Brad Kitkowski is the owner and manager of Isola, a restaurant in its third year as a warm and welcoming year-round Shelter Island refuge of rustic Italian fare.
But Brad’s working life has not always been hospitality and good times. In his 30s, a couple of years into a successful career at Willis Group, a multinational insurance brokerage, he accepted a new job as managing director with a high-powered, privately held firm.
“Seven days into the job I thought I made a mistake,” he said. “I had to figure out how to be me, and survive.”
He managed to last in the job for two and half years by focusing on understanding the business, and positioning himself with executive management. “You are a product of what you’ve gone through,” he said.” You’ve got to learn from everything. Did I have bad dreams for 60 days after I left? Yes. Took a little bit to shake it all off.”
Brad grew up in Ohio, the middle child in a family with three brothers and a sister. He moved to Florida with his mother just before his senior year of high school, went to junior college for a year and a half, and then to the University of Florida at Gainesville, a place he fell for immediately.
The Kitkowskis were long-time Notre Dame fans, so when Brad began “bleeding orange and blue” during the second half of his first University of Florida football game, his siblings figured he had seceded from the family. Patrons of Isola will find evidence of Brad’s continuing dedication to all things Gator in the décor, including the distinctive blue of the Isola logo, which could evoke the Mediterranean Sea, or could be Pantone PMS 287 C (also known as Gator blue).
Brad was in his senior year of college when he was offered an interview for a sales position at E-One, a manufacturer of fire and rescue equipment, whose slogan is “Kickin’ Ash Since 1974.”
Unfortunately, when he walked into the interview, he thought the position was in medical sales. “I had to admit it, I had no idea what the company did,” he said. “They liked the way I recovered, and I got a second interview.”
He started out as a product manager for tankers, and still in his 20s, became a product manager for a petrochemical and refinery business, and was then promoted to regional manager based in Amsterdam, with a territory that took in most of the Middle East and all of Africa. For five years in the mid 1990s, he called on accounts from Turkey to South Africa, still a junior person, with a junior salary to match.
“My expense account was four times my salary,” Brad said. “But I still know 15-20 words in a dozen languages, and I saw Mt. Kilimanjaro, and Victoria Falls.”
It was a life changing experience, but he felt something lacking. “I was not grounded in any way,” he said.
He resigned, and moved back to Central Florida where he got married and went to work for a company that did employee outsourcing for small and medium businesses.
Brad’s son Bailey was born in Sarasota, Fla., but by 2002, his marriage to Bailey’s mother was over. He moved to Manhattan, his ex-wife to Long Island, and Bailey lived with both. Brad calls Bailey “the most consistent person in my life.”
Brad’s move to New York marked his shift to a new line of work, since he had been recruited to work for Willis Group as a senior vice president managing a retail division of the commercial insurance brokerage where he made his career.
He made dinner, too. “When I moved to Manhattan I really got into food,” Brad said. “My son was with me every weekend, every vacation. I made goulash, chicken and noodles. I recreated my mom’s dishes.”
He discovered Shelter Island around the same time, and still remembers the anxiety of a newcomer on his first ride on the ferry. “Was I in the right lane?” he said.
But he soon felt at once that this place is heaven: “I always say, people either get it or they don’t.”
Brad had been a summer visitor for about 10 years before he thought about opening a restaurant here. His grandparents owned a restaurant when he was growing up, the site of his first beer and his first job, as a dishwasher. He’d also dipped his toe into restaurant management in Manhattan.
On Shelter Island, he got to know the Rando family, who owned Sweet Tomato’s, located in the 100-plus year-old Victorian in the Heights where Isola now operates. The building once housed a butcher and grocery, and for the last 30 years or so a series of restaurants, including The Cook, Chamberlains, and Sweet Tomato’s. To make it work, Brad needed to buy the building, and for that he needed a partner, his friend Anthony Killough.
The first years of Isola were not without bumps. “The first summer we were blessed with a great chef but we made every mistake in the book,” he remembered. Staffing, the bane of every restaurateur operating in a mostly-summer economy, was challenging. “We had some misfires,” Brad said.
Keeping the lights on for the entire winter was counter intuitive, and proved to be a stroke of genius. “I stayed open the first winter and then I knew people,” he said. “You make progress here through word of mouth. The reality is you’ve got to earn the respect of the people who are here.”
Operating year-round also helped him build a strong staff. “We are a place that has pretty darn good service and the service is because we have pretty darn good people,” he said.
Brad still keeps his hand in the insurance business, but his heart, and increasingly his home, is on Shelter Island, providing hospitality for friends and family. “I got a chance to do something that I love. I get to go out every night.”
What do you always have with you? My Shelter Island bracelet.
Favorite place on Shelter Island? The North Ferry, because it means I’m back.
Favorite place not on Shelter Island? Manhattan.
When was the last time you were elated? When I realized that Isola made it, we are going to be here for awhile.
What exasperates you? Narcissists who distort things for their own benefit.
When was the last time you were afraid? When I had a laydown-MRI. I had to figure that one out.
What is the best day of the year on Shelter Island? Memorial Day.
Favorite movie? ‘The Grand Budapest Hotel.’
Favorite food? Isola’s lasagna.