences and upsells.” That’s not the exact wording, but it’s the gist. There’s a link, and clicking it already recognizes your phone number as your username — you just get a six-digit magic code, no password to create, nothing to download, and you’re in.

Now you have a personalized, Disney-app-style experience specific to your stay. You can add the rest of your group, which removes the friction of having to relay information to everyone yourself. I call that role the “party captain” — the person who booked the property, the booker guest — because in larger groups, that person otherwise has to organize and inform everyone else. Adding the rest of the group to the portal removes that communication bottleneck, and just as importantly, it captures everyone’s information — phone number, email — not just the booker’s.

06:44 – Navigating Airbnb’s Communication Restrictions

Annie: The million-dollar question on everyone’s mind right now is Airbnb’s new rollout around off-platform booking and being told you’re not supposed to communicate with guests directly. We touched on this a bit at VRMA Nation, and honestly it feels a little dystopian — you have the property, the guest is staying in your property, but you’re not allowed to actually speak to them. How do you see Lasoh working for hosts in that scenario, where they’re listing on Airbnb but facing that restriction?

Orlie Benjamin: I think the history of this industry is that operators and guests have existed since before Airbnb, and Airbnb has inserted itself into that value chain — which is smart, honestly. It’s a marketplace, similar to how Amazon works: people have been buying and selling forever, and now there’s this intermediation layer.

But I think there’s a real distinction here, and honestly it’s very much a legal question. I’d love to see the FTC, the DOJ, or an attorney general look into whether this is anti-competitive, because it feels like a restriction of trade to me — as an unofficial opinion. All of Airbnb’s terms and conditions route to arbitration; there’s no litigation on record anyone can point to. I genuinely think it’s a rule with no teeth. They could remove someone from the platform, but I don’t think there’s real legal teeth behind it. Again, unofficially — I did go to law school, but this isn’t a legal opinion. The reality is operators are the ones bringing customers into their business. Airbnb doesn’t control the inventory, doesn’t own the assets, and there’s a real question about what level of control they think they can exercise over other people’s businesses. It’s a step beyond being a distribution channel — it’s operating with a level of control that’s pretty unprecedented.

Annie: You’re preaching to the choir — we agree completely. Beyond the legal question, though, there’s the practical risk: Airbnb’s ability to strip listings can put a person or company out of business overnight, especially operators who are 100% dependent on Airbnb for bookings. We understand the bigger-picture advice is to diversify and push toward direct bookings, but in the meantime — if you’re not supposed to be collecting emails from guests, are you still asking for them, or doing something different for Airbnb guests specifically? We’re genuinely asking every guest-app founder we talk to this question right now.

Orlie Benjamin: Let’s see if my own property gets taken off Airbnb after this interview — but I’ll tell you exactly how I’m doing it. And yes, I know a lot of Airbnb people listen to this podcast, so I’ll just put that out there.

Lasoh turns Airbnb into lead generation. Here’s how: a booking comes in through Airbnb, goes to the PMS. The PMS is the intermediary between Lasoh and Airbnb — there’s no direct connection between Lasoh and Airbnb at all. There’s no way for Airbnb to know what Lasoh is doing, just like there’s no way for Airbnb to know if a property manager has a real-life conversation with their guest, because it’s not happening on the Airbnb platform. There’s a whole world that happens outside of Airbnb that Airbnb has no jurisdiction over, legally speaking.

What Lasoh is doing is simply leveraging PMS integrations, the same way a PMS can integrate with any other software, to give the operator an optional platform for optional things. The marketing opt-in is optional. The value the digital portal provides is meant to genuinely help the guest, and in doing so it captures marketable guest information — but happy guests actually want to be marketed to. They want to come back, they want to tell their friends. It’s a consensual process; nobody’s forced into it for anything essential, like a door code. The booking still lives entirely on Airbnb — the portal just adds value that Airbnb itself doesn’t provide.

Annie: And what does the marketing side actually look like — what can people do with Lasoh to remarket to their guests?

11:29 – Retention Marketing, Not Acquisition

Orlie Benjamin: Lasoh’s specific focus isn’t acquisition marketing — that’s where Airbnb excels. Anyone running a direct booking page is probably already doing something on the acquisition side, like pay-per-click or SEO. What Lasoh helps with is retention marketing and organic marketing.

For example, every guest who logs into the portal gets asked, at the end of their stay, “How was your stay?” — not just the booker. If the rating is a four or five, they’re routed straight to leave a Google review, which drives a lot of organic search ranking value. If the rating is a one through three, it triggers more of a net-promoter-style follow-up: “What can we do better? Please give us feedback.” This is a very standard playbook in retail — Trustpilot specializes in exactly this — and I’ve just brought that same approach into vacation rentals.

There’s also a CRM component. If you only use the guest portal, that data lives in an exportable spreadsheet. But if you want to go a level further, you can drop it into the CRM we provide and actually run segmented campaigns — for example, “Hey Alex, it’s been nine months since you celebrated your birthday with us. We’d love to have you back — here’s 10% off to celebrate again.” That kind of message only works if you know who the guest is, when they came, and why they came. And there’s no way to do this manually at scale — that’s exactly why large companies invest in marketing technology: automation at scale.

Annie: You’ve been working on this for a while — I think we met a couple of months ago, when you were still working through some of the process. You’ve recently launched your website, Lasoh.io. What does an actual launch look like from here? Are you targeting a specific profile of operator — hosts in general, enterprise operators, or the whole spectrum?

14:12 – Who Lasoh Is Built For

Orlie Benjamin: I’ve purposely been using the word “operator,” because whether someone identifies as a property manager or a host, they’re all operating a business at some level, and I don’t think the label matters. Honestly, I don’t think it’s about portfolio size — it’s about the life stage and sophistication of the business model.

Anyone with a direct booking site, anyone with a PMS, is relevant for Lasoh, because at that point they’ve already committed to owning their book of business through some direct channel, and they’ve found value in operational technology that lets them run things in a more sophisticated way. There are operators out there with hundreds of Airbnb units who don’t use a PMS at all, and there are operators with two units who have a direct booking site and a PMS. It’s not about size — it’s about how seriously they’re trying to diversify their distribution strategy so they’re not entirely reliant on one OTA. If someone is fully reliant on Airbnb for their business, they haven’t taken the steps to mitigate that risk. Channel diversification, risk mitigation, and owning your customer relationship — those are the marks of a more sophisticated operator.

Annie: Exactly the things we love to talk about. We’ve heard so many horror stories about people with all their eggs in one channel, and then overnight their account gets suspended and they go from making a million dollars a year to nothing, with no recourse — stuck in a black hole of unanswered questions. We always emphasize diversification, but also owning your guest relationship. You got into this business to provide a service to somebody — why wouldn’t you want to build on that connection, rather than just waiting for a channel to send you business?

16:29 – Learning From the Hotel Industry’s Playbook

Orlie Benjamin: This isn’t a new story. We’ve already seen it play out in hotels. Expedia and Orbitz sent business to hotels as distribution channels, and hotels eventually woke up and said, “We’re going to build loyalty programs, digital apps, value-adds — we’re going to own our guest and the relationship.” I’ll say the word “Marriott app” — it’s downloadable, sure, partly because of brand loyalty, but Lasoh isn’t meant to be an app that lives permanently on your phone. It’s a web app, because it’s a fractional software offering across many different brands, and I just don’t think people are going to download a dedicated app for one vacation. But they will engage on their phone if it gives them value at the right time and place.

Look at Marriott’s stock price, look at their 10-K — roughly 80% of their revenue comes from about 20% of their customers, because they own that guest relationship, drive repeat bookings, and maximize revenue per guest. It’s obviously not the same scale as an operator running a handful of units versus a multi-billion-dollar hotel chain, but the playbook still applies. This industry is young, there’s going to be a lot of consolidation, and whoever wins will be operating at a higher level of sophistication — not entirely white-labeling their book of business to Airbnb. There’s a reason people say “I stayed in an Airbnb,” not “I stayed in a vacation rental” — Airbnb has effectively owned the brand from the customer’s perspective. Vacation rentals aren’t brands if they come in exclusively through Airbnb and the operator never establishes an identity of their own.

Annie: A hundred percent. We talk about this as the difference between hunting and farming when it comes to customer acquisition. People come to me all the time saying they want to get into direct bookings, and if it’s a small operator, they immediately want to jump into PPC and email marketing. I always say — you have to crawl, then run, to get there. I’ve managed a $2 million-a-year marketing budget at 95% book-direct, and I’ve also seen it from the small-scale side, where the lowest-hanging fruit is simply the customers you already have. Getting them to leave a review or refer a friend — that’s a win, even if they never come back themselves. And having the technology to facilitate that at scale is really important. Every guest who comes through Airbnb, Vrbo, whatever platform, becomes part of a system that gives them the chance to review you, share content, or refer their friends and family. That’s farming. Once that’s working, you can invest in hunting — go get new business, because you’ve got a foundation behind you. It’s a balance between the two.

What’s fascinating to me is that Annie and I have spent years working with professionally managed, large operators for whom this is all commonplace — but for Airbnb-only hosts, this is all brand new. They’ve never even thought about it, because all they’ve known is running “an Airbnb business.” A lot of these people are genuinely smart business people who’ve done other things in their careers, but somewhere along the way they’ve boxed themselves into thinking this is the business, without stepping back to see there’s still real economics involved in how you actually get customers.

20:33 – The CPG and Target Analogy

Orlie Benjamin: When I think about the evolution of business models — take consumer packaged goods, CPG, as an example. Back in the day, since you couldn’t easily distribute your own product, the strategy was just to be really good at making it. That’s completely broken now, because direct-to-consumer has become possible — Shopify removed the barriers to entry for anyone to sell directly.

That’s the same evolution I see coming to this industry, using the Airbnb-and-Amazon analogy, or even Target. Target predates Amazon — it’s a retailer that sources products from other businesses. There’s a distinction between businesses and brands: businesses rely heavily on Target’s distribution, but a direct-to-consumer-minded brand wants to own its customer relationship. It’ll be really hard to get me to go to crest.com to buy toothpaste. But if it’s Magnolia Home, I would absolutely shop their line directly on their website instead of walking into Target.

So the question becomes: would a customer choose to book direct on their own? There are a lot of reasons they might. First, saving 15% off the Airbnb price is a pretty compelling economic reason on its own. Second, think about what Airbnb really is beyond a marketplace — it’s a trust economy. No one would let a stranger stay unattended in their home, and no traveler would stay in a stranger’s home either, without some system establishing trust. That’s great for a first-time transaction. But once a guest has had a great experience with an operator who has a portfolio of properties and a consistent brand — ski destinations, beach destinations, whatever it is — and they know they can rely on a similar experience each time, going direct becomes a no-brainer. That guest just needs to be engaged with in the right way. It’s classic digital marketing.

Annie: I think that’s the root of why Airbnb is doing what they’re doing — they’ve seen what happened with hotels, and now that these operators are building real businesses of their own, Airbnb realizes they could lose some of that “empire” to direct bookings. It’s a smart, savvy move on their part. Whether it actually holds up legally is another question, but it feels disingenuous to call it a partnership if you’re essentially saying, “We’ll send you the business, but act like the guest was never there once they arrive.” You can’t provide that level of service without connecting with people — it’s just not who we are as an industry.

Orlie Benjamin: It’s a classic bargaining-power dynamic. Airbnb is a $90 billion software company, and those operators have one or two units. What can the little guy really do?

Annie: Exactly — not much.

Orlie Benjamin: They can level up. They can take their own approach if they’re willing to put in the work — and a very small operator might reasonably decide it’s not worth it for them. But once you’re at scale — three, five, ten, a hundred units — the economics change. At that point, owning your business is a no-brainer.

Annie: A lot of operators reach that scale without ever really planning for it, and then find themselves beholden to one way of operating without realizing they had other options. That’s something Alex and I talk about constantly — how do you educate people from their very first unit onward, so they have a plan for what changes at unit two, three, four, or when they decide to sell? A lot of people just don’t know what else is out there. There’s been so much focus on “building your empire around the sun” that they’ve never noticed the other planets.

Alex: That would make a great conference session title — “Building Your Empire Around the Airbnb Sun.”

25:32 – Sponsor Break: Boom

Alex: We’ll be back in just a minute, but first, a word from our premier brand sponsor, Boom.

Hey everyone, it’s Alex, and I’m so excited to announce that Boom is back as our premier brand sponsor of the podcast. If you’ve been following the show, you know how much we believe in Boom and what they’re building — the world’s first AI-powered property management system. Now they’re unveiling something huge: the launch of their fully integrated, AI-powered trust accounting.

If you’re a property manager, you already know manual reconciliation is one of the biggest pain points in the business — most PMS platforms aren’t connected to your bank account, which means more manual work, more headaches, and a higher risk of costly errors. Boom fixes that, bringing reservations, income, expenses, and operations together under one connected ecosystem, and now with trust accounting built in, your finances, operations, and banking finally work together.

And it’s all powered by AI — payouts from platforms like Airbnb and Booking.com are automatically matched to the correct reservations using dates and transaction data, so there’s less chasing down numbers and more time running your business. You also get clean, detailed P&Ls for each property, region, or your entire portfolio, all visible in one simple dashboard — the first thing you’ll want to check every morning. Boom’s Trust Accounting was built for how property managers actually work today: real-time insights, full transparency, everything in one place. Check it out for yourself at boomnow.com, schedule a demo, and let them know you heard about Boom on the Alex and Annie podcast.

27:00 – Upsells and Airbnb’s New Experiences Feature

Annie: I’m curious on two fronts — first, I know upsells are something Lasoh offers, so tell us more about that. And second, what do you think about Airbnb’s new “Experiences” feature, which seems to take some of that upsell opportunity away from platforms and hosts?

Orlie Benjamin: It’s classic intermediation. First, Airbnb positioned itself between the guest and the host as a marketplace — and honestly, I get why. The way you make money is how many customers you have, how much they spend per transaction, and how often they come back. Airbnb has essentially maxed out on new customers — they have 450 million guests, 7.7 million units, and 5 million operators on the platform. So now they have to focus on spend per transaction and repeat frequency.

Spend per transaction makes a lot of sense once you realize about 30% of a vacation budget goes to lodging, and the other 70% goes to everything else. They’re going after the bigger pie, because they’ve already largely captured the vacation-rental-lodging pie — and 20 to 40% of hotel revenue comes from food and beverage. None of this is new; these are existing playbooks being adapted to lodging disruption. Airbnb is a publicly traded company that needs to keep growing for its stock price, and the next frontier is the rest of the stay beyond just lodging — the whole trip, the whole experience.

But there’s only so much of a slice to go around. The person actually providing the service — the massage therapist, the chef — needs to get paid. The guest is going to pay something. If Airbnb takes a cut as a third party, the host ends up fourth in line, with nothing left. Hosts can absolutely do this themselves if they get smart about it — that’s part of what the experiences component of Lasoh is designed to do: enable operators to set up those relationships directly and run their own experiences, keeping the revenue themselves. And it’s not just Lasoh doing this — there are some great software companies building real experience infrastructure. Lasoh will never try to be that kind of experience-marketplace infrastructure itself; it’s more the e-commerce environment where operators can bring the whole guest experience together in one place, without Lasoh taking a cut.

Annie: So what’s the payment model — a flat fee per property per month?

Orlie Benjamin: It’s a SaaS platform, priced per unit, per month.

30:04 – Go-to-Market Strategy

Annie: Back to the launch — do you have campaigns lined up? I know you launched the website, and you shared a great little promo video with me earlier. How do you plan to reach these operators?

Orlie Benjamin: That’s the thing I should be good at — this is literally my background. Tech, I’m still figuring out. [laughs] In all seriousness, my commercialization strategy is three-pronged.

First, PMS integrations. Marketplaces exist, and operators need their tech to work together — it just has to. We already have several integrations in place, though I won’t list them here since we’ll likely have more by the time this airs — check the website for the most up-to-date list. That’s table stakes.

Second, I plan to partner with other businesses in the industry that share the same customer but offer a different value proposition, because cross-marketing is powerful. Take Epicurate as an example — I just met them at VRMA Nation. They match vetted chefs and other service providers with operators by location. What happens, though, when an operator has seven other vendor relationships to communicate to a guest — do you send seven separate email links? That’s a terrible guest journey. Lasoh provides one source of truth, like a Marriott or Disney app, where guests can navigate everything in one place, and there’s no charge to Epicurate or the operator to link into Lasoh. It’s part of the value of owning your own digital guest experience — for me it’s about partnering with others so that one plus one equals three.

And finally, traditional sales and marketing. I’m working with a couple of people on content creation — we just shot some content at my cabin, and we’re putting together thought leadership pieces. I’ll be personally putting out a lot of content on LinkedIn, and Lasoh will build its own marketing presence over time. Conferences matter too, and targeted, meaningful outbound sales — nobody wants to be spammed with a cold intro that has nothing relevant to say. For me it’s about being precise: finding operators who already have PMS software and direct booking sites, because if someone only lists on Airbnb, they’re still a few steps away from being ready for Lasoh.

Annie: I’d actually argue that’s really your core audience, though — the people with direct booking sites already know what they’re doing one way or another. The much larger mass of operators out there aren’t at that point yet, and even without a direct booking site, if your system supports texting and email — and I’m not even sure it does — it’s wild to say this, but even sending guests back to their Airbnb listing to rebook is still a win, since it drives more bookings back. Obviously the goal is direct, but in the meantime, before someone’s set up with something like a Mark Boolean-style easily spun-up website, there’s still a crawl-run path forward here.

Orlie Benjamin: If someone with an Airbnb-only listing just wants basic email and text capability, they can go grab a Mailchimp — they don’t need what I built. What I’ve built is specifically for an operator who wants to own their book of business and focus on the combination of direct bookings and channel revenue together. It’ll never be 100% direct bookings unless you’re exceptional at marketing — it’ll always be some mix. But shifting that mix matters, and it’s not just about the mix, it’s about occupancy rate. The average occupancy rate for a vacation rental is about 55%.

People go to Airbnb when they have high purchase intent in high-demand windows — but what about the off-season and shoulder season? That’s when your existing guests come back, because you reminded them of a special deal, a special event, or just genuine value. It doesn’t have to be a discount — Annie and I were bantering about this on LinkedIn recently — find other ways to provide value and fill up the calendar. Don’t settle for a 55% occupancy Airbnb-only business.

35:37 – Lessons From American Airlines, Victoria’s Secret, and NetJets

Annie: I’m curious about your corporate days at Victoria’s Secret and NetJets — you must have some good stories.

Orlie Benjamin: I can’t tell you the fun stories on this podcast — we’ll have to save those for the next conference. Next week, actually, at the executive summit in Miami.

Annie: Fair enough. What are some of the bigger lessons you learned in those roles that you’re applying now, beyond what we’ve already covered?

Orlie Benjamin: Fundamentally, American Airlines, Victoria’s Secret, and NetJets all have significant distribution components, and all three are incredibly good at owning their book of business, being vertically integrated, and maximizing revenue through customer relationships. Their marketing departments are excellent. At NetJets, the retention rate of their “owners” — customers with fractional jet shares — was 85% on a three-year contract term, and these are people spending $5 million each. That was a while ago, so who knows, it might be even higher now.

At Victoria’s Secret, some of the philosophies I carried forward were around being a business that can defend itself. The more you rely on distribution, the less control you have over your value chain and your business stability. As a publicly traded company, you need stability and control over revenue to maintain a healthy stock price — that’s how you stay in business. The underlying philosophy is deeply customer-centric: understand your customer, know their pain points, actually listen when something’s wrong, and pivot the business if it makes sense. A lot of great corporations start by identifying a customer’s pain, finding a way to provide value, and building a business model around that — the money follows good strategy, not the other way around.

Something interesting about American Airlines, similar to Marriott, is that distribution aside, roughly 20% of customers drove 80% of revenue, thanks to a combination of hub-and-spoke geography and genuine loyalty. There’s nothing more of a commodity than airfare — if three airlines fly the same route, you’re picking based on price unless there’s something else differentiating them. That lesson is really relevant to vacation rentals: if you can differentiate on something beyond price — a cool amenity like a sauna, a pickleball court, some other value-add — you don’t always have to compete on price alone.

Airlines actually figured out how to compete without constant price wars taking each other down. I once worked with a former United revenue manager while I was at an Expedia-affiliated company, and it fascinated me — I’d never realized airlines even had dedicated revenue managers. The math they run daily, factoring in weather, events, and competitor pricing, is remarkably similar to hotel revenue management, just applied to a different commodity — and much more sophisticated than I expected.

I actually worked in revenue management at American Airlines myself, including managing the Priceline channel, which is considered a liquidation or “opaque” channel. I have some promotional strategy plans for Lasoh inspired by that, which will come later. On the revenue management side, airline prices change up to four times a day on weekdays, twice on weekends — and you can override the system. It’s essentially operations research, and honestly I think it’s more complex than hotels, because there are fewer players and the market is more consolidated, so the swings can be dramatic. Sometimes someone would accidentally price a ticket at $25 instead of $250, and the whole system would react — “one airline just priced this route at $25, so ours needs to match.” Add in fuel prices and other factors hotel operators never have to think about day-to-day.

Annie: Interesting — I’d have assumed there was some cost-based floor to it.

Orlie Benjamin: No — it’s entirely competitive, purely supply and demand. There’s no cost-based strategy layered on top of it.

40:47 – The Untapped Opportunity in Loyalty and Points

Annie: We talk about this on the show occasionally, but I think loyalty and points programs are probably the biggest thing independent or small-destination vacation rental managers haven’t figured out yet. A few companies are experimenting with it, but no one’s really cracked how to drive meaningful business through it. You mentioned earlier that people will switch airlines — they will, but I know Annie personally will always fly Delta because of her points.

Annie: I’ll fly American because I can call someone internally, and I’ll fly Southwest for a direct flight to Nashville, but otherwise it’s Delta. Points have been a real driver — Vrbo’s Homes and Villas, who we recently had on the show, and a few larger companies entering the space understand this and have integrated it a bit better. But I think there’s a huge opportunity for someone to really own the loyalty and points game in vacation rentals. We actually met with Simon Lehmann probably seven years ago, when I was at Condo World, and asked him for his thoughts on loyalty — and it’s genuinely tough. We were multi-destination at the time, and even within a single destination, your portfolio doesn’t pay out the same commission across every property. If you give a blanket point value, you risk shooting yourself in the foot on customer acquisition and retention costs. It’s a real matrix, and I don’t think anyone’s fully solved it — but it’s a big opportunity sitting there.

Orlie Benjamin: I think about this all the time. I think the only real way to do it is by spend — that’s what Southwest has always done, and other airlines have moved that direction too. There’s a question of how much a point is worth, and a separate question of how you can redeem it — those are two completely different problems. I’m honestly a bit of a points junkie myself now — Journey has come out, and The Points Guy — I’m blanking on his full name, Brian something — they’re trying to crack this, and I’m curious to see what they do. I think there’s room for a few players.

There’s also the question of who actually receives the points — the person who books the property? What happens with multiple guests staying together? In a hotel room, one person typically gets credit for everyone, but this industry is different, since about 50% of U.S. vacation rental inventory is large homes. So maybe there’s an entirely different model out there, based on stays and other kinds of value, rather than who happened to book it. I’m still noodling on it — there’s a lot of work ahead.

Annie: Your mind is clearly spinning on it — I’ll let that marinate with you and circle back later.

Orlie Benjamin: I have a strong point of view, but in terms of priority order, I need to focus on fundamentals first. And honestly, the one thing we haven’t talked about yet is AI. AI is going to change the game. I think it can make marketing really easy for people who know nothing about marketing, because it can suggest the right moves — turning marketing into a push system rather than a pull system. It’s another area I’m noodling on, but fundamentals come first.

44:00 – Where AI Fits Into Lasoh — Carefully

Annie: How do you see Lasoh using AI right now, and how do you see that evolving?

Orlie Benjamin: Honestly, we don’t use it much yet, and that’s intentional. AI trained poOrlie can be more harmful than no AI at all. Training a model well is genuinely difficult, and that’s part of why the CRM and data capture piece matters so much to me — the more the AI actually knows about the guest, the better it can perform. So I want to focus first on getting the right sample data into the infrastructure, then train it carefully on specific use cases. It has to be right, or it shouldn’t ship at all — there’s a lot of sloppy AI out there, especially in communication, and at this point dealing with a bad bot is more frustrating than just waiting for a human response.

Annie: Completely agree — if you get wrong information and it keeps repeating that wrong information, that’s worse than no automation at all.

Orlie Benjamin: Exactly — you have to do it right.

Alex: I say this to people all the time — I see real value in some AI applications, but I also worry. I was reading an article recently about college students relying on it so heavily that by the time they reach college they may never learn how to actually research or write a paper themselves, because they’re so dependent on the tool. Our friend Amber’s been doing training with people on using AI to build a foundational framework, but still infusing your own voice — because AI can’t do that for you, and you shouldn’t let it. Instead, people are handing themselves over to it completely — “well, it looks spelled right, so it must be fine” — when in reality a lot of AI-generated communication has bad grammar, wrong tone, or just wrong information.

Annie: It’s honestly a little frightening when you think about how bad actors could use it — falsifying news, spreading disinformation that could have real consequences. That’s the part that genuinely worries me; I have that doomsday instinct in the back of my mind, and AI has brought it right to the forefront.

Alex: It’s funny how differently we each think about it — when we talk about AI, you go straight to the risks, and I go straight to efficiency. Neither of us is wrong, but that’s the conversation everyone’s having right now: how are we even supposed to be thinking about this?

Orlie Benjamin: That probably makes you two a good team — built-in point and counterpoint.

Annie: For sure, we definitely are.

46:11 – A Lighter Note: Asking AI About Yourself

Orlie Benjamin: Have you two ever asked ChatGPT to describe you?

Alex: Oh yeah — mine was spot on.

Annie: Mine was not spot on at all.

Orlie Benjamin: What’s interesting is that it can only summarize what’s already out there — if the source information is inaccurate or misunderstood, the summary will be wrong too. Any journalist knows how much primary sources matter. Going back to the idea of intermediation — a GPT interface is, by definition, an intermediary. It removes the critical thinking step of asking, “Is this a primary source? Is this even accurate?” AI can’t reliably judge good versus bad or right versus wrong right now — it just digests a huge amount of material and produces something. If a college student never goes back to check the primary source, the disinformation risk is genuinely frightening, because people are losing that critical-thinking muscle. That’s really where I land on it.

Annie: Funny you bring that up — we actually did this together back in February in Nashville. We put our own names into ChatGPT with some extra prompts, kind of roasting each other, and it surfaced things that made us go, “Wait, how did it even find that?” Nothing bad, just surprising. But it does make you realize — someone could put something obscure on the internet, seen by almost nobody, and it could still become the “source of truth” that an AI pulls from, simply because it found it quickly. And nobody double-checks it, because “ChatGPT said it,” so it must be true — like people used to say about the internet in general.

Orlie Benjamin: I actually believe in both of your perspectives. As much risk as I see, I see real reward too. I’m mindful about what I let my nine-year-old son engage with technologically, but I also don’t want him growing up without any exposure to it — he has to learn to be responsible with it, which, as a nine-year-old, takes a lot of guidance. Honestly, it’s hard for us as adults too. There’s so much to process, and only time will tell where things stand six months, or even six days, from now. We’re at a wild inflection point in technology — think about how far we’ve come since before the iPhone existed. Lots of good things coming, alongside a lot to figure out.

Annie: When I moved to Myrtle Beach in 2007, most people I knew didn’t even have a Facebook page yet. I worked at a marketing company right as businesses were starting to think about having a business Facebook page, and none of us really understood what that meant. Someone joked, “That’s like selling somebody a library card — it’s free, you can’t sell it to them.” But you still had to teach people how to actually use it. It’s wild to think how fast things have moved since then — what will things even look like fifteen years from now?

Alex: Honestly, that’s a little scary.

Orlie Benjamin: I’ll agree with you there — scary, but exciting too.

51:01 – Closing and How to Connect

Alex: Orlie, we’re so excited for you, and it’s been such a pleasure getting to know you. I know a lot of people listening will want to learn more. What’s the best way for people to get in touch?

Orlie Benjamin: The website already has a lot of information about what Lasoh does. You can book a demo call or connect with me directly through the Calendly link in the site’s call to action, or find me on LinkedIn through my profile. I’m specifically looking to connect with early-adopter-minded operators who are willing to be a little contrarian and take real ownership of their book of business. If that’s you, I want to talk — I want to be pushed, I want real discussions, and if the product feels like a genuine fit, I’d love for them to use it and give me feedback too. Lasoh is going to be very customer-centric — complaints will turn directly into product development, because I believe fixing real customer pain is good business strategy, full stop.

Annie: Our friend Boogie always says feedback is a gift — take it for what it’s worth.

Alex: That’s a great attitude to have, genuinely. I think that mindset will be your ticket to success — you’ve got the right ingredients, the know-how, and the willingness to stay open to what’s working and what isn’t.

Annie: We’re so glad we met you, and we’re excited to keep running into you at conferences going forward. Thanks again for coming on the show — we can’t wait to watch where you take Lasoh.

Alex: If anyone wants to get in touch with Annie and me, you can go to alexandanniepodcast.com. Until next time, thanks everybody.