While on tour with his younger brother’s punk band in Europe, complimentary food platters inspired James DiSabatino ‘09 to make a living off selling cheese and bread.

DiSabatino traveled with the band The Carrier from 2007 to 2010 in between school vacations. He said he was responsible for managing the logistics. 

“They would give us these really nice tables of bread, cheese, Nutella, and pickles,” he said in an interview. “Someone had the idea that we should just make grilled cheese for a living.”

The idea of making grilled cheese for a living stuck with DiSabatino—he opened Roxy’s Grilled Cheese in March 2011 after he returned to the U.S. DiSabatino now boasts two Roxy’s food trucks and two Roxy’s restaurants in the Greater Boston area, in addition to another vegan and vegetarian joint. 

The Roxy’s food truck was featured on the second season of “The Great Food Truck Race” in 2011, and Eater Boston ranked Roxy’s the sixth best grilled cheese place near Boston in 2017. 

But before DiSabatino began his adventure into the food industry, he planned on getting a job related to his marketing degree. 

“I had applied to some jobs and stuff, but this was right when that recession happened [in 2009 and 2010] so no one would hire me,” DiSabatino said. “I even applied for $8-an-hour internships and didn’t get them.”

He landed an interview with a small law firm, but said all he can remember about the meeting was how uncomfortable he felt in his suit and the hum of the lights—which is why he declined the second interview. 

DiSabatino and his friends looked at restaurant spaces for their grilled cheese place, but he said all the leases were too expensive and they did not have enough experience. 

“This was right when food trucks in L.A. and New York were starting to pop up, so I thought a food truck could be cool,” he said. 

DiSabatino said he felt drawn to the food truck idea, but Boston did not allow them at the time. However, DiSabatino found a $45,000 food truck on Craigslist and swindled his way out of paying for it upfront. 

“I talked him down to $44,000, but I didn’t even have the money at the time,” DiSabatino said. “I ended up keeping the truck for a probably illegal amount of time before I paid for it—I was working my ass off, working doubles every day at a bar in Cambridge, and I was only eating at my mom’s house and not spending any money.”

Eventually, DiSabatino got licensed as having a food cart, instead of a food truck, through Boston’s Parks and Recreation Department. He paid for the license up front so that it would be harder for the city to take it away, he said. 

As DiSabatino finalized the menu for his truck, he conducted market research by cooking for his friends and family.

“I think we knew we wanted to do something better, we didn’t want to do cheap food—we wanted to find nice bread and use good cheese,” DiSabatino said. “There are a lot of really tacky trucks out there that have a good name, but their food sucks, and we didn’t want to be that at all.”

DiSabatino said he does not want to relive Roxy’s opening day in Cleveland Circle. The morning got off to a rough start as they drove the truck from Saugus—where his mom lives—to their kitchen in Jamaica Plain.

“Trucks can’t go under bridges or under tunnels, so you have to take the long way,” DiSabatino said. “It would normally take an hour to get to Jamaica Plain, but that day there was a bank robbery on the route, so it took two and a half hours to get to our kitchen and start making the food.”

When the truck finally reached Cleveland Circle around 8 p.m., the already-forming line made DiSabatino second-guess everything. 

“I was like, ‘No, we are not ready for this,’” DiSabatino said. “We had no systems in place, and it took so long for people’s food to come out.”

He said that, initially, he wasn’t prepared for the cleaning, accounting, maintenance, and cooking that came with running a food truck. 

“I did not learn anything that prepared me for that,” DiSabatino said. “School is cool, and it helps you adjust socially, but a lot of people open restaurants that really suck, so the first thing you have to have is some self-awareness.”

A year and a half later, he opened his second food truck, and in 2014 he opened a Roxy’s restaurant in Allston to avoid paying rent for their kitchen in Jamaica Plain.

“We were looking at Fenway, Cambridge, Somerville, even Salem, and my friend who was working for the city said Roxy’s should really be in Allston,” DiSabatino said. “I was like, ‘I hung out there too much in college and have some bad memories, I don’t know if I really want to be there’—but then we found a space and said, ‘We really should be here.’”

DiSabatino said he values the customers that have been coming to Roxy’s since the beginning. 

Helen Carpenter first came to a Roxy’s food truck eight years ago, and she now visits their trucks and restaurants—in Allston and Central Square—every few months.

“I first tried a grilled cheese, and it was really good,” she said while waiting in line at the Central Square restaurant. “I’m a sucker for grilled cheese.”

Montgomery Smith has been working at Roxy’s Central Square location since she moved to Allston in September for graduate school at Boston University. She said she is already getting to know the regular customers.

“It’s very relaxed and community-based—the same people come in all the time,” she said. 

While grilled cheese might seem like a simple menu item, for DiSabatino, it’s way more than that.

“I love what it represents, and it is fun to make,” DiSabatino said. “You have to be patient—it’s like science. Sometimes when I go to restaurants, I’ll order their grilled cheese. Not to do research, but because it is a pretty solid choice.”

On top of grilled cheeses, Roxy’s also offers burgers and vegan sandwiches. Smith said even the classic grilled cheese is more than the average product. 

“Even with the classic grilled cheese, we use three cheeses, so we spice it up,” she said. “The main impression I have is that our menu is vast, and it really does have options for everyone.

In 2015, DiSabatino and his partner opened Whole Heart Provisions, a vegetarian and vegan restaurant. Whole Heart Provisions has locations in Allston, Central Square, and Harvard Square.

“I was changing the way I ate, and I realized I didn’t want to eat Roxy’s all day,” he said. “I was looking for healthier stuff to eat, like vegetarian stuff, and it was all crazy expensive and not that good.”

Now, DiSabatino works between Roxy’s and Whole Heart Provisions, with different goals than when he founded his first food truck. 

“On day one, my goal was to make it home to go to sleep,” he said. “It was survival because it is really hard to make money with a food truck company in a city that is cold most of the year. Now I mentor people and help them get to where they are going next—a lot of people who work for us are students, so it is cool to talk to them, see what they are doing with their lives and where they want to go.”