Gregory Henderson: Fantastical Forays + the Digital Sphere
The Peak talks to one-half of the dynamic duo behind the Roxbury Experience, the world-renowned luxury escape.
Gregory Henderson is co-owner & proprietor of The Roxbury Motel and The Roxbury at Stratton Falls with his partner, Joe Massa. Thanks to this dynamic duo, the quiet Catskills hamlet of Roxbury is now home to two of the most fantastical luxury escapes ever imagined. With a worldwide reputation, people come from all corners of the planet to sleep in out-of-this-world rooms: The Digs Cottage, Cinderella’s Gown, Crown of the Pendragon, Faerie Forest, Terrazza of the Titans, Galileo’s Gate, The Lost Horizon.... “Theme hotel” does not begin to explain what began as a 10-room roadside motel renovation on a back road 3+ hours north of NYC and has grown, expanding 4x over. Just as Covid-19 hit the state, Gregory and Joe opened the Roxbury at Stratton Falls, just down the road from the Roxbury Motel. While not the most opportune time to launch a new venture, the resort has captured the imaginations of a homebound world—generating a staggering list of accolades from the CBS Morning Show, Conde Nast Traveler, Travel & Leisure, New York Times Forbes, Martha Stewart, and many more.
The Roxbury Motel and the Roxbury at Stratton Falls are both such fantastical places—fantastic escapes from the real world. Where did the idea to start the business come from? The idea has morphed and grown and been elaborated upon over the years. We didn't wake up one day and say, “Oh, we're going to become hoteliers and build theme rooms that delve into fantasy.” It evolved. The original concept for the motel was mainly not unlike what many people who live in New York city are doing right now as a result of COVID. We were looking for a way to change our lives, to find a way to leave the city. We had been wanting to do that for a while, and 9/11 finished us off. We already had a small weekend cabin in Andes, which is where we still live to this day. And we began toying around with different ideas of what we could do if we sold our Manhattan apartment—what that could finance.
We had talked about becoming innkeepers. We knew that it would be a lot of work, although we had no idea at the time, but we looked at it as an opportunity to be creative together as a couple, because we had spent our last five years in the city apart from each other in different careers. I was working on Wall Street at that time. Prior to that, for the first 10 years of our relationship, we were in theater together. Although we were poor and struggling—all the cliches—we realized looking back on it that we were happiest when we were creating together. So, the original 10-room roadside motel was an experiment in whether or not it would succeed, and could we be creative and have fun with it.
Photo by Nils Schlebusch
With the original rooms, we paid tribute to back when the roadside motel did not have a negative connotation, when the Catskills were still in their heyday in the sixties. We were having fun with the concept of mid-century modern, which, in the early 2000s was just beginning to have a comeback. It was still kind of grandma's furniture. We did one room like that. We called it the Austin Powers suite. It was our only theme suite at the time. What we thought was over the top, people just ate it up. There have been different extensions of progressions over the years, four more new construction projects after the first motel, the latest being the Roxbury at Stratton Falls.
Photo by Nils Schlebusch
How do creativity and business work together for you? How do they inform each other? The whole nature of our business is fed through the creative process much as I just described to you in the history of how it happened. We started this business so that we could be creative.
The creativity has led to its success. It has always been successful. But there were times when we were just breaking even, particularly when Airbnb first took hold and began to dominate the area and everybody and their dog were renting out their houses in the Catskills. That definitely affected us. But since we built Roxbury at Stratton Falls and pulled ourselves out of the pandemic, right now you can't even get a room until 2022.
Photo by Nils Schlebusch
But it was always all about the creativity. If it had been all about business, there's no way we would've done what we've done. There's a reason that hotels standardize. So many hotels are franchises with standardized rooms, even boutique hotels. Usually, they put the money into the lobby, or the pool area, or whatever, and yes, maybe the rooms are interesting and fun, but in general, most of the rooms are all the same. They don't go into detail to the level that we do. And there's a reason for that. Because it's difficult to make the business model work. So we just keep hoping and risking that we will continue to be profitable because people will respond to our creativity.
How does the web help your business? From day one, the web has made our business easier. You know, we opened back in 2004 when two things were still relatively new: booking directly online and online reservation systems that were integrated with your website. Now, of course, by the end of the 2000s it wasn't a new concept anymore, but the power of a fully integrated website—definitely needed then—still wasn't anything like it is today.
How did the web help your business adapt to the upheaval of the pandemic? I don't know how we would have done it without the web. We published our COVID-19 safety operating guidelines on our website and offered a printable PDF. Countless people have told us—literally countless, to this day we still hear it—that they chose to come to us because of the amount of effort that we put into writing our COVID operating guidelines. It's like three pages single-spaced. I mean, I like entities like TripAdvisor where you can go and find out about hotels, but most of our guests still come to us directly through our website.
The web also helped us automate quickly, and make a variety of things contactless, which was particularly important in the early stages of the pandemic. So important, because everybody was obsessed and afraid. Now, they're learning that it's very difficult to get the virus through surface contact. But remember, people were washing their groceries then. So, it helped us automate the whole check-in procedure and scheduling services like socially distanced time in the pool, sauna, and hot tub. It also helped with breakfast. Prior to the pandemic, we used to serve an extensive continental breakfast. Everything was wide-open and people stood in line for it. We converted all of that online. People could place their orders before they even arrived, and their breakfast bags would be delivered to their rooms in the morning. It made them feel so much safer.
Has your online presence grown over time? Yes. Social media changed everything. It plays into our theater backgrounds and our desires to still perform. I suppose social media is my outlet. I mean, it's also a curse sometimes because it's a lot of work to come up with content to keep people entertained. But it's something that we enjoy. And there's no question that it has revolutionized our ability to communicate with our tribe.
Photo by Nils Schlebusch
It's not surprising that you use social media in really clever and creative ways to engage people, even your employees. Is there a strategy behind it? I feel it's important to post every day, not more than once a day, and it's important to post at the same time each day. I've learned that people look for it now, at the right time. And, with Instagram stories, I tend to like to tell a story with my stories. So, it depends on when people pick them up. I try to post between five and eight pm every night. And, if the ones from the previous day have not run out already, I actually delete them so that we’re starting fresh with the beginning of that day’s stories.
As far as strategy for creative, it's just really what appeals to me that day. Although the overall strategy to keep in mind is that we're selling rooms and I'm always nervous about posting too much personal content. I don't want to appear like so many social media influencers full of their own ego. I suppose that there's an element of that—I'm an actor at heart. But I've asked, and it seems like the overwhelming majority of followers always say, no, they love the personal stuff. They love to see the people behind our brand. So, it's important for us to make sure that we have a mix of photos of the rooms and the resort—literally, the Roxbury Experience—combined with the behind the scenes running of the Roxbury, and also a little bit about our personal lives.
Photo by Nils Schlebusch
Do you have any frustrations or worries or paranoia about conducting business or life online? There are trolls out there, knock on wood. We haven't had that many, but there's a handful. And, you know, when you're in the business—when the whole crux of your business is based on making people happy—and you combine that with being people who are probably overly sensitive about making people happy… When you get people being negative, or too literal on social media, it can be hurtful. I think we've gone too far with online reviews and people being able to just voice whatever they want. The vast majority of our reviews are beautifully positive, and they mean the world to us. But I think, like a lot of us, we tend to obsess about the ones that aren't, and people can be really mean online.
In a world where it's all based on an algorithm as to how many stars you've got, a one-star review can really hurt your ratings. I think it’s getting a little bit better. For instance, TripAdvisor has realized their business model doesn't work that well. I think they learned that they need to go beyond people just being able to post reviews. They need to sell rooms and make money in other ways. And, I think the general public has gotten a lot savvier about reading between the lines with reviews.
The business owner has the ability to write in response to any reviews, but it's not the same.
Do you do that—respond? I can't keep up with all of the posts but if there is a negative one, if there's something that is really off or really not nice, then yes. I feel like it's something that needs to be corrected. Absolutely. You know, I respond in a very positive way. But there are some things we just can’t do anything about. Like, we’re in a rural area or there aren’t enough restaurants.
Do you have any goals or hopes for your digital presence? Yes. I need to automate even more. I need to stay current with the contactless trend that is everywhere with bar codes, scanning codes, so that people can go up to signs around our property, where they can scan the barcode on it for different things, like things to do, places to go, restaurants, or whatever. And I need to update some of our packages and offerings. Our great new website is still relatively new. And just keeping up with new content for it is a full-time job. The problem is, I guess I’m a bit of a control freak. Someone having the same voice as me, writing for the web, would be hard.
For more on The Roxbury Motel and The Roxbury at Stratton Falls , visit theroxburyexperience.com.