Grad finds purpose mentoring entrepreneurs
Information technology and MBA alumnus Aaron Foss teaches at correctional facilities
Aaron Foss ’00 (information technology), ’01 (MBA) remembers his first trip into a prison, nervously crossing the long, narrow bridge into New York City’s infamous Rikers Island. As he followed corrections staff through a gymnasium where participants were gathering, he was met with surprising warmth.
Foss is, in his words, a retired entrepreneur. A five-time founder, he successfully created and sold companies, including Nomorobo, an award-winning service that has blocked millions of robocalls nationwide, and SideTour, a marketplace that helped people discover local activities.
But entrepreneurs never really retire. He is taking all the lessons learned and finding purpose in passing it on to a new generation of entrepreneurs.
He’s spent the last decade volunteering and supporting Defy Ventures, a national nonprofit grounded in criminal justice reform through entrepreneurship. Through its programs, the participants move through a structured curriculum that covers simple business practices.
In correctional facilities, volunteers like Foss lead small-group sessions where participants workshop ideas, practice pitch presentations, and receive individualized feedback. The program’s goal is to lower recidivism by offering a clear path toward legitimate work.
Working with incarcerated populations in the New York-Connecticut-New Jersey tri-state area, Foss spends his days fixing résumés and listening to pitches.
His introduction to Defy came through Techstars, an accelerator that guided an earlier venture. When Defy representatives visited a founders’ conference in 2015, Foss immediately connected with their mission.
“They found me,” Foss said. “We both believe that entrepreneurship doesn’t care who you are, your background, your gender, your neighborhood. It just cares that you put in the work.”
As soon as his company’s acquisition was finalized and the funds cleared, he went right to work. Some moments have stayed with him over the years. At a women’s facility in Connecticut, two participants sat down back-to-back during a rotating mentorship session. Both had worked fast-food jobs at McDonald’s and Taco Bell. One of the women struggled to explain how she stood out until Foss flipped the page and found a list of responsibilities she’d taken on through a puppy-to-prison volunteer program.
“She coordinated visits from outside organizations and supervised peers,” Foss said. “I told her, ‘This is leadership.’”
In addition to in-facility mentoring, Foss also serves on Defy’s investment committee. After release, the organization continues to support its participants through virtual mentoring and access to small grants, up to $10,000, that help launch service-based businesses.
What has struck Foss most about his volunteer work is how openly he is received in facilities. Participants often thank him simply for showing up or for treating them with a level of respect they don’t always experience. Those interactions, he said, reaffirm the importance of consistency, empathy, and direct human connection.
“There are a lot of good people who made bad choices,” Foss said. “My job is the rehabilitation side, and being a part of that person’s second chance is incredibly meaningful to me.”
