Each semester, Northeastern's Entrepreneurs Club brings Boston innovators and students together for coffee and a discussion in their "Coffee Meets..." series. To kick off this year, the club hosted James DiSabatino, the creator of one of Boston's iconic food trucks and restaurants: Roxy's Grilled Cheese. Over some coffee, tea, and snacks, we learned about James' background and his advice about starting a business.

Getting His Start

Photo courtesy of Joe Thomas

At only 22 years old, the Emerson grad bought a food truck on Craigslist to sell grilled cheese sandwiches. We were all curious, why grilled cheese? Basically, James said, it was unique and versatile. Nobody was doing it and he saw the potential to get creative with different breads, cheeses, and extras. His favorite grilled cheese though? Just cheese. Simple. Preferably with some tomato soup.

Early Challenges

Photo courtesy of Joe Thomas

James started his food truck business in Boston at time when the city had regulations against food truck vending. He shares he had to be quite creative to obtain a permit and begin operating his truck, and that it took a lot of perseverance to show the city the benefits of a booming food truck scene. Today, Boston has countless food trucks on its streets, and James' pioneering work building up Roxy's served to pave the way for the success of the vendors we know today. When asked about his thoughts on how his work essentially created competition for himself, James responded that building each other up and promoting a truck-friendly city is beneficial to all the businesses involved; it wouldn't be any fun to be the only one.


Roxy's got a big break in 2011 when James and his team competed on Food Network's The Great Food Truck Race. It really helped get the word out about the business to a larger audience, and showed the Roxy's team the growing potential of their truck.

By 2014, Roxy's was outgrowing their truck and shared kitchen space, so James and his team took the leap to open a brick and mortar location in Allston. Still going strong today, the restaurant accompanies their grilled cheeses with burgers, hot dogs, and beers.

Today, Roxy's has two other brick and mortar locations; one in Lynnfield and one in Central Square as part of the A4cade collaboration with Area Four.


Photo courtesy of Joe Thomas

As the business has expanded, James reflects that his specific job has shifted to the business and management side, as he now delegates things he used to do in early days to his growing team of employees. But he is proud to say he remains the visionary of the company, the motivator who has not forgotten one of the main reasons he started a food truck: to foster a more personal connection with his customers.

When asked in general for advice about starting a business, James said he wished he asked for help earlier instead of pretending he knew everything. He learned later on that people, especially those who have found success, are often very willing and eager to share experiences and advice to budding entrepreneurs.  

James also discussed his approach to branding and social media by saying that he really doesn't have a set strategy. While some companies very successfully research and plan, James says he and his team have always just chosen the colors they think look good, posted photos that they find appetizing, and used their Twitter and Facebook to connect with their community. There are different approaches to handling such aspects of a business, and this way works well for Roxy's.

The Future

toast, sandwich, cheese, bread, french toast
Nancy Chen

In addition to building up Roxy's, James teamed up with Boston chef Becca Arnold to create a restaurant serving up a quite different cuisine: vegan food. Located right next to Roxy's in Allston, Whole Heart Provisions is all about veggies and James commends his partner Becca's creative approach to expose Bostonians to unfamiliar, healthy, delicious ingredients.

Most recently, Roxy's has paired up with Area Four to create the A4cade arcade-bar experience that has taken over Central Square recently. You can't beat grilled cheese, pizza, beers, and arcade games!

James is always thinking of fun, new ways to grow his business (like this week's Cheddar Broccoli grilled cheese!) and we're excited to see where it takes him next. Thank you to James for chatting with us and answering our questions, and for the Entrepreneurs Club for facilitating the conversation!