By Charlie Pogacar
When Lynn Humphreys and Brandon Bruner opened a Lynn’s Chicago Pizza brick-and-mortar store in the Woodlawn neighborhood of Chicago, they knew it was a longshot. They wanted to bring their pop-up, deep-dish pizza brand to a food desert on the city’s South Side, fully aware they’d be one of the first—and only—restaurants in the area.
So when, just 15 months after opening, Bruner had to close the shop, he didn’t view it as a failure. He viewed it as a learning experience—one that produced valuable data for a future pitch deck.
“For us, the biggest thing that came out of it was proof of concept,” Bruner said. “Real numbers, real sales. We sold almost $300,000 worth of pizza in about 15 months.”
That number matters to Bruner, because it tells a more complicated story than “a pizzeria opened and, 15 months later, it closed.” The brand’s physical shop proved there was demand for his product—foodies flocked to the neighborhood to try his highly acclaimed pies. The pizzeria accrued over 10,000 followers on Instagram in the process.
But what Lynn’s couldn’t overcome was the lack of foot traffic. When the restaurant opened, Bruner and Humphrey held optimism tied to nearby development, including the long-anticipated Obama Presidential Center. They hoped Lynn’s could hang on until the surrounding area caught up, but that proved challenging. “There’s a reason it’s hard to be first,” he said. “You need deeper pockets to hold on. And we just didn’t have them.”
Rather than walk away from the brand, Bruner has decided to take it back to its roots while he hits the reset button. Today, Lynn’s Chicago Pizza exists as a catering and pop-up concept, operating out of shared kitchens with minimal overhead. He’s also launched a side project selling pasta kits and lasagnas—anything that allows him to keep cooking while he fundraises and eyes possible new locations.
At the same time, Bruner is doing something else: taking his deep dish on the road. After a strong reception at Varasano’s Pizzeria in Atlanta, Bruner realized the pop-up format could do more than generate short-term cash. It could build awareness and keep the Lynn’s Chicago Pizza name alive while he raises capital for his next brick-and-mortar play.
“In Atlanta, people were like, ‘This is better than home,’” he said. “Chicago people are everywhere—and they miss this pizza.”
That realization has shaped his roadmap. Bruner is targeting cities with large Chicago transplants—like Atlanta, Houston and Phoenix—using pop-ups as both market tests and brand builders.
Ultimately, Bruner’s long-term vision looks different from Lynn’s original footprint. The next step, he hopes, is a smaller slice shop in a higher-traffic South Side neighborhood like Bronzeville or Hyde Park—areas with customers jonesing for handcrafted food. From there, he imagines a flagship pizzeria anchoring the brand, with faster-format slice shops serving surrounding communities.
“In my neighborhood, speed matters,” Bruner said. “People are used to food in minutes. That doesn’t mean they don’t deserve quality—it means you have to meet them where they are.”
For now, Bruner is focused on momentum—showing up in other cities, collaborating with other operators and keeping Lynn’s Chicago Pizza visible while he works toward the next opening.
“It would’ve been easy to close and disappear,” he said. “But this is something I built. We started in our home kitchen. Going backward to go forward—that’s how I’m looking at it.”
