A Journey of Leadership with President and CEO Stanley Richards

A Journey of Leadership with President and CEO Stanley Richards

08/13/2025

As the President and CEO of The Fortune Society, Stanley Richards is a pillar of the Fortune community. Stanley was first hired in 1991 and has remained committed to serving individuals impacted by the criminal legal system ever since.   

We sat down with Stanley to learn more about his years at Fortune and how he has grown into the remarkable leader we know today.   

Very early on, Stanley learned that Fortune is unlike many other reentry organizations. He felt aligned with Fortune’s commitment to every participant’s wellbeing, whether they just walked through the doors or they’re coming back for assistance ten years later.   

“Fortune is a place that, when you walk in here, you can see the work happening,” Stanley said. “But it's also about how people feel connected to this community and why we do the work that we do. That has always brought me back to Fortune. It's what drives me in this work.”

Stanley’s first role at Fortune was with Admissions, formerly known as the Counseling Unit, as a counselor. He welcomed new participants to Fortune, conducted intakes and connected people with necessary services at the agency. Stanley described this work as the joy of his life, and he is proud that this was the starting point of his career in criminal legal system reform.  

“I made the decision when I was incarcerated to dedicate my life to helping others realize that they didn’t have to live in a cycle of incarceration,” Stanley explained. “I wanted to find an organization where I could offer what I’ve learned and the skills that I was bringing to the table.”  

Stanley’s first role at Fortune was with Admissions, formerly known as the Counseling Unit, as a counselor. He welcomed new participants to Fortune, conducted intakes and connected people with necessary services at the agency. Stanley described this work as the joy of his life, and he is proud that this was the starting point of his career in criminal legal system reform.  

“I made the decision when I was incarcerated to dedicate my life to helping others realize that they didn’t have to live in a cycle of incarceration,” Stanley explained. “I wanted to find an organization where I could offer what I’ve learned and the skills that I was bringing to the table.”  

Stanley noted the incredible value of working within Fortune’s various programs, and his experience informs how he approaches his work now. Having had a hand in Admissions, Employment Services and Education, and various other programs, Stanley understands how our services work together to best serve participants

“Every program we have, I have been involved with either growing it or starting it,” Stanley explained. “All the roles I had, going back to when we first launched the Drop-in Center, or when we opened the Castle. It all provided me the opportunity to see how serving the full range of needs of our participants can have generational impact. When you think about the vision of how all these pieces work together, we have created a place where you can come in any door and get access to the community and get everything you need.”  

During his time at Fortune, Stanley has drawn from his lived experience to deliver quality care and support to participants. Whether he worked in Admissions, Employment Services, or, as he now serves, as President and CEO, he consistently approaches his work with sensitivity and understanding.   

“My philosophy is, you show up in the way you want people to show up, and you treat people the way you want to be treated,” Stanley said. “You see people not from a place of deficit or what they did wrong, but from a place of understanding that they have what it takes to succeed.” 

That philosophy applies to how he leads Fortune and how he engages with staff and participants.  Stanley can be seen walking around our multiple sites, talking and checking in with staff and participants, and always extending time to listen and engage.  He often quotes one of his mentors and friend, Kenneth Sole – “The health of pathology of those in authority will be manifested in those with lessor authority”, and adds that “For those of us leading organizations, directing programs or providing services like running a group, we must show up in ways that affirm the best in people.”   

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