Jimi Rando, operator of Sweet Tomato’s restaurant in Shelter Island Heights, is a natural at what he does.
“What I love is what people do in life. They work, they take care of their family, and for certain amounts of time they go out and have a drink and tell jokes,” he said last week at his restaurant as crooners sang Great American Songbook classics on the audio system. “I get paid to do that. When it’s show time, my job is to be social.”
He and his younger but “way more mature” brother Anthony, now a Shelter Island Town police officer, took over the business in 2008, five years after their mother Mary and father James had launched it.
Originally from the Bronx and Brooklyn, respectively, both Rando parents had family roots in the Long Beach and Island Park area, where Jimi grew up and where his father runs his own auto body business, Smooth Edge Collision.
They opened Sweet Tomato’s in 2003 “as kind of a hobby,” Jimi said, about six years after they’d come to the Island for the first time during a weekend getaway to Greenport and had run into broker Hannah Dinkel. By the end of the day, Jimi’s father had made an offer on a house on St. Mary’s Road, which he and his sons spent weekends rebuilding, right down to new I-beams.
Jimi wasn’t keen on Shelter Island then. “I preferred the city,” he said. The Island was “very quaint back then.”
The eldest of Mary Rando’s three children, Jimi was born in the Bronx in January 1982. She was a secretary on Wall Street and a waitress, doing “whatever she had to do” to make a living in those days. When she married James Rando when Jimi was four, James soon adopted the boy, who has never thought of him as anything except his father.
Growing up, Jimi worked at his dad’s auto body shop. “Of course I hated it,” he said without a trace of rancor, but “it helped me develop a real work ethos. My father always said to me that college is not for everybody. ‘You do not have to go to college but you do have to make money,’ he told me.”
After graduating from West Hempstead High School, he did go to SUNY Oneonta for a semester but “for the wrong reason,” he said. “At the time, it was listed by Playboy as the number-one party school in America.”
He went back to Long Beach to live with his grandmother — “The closest person in the world to me besides my mother,” he said — because of her declining health. He held down several jobs: opening the Romantic Bean coffee shop every morning; working at Whitbread Sons Lumber Yard all day; heading either to the Long Beach Starbucks or Pop’s Wines & Spirits to work into the night.
He tried living on Shelter Island for the first time after his grandmother passed away and his parents had opened their restaurant. “It really wasn’t for me,” he said. “It was too seasonal for me to be out here.” So he moved into an apartment in Island Park that he and his best friend Jesse Goodman built in the basement of the Goodman house. He landed a job at Sutton Place Great American Bar & Grill in Long Beach, where he “got bumped up really fast, from busboy to food runner to waiter in a few weeks.”
He excelled at waiting tables, he said, “because I love people” and that’s what the restaurant business is all about. “You can’t fake that. You like people or you don’t.”
At the same time, he worked at Jimmy Ryan’s Bar in Throgs Neck and a legendary deli there called Cafaro’s, doing short-order cooking, working the counter, managing inventory, opening up and closing.
He spent five years at Marina Del Rey, a catering hall on Tremont Avenue with a staff of 120 waiters. “Within a month, I was head waiter,” Jimi said. “I always worked. I kept my head down. I was not there to make friends. I was there to make money.” Soon training the wait staff, he was promoted to captain after only six months.
He was especially inspired by two maître d’ there, Joe Savino and Joey Orso. Joe was “the best maître d’ on the planet Earth,” Jimi said. “He’d remember your wife’s middle name if you came back 10 years after your daughter’s Sweet 16 party to have her wedding.” He and Joey Orso were just “two Italian guys from the Bronx, just two neighborhood guys who weren’t great at any one thing but always kept hospitality in mind.”
His mom, having beaten cancer twice, fell ill with multiple sclerosis and soon needed help running Sweet Tomato’s. “She’s tough and resilient but she couldn’t be here every day,” said her son. “To make a small business work, especially a restaurant, you have to be here every single day. You are the difference, no matter what, in a small business.”
He and Anthony took over in 2008, renting the building from their parents. They skipped salaries in order to hire Alfredo Alverez — a nationally known chef and restaurant consultant — to work with them for two summers, teaching them everything from quality control, “how to cut costs without cutting corners” and how to make their own pastas. After overcoming zoning issues, they put in a brick pizza oven, which Jimi and his father went to Italy to buy and learn to use.
“I didn’t plan on being here this long but my brother had some great ideas and I saw the way he matured business-wise,” Jimi said. “This little kid really had such good vision, being open in the winter … He said nobody opens because everyone says nobody’s out here. If nothing’s open, why be here? So if I were open two, three years, that’s when we’ll see if people will come out.
“But for Vine Street being there, there’s no way Anthony and I could have done it. They proved it … They had a concept, a mission, and they stuck to do it. They didn’t get thwarted by a few bad winters, a few bad weeks. They understand the ups and downs of the business. It really is a dynamic equilibrium … and as long as the level point is a little bit better than last year, then you’re doing okay.”
On July 11, 2008, they had their grand reopening, with a free, family-style, random-seating meal for 60 local opinion makers — from real estate agents and B&B owners to people from the ferry companies. The next Saturday, they served 120 dinners, up more than 50 percent from the typical draw.
A single guy with an apartment in the city, he heads into New York after the dinner push every Sunday — not just for the nightlife. He’s planning to make a career of restaurant consulting, just like Alfredo Alverez, so he’s taking a full load of courses at the Institute of Culinary Education.
It’s not that he intends to let go of Sweet Tomato’s. In fact, he’s looking forward to his brother coming back to work.
“He’ll retire at 43,” Jimi said. “He’s going to pick up where he left off. I do feel like I’m doing this for us. He put sweat and tears and love and life into this. He wants to see this place succeed more than I do.”