Why I Volunteered to Spend a Day in Prison

by Nick D’Antonio

Along the beautiful coast of California’s Del Norte County, bumping up against the Oregon state line, is a small town of only 7,600 people. For more than its landscape or geography, the town of Crescent City is unique. Nearly a quarter of those who call Crescent City home will see little of the Pacific waves that crash against the coast day in and day out. That’s because they reside at Pelican Bay State Prison — a super-max prison with nearly 2,600 incarcerated men.

I joined 60 other volunteers with S+ Catalyst Defy Ventures, a prison entrepreneurship and character development program for incarcerated men and women. Pelican Bay, one of the most remote prisons in the state, has struggled to launch programming of any kind, and men serving time are starving for meaningful activity. Without it, they often resort to what they thought — violence.

Defy Ventures recently launched programming at Pelican Bay and hosted a business coaching day where volunteers work directly with Defy’s “entrepreneurs-in-training” (EITs) on business-related skills, like resume building, personal statement drafting, and business ideology.

The day started with one young man named Anthony* sharing his testimony. Through three preceding days of personal coaching, Anthony became comfortable and confident sharing his story. With the support of a friend by his side, Anthony stood up in front of both volunteers and fellow EITs. By age six, he had watched his mother overdose on his couch, seen a dead body, and witnessed a murder. Understanding the course of tragic events Anthony experienced so early in his life transformed him in my mind from an inmate in a high-security prison to a young man not that different from me, filled with pain from an upbringing that carved a different path.

Step to the Line

We then moved to Defy’s most unifying activity, Step to the Line, an exercise designed to promote equality, identify inequities among the group, and create an atmosphere of vulnerability, respect, and humility. Catherine Hoke, the executive director of Defy, flawlessly facilitated the exercise as men and women silently stepped forward in response to statements from, “I’ve been in love” or “I dropped out of high school” to more difficult ones like “I was born to a teenage parent” or “I grew up in poverty.” The exercise proved instrumental in breaking down invisible barriers between EITs and volunteers, reminding us of the humanity of every individual and unmasking the power of privilege in determining one’s path. As volunteers and EITs shed their shame, pride, and embarrassment, true empathy was formed and with that, a bond.

“As I stepped to the line, I looked at him, and he had so much compassion in his eyes like he was saying to me, ‘I can’t believe this happened to you, I’m so sorry.’ It hit me like a ton of bricks,” shared Candace*, a volunteer visiting prison for the first time with me. As we volunteered over the course of the day together, Candace shared how her entire perspective of prison and incarcerated individuals changed drastically. “I didn’t have expectations going into prison. I couldn’t even conjure them up. But, I did have biases. [Through my experience] I was able to see the humanity in these guys, to see them as real people with a lot of pain and a lot of hurt.”

Candace later sat down with two EITs to work with them on their personal statements and resumes. The compassion between two racial rivals in the prison was unexpected and disarming. “I was in a group with a Hispanic man and a black man, which in prison don’t mix. One was having a really hard time sharing his personal statement. He couldn’t sit still or look me in the eye. The other EIT very gently reached out his hand over the other’s and said, ‘You got this.’ He looked me straight in the eye and delivered his personal statement. How Defy does it — I don’t know. I have no idea.”

The Intangible Transformation

Defy Ventures operates several different programs for both currently and formerly incarcerated men and women. Programs range from entrepreneurship training, MBA coursework, intense character and personal development, job placement, executive mentorship, startup incubation, and business pitch competitions with prizes of up to $15,000 in start-up capital. One of the most powerful aspects of Defy’s programming is what’s intangible. The personal and character transformation that occurs when men and women — who have been hidden from society and ignored — realize they have valuable gifts and talents to contribute to others is worth far more than any business start-up grant they can earn.

One EIT shared about the impact of Defy in changing his own life. “You know, before you guys came and before I got involved with Defy, I thought nobody cared about me, so I’m not going to care about them. I can’t believe you guys care so much. We’re supposed to be a forgotten community in the middle of nowhere, out of sight. You came here to show how much you care. This is going to stay with me the rest of my life.”

Those eight hours that I spent at Pelican Bay won’t be my last time in prison, and it probably won’t be Candace’s last time either. I looked at fellow human beings, born with flesh and blood just like myself, asking for a chance to prove themselves. They deserve that chance. Not one EIT that I spoke to didn’t own why they were there. There were no excuses despite the challenges they faced. Not one of them, like Anthony, wrote off their incarceration as a product of circumstance. Offering support and a second chance, Defy asks EITs to take ownership of their actions, and they do. I plan to step to the line and help with that second chance.

At Stand Together, we’re committed to helping Defy provide second chances to incarcerated men, women, and children across the United States. Currently serving EITs, in New York, California, and Nebraska, Defy has aspirations for programming across the entire United States.

As Candace reflected on her first prison experience and the compassion she found for incarcerated men and women, she shared, “It’s very socially acceptable and amenable to get involved with children. They’re innocent. They have opportunities. You look at a group of gentlemen who have criminal histories — why would I invest in them? Well, because if we don’t, who will?”

• Names have been changed to honor the privacy of the individuals mentioned.

Nick D’Antonio is a director of strategic partnerships at Stand Together, where he sources, analyzes, and manages venture philanthropy investments, working alongside organizations on their path to meaningful change. Nick is a graduate of the Kogod School of Business at American University and a certified project management professional by the Project Management Institute.