Boston People More People

James DiSabatino

King of Cheese

By Emily Wright

Behind wire-trimmed lenses, set in licorice-black frames – standard hipster issue – James DiSabatino’s eyes turned up at the corners. His lips, highlighted by a manicured auburn beard, followed suit.

DiSabatino paused mid-sentence to watch a pair of customers step up to the counter of Roxy’s Grilled Cheese for what appeared to be the first time. One woman, with the excitement of a schoolgirl at a Taylor Swift concert, exclaimed, “Oh! They have tomato soup!”

“It’s not like Boloco,” DiSabatino said, laughing as he referenced the standard “beans and rice” burrito options splashed across the local chain’s menu boards.

There’s nothing standard about the menu options or the decor at Roxy’s Allston brick-and-mortar location.

“For me, it’s as important to be different from the next guy, as it is to make money,” DiSabatino says.

Sandwiched between eclectic spots like vegetarian haven Root and sister restaurants Lone Star Taco Bar and Deep Ellum, the 30-seat Roxy’s, with its chocolate brown walls, cheddar cheese yellow subway tiles, and classic arcade game corner, has enough unique offerings to separate it from its competition.

Roxy’s has garnered a loyal following by featuring staples like the Quebecois delicacy, poutine, and its mood-themed daily specials like the Nikki [sic] Minaj aka the Truffle Butter Burger (truffle, butter, steak seasoning, crispy onions, and Justin’s sauce) keep visitors guessing.

Building a community has always been a high priority for DiSabatino, and as soon as he realized he’d dissed Boloco’s offerings during an interview, he tried to take it back.

“No, don’t say that,” he blurted out. “I like Boloco.”

DiSabatino’s quick-witted snark and constant mindfulness are just two of his many personality traits mirrored in the brand, and evident in everything from Roxy’s quippy posters to its dedication to feeding folks with restrictive diets.

This wasn’t by chance.

DiSabatino has carefully calculated, and in certain cases hand-crafted, everything in and around Roxy’s since he dreamt up the original idea more than five years ago. He admits, perhaps to a fault, that he thinks nonstop about the restaurant and its two sister food trucks.

“I’m always doing Roxy’s stuff,” DiSabatino said.

That’s because he has his hands in everything from curating custom playlists (for example, he doesn’t love it when Blink-182 comes on when he’s giving an interview at the restaurant), to posting on social media.

“I’m very proprietary about it,” DiSabatino said of Roxy’s Twitter presence. “The same way a chef would be proprietary about their recipes, you know? I think that you can’t just hand it off — at least our brand — you can’t just hand it off to an intern.”

His efforts to connect with each customer from the truck’s first days on the road (he still tries to get behind the counter and in the kitchen whenever he can), both in-person and via social media, have helped build a following of more than 15,000 on Twitter and close to 12,000 likes on Facebook.

“I really like being part of the conversation. How much work does it take for me to talk to people? Like, nothing. I could just be looking at my phone and do it. Easy.”

Not everything came to DiSabatino as easily as his social media presence. Up until “very recently,” the 5-foot-9 Revere native kept a pillow in the back seat of his 2010 Nissan Versa to remind himself of the nights he spent sleeping there, with the compact car’s engine running to keep warm.

“I don’t want to relive that ever again,” DiSabatino said of the early Roxy’s days. “I’m not saying, ‘Oh, I’m so glad I did that.’ I hated that. I did not like that.”

When Roxy’s first truck opened on March 3, 2011, operating under a food cart permit given by the city of Boston’s Parks & Recreation Department, DiSabatino began putting in 17-hour workdays just to stay afloat. He realized quickly that his daily commute was going to take a toll.

Mornings started with driving the truck from his home in Saugus to the company’s prep space in Jamaica Plain, before setting up shop in Brighton (Roxy’s first home base, 5 miles from downtown Boston). There, he’d spend the full day behind the grill, before returning to Jamaica Plain to clean the truck, and finally retiring in Jamaica Plain. It was a commute (and early business model), that was not sustainable.

“There was a point where I thought I was going to lose it,” DiSabatino remembers.

“Some nights, I would only have three hours between when I needed to leave and come back, so if I drove the truck back, and then drove the truck back to Jamaica Plain, that would only give me about an hour to sleep. So I’m like, ‘Well, I can just sleep in my car, and get three hours.’”

Five days a week, DiSabatino would serve the families and college students that live in Cleveland Circle, an area he was initially nervous wouldn’t be receptive to the now infamous Roxy’s tattooed girl emblazoned on the side of its truck.

The other two days a week he would bartend in order to pay his bills.

“I felt like I was a slave in a world that I didn’t know existed,” he said. “I didn’t know what was going on.”

He ended up getting an overwhelmingly positive response from his first customers, despite not knowing what he was doing in the beginning.

“It was just kind of an experiment, I thought it would just be a really fun project to do, and it ended up turning into a lot more than I thought it was going to be,” DiSabatino said.

Rather than sleeping in his car, DiSabatino now returns home to a one-bedroom apartment in Somerville’s Winter Hill, which he shares with girlfriend and Sarma chef Rebecca Arnold. Last week, Roxy’s celebrated its four-year anniversary, and DiSabatino recently sent out 50 W-2s to the brand’s employees for 2014. He ballparks that the brand brought in somewhere around $1.5 million in revenue last year, and he has plans to open two additional Roxy’s restaurants by the end of the year.

Things are looking up from those early days.

“There’s good opportunities for us, and there’s great opportunities for us, which I’m fortunate to have,” DiSabatino said of the business’s current state. “My goal is to pursue the great ones, and take a look at the good ones.”

The opportunities started arising back in April 2011, when DiSabatino hit the road with his brother Mike and a former Roxy’s chef to take part in Food Network’s second season of The Great Food Truck Race. The guys and Roxy’s made it to the semi-finals over their seven weeks of filming before returning to Boston, where the food truck game was rapidly changing.

“As soon as we got back to Boston from the TV show, the [Wicked Good Food] program opened itself up to traveling around the city, so we were on national TV and in 10 different locations in Boston, basically at the same time,” DiSabatino said of the “fairy tale” way things came together. “We were pretty popular for a while.”

A year later, James and Mike DiSabatino were operating two trucks and looking for a brick-and-mortar location.

Mike, a Le Cordon Bleu–trained chef who currently serves as a Roxy’s manager and menu developer, is partially responsible for the creation of the brand. While attending Emerson College, James (16 months Mike’s senior) was tasked with accompanying Mike’s punk rock band, The Carrier, on national and international tours.

“I was the only responsible person to go over there with him,” James said. “And I think that experience, doing that for a couple years on summer vacations, winter vacations, spring vacations from school, inspired me to do something like this.”

After returning from one of The Carrier’s European tours, James was hit with the idea for his now burgeoning brand.

“All these cities that we were going to every day would have these big tables of bread and cheese out for us everywhere we went,” James remembered. “It was like, you were traveling in a van for 10 hours with a bunch of guys. The best thing you could come to is a full table of carbohydrates and cheese.”

Mike recalls James as always being “kind of a wild ideas guy.”

“Even back to when we were 14, 15 years old, and we were traveling a bunch, and he just had all these wild ideas,” Mike said. “Let’s open up a bar, let’s open up a restaurant, and we actually went back and forth, and the idea was born: ‘Well, why don’t we start a food truck?’”

While finishing up his final semester at Emerson in December 2009, James began working with graphic designer and friend Holly Gordon to come up with the brand’s logo, while at the same time creating a rough outline of a Roxy’s business model in his head.

“I didn’t write anything down on paper,” James said. “I just wanted to do something cool, and see where it would go, which I think is a very Emerson thing to do by the way.”

Once he had the concept, he began searching for a truck.

It took more than five months before James found a hot dog truck on Craigslist that even came close to suiting his needs. In order to pay the for the $46,000 truck, James drained his savings, and borrowed $20,000 from his dad — a loan he still isn’t sure he’s paid off.

“No matter what, I’ll always owe him something,” he said.

Then, he sank another $5,000 or $6,000 into outfitting the truck for making grilled cheese.

Initially James’s dad, Jeff DiSabatino, was a taken aback by his son’s business idea.

“When he told me he was going to open a food truck, I was surprised, but I told him I’d support him with whatever ventures or whatever avenue he’d taken,” Jeff said. “I’ve always pretty much been behind him and believed in what he’s been doing and wanted to do.”

Jeff is impressed with how far his son has taken the business in such a short amount of time.

“Even though I’m a 60-year-old man, and my son is 27, I still tell him he inspires me by what he does,” Jeff remarked. “Instead of a parent inspiring a child, this is the opposite.”

James told his father at a young age that he wanted to go into business for himself.

“At the dinner table when he was 14, [James] had said to myself and my girlfriend that he wasn’t going to work for anybody else, and he was going to be a millionaire before he was 30,” Jeff remembered. “I sometimes remind him of that.”

James’s mother Annmarie DiSabatino attributes his work ethic, which she thinks he inherited from his dad, to his success.

“He’s always been such a forward-thinking person,” Annmarie said.

The menu he and Mike create is full of what they’ve tested (and tested) and dubbed the best ingredients, like pain de mie from Iggy’s Bread and Roxy’s from-scratch guacamole. They’ve also embraced the use of mayonnaise on the outside of the bread to get the perfect sear.

There’s even a three-and-a-half minute grill science to getting the cheese to melt just right.

“I’m not just okay with people doing mediocre jobs at things,” he said. “I just think if you’re not going to do the best job that you can, why do it at all? What’s your motivation for doing something besides just doing a great job?”

The passion he has for growing the Roxy’s brand is what gets James out of bed every day.

“This is what I want to do right now,” he says. “I think when I first started this, before we opened, before I had any expectations, I said, ‘This is going to be the thing I look back on and say, ‘This is what I did in my 20s.’ And now I’m 27, and I’m starting to think this is going to go longer than that.”

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