Vlad: For those who have no idea about you or your company, can you introduce who you are, what you do, and why people should choose you?
Rick: My name is Rick Kenworthy. I'm the co-founder and CEO of Travli Hospitality, based in Scottsdale, Arizona. We're primarily a luxury-based vacation home management platform. We manage a little over $200 million in assets, more than 112 properties currently, and we're growing daily.
Vlad: How do you see the market now? Everyone talks about change, and guest expectations keep rising while reality often lags. How do you keep up when everything moves so fast?
Rick: We've adopted AI in a lot of the operational elements, but not so much in the guest-facing side - the communications. We believe people dealing with people is still the way to go, especially in high-end hospitality. But we've embraced AI on the backend: automations, tech support, all those things. So we have a good blend of human interaction and automated AI function. A lot of our competitors have gone all the way down the AI path - you see influencers and so-called experts online pitching a fully automated Airbnb or vacation management system. That probably works in the budget sector, but I don't think a full AI model works in luxury hospitality. The margins are greater when you automate everything, sure. But think about my own frustration trying to service my vehicle through AI, or waiting on hold with my internet provider - I'm not going to subject my guests to that until it's perfect. I'm not saying we won't evolve toward a greater percentage of AI in operations, but right now we still believe people dealing with people on the actual hospitality side, using AI behind the scenes.
Vlad: What is something you understand about luxury short-term rentals that most property management companies get wrong?
Rick: A big part is forgetting that when you're a short-term rental manager, you're managing people's experiences. We've evolved into a world where people are removing the vacation part of the vacation rental industry. Their vacations are predicated on your support systems. When we talk about the value of a portfolio, at the end of the day none of it exists without the guests. If you're not very guest-forward in how you run your company, you just can't be successful. In a budget category you can probably get away with it because expectations are lower. But the mistake everyone's making is getting sold on everything automated - AI, chatbots - thinking they can cut corners or skip steps. AI has actually made it easier for everyone to cut corners. That said, we use AI a lot. We've trained our LLMs to understand Airbnb's algorithms and policy - we upload policy changes all the time, and as a pro host we get better information straight from the platforms. Once your LLMs understand that, things like listing descriptions, titles, and the SEO component of visibility become much easier. And basic automations - sending check-in instructions, coordinating cleanings - none of that is guest-facing. So we lean on AI a lot. It's just our touch points, our communication with guests, that stay people dealing with people.
Vlad: If you looked back 10 years, what advice would you give yourself - not to simplify the process, but the tough lessons?
Rick: I'd tell myself to trust the process more, to delegate and let your support staff do what they're there to do. One mistake early on was trying to wear every single hat. That works at eight, nine, ten properties. At a hundred, it simply doesn't - you wear yourself thin or implode from the inside out. After Covid we had a big boom of prospects and investors wanting to be in Arizona - a bit of a gold rush, though we joke now it was the fool's gold rush. We saw competitors our size take every single client that came knocking, and they didn't have the infrastructure to support it, so a lot of them imploded. We've always hired first, put the pieces in place, then expanded the portfolio and pushed marketing for new clients. So 10 years back: trust the process, don't try to do every single thing, nurture your people and coach them into positions that make your life easier. We practice that now - it just took 10 years and a lot of sleepless nights to get there.
Vlad: Did you ever have a survival-mode period, and when did the company really start to scale?
Rick: It's hard to pinpoint. My wife and I teamed up and got to about nine properties while we both still had regular jobs. It became so cumbersome it was affecting my day job, and that was the lightbulb moment - decide whether this is a real business or stays a side hustle. That was August of 2020. Everything was growing, so I jumped in full-time, and that's when we really developed a team, infrastructure, and policies - all the things a real business should have, with no experience doing it. A lot of trial and error, and honestly a lot of failure, came with that.
Vlad: How do you keep the guest experience high while protecting margins so operational costs don't blow up?
Rick: Keeping the human element in. The reality is, with the way society is structured, you wouldn't have margins if you couldn't use overseas virtual assistance and still keep the people element. If we paid Arizona prices for every person handling guest touch points, it would be extremely difficult. So you find the balance: the cheapest option is a chatbot or purely AI on a subscription; the next least expensive is utilising talented people overseas. We've gone that direction for now - that's where hospitality comes first, real people dealing with real people. It's a debatable subject in my position, because some people tout their margins but aren't as highly rated or don't get as much repeat clientele. There are tradeoffs. We get a lot of repeat guests because they appreciate dealing with real people - not phone prompts, option one, option two - a real person who understands a real issue and comes up with a real solution. We'll hang onto that model as long as it's sustainable. It's a place where you could have heated discussions with a lot of managers about what's more important: your bottom line or the happiness of your guests. Because if your reviews dwindle, that goes directly to your visibility, which goes right back to your bottom line.
Vlad: When Airbnb or the OTAs change a rule or fee, how much does that mess with the company?
Rick: When Airbnb changed their fee structure, it was actually welcomed to an extent. We'd all prefer it was less, but moving fees from the guest side to the host side let you, if you know what you're doing, compensate in an invisible way. For years guests were trained to expect taxes and fees stacked at checkout. Our data supports that more travelers now appreciate the one-fee model - at the end of the day, all the OTAs charge commissions, they all have to make money. We play mostly in Airbnb's world because they're the prominent OTA in Arizona, so everything we do caters to how Airbnb operates. When they made that switch, they also pivoted toward supporting pro hosts with a proven track record. Those two things together contributed to a record first six months by a wide margin. Everyone in the blogs and Facebook groups is crying about the 15.5%, but if you mark it up correctly the price to the consumer is the same - it's just how it's portrayed. Consumers appreciate seeing the true nightly rate with everything included except taxes. It created more trust, and it's been a welcome change. You'd wish the OTAs charged less, but your business relies on them, so you pivot - and if you pivot the right way, it actually made life a little easier.
Vlad: It's hard to build direct bookings now - you need to be active on social, because no one searches a specific hotel name unless something caught their attention. Moving traffic from OTA to direct is tough.
Rick: A lot of people try to pivot to direct - "let's fire Airbnb and build on direct bookings." But you need a massive marketing budget to go against a VRBO or Airbnb for those bookings. It's easier to market to your previous guests within the confines of policy, but it's not as simple as flipping a switch. There's a lot of risk, too. When we first turned on direct bookings, we weren't ready - one of the failures we learned important lessons from. If you don't have good security protocols, fraud detection, and identity verification, you can get burned fast. So the random person with 10 properties who signs up for a PMS, sees they have a direct booking site, and pushes it hard on social media is opening themselves up to a whole set of issues. You have to get ahead of that before you take the leap, because doing it in haste can really hurt.
Vlad: Airbnb and Booking.com invest billions in marketing every year. What makes a guest choose one listing over the other hundred - reviews, the view, price?
Rick: A clear understanding of each platform's algorithm is the most important, because that triggers your visibility. Using Airbnb as the example - play by their rulebook and everything else falls into place. You need to understand what makes your properties show up more often than competitors. That's the baseline. Then the aesthetic component: if you're passing off iPhone photos as professional, you're not getting the right angles or understanding the hero photo and the four that follow, the photo-tour flow that starts at the front door and works through the property. You can show up first, but you need something to catch attention. Then, when guests narrow it to one or two properties, you differentiate: professionally managed, an infrastructure, a prep team, a cleaning crew, inspections, quality checks - all the things that come from renting from a brand rather than an individual. And then reviews. If you're a guest favorite or top-tier, those properties stand out by default. We have a "first five" rule and A/B test new listings over the first couple of weeks to learn which combination of photos and titles converts. We're at almost 11,000 reviews and still over 4.9 stars - the only Arizona management company with that volume that maintains Superhost status - so we have a bit of an unfair visibility advantage by default. But if you're showing up on page 12, 13, 20, your only way to the top is being the cheapest and hoping people filter by price. And that's seasonal - Arizona summers have a catastrophic drop-off, so if you don't diversify into midterm stays and use all the discounts and triggers, you'll fail instantly. Visibility is king, visibility comes from conversion, and if you're not converting, you're not visible - you're done. Your only way to combat that is price, which is a negative on your bottom line.
Vlad: If you had a magic wand to remove one thing from the market, what would it be?
Rick: The cliché answer would be regulation, but most regulation is welcomed. What I'd really wish away is the operators who make the rest of us look bad - absentee owners, uninvested owners, and by uninvested I don't just mean money, I mean mentally. I wish we could cut out the 30% of competition that isn't operating at a level that exudes hospitality, so the rest of us who take it seriously can thrive. We're in one of the top five or six most competitive markets in the country, and honestly we look at 30% of them as barely existing - poorly managed, no infrastructure, horrible marketing, dated, deferred maintenance. Most of those properties come up for sale eventually anyway. But I'd eliminate the components of our industry that make those of us who take it seriously look bad.
Vlad: How do you see the market over the next few months?
Rick: The short-term rental industry changes almost every single day, and every market is different, so it's hard to say globally. I do see this wave of people pitching AI-run businesses, and I fear it'll bring the quality of our industry down. I saw two of them this morning - "I'll find an independent operator, steal his photos, use AI to create a dynamic video, and sell him management." That's not real. You can enhance photos and make properties look better than they are, get a boost in conversion, but then guests show up and the property doesn't match, and that only hurts you. I think fully automated management - in Scottsdale or any market - will bring quality down and hurt us all initially, but it'll probably rebound because it's not sustainable. Everything automated by AI leaves too many touch points uncovered, and people will steer away from companies that operate that way. Regulation is getting more aggressive in most jurisdictions. Our market in the next few months - it's summer, so it's brutal here, and we count down to Labor Day when our season returns. But we're experiencing record growth. Owners in Arizona want to work with us because they see our marketing and I'm very transparent - I share numbers and I won't tell someone their property is something it's not just to get a contract. We probably say no three times for every yes; it has to be a good fit from the property and the owner, it has to vibrate on the relationship first. For the first time - Q1 and Q2 of 2026 - we saw an increase in every KPI we track: occupancy, average nightly rate, length of stay, lead times, and RevPAR. That's the first time in five years all five were positive, which is a good sign, and we're seeing some of the operators who aren't up to par falling out.
Vlad: Where can people find more about your company?
Rick: Our website is gotravely.com - T-R-A-V-E-L-Y. I publish blogs often for other operators, digging into trends, mostly in our market, but there's a lot hosts can take away. The links to social are there. We're launching new products and initiatives all the time, and I'm never afraid to mentor - I mentor a couple of smaller managers to help them avoid the mistakes I made growing.
Vlad: There's a lot of really good content. Rick, thank you so much for everything you shared today - I'll put your links in the description.
Rick: Thank you.
