As I walked out of the gates of the medium security California City Federal Correctional Facility as a free man, I thought to myself, “I can’t wait to go back.” My psyche was permanently changed by the experience. But I wasn’t serving time - I was serving as a volunteer.
My day in prison was made possible by Defy Ventures, a nonprofit that is working to solve the mass incarceration problem in America, and my desire to go back was made possible by privilege. While the idea of volunteers swooping into prisons to save the day is romantic, the reality is our prison system is unmistakably broken. It breaks the future of inmates, the hope of families, the wellbeing of communities, and the budgets of governments.
So what could a social impact executive slash hip-hop artist, alongside executives from other industries, do about such a daunting problem? We walked through the doors of Cal City with a belief that our business acumen would transform the lives of the prison’s up-and-coming entrepreneurs. These “Entrepreneurs in Training,” or EITs, were prepped by Defy Ventures’ intensive training program and were developing businesses that would be launched upon their release from prison. So we buttoned up our shirts, dusted off our oxfords, painfully turned off our constantly buzzing cellphones, and allowed the gates to shut behind us.
The deafening crash of metal in movies about jail is no exaggeration. We entered a facility devoid of color and heavy on procedure. Each door required an escort and would only open after the sliding metal bars closed behind us. Coming from a world where we are used to accessing information, transportation, and resources within seconds, we felt trapped. But as I walked into a large room of inmates with startup founders, hedge fund managers, and venture capitalists by my side, I quickly learned what imprisonment means for leaders.
We learned what Emotional Intelligence really means.
We started the day with an icebreaker called “Step to the Line.” When the moderator read a statement that was true for ourselves, we stepped forward to a line of masking tape across the barren concrete floor. For example, I stepped forward when she read, “I love hip-hop music.”
The volunteers were placed on one side of the line and the inmates created a sea of blue on the other. When the moderator said, “I’ve been incarcerated,” the inmates stepped forward while most volunteers stayed back. But when she said, “I’ve committed a criminal act,” or “I’ve lost someone I love,” or “there are times when I feel ashamed of myself,” the line was full with people standing shoulder to shoulder, representing an array of colors and experiences.
Not a word was spoken by the inmates or volunteers during this time, because our eyes and hearts connected on that line. On that line, we discovered the inequity of a system that punishes people without means when they make mistakes. On that line, we discovered the similarities between millionaire venture capitalists and OGs who have served 20 years. On that line, we discovered that people don’t bond through resumes, but humanity.
You can’t lead people and drive for positive change unless you truly understand people and why change is so necessary. That knowledge doesn’t emerge through books or conferences or corporate roundtables. It emerges when you stand on that line with inmates.
We discovered our nation’s greatest source of untapped talent.
An EIT stepped to the stage with a brochure for his new business, a strategy to drive revenue, and over 15 years of incarceration under his belt. As the panel of judges peppered him with questions about local competition, salary structures, capital costs, and branding, he knocked out each one with the confidence of a seasoned executive.
But his time in prison isn’t what sets him apart from the average Silicon Valley or New York entrepreneur. He showered the volunteers and prison and Defy Ventures staff with gratitude for the opportunity to rebuild his life and transform his hustle. He demonstrated the hunger that you can only tap when your back is firmly against the wall and everyone has counted you out. He outlined a comprehensive plan to hire other EITs - not to find cheap labor, but because he wants to send a message to the world about the talent that we are relinquishing behind bars.
I’ve spoken with Department of Corrections officials in other states who won’t allow inmates to hug each other. I’ve heard community members call young teenagers of color who have been jailed for petit larceny “thugs with no hope for the future.” I’ve seen elected officials pat themselves on the back for being tough on crime as opposed to investing in rehabilitation.
That isn’t leadership. Leadership is going to where the talent is and cultivating it. That means in-prison training, ongoing mentorship, and paths to productivity. You don’t discover opportunities to tap an emerging pool of talent by reading the latest report about our rising prison population. You do it by giving inmates a chance and allowing yourself to be amazed.
We became accountable for more than we ever imagined.
During the event, I had the opportunity to perform my new song “Our Time” with two of the EITs. It’s a song about seizing the moment through our determination and passion, and I’ve never had more fun performing it. Afterwards, I spoke with one of my co-performers who told me about his plans after he leaves prison on October 18th.
He told me that he used to be a gang leader with a massive drug distribution network. He “beat death” three times - once in the shootout that led to his incarceration, and twice when the prosecutor tried to give him a life sentence. He lost his family and his friends. He was told he was getting what he deserved.
After years of anger while sitting behind bars, he was dismayed to see a younger generation following his path. He pivoted and started teaching inmates about the power of hip-hop music to express yourself in positive ways. He became an EIT and buried himself in classes taught by Harvard and Stanford business professors. Now viewed as a role model, he plans to start a nonprofit that brings hip-hop to prisons so inmates can experience the same transformation he did. He’ll even do it for free, because his newfound mission is too important to fail.
His story was a reminder to me that my music has to be more than pressing play. A reminder that my leadership has to be more than green lights on a scorecard. My bond with this EIT, forged through music and a day in prison, will be a constant reminder that my music and leadership will only hold value when I inspire others and help to transform a system.
Walking out of Cal City, all of us were still on the line. We could still see the inmates across from us with tears in their eyes as they heard, “by the age of 18 I learned that I couldn’t trust anyone,” and they glumly paced toward the line. We felt the reverberations of cheers, hugs, and high fives of EITs who received business certificates from Baylor University - the first time many of them had ever attained an academic achievement. And we understood Martin Luther King, Jr.’s “fierce urgency of now” like never before, because neither the EIT program, nor leaders going to prison, is the norm in America.
Let’s change that. Let’s go to prison. Our humanity is on the line.