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How Did you Get that F*&%ng Awesome Job?
Ready Made Magazine
December-January, 2009

Greg Henderson and his partner, Joseph Massa, left successful careers on Wall Street to chase a crazy dream: opening a boutique hotel known for ’60s and ’70s space-age decor in an old motel building in the Catskill region of upstate New York—an area not exactly known for its edginess. Now in the midst of their second expansion, they’re so glad they did.

Name: Greg Henderson
Occupation: Hotelier, co-owner of the Roxbury Motel
Location: Roxbury, NY in the Catskill Mountain region of New York State
Age: 45
First Job: Babysitting some brats down the street who would punch me in the nose because they knew it would bleed easily
Best Job: What I’m doing right now! Touring the country doing my own one-man show for five years was pretty darn exciting as well, but everything looks better in hindsight. If I really put myself in the same place that I was back then, I would never want to go back to the anxiety and fear involved with never knowing where my next meal was coming from. Owning and operating The Roxbury gives me the best of both worlds. It’s just like theater in that we have cool sets, a “fantasy” world that is created by our whimsical design, a receptive audience, and the occasional standing ovation from extremely satisfied guests.
Greatest Professional Challenge: Having the guts to leave a lucrative job on Wall Street to open a crazy boutique hotel in a very rural area full of “antiquey doily” B&B’s.

1. Hi, Greg Henderson. How did you get that f*&%ing awesome job?
Whew! How do I put all of it into words? I guess you could say that everything in my life up until opening The Roxbury “brought” me here. I got a degree in business from Georgetown University in the 80’s, majoring in International Management and Marketing. But the thought of being what I thought at the time as “just a businessman” for the rest of my life petrified me, so I pursued my real passion in the theater and moved to New York City, where I received a degree in acting from The American Academy of Dramatic Arts. I was a working actor for 10 years, the last five years of which I toured in a one-man show which played 14 different cities. While acting, I met my life partner who was the artistic director of a theater company in NYC. We built and painted the sets, wrote the plays, acted and directed in them, and provided the marketing and PR for them. I started panicking, though, in my mid-30’s that I would never be able to afford basics like health insurance and decent food, so I allowed myself to get sucked into the world of money through a temp job that turned into big bucks. Within two years I was a vice president on Wall Street, asking myself how I got there and what had happened to all of the creativity and passion. With the newfound wealth we bought a small weekend home in the Catskills and fell in love with the beauty of the area. Then after five years on Wall Street I realized that I had to find a way out or, well, uhm, die… My partner Joseph and I missed the struggling years of “creating beauty” on the stage, so we started looking for what we could do. We realized that if we sold our Manhattan apartment we would have just enough money to open some kind of small business in the Catskills where the mortgage on our weekend home was quite small. A friend told us about a run-down roadside motel that was for sale so we went and looked at it and the rest is history. It took a year after that to “take the plunge” and move upstate and then a year of renovations to the motel. Daily anxiety attacks as well. Will the people come? Will we lose everything and go bankrupt? But the people did come and (knock on wood) still do. We’re now on our second expansion.

2. What’s distinctive about the Roxbury, and where’d you get the idea?
My catch phrase for The Roxbury is “whimsical elegance.” We’re certainly not the first hotel to come up with the idea of creating theme rooms, but I think we’re one of the only hotels that combines the trend of creating a “boutique” atmosphere with also creating a whimsical “theatrical” experience that does not allow itself to fall too far into the kitsch factor. The design for most of our rooms is inspired by TV shows, films and cartoons from the 1960s and 1970s. I guess you could say that we’re re-creating the fantasies of our childhood. I always wanted to live in the bottle from I Dream of Jeannie, so I grew up and built my own bottle. The concept resonates with many people, even if they are too young to remember some of the shows that have been our inspiration (like The Flintstones, The Jetsons, Bewitched, The Partridge Family, etc.). It’s very important to note, though, that we do not recreate real sets from the shows—we could get into trouble for that. We’re just “inspired” by them. Their colors, their textures, their moods, their atmosphere translate into the design for a room.

3. Did you have a background in the hospitality business before you started your hotel? If not, what made you feel emboldened to do it?
I had never done a single thing in the hospitality business. Never worked in a restaurant or hotel or catering company. But I loved staying in fun hotels and I’ve always loved design. I know what I want from a luxury hotel and I know what I want in customer service. It’s just common sense. Being an actor at heart, I suppose there is also that inherent need to please people and get their applause. The hotel business that we have created is very similar to that. Pampering people and giving them an experience that takes them away from their normal lives is very similar to being on stage.

4. When did you know you wanted to own your own business?
September 11 was the final straw. Working downtown during that period pushed me over the edge in many ways. I knew I was miserable but prior to 9/11 I was afraid to take the risk and start my own business. 9/11 taught me how short and precious life is and that you have to just go for it.

5. Did you have any inspirations when you were designing the place?
Yes, my childhood! I don’t really remember the 60’s, but I certainly remember the 70’s and I’ve always been attracted to that era. The “groovy,” psychedelic, modern, colorful, micro-mini-skirt-world that erupted in the 60’s was revolutionary at the time. The world had never seen anything like it. It was about youth and fun and whimsy and why not. The world of design is embracing that era again right now I think because the economy has made us all need some fun in our lives. Back in 2003, we decorated our first suite in bright oranges and yellows and black and zebra prints with lots of acrylic space age furniture and called it The Shagadellic and and we were petrified that guests would think that it was “too much.” Not only did they not think it was “too much,” they wanted more! We learned then that people need an escape from their everyday worlds and are very attracted to design. Even if it’s not how they would decorate their own house, it’s fun to stay in a fantasy place for a few days and escape!

6. What were the steps you had to go through between having the idea for the Roxbury, and making it real? Skills you had to acquire, hurdles you had to jump through, loans you had to nail down?
There were daily meltdowns caused from turning a rundown, not-up-to-code building into a functioning hotel. There were so many things that we knew nothing about: Oh didn’t you know you needed a handicapped accessible room? Didn’t you know that if you’re going to serve a hot breakfast you need to have a full commercial kitchen? Didn’t you know that you can’t just buy wine and give it to guests, you have to have a hotel wine and beer license? Didn’t you know that you need a manager on the premises 24 hours a day because you have more than 10 rooms? Didn’t you know that in order to get approved for the loan, we need a million dollar life insurance policy on you? Didn’t you know that if you build that close to the river you have to get approval from NYC’s DEP and you’ll probably need to put in a $100,000 stormwater pollution system? Didn’t you know that code says this, code says that?

7. What is your typical day like?
One of the best things that we did in the beginning was investing in a web-based reservation system. We no longer live on the property, but we can still access its reservation system all over the world 24 hours a day. What that means is that I’m on the computer WAY too much. Up at 5:30 checking reservations and checking them again before we go to bed at night. There really is no “typical” day in the hotel business because you’re in the business of having people “stay” with you overnight and anytime you get people together, life is constantly happening all around you. There are the normal things like making sure flowers and chocolates and wine and sheets and towels and soaps and comforters and other items are purchased and kept clean and on and on, but then there are the other unexpected things like a woman going into labor in room 5 and helping her husband time the contractions until the ambulance comes or the guy in #14 who has just proposed to his girlfriend and she says no and he’s in the office crying and asking you what to do. You become a part of everyone’s life for the few days they are here and sometimes, in the case of repeat guests, you make great new friends.

8. What are the biggest pleasures of the job? What could you do without?
As I’ve alluded to already, the biggest pleasure is seeing a happy guest. Sometimes even an ecstatic guest. It’s better than applause on a stage because it lasts longer. Seeing them happy all weekend is the best! Or watching their progression from tired and stressed-out and anxiety-ridden when they arrive on Friday night to relaxed and smiling and rested when they check out on Sunday morning. There is nothing quite like the fulfillment associated with that. I will say, though, that sometimes I could do without the 24/7 aspect of it. It’s not that we’re ALWAYS on duty, but when the phone rings after 10:00pm at night, our hearts sink and our stomachs drop because more than likely that means that there is a problem at the hotel.

9. What advice would you give to someone who wanted to do something similar to what you’ve done?
DO IT! Life is too short and too precious to do something that you don’t like. All of the old adages and clichés are true. If you have a passion for it and you often forget that it’s “work” that you’re doing, then you’ll be successful.

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