But today, Schilling is right in the middle of one of the most competitive House races in the 2010 congressional midterm elections, running to unseat two-term Democratic incumbent Rep. Phil Hare in Illinois' 17th District.
"I'm a guy that for the last 14 years I've fired up, from the ground up, my small pizza store, and, you know, worked my fingers to the bone, and, you know, had for the first three or four years really struggled to get by," Schilling said in an interview with ABC News.
Following the 2008 presidential election, Schilling says he began considering a run for the House.
"We're just starting to get our head above water and the government wants to come in and raise taxes and, you know, I just figured now's the time to do something rather than just sit around and complain," Schilling said "The big thing I looked at ? the big picture as a husband, a dad and a small business owner,?we trust that the government, our elected officials, are going to go in and do what's in the best interest of our country, and I did not see that happening, so for the first time in my life I decided to run for an office."
Schilling, whose favorite kind of pizza is "Jalapeno Garden" (sausage, onion, tomato, mozzarella and jalapenos) started his restaurant businesses almost 14 years ago. The pizzeria employs eight employees, including three of his own children. His tight bond with his family is evident in his campaign as well, which is run by his oldest son, Terry.
While polls show the race as a toss-up, Schilling says his congressional campaign is built at the grassroots level -- and about one-third of his campaign volunteers are registered Democrats.
Republican campaign sources say the Schilling-Hare race reflects the kind of trouble Democrats are having in Midwest congressional races.
Pizza Party or Tea Party
"It's a really great thing because we're seeing more and more people are voting for a person rather than a party, and that's exactly what we were hoping to have happen," Schilling said.
While he has endorsements from former Massachusetts governor Mitt Romney, the U.S. Chamber of Commerce and even "Joe the Plumber" (Samuel Wurzelbacher of 2008 fame), Schilling says he considers himself a Reagan Republican and enjoys support from the Tea Party.
"It's a great organization," Schilling said. "The media tends to villianize them, but, you know, if you go back to basics, you know, Tea Party stands for 'Taxed Enough Already.' They're for smaller government, less spending. I mean, if you stick with what they're set up for, you know they're a pretty good organization, and it's another thing similar to our campaign, it's just conservatives in general, from age 18 all the way up to 88 years old is the oldest guy that I've seen out there. And it's just Americans that are saying 'Hey, we do not like the direction that this administration has taken our country and we're going to fight to take it back.'"