One summer evening while sipping wine with friends in Jamaica, Anna Kay von Dueszeln and her pals hit upon the idea to open their own wine and cheese shop.

“Our idea, which sounded really good over wine, was to dabble in wine and cheese,” Anna Kay says. “This was about 10 years ago when we first discussed the idea, and my only experience at the time in the hospitality business was that I liked wine and cheese!”

But backed by partners and friends, and a zest to go for it, they opened a small retail outlet in Kingston, Jamaica. After which, there was no looking back!

“We grew organically from that small retail shop into two full-fledged restaurants, and we’re considering opening a third location, with 50 employees,” says Anna Kay, co-owner and managing director of Uncorked of Jamaica.

In this week’s Q&A with Boxerbrand blog Recipe for Success, Anna Kay describes the journey that began with a fun idea over drinks.

Q: How did Uncorked get its start?

My friends and I were having wine one night and we thought it sounded fun to open a wine and cheese shop. We thought we’d just dabble.

But the great American investor Warren Buffett says he only invests in things he personally likes, and I thought that was a good model to follow.

Q: How did you grow from a retail shop to two restaurants?

The whole thing happened organically. We opened the retail shop in 2011 in a small space in Kingston. As we attracted customers, over time, the customers started to ask us for more. First, they asked us for some tables and chairs so they could sit and sip their wine. After they did that, they began asking us for menu items.

After two years, we moved to a larger space in Montego Bay, put in a kitchen, and developed a menu that paired well with our wines and cheeses.

At first, we were just a small shop to sit and sip wine and eat cheese. But our customers demanded more. Now our niche appeals to customers who want to dine out on their way home. These customers prefer to entertain their guests more at Uncorked than they do in their own dining rooms. In a sense, we’ve become our customer’s dining room.

Q: You’ve described your menu as eclectic.

We have all sorts of salads and recently started a bowl, where customers choose the ingredients they want to fill it with. We offer three to four fish dishes and do gourmet burgers with beef and lamb, and have a lot of hors d’oeuvres that do very well. All the menu items we offer have a Jamaican vibe to them and go nicely with our great wines and cheeses.

Q: You make it all sound so easy!

It’s not easy at all! Just the operational challenges we face every single day are considerable. Running a restaurant in Jamaica is different than in the US. For example, if our equipment breaks down, it can take us weeks to replace it, whereas, in the US, equipment can be replaced in 24 hours.

The dry goods come in by ship and take two weeks, and our cheese is flown in, and requires we navigate lots of shifting red tape.

We employ 50 people now, and that’s 50 separate lives and separate issues. Love, love, love them, they’re a huge part of our success, but  it can be a challenge too, because no single life goes in a straight line, so there’s always considerations to be made.

Q: How did you attract your first customers?

When we started, we all had a large network of friends. And we grew our customers through word-of-mouth and I also used Constant Contact to update our customers on specials.

We’re a very small society of people who know each other, so there’s always a familiar face at Uncorked. Women feel comfortable coming in alone. We hear all the time we’re like Cheers in Boston. (Cheers in Boston was the inspiration for a popular TV show in the 80s, and its slogan, “A place where everybody knows your name).

We have a community of Jamaicans and also kids from Europe and the US who are very comfortable in a wine bar space.

Q: What advice do you have for someone who is inspired to open their own wine bar?

Sober up! (Laughing). I would say that it can be done and done well. I had no idea what we were doing when we first started this. I’d never worked retail. I’d never cut a piece of cheese. But, I knew great product and how to sell it. — Uncorked Jamaica uses Boxerbrand’s Shimmer Line in its table presentation line. Thank you!