Michelle Freeman—the 50-year-old CEO of the Carl M. Freeman Companies—is open about the pains that life has thrust upon her. “I learned from both men I loved that lives are what matter, not stuff,” she says. “It’s scary to be honest, but if you are, change comes. Somehow, if my pain helps someone else, it’s not in vain.”
That pain included addiction, poverty and accidents that killed her husband and, later, her boyfriend. “I wouldn’t wish this on anybody,” she says. “I try not to look at myself as a victim.” It all made her grow in “wisdom, friendship, love, connections and empathy.” It grounded her, too. “Every time I’m at the Freeman Stage, I pick up chairs, make coffee, do whatever it takes to be real.”
The first pain was addiction. “I don’t ever remember drinking normally,” she says, “and my drug use followed that trajectory.” She became clean and sober at age 20.
After dropping out of college, she became a mother at 23. The father didn’t provide much support, but her family, friends and faith did. Freeman juggled multiple jobs: waitressing at her parents’ restaurant (she was born a DiFebo, the family behind Feby’s Fishery in Wilmington) and at Fran O’Brien’s in Rehoboth Beach and selling real estate. “I did whatever I could to make financial ends meet,” Freeman says, though she still needed food stamps.
Over the years, Freeman built a better life that included better-paying work, a fairy-tale marriage to Joshua M. Freeman—scion of the company that developed Sea Colony in Bethany—and two more children. Then tragedy struck—twice. In 2006, Josh was killed in a helicopter crash. In 2014, Freeman’s first serious boyfriend since Josh’s death, local restaurateur Matt Haley, died after a motorcycle accident in India.
Such pains inspired Freeman to pay it forward to her staff. “It colors everything about the experience of working for Freeman,” she says. She stresses good deeds and philanthropy through two charitable foundations, gender equality in pay, empowering people to speak up and wrapping it all in a “safe and fun workplace.”