Now and then, Diana Willis thinks wistfully about the fact that she never finished college. But the Beaumont, Texas, native has never regretted the path her professional life was set on, thanks to a mentor who saw a little something extra in Willis back in the mid-’80s. “I was 20, going to school and working at a hotel,” Willis remembers. “I came to know one of our frequent travelers, who worked at a property management company. She offered me a good position, trained me, invested in me, took a chance on me. I don’t think I’ve stopped learning ever since—I just haven’t done it formally.”
A lot of that learning, less structured though it may have been, has happened alongside her husband, Scott, her high school sweetheart. He was director of operations for a McDonald’s franchise when they married in 1986; nine years later, the two bought a franchise near Little Rock, Arkansas. “That’s when we became business partners. We had to learn how to divide and conquer, basically building the model for what we’d do in the future,” Willis says. Over time, they came to realize that Diana was good at community building and leading a sales team, while Scott’s skills were more in line with the human resources and financial sides of things. Additionally, “When we started, I was the student and he was the teacher,” Willis says. “But at a certain point, we switched roles. That’s what happens when you grow.” Five years later, the couple decided to invest the knowledge they’d accumulated in their McDonald’s years in a risky venture. They moved to Fort Myers to open the first of their Jason’s Deli franchises, which started slinging salads and sandwiches to locals in 2001. It was a daunting undertaking, but the change provided the Willises with just the right landscape in which to continue raising their young sons, and to take on the new learning challenges that inevitably crop up around building an empire of one’s own. “This was a community we knew we could get involved with,” Willis says. Since launching their first deli, they’ve systematically gone on to open locations in Naples, Cape Coral, Port Charlotte, Sarasota and, just last year, a second Fort Myers location, on Alico Road.
Along the way, Willis has eagerly sought opportunities to improve herself as a boss, as well as to pass along some of her accumulated wisdom. “I had the chance to lead when I was young, and to make mistakes doing it, which gave me the foundation to be a good business person,” she says. “Now I can teach other people.” She works one-on-one with some students at the Pace Center for Girls, which gives at-risk teens an educational leg up. She also personally encourages and guides her 300 employees, a few of whom she hopes will eventually rise to leadership roles that will “help us not be so hands-on at the delis one of these days,” Willis says. One of the up-and-comers in the ranks may well be her older son, Brandon. He recently moved back home, after finishing college and garnering a few industry experiences of his own, to work alongside his parents.
In the 17 years she’s lived and operated in Fort Myers, Willis has learned perhaps the most gratifying lesson of all: that there’s validation to be sought among, and given by, her neighbors. “I call it ‘Old Home Week’ when I work in one of the delis,” she says. “And every time, I see people who are still dining with us multiple times a week. I know their comings and goings, their highs and lows. It’s heartwarming to know they now consider us a part of the family.”