From 3% to 15%: Why Platform Fees Changed My Business Strategy with Orlie Benjamin

Airbnb’s latest fee structure changes everything—but are you ready to take control? Orlie Benjamin, founder of Lasoh and former marketing leader, breaks down why now is the moment for vacation rental operators to build their own direct booking infrastructure.

Transcript

00:00 – Cold Open

Orlie Benjamin: Be really clear on your strategy. There’s a lot changing right now around Airbnb, and I’m genuinely curious to see what Vrbo does — Vrbo has a real moment to shine right now if they choose to take it. But if you’re going to say, “I’m all in on Airbnb, I don’t want to invest in direct booking infrastructure,” then be all in on Airbnb, and make sure the math works around these platform fee differences.

If instead you’re committed to diversifying your distribution and going direct, decide exactly what your plan is and what your next step is, and commit to it. For some people that’s a direct booking site. For others it’s getting a PMS. For others it’s simply gathering contact information. And for some, it’s taking that contact information and actually doing something with it — engaging with their customers. It depends on where you are in your direct booking journey. But whatever it is, be clear on your distribution plan, know your next step, and commit to it.

01:08 – Sponsor Message: Crafted Stays

Gil (Host): Before we bring on our guest, I want to talk about something I’ve been hearing constantly from hosts. It’s the same thing every time: “I know my website isn’t converting, but I can’t afford $8,000 for an agency to rebuild it.” Here’s the problem — you’re running marketing, driving traffic, putting in real effort, but if your site isn’t built to convert, you’re essentially lighting your energy and money on fire. And even if you could afford a custom agency build, every time you want to test something or make a change, you’re paying them again. You can’t iterate, you can’t test, you can’t really improve.

You don’t need a custom $10,000 website to get conversion rates that actually matter — you just need the right platform. That’s why I built Crafted Stays. It’s purpose-built for short-term rentals, designed from the ground up to help you drive more direct bookings, turn traffic into actual bookings, and keep testing and improving as you learn — all on the platform, without having to learn something new. If you want to get started, go to craftedstays.co and start your free trial.

02:07 – Welcome to the Book Solid Show

Gil: Now let’s bring on our guest and dive deep into hospitality and marketing. Hey folks, welcome back to the Book Solid Show, the podcast where we bring on top operators to discuss marketing, revenue management, and direct bookings. On today’s show, I have the pleasure of interviewing Orlie Benjamin, founder of Lasoh, a new marketing platform specifically built for the short-term rental space.

We’re going to talk about why she started the business in the first place, the gap she sees in the market, how she’s launching it, some of the changes happening within the OTAs that are driving huge momentum toward direct bookings, and the ideology behind building a SaaS company versus a consulting agency — we get to nerd out a bit on that. It’s a real pleasure to have her walk through the early days of Lasoh and what she’s building. Let’s bring her in. Orlie, welcome to the show.

Orlie Benjamin: Hi Gil, thanks for having me.

Gil: Good to finally get you on — it’s great to have another entrepreneur in the hospitality tech space on the show.

Orlie Benjamin: I know we’ll have an easy conversation, since we’ve talked a lot before this. Looking forward to it.

Gil: To kick us off, would you mind giving folks an introduction to who you are?

03:21 – What Lasoh Does

Orlie Benjamin: Sure — my name is Orlie Benjamin. I’m the founder and CEO of a software platform for the vacation rental industry called Lasoh. It’s a guest experience and marketing technology platform that enables operators to own their book of business, reduce dependence on Airbnb, and maximize revenue.

Gil: Tell us a bit more about the software — what’s it actually doing behind the scenes? What problem are you solving?

Orlie Benjamin: The core problem is that operators using booking platforms aren’t able to own their book of business, because platforms like Airbnb are purposefully disintermediating the relationship between guests and hosts. Lasoh turns Vrbo or Airbnb into lead generation, because it captures contact information for the entire group staying at the property — not just the booker — starting at the point of booking, not arrival.

Once an operator has that contact information, they can sell guests more things, improve the stay, and build a relationship that can turn into real fandom. Knowing the customer and being able to reach them comes first. From there, Lasoh helps operators maximize revenue through upsells and e-commerce-style experiences. Once the stay ends, it helps operators collect reviews from the whole group, which improves search and generative engine optimization — we have a proprietary Google review flow that filters out negative feedback so only positive reviews make it onto the internet. From there, it’s more traditional marketing: CRM infrastructure to manage contacts, plus simplified email and text campaigns built from templates, so operators can essentially “shop” for the campaign they want instead of building it from scratch.

05:46 – Orlie’s Path Into Vacation Rentals

Gil: You’re an operator yourself. What led you down this path? Give us a bit of backstory on where you came from and what led you to invest in building this company.

Orlie Benjamin: Professionally, my whole background has been in customer-centric roles at Fortune 500 companies. I worked in pricing strategy at American Airlines, where I managed the Priceline channel and a lot of the revenue-maximization innovation at the time. Then I moved to Victoria’s Secret, working in omnichannel marketing strategy — a mix of digital and in-person marketing strategy and implementation. After that, I went to NetJets, a private jet company owned by Berkshire Hathaway, where my job was designing the digital experience for billionaires.

My whole career has really been about identifying a customer’s pain point and figuring out how to deliver value through some combination of knowing the customer and applying digital technology. When I built my own vacation rental business, the first thing I looked for was a marketing tech stack, because I’d always worked in businesses where owning the customer relationship was central. Owning a book of business is essentially building an annuity — when customers come back, you need to do less acquisition marketing, because existing customers compound over time into high lifetime value: they return, they tell their friends, and your marketing effort actually decreases over time as you nurture them.

I realized pretty quickly there wasn’t a marketing tech stack built specifically for this industry that could achieve what I wanted, using the same playbooks I’d used in corporate America. So I cobbled together a tech stack on my own, and quickly found that third-party software just wasn’t working — a lot of CRMs out there are built for sales teams, not nurture marketers, and there were use cases specific to vacation rental management that would’ve required serious custom engineering to make any off-the-shelf stack work. That’s when I decided to build it myself, especially after talking to other operators who articulated the exact same need. Between my corporate experience, my passion for hospitality, and seeing real demand, it just made sense as something I had both the interest and the skill to pursue.

08:47 – Frankenstein Tech Stacks

Gil: That’s interesting — I come from an e-commerce and SaaS background myself, and I completely agree. In those industries, there’s genuinely purpose-built software for marketing, and the tech stacks really differ by industry. In ours, you’re right — there’s nothing purpose-built for our specific workflows and touchpoints. I’m curious what you’ve seen people cobble together, and where it tends to fall apart.

Orlie Benjamin: I’ve seen so many different “Frankenstein” setups while doing discovery. Some more sophisticated operators try using Airtable as a CRM, but it falls short because you can only create so many Zaps connecting Airtable to email marketing software, and there’s no real bidirectional enhancement happening the way there should be.

I’ve also seen setups that don’t work as intended, because people don’t have access to software engineering — they have a wish list for how something should work, but there are gaps, because hiring a software engineer to build something custom is expensive, and most vacation rental operators aren’t technical and don’t have engineers on hand. So I’ve seen a lot of off-the-shelf email tools like Mailchimp, sometimes Klaviyo, which is really built for e-commerce, and I’ve seen operators leaning heavily on point solutions specific to the industry combined with a lot of spend on consultants — consultants managing various campaigns, but hand-coding those campaigns individually. A lot of money ends up going not to technology, but to consultants manually bringing a vision to life. So from my view, the tech isn’t really serving people, and there’s a lot of bespoke consulting happening that could be simplified if that same expertise could operate purpose-built software instead of tactically building everything from scratch.

Gil: Is your goal to enable property managers to handle this themselves, or do you still see a world where consultants keep running the marketing, just using a purpose-built tech stack?

11:42 – Consultants vs. In-House: Both Paths Are Valid

Orlie Benjamin: I think both scenarios are viable — it depends on the business and what resources they want to keep in-house versus outsource. A larger operator might reasonably bring marketing in-house if the technology makes it easy enough to operate, especially if they can afford the salary and the economies of scale work. But I actually think a lot of marketing consultants will end up using our software too, because they’ll finally have real tools to work with — consultants aren’t engineers, and they’ve always had wishes for how things should work that existing software couldn’t support. This gives them a broader toolkit to deliver better outcomes for their operator clients. So I think it’ll go both ways, depending on the operator’s size, internal capability, and business strategy.

Gil: What was your original inspiration for starting this? Was it other industries, other software you’d seen, where you thought, “I wish we had this in our space”? Where did the idea actually come from?

13:00 – Where the Idea Came From

Orlie Benjamin: Honestly, it came from everywhere I’ve worked. At NetJets, we built a proprietary guest experience portal — that was literally part of my role, designing the private jet experience from booking to rebooking. That concept of the guest journey and owner journey was something I’d already lived. At Victoria’s Secret, it felt completely natural to want to own customer data, segment customers, and think in terms of journeys — I understood the value of well-segmented messaging and promotions from seeing it work in retail, and I wanted to bring that capability here.

From American Airlines and pricing strategy, it’s really all about revenue maximization. Look at PriceLabs — they’re crushing it, with something like 450,000 units using their software, more than any PMS, purely because of the value in optimizing nightly pricing. But revenue maximization is about so much more than just how much someone spends per stay. It’s how often a guest comes back, how much they spend per trip — nightly price is one lever, but there are others: upsells, concierge-level offerings, even e-commerce-izing parts of the trip. I’ve seen so much untapped opportunity here that I’ve watched work firsthand in Fortune 500 companies, and it makes sense this industry isn’t there yet — direct booking as a real concept, both through Airbnb and PMS providers, has really only existed for about ten years, and taking on that responsibility as an operator is a big commitment when Airbnb offers such a convenient platform.

But now, with the pricing changes happening — platform fees moving from being blended between host and guest to being borne entirely by the host — that’s a huge margin shift, going from roughly 3% to around 15.5% of gross income, not net, which is also an important distinction. That changes the marketing budget analysis completely, because operators are no longer just handing Airbnb 3% of their business for lead generation — now it’s 15.5%. That gives operators a lot more margin to justify going direct, if they’re willing to put in the work. So really, nothing Lasoh is doing is new or crazy — it already works in other industries. This industry has just been underserved.

15:57 – The Missing Playbook: LTV and Repeat Bookings

Gil: I think our industry is largely figuring out marketing from the ground up, without a real playbook or toolset. In SaaS or e-commerce, there’s a distinct playbook and clear KPIs. You mentioned LTV — in retail and e-commerce, that’s something we think about constantly. It’s not just the one checkout — it’s repeat purchase rate, how quickly customers come back. For a lot of hosts and property managers, LTV is essentially treated as equal to one single stay, which is actually pretty wrong when you compare it to how a big hotel chain thinks about a single guest.

Orlie Benjamin: Exactly. Before I even committed to building this software, I did real research — I surveyed over 100 operators, and less than 20% actively monitor repeat booking rates. And even the ones who do will tell you they’re not fully confident in how accurate that number is, because you have to decide what actually counts as a repeat booking. If Jill books the first stay and Jack books the next stay for the same group, they’re both guests, both customers — but is that a repeat booking? I’d say yes, but most operators don’t even have visibility into who’s actually staying at the property to make that determination in the first place. That’s part of what I’m trying to solve — giving operators a clearer picture of who their customers actually are, and what their real repeat booking rate is.

Going back to lifetime value — in retail, the way you make money is number of customers, multiplied by number of visits, multiplied by average spend per visit. Multiply those three together and you get customer value, over whatever time horizon you’re measuring — a year, a lifetime. But so much of the vacation rental business is fixated on that single visit. No one’s tracking spend per visit, no one’s tracking visits per guest. To me, those are genuine white spaces — real opportunities to maximize revenue. Look at how much demand there is for PriceLabs, and that’s just one lever: nightly price. There are so many other levers that simply aren’t accessible yet without a huge amount of sophistication and elbow grease, and unlocking those is exactly what needs to happen for operators.

19:23 – Where Lasoh Is Today, and What’s Next

Gil: You’ve been working on this for a while now — how has progress gone in terms of capabilities, and what do you see happening over the next year to close some of those use-case gaps?

Orlie Benjamin: I’m happy with what I’d call our 1.0 product. There’s a lot more I want to build, but I think 1.0 delivers real value on its own — it’s really focused on data capture and e-commerce-izing the guest journey. The next product is the marketing tech stack, which we’re actively building right now, and we’ll be beta testing it with an early group of customers. If anyone listening wants to be an early beta tester, reach out — we’re always looking to design alongside customers.

Even though I’m an operator myself, it’s really important to me to design with design partners — listening to different customers’ use cases and building for the industry, not just my own opinions, because that would just be “me-marketing.” I don’t assume I know everything; it’s better to listen to other people’s pain points to drive better product strategy. So while there’s a lot I want to build, I want to make sure what we build actually aligns to real pain points guests and operators have, and a lot of our prioritization is going to be driven directly by that feedback.

Gil: As you build this out, how much is focused on the platform and capabilities versus eventually offering some kind of service layer? Do you see yourself going down the services path, or staying purely on the enablement/technology side?

21:22 – Software vs. Services: Staying in the Software Lane

Orlie Benjamin: Great question — my objective is to be a software company. I’ve seen scenarios where some service enablement is necessary for success. HubSpot’s a good example — it’s a software company, but it certifies service providers who are trained to operate the software properly. I could see a world where Lasoh builds relationships with marketing consultants who become “Lasoh certified,” meaning they know how to operate the software on behalf of clients. I don’t see a world where we build our own in-house consulting arm, unless there’s some genuinely unique use case that the existing ecosystem of consultants just can’t cover.

Even now, if Lasoh alone doesn’t solve someone’s problem, I’ll say, “Let me connect you with someone who can get you to where you need to be.” A lot of my calls actually end with me connecting a potential customer to a marketing consultant. It’s a genuinely complementary relationship, because a system without someone driving the strategy behind it isn’t particularly useful. It’s like buying a beautiful manual-transmission Ferrari but not knowing how to drive stick — if you can drive stick, you’re ready to go; if you can’t, you’ve got a system you can’t use. The system is only as good as the people operating it.

Gil: We have a similar mindset at Crafted Stays — we try to make things easily accessible for whoever’s on the other end, and we deliberately avoid the services side. If someone asks me to help with email marketing or branding, we probably could, but honestly there are people who can do it ten times better than we could.

23:57 – Why Software and Services Don’t Mix Well

Orlie Benjamin: I’d much rather refer people to trusted partners who already do that as their bread and butter. It’s actually a really symbiotic relationship — they get to know the platform, they often serve multiple clients on it, and they can handle specific use cases far better than we could ourselves.

I agree with that approach completely. It’s genuinely hard to be both a services business and a software business — they require completely different capabilities. One is selling a product, the other is selling time. The whole point of a software business is selling something infinitely scalable. Having a strong working relationship with industry experts who understand marketing, and who can become grassroots promoters of your product, is just smarter than trying to build your own in-house marketing agency. I actually did consulting for a year, and I realized I don’t want to be in the consulting business — I want to be in the software business.

Gil: It also almost forces you to mature the platform faster. When you hit a problem, you can either throw manpower at it or build a scalable solution using technology. Staying focused on building the most mature platform forces you to constantly ask, “How do I solve this not just for one person, but for a whole market of people?” That’s how I think about it.

25:18 – Strategy Is Also What You Don’t Do

Orlie Benjamin: Completely agree. I actually think strategy isn’t only about what you do — it’s equally about what you don’t do. In consulting, everything can be bespoke and fully customized. In software, you have to be really disciplined about what actually serves the most people, and consciously avoid what would just be a distraction. It’s almost like comparing mass-produced fashion — a product that works well for most people, at an affordable, scalable price — to couture, which is fully custom, expensive, but perfect for one person. That’s a decent analogy for custom-made versus mass-made in this context.

Gil: That example about consultants patching problems with manpower — that’s actually exactly how direct booking websites used to get built for our industry before Crafted Stays. It was all bespoke, someone hand-coding a one-off instance for each client. I see a ton of inefficiency in that, especially when the same templates get reused over and over anyway. I think in your world too, people are cobbling different systems together without really leaning on lessons about how to build this sustainably. I think over the next few years, platforms like ours will mature the way PMSs have — to the point where people come to expect certain baseline functionality across every provider.

27:23 – Maturity, Backend Infrastructure, and the WordPress Comparison

Orlie Benjamin: A mature PMS anticipates your needs and has already solved for them, where a less mature one is still figuring out what those needs even are. Going back to your earlier question — I actually don’t see too many fully custom websites failing because of custom requirements. I see a lot of gaps, because it’s relatively easy for a web developer to build a visual, custom website. But once you start stacking together technology that requires real backend data infrastructure alongside a front-end interface, that’s often too heavy a lift for operators to pull off. So instead of those wishes becoming reality, there’s often just no real engineering behind the use cases people want, and it simply doesn’t get built. A lot of point solutions — sometimes industry-specific, sometimes not — end up stitched together with real gaps, functionally getting close to the goal but never quite matching what a properly integrated system could deliver.

Gil: I’d actually argue that even in the direct booking space, probably half our engineering team is focused purely on backend, non-visual infrastructure — because that’s what actually makes it easy for people to set up the sites they want, or ensures seamless integrations. I see some of what people build with WordPress plugins, and I’m not surprised it’s buggy, because it was never designed to be built that way. It’s a lot easier building something from the ground up for these specific use cases, like what you’re describing.

Orlie Benjamin: What’s nice about direct booking websites specifically is that 85–90% of the use cases are basically the same across operators, and there’s a lot more stability plugging directly into a PMS or email software than relying on something like WordPress, which is constantly pushing open-source updates that require regression testing and inevitably break things — it’s a huge ongoing web development investment. I actually have a custom WordPress site myself, and I probably spend more maintaining it than I would if I just switched to Crafted Stays, which we’ve talked about — I need to make that switch, honestly, for simplicity and cost savings, because of the scalability you get once someone’s already anticipated the needs of a typical website and packaged it up for you.

29:59 – SaaS Incentives vs. Consulting Incentives

Gil: I think that same principle applies to your platform as it matures over time. As you roll out 2.0 and run marketing campaigns on behalf of property managers, that stack, the use cases, and the capabilities are all going to keep improving. The nice thing about SaaS is that because you’re billing on subscription, you’re constantly incentivized to keep adding value. As entrepreneurs, we’re encouraged to keep maturing the platform. It’s almost inverted with consulting — you deliver one piece of software, maybe a hosting fee, but most of the money is upfront. With SaaS, you’re constantly proving ongoing ROI, which for me is actually a great incentive structure.

Orlie Benjamin: Consulting as a business model has essentially zero barrier to entry and immediate cash flow, but it’s completely capped in scalability, because you only have so much time to sell. Software is the exact opposite — real barriers to entry, since you have to invest in building it, but in theory unlimited scalability if your addressable market is large enough. The trade-off is you have to make the right bets early, or you’ve built the wrong thing and none of it matters. Different risk-reward profiles entirely.

31:37 – Airbnb’s Recent Changes and the Surge in Direct Booking Demand

Gil: What have you seen recently? I’ve noticed a lot of change over the past five to eight months, specifically with Airbnb, and I think Vrbo’s made some moves too. Have you seen higher demand or desire on your side to go direct?

Orlie Benjamin: The time is now, honestly. A couple of big Airbnb changes stand out — the shift in the platform fee structure. Traditionally it’s been roughly 3% for the host and 15% for the guest, and now they’re consolidating those fees onto the host side — I believe effective October 27th of this year, which by the time this airs is only about a month out from us recording. That’s going to change everything.

There’s also chatter about beta-testing masked phone numbers, so guests’ actual phone numbers are never shared and are entirely controlled by the Airbnb platform, along with a variety of changes around chargebacks and other risk-mitigation measures. Airbnb has done more in the last three months to reduce operator control than it’s done in the previous ten years combined, which I think is a really clear signal — Airbnb feels it now has enough operators locked into the platform that it doesn’t need to worry about them leaving, and it’s optimizing heavily for the guest experience, since that’s where most of the money comes from.

It actually mirrors what Uber’s done with drivers — changing the pricing structure and the relationship drivers have with riders. The key difference is that an Uber driver has a real interpersonal moment with the passenger in the car, if they choose to engage, and that human connection largely doesn’t exist for vacation rental operators, since most are remote. Operators are definitely waking up to the risk of an intermediated distribution channel, because going from a 3% cut to 15.5% can flip a business’s economics upside down depending on their margins. You could reframe that 15.5% as your marketing budget — you either hand it to Airbnb, or you build your own direct-to-consumer capabilities for probably less than that. It fundamentally changes the unit economics: 3% is negligible, 15% is sizable. I think direct booking demand is genuinely exploding right now, because nobody wants to be stuck handing over 15.5% of their margin with zero control over chargebacks or communication, where a fraud claim can suddenly become entirely your problem.

35:11 – Reframing Commission Fees as a Marketing Budget

Gil: That’s such a good point about commission fees essentially being an inverse marketing budget. If I look at just one of my properties, if 100% of its bookings came from one OTA, that would be roughly $20,000 a year in commissions — which is actually a pretty sizable marketing budget if I redirected it toward my own marketing.

Orlie Benjamin: I have a fairly sizable direct booking pipeline myself, and I can tell you I spend way less than 20% of my margin on marketing — some of that’s because I know how to run it efficiently, sure, but 20% is a huge amount to spend on marketing. A lot of businesses don’t even hit that.

Gil: Sorry, I meant $20,000 specifically, not 20%.

Orlie Benjamin: Ah, got it — either way, it’s worth comparing that dollar figure to what Airbnb effectively costs as a marketing channel.

Gil: Right, and what people don’t realize is that’s $20,000 every single year, indefinitely, if 100% of bookings keep coming through Airbnb.

Orlie Benjamin: And there’s an opportunity cost too — without owning that customer data, those guests never turn into an annuity that reduces how much you need to market going forward. In my own experience, direct bookings actually fill in the less desirable parts of my booking calendar. My Airbnb bookings cluster around peak, high-intent periods — summer, fall — but my winter and weekday bookings are overwhelmingly direct, because someone is choosing to stay at my property based on demand I’ve created, rather than stumbling across white-labeled inventory on Airbnb. Once you flip the script from being discovered inventory to actively generating your own demand, your occupancy rate goes way up, and that changes everything.

The average U.S. vacation rental occupancy rate is around 55%. If you move that to 65%, your costs barely change at all — mortgage, cleaning fees, maybe a little variable cost on amenities — otherwise it’s almost pure profit. That’s where marketing has enormous upside: demand generation. I’d genuinely love to hear from anyone listening who feels they have a healthy direct booking business — how much real demand are they generating themselves, versus just reacting to someone’s Airbnb search? Being able to generate your own demand is an incredibly powerful position to be in.

38:26 – Compounding Revenue vs. Renting Attention Every Year

Gil: I’ve noticed that property managers driving significant direct bookings run a completely different marketing strategy overall. They’re less anxious about reviews, less obsessed with ranking on page one — sure, they still want it, but a lot of their revenue is compounding revenue they’ve built over years. That’s probably the biggest difference: you’re not paying that $20K annually forever. You might invest heavily in year one — consulting, campaign-building — but by year two or three, you’ve built a much larger email list, a more loyal following on Instagram, and your messaging is dialed in. That’s where I see the real compounding impact on direct bookings. Compare that to OTAs, where you could be a host for ten years, get a couple of bad reviews, and watch it all tank, with essentially no accumulated equity beyond maybe a Superhost badge.

Orlie Benjamin: Completely agree, especially for anyone thinking about eventually selling their business — part of that business’s asset value is literally the rolodex of customers. There’s real intellectual property in that. It’s not just having an Airbnb listing and a website — it’s the ability to turn an existing customer base into an annuity. That’s what good marketing and demand generation actually do, and it puts a much higher multiple on the business, because it ties directly back to lifetime value and repeat business — which is recurring revenue. And recurring revenue is every investor’s favorite word, whether it’s ARR or MRR in SaaS terms, or repeat bookings in vacation rentals. It’s probably the single most important KPI for evaluating the underlying health of your demand, because every repeat booking is that much less demand generation you have to do — and that much less reliance on Airbnb.

40:49 – Learning From Boutique Hotels

Gil: It’s interesting — if you ever talk to a boutique hotel manager, the way they think about delivering service and bringing guests back is very different from how the short-term rental world has traditionally operated. Things are starting to shift, but I’m always fascinated by how boutique hotel managers run their operations — it feels like a nice hybrid between large-scale hospitality and a scrappier, more personal approach.

Orlie Benjamin: It’s funny — people often describe me as “property tech,” and I always push back on that. This isn’t just a property asset class — it’s a hospitality business, and a hospitality business is fundamentally an experience business. An operator’s job isn’t just financial viability and tight operations; it’s also creating demand. You could run the tightest operation possible with a low occupancy rate and still not be winning.

41:57 – Brand as a Promise, Not a Logo

Orlie Benjamin: A lot of this comes down to brand, and when I say brand, I don’t mean logo, font, and color palette. A brand is fundamentally the promise you make and your ability to deliver on that promise. A great boutique hotel sets an expectation and delivers on it consistently through the experience — every touchpoint is part of the brand’s value proposition. That’s part of why guest experience matters so much: it’s literally how you build trust.

When a guest arrives already having had a positive experience before their stay even starts, there’s goodwill already banked. If something small goes wrong later — something minor, something forgivable — you don’t get the same reactive frustration from that guest, because the positive goodwill is already there. That’s brand building. And branding is also fundamentally about being memorable — yes, operators should have logos and names people recognize, but the real work is making and consistently delivering on a promise. It’s not just a design exercise; it’s experience strategy and experience design.

That’s what’s genuinely exciting about hospitality — great hospitality brands set an expectation and deliver on it consistently. And when you really think about what Airbnb is, it’s fundamentally a trust economy — no one would ever stay in a stranger’s house without some baseline sense of trust. The way to reduce your dependence on Airbnb is to build your own trust economy — through consistently great delivery of an experience your guests love enough to talk about with friends, rave about on social media, and become genuine superfans over. That’s all branding, built entirely around the experience.

44:02 – Where the Name “Lasoh” Came From

Gil: Curious tangent — where did the name Lasoh come from?

Orlie Benjamin: It’s a deliberate misspelling of a cowboy’s rope, because — like we were just talking about — I feel like you have to wrangle everything together. There’s this whole journey from the point a guest books to the point they rebook, and it all has to be wrangled into one cohesive experience. Practically speaking, you also can’t buy a normally spelled domain name anymore, so I just misspelled “Lasoh” slightly — which, funny enough, trips a lot of people up phonetically. But really, it’s about wrangling everything together into one place.

Gil: I like that. Alright, Orlie, we usually close the show with three questions. First — what’s a good book recommendation? I’ve been reading a lot lately and I’m always looking for the next good one.

44:53 – Closing Question 1: Book Recommendations

Orlie Benjamin: Have you read The Lean Startup?

Gil: I have — it’s probably been 12 years since I picked it up.

Orlie Benjamin: I’d put it near the top of your list, mostly because at this stage as founders, it’s genuinely useful to refresh yourself on the why behind your business — how you’re commercializing, what your strategy actually is. It’s maybe less directly relevant for the general audience of this podcast, since many of them aren’t building startups, but I think it still applies broadly because it’s really about the fundamentals of entrepreneurship. I’m actually rereading it right now for the second time — that’s how good I think it is.

Gil: It’s been a while, but I remember the core premise — proving out your value proposition and business viability without having to build everything at once and deliver some big-bang launch. It’s about piecing things together in the scrappiest way possible.

Orlie Benjamin: One of the really important points in the book is knowing when you’ve built enough to actually scale at speed. That inflection point is genuinely hard to pinpoint — how do you know you have enough customer traction to say “this is validated, I can go faster,” versus this isn’t validated yet and you’re just moving too fast, and the wheels are going to come off? That’s a critical moment for any early-stage business, and it’s probably very relevant to where you are right now — you have paying customers, a solid early product. Could you throw fuel on the fire right now and everything scales, or would the wheels come off?

Gil: I feel pretty confident, honestly.

Orlie Benjamin: Good — then maybe this isn’t the exact right book for you right now, but it’s probably still worth revisiting as a reminder, even after seven startups.

I’ll throw out a second one, also maybe less directly relevant to your audience — it’s called Tribal Leadership. What I like about it is the idea that birds flock, fish school, and humans tribe. It explores how a tribe tends to be somewhere between 20 and 150 people, and how there are distinct cultural patterns within tribes. We build tribes as leaders of our own organizations, and we also build them through partnerships and customers. Thinking about people as tribes with shared values is genuinely interesting when you’re thinking about how to influence behavior.

Gil: Haven’t heard that one — definitely want to pick it up.

48:04 – Closing Question 2: Mindset Advice for Starting Something New

Gil: Second question — what’s one piece of mindset advice you’d give someone starting something completely new?

Orlie Benjamin: Just do it. It’s okay if it’s bad at first — it probably will be — just keep going. I’d call myself a recovered perfectionist, and so much value comes from just making progress, even if it’s not right the first time. Accept the mess, treat everything as either a win or a learning opportunity, not a binary win-or-lose. Get out there, stay open-minded and flexible, and flow with it until it starts to make sense. Fear about starting, or feeling like you’re not ready — ironically, that’s the worst outcome, because it means you do nothing. So just go do it, be okay with being wrong, fix it, and get better.

Gil: I tell my ten-year-old son this constantly while he’s learning sports — none of these professional athletes walked onto the field already perfect. They worked at it.

Orlie Benjamin: Exactly, and you can’t improve until you take that first step. I still remember the very early days of Crafted Stays, and it’s nothing like what it is now. If I’d let myself get intimidated by everything I’d eventually need to build, I probably wouldn’t have stuck with it. Just putting on blinders and focusing on the next immediate step was genuinely what made it possible for me to take the plunge.

49:50 – Closing Question 3: Tactical Advice for Direct Bookings

Gil: Last question — what’s one tactical takeaway for someone either just starting with direct bookings, or trying to amplify what they already have?

Orlie Benjamin: First, be really clear on your strategy. A lot is shifting right now with Airbnb — I’m genuinely curious what Vrbo does with this moment. But if you’re deciding to stay fully committed to Airbnb and skip direct booking infrastructure entirely, then go all in and make sure the math on these platform fee changes actually works for you. If you’re committed to diversifying and going direct, decide exactly what your plan and next step are, and commit to it — for some, that’s a direct booking site; for others, it’s getting a PMS; for others, it’s simply gathering contact information; and for some, it’s actually using that contact information to engage customers. It depends entirely on where you are in that journey. But whatever it is, be clear on your plan and commit to your next step.

Going back to my “just do it” point — it’s really easy to have a plan you never actually execute, while time keeps passing, and you can never manufacture more of it. So operate with a real sense of urgency, commit to your next step, and go do it.

Gil: And for folks who aren’t sure how to navigate that, on the Crafted Stays website we actually have a guidebook covering the fundamentals — starting with having a PMS in place, then your website, branding, and marketing, understanding your overall infrastructure. If you’re not sure what your next step is, take a look at that, figure out where you stand on the fundamentals, and take that next action step.

Orlie Benjamin: I’d say to anyone listening — I’m not in the consulting business, but you can book a free demo with me on my website, and I’ll listen to where you actually are in your business. Even if Lasoh isn’t the right fit, I’ll connect you with someone who can help you get to your next step. I’ve talked to plenty of operators who don’t have a PMS yet, or a direct booking site yet, and since Lasoh requires a PMS, it’s not something they can use right away — it comes later in the direct booking journey. But I’ll gladly spend 45 minutes doing discovery with you on your plan and next steps, regardless of whether Lasoh ends up being the right fit.

53:53 – How to Connect With Orlie

Gil: That’s awesome. Where can folks learn more about you and follow along?

Orlie Benjamin: You can find me on LinkedIn under my name, Orlie Benjamin — that’s my personal page. There’s also a Lasoh LinkedIn page. The Lasoh website is Lasoh.io, and we’re active across a few social channels for both the Lasoh business and the content I put out around marketing and educating vacation rental operators on distribution strategy — Instagram, Facebook, a handful of places. Hopefully some of those get tagged in the podcast notes so people can find them easily. I’m very active on LinkedIn and will respond if you reach out. My email is Orlie — spelled O-R-L-I — at Lasoh, spelled the “incorrect” way, dot io. So feel free to message me that way too.

Gil: I’ll drop all of those links into the show notes so people can just click through instead of copying and spelling things out themselves. Orlie, it’s been a huge pleasure having you on — thanks for walking us through why you started this company, the gap you see in the market, and why now is such a ripe moment for operators to think seriously about direct bookings, or decide deliberately to double down on OTAs, and how to succeed either way. Really appreciate you sharing all of that.

Orlie Benjamin: Thanks for having me — always fun to talk with you. I know we share a lot of similar philosophies, and I’d genuinely challenge anyone listening to come challenge me too. I love a good intelligent debate, so come find me and push back on my ideas — I’d love to hear what I’m missing. Seriously.

Gil: Awesome — thanks, bye!

Orlie Benjamin: Bye, thank you!