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.'"
Schilling and his opponent Hare coincidentally share some biographical connections. Both are from Rock Island, Illinois, both attended the same Catholic high school, and both attended Black Hawk College near the Quad Cities. But Schilling says the similarities end there.
"We have a lot of career politicians. Like the guy that's going to be unelected on November 2. You know, this is all [Hare] knows. He's never run a business, doesn't know when to stop spending money, he's never had to balance a budget or meet a payroll. And that's something that I bring to table that's much needed in the country today," Schilling said.
If elected, Schilling promises to abide by an informal contract he's made with the 17th district of Illinois, including a self-imposed eight-year term limit in the House, rejecting the congressional pension plan and donating any congressional pay raises to charities in his home district.
Schilling Touts Small Business Credentials
"We're going to give a lot better service than what's going on right now. I'm going in to serve. I'm not going in to make a career and that's the big difference between the two of us," Schilling said.
While President Obama's successful presidential campaign may have motivated Schilling to seek public office, he's not exactly a fan of No. 44.
"I think [President Obama's] done actually not very well at all," Schilling said. "He's an excellent campaigner, but you know, it's time to stop the vacations, stop the golfing and it's time to get to work and run this country."
"We've got the jobs numbers out again. We're still at 9.6 percent [unemployment]. We spent a trillion dollars of money promising us that unemployment wasn't going over eight percent. I believe the stimulus failed, and I think that until [President Obama] decides to help create an environment that's going to be favorable towards small business, I think that it's just going to continue to go down the wrong path," Schilling said.
Schilling says that during the financial crisis, business at the pizzeria has dropped about 20 percent. If the Bush-era tax cuts expire at the end of the year, he predicts he would have to lay off at least one of his eight employees ? most likely one of his own children.
"As a small business owner, I understand that if they give me another tax ? and this is why this is so important we don't get any tax increases ? is there's only so much you can charge for your product, and then people have to stop buying because we're in a downturn economy."
When asked what he thinks about the GOP's proposed legislative agenda "A Pledge to America," Schilling says it's "a good start" but that "it needs to go a little more in depth."
"One of the things I did like is that they talked about any bill that comes to the floor before they vote on it, they check to make sure it's a constitutional bill," Schilling said.
Schilling said he's opposed to the health care reform bill signed into law by President Obama earlier this year, and calls it "a tax bill" wrapped with "a few pieces of Health Care reform."
"I do not believe that the government can force anybody to buy any product throughout the country, and I think that that's something that's important, and one of the reasons why we've lost our way," Schilling said. "If it was a good thing for the American people, it would not have been done behind closed doors. They would have read the bill before they passed it."
Asked what his highest priority would be after he's sworn into office, Schilling says Congress's primary objective should be to create some stability in the market for small businesses, repeal the health care bill and shut down Cap and Trade legislation, which he says could cost the United States more than five million jobs.
"I call it the China and India jobs bill because it's just going to put a hurt on our companies, on our employees, and then seniors and the poor folks in our country are going to get hit with an additional tax," Schilling said. "It's going to be a national energy tax is what it is, and you know, right now, I don't believe there's anybody in this country right now that can afford any new taxes."