Like many young people trying to make a living in East Hampton, Ben Dollinger has many jobs.
Unlike many of his peers, he and his wife, Leah, own their own home. That’s quite an accomplishment, considering a starter home here may buy a mansion in other parts of the country.
When Mr. Dollinger says he hustled to save enough money, he isn’t kidding. You could say Mr. Dollinger got his start with Benjie’s Chocolate Cookie Stand but, he said with a laugh, “My mother did all the work. I was just the face of the business.” In addition to selling cookies for a while, he started caddying at the Maidstone Golf Club at age 12 during the day. In later years, he also was parking cars at the Maidstone Arms Restaurant and at the nightclub on Three Mile Harbor Road at night.
“In high school, I’d park cars until 5 a.m. then go straight to caddying at the Maidstone and back again,” he said, “I’d hustle for cash. I loved it. I still do.”
To this day, he caddies part-time for the fringe benefit of playing the exclusive club’s course. The bigger benefit was learning to play the game for free. He also keeps a part-time lifeguard job for a highly coveted village beach sticker. And if he’s not on the lifeguard stand, you may see him on the beach setting up a clam bake for Claws on Wheels, another job he’s held onto for years.
Mr. Dollinger looks like a typical all-American athlete. He attended Green Mountain College in Vermont, where he raced with the ski team, and spent three semesters abroad in Australia, Costa Rica and Mexico’s Baja Peninsula. It’s no coincidence that all locations have great surf and he is a surfer.
Tall and blond, his good looks did not go unnoticed by photographer Bruce Webber at a chance meeting in East Hampton after he had returned from college. Mr. Webber, the world’s most celebrated fashion photographer, put together a modeling portfolio for Mr. Dollinger. Click Modeling Agency signed him on the spot and he was soon modeling for the likes of Ralph Lauren. At one point, his image was plastered on billboards everywhere, thanks to Abercrombie and Fitch.
Mr. Dollinger followed the natural progression for most fashion models and took acting lessons, from actor and East Hampton resident Michael Nori. In between his many jobs, he went on auditions in the city but he decided it wasn’t worth his time commuting for jobs he was not sure he would get in the end.
“Maybe it would have been different if I had moved into the city or to Los Angeles but Leah wasn’t having any of that,” he said of his bride, a yoga instructor.
Leah Kinney was a year behind Mr. Dollinger in East Hampton High School and asked him to her junior prom. “I didn’t know her at all, but she was hot.”
The couple didn’t see each other while they were away at college but, when they both returned home, they started dating again and got married last year.
At 30, Mr. Dollinger said he is too old to get much more modeling but he still works in fashion, producing magazine advertisements and editorials. Although he is older now, his work schedule is just as hectic as it was when he was a teenager. Take last week, for example.
Mr. Dollinger worked construction during the day, and then he went to a bartending job at Rowdy Hall. After his shift, in the middle of the night, he drove his car into the city and slept on a friend’s cot in Greenwich Village for 45 minutes.
He got up before dawn and went to the Condé Naste building in midtown Manhattan, where he loaded a wardrobe of summer dresses into a mobile home for a Gentleman’s Quarterly spread and went on location in Fort Greene, Brooklyn. From Brooklyn, he drove the mobile home back to East Hampton. The next morning, he was at photographer Peter Beard’s house in Montauk for another shoot. He then drove the mobile home back to the city, got his car and drove home. The following day, he worked carpentry again with his father, general contractor Herb Dollinger.
“I said I’d never work for my dad. He yells a lot but I like that my father is teaching me a trade. I know someday I’ll appreciate spending so much time with him,” he laughed.
“I’m hoping one day to have everything move in the same direction,” he said of his multiple careers. “I just got my real estate license, so it will probably be in building and real estate. That seems to be the thing I know most about.”
As soon as he bought their home in Clearwater Beach, he renovated it and rented it out for the summer while the couple moved back in with his mother.
It may be tough living here, but he has traveled the world and has realized that East Hampton is where he wants to be.
“I’m lucky we’re not stuck in a bad cycle. I see a lot of young people here who live beyond their means, trying to get out of debt and paying rent or too afraid to make a move.”
“We’re not stuck here, we chose to be here,” he said.