Dale Schwartz ’83 is upping his game with Pinstripes, a rapidly expanding restaurant group.
As a boy growing up in Cleveland, Dale Schwartz ’83 spent his summers participating in weekly kids’ bowling leagues. He hung out with friends and ordered hamburgers, milkshakes, and fries from the burger place next door. The memories of the fun he had lingered with Schwartz even as an adult. But he thought he could improve the experience — which is why, in 2007, he founded Pinstripes, a Chicago-based restaurant group that combines bowling, bocce, and high-quality American-Italian cuisine. “The challenge from day one,” Schwartz says, “was to redefine the bowling space.”
Turns out, he wasn’t the only one yearning for nostalgic fun and great food. Since opening the first Pinstripes in Northbrook, a suburb of Chicago, the company has expanded to 13 locations in nine states. In the next 15 to 20 years, Schwartz intends to open 100 to 150 more in the United States and overseas.
A natural entrepreneur, Schwartz got his first taste of running a company at 17, when he started an asphalt seal-coating business with his brother. For nine months of the year, Schwartz was double majoring in political science and philosophy at Colgate (as well as being a “backup–back up” quarterback for the football team). In the summers, he and his brother ran the business. They sealed 11 driveways the first year, and continued running the business for 10 years, eventually doing about 1,000 driveways annually.
After graduation, Schwartz’s career followed a varied path. He worked in mergers and acquisitions at Morgan Stanley for two years, earned his MBA at Harvard Business School, and then spent four years at the private equity firm Odyssey Partners. While living in New York and working for Odyssey, he tried to buy a bowling alley on the Upper West Side with a couple of buddies (including Glenn Taitz ’82). It didn’t work out, but he coined the name Pinstripes then, a play on bowling pins and the upscale pinstripe suits he wore to work.
Schwartz eventually left New York and bounced around the country working in the biotech industry before cofounding Pharmaca, an integrative pharmacy chain in the late 1990s. Pharmaca now has 28 locations across the United States, but Schwartz left after seven years as co-CEO because he longed to run a business on his own. “I kept dreaming about Pinstripes,” he says.
At that point, Schwartz was ready to get the ball rolling and spent the next two years putting plans in motion. He interviewed candidates for general manager and executive chef and assembled an executive team. After visiting Campo di Bocce in Los Gatos, Calif., he decided to also include bocce, which was similar to the lawn bowling he loved during golf trips to Scotland with Colgate friends. He signed a lease for a 38,000-square-foot space, installed 18 bowling lanes and 10 bocce courts, and opened the Northbrook location in 2007. The menu includes wood-fired pizzas, maple-glazed salmon, and seasonal, house-made gelato, accompanied by a list of fine Italian and American wines.
The company opened its second Chicago location on Sept. 22, 2008, a week after the subprime mortgage crisis began. “We survived 2008 and the economic downturn in a slightly similar way to how we survived COVID this last year,” Schwartz says. “We had to tighten our belts and work harder. We didn’t want to sacrifice the quality of our food or make the easy cuts. We just muscled through.”
Schwartz has been pursuing expansion plans by entering into strategic partnerships with major real estate developers. These partnerships include plans to open a handful of new locations in 2022 and more thereafter.
His plans are ambitious, fueled by a spirit that still lingers from his student-athlete days. “I like competing,” he says, “and, when possible, I like winning.”