Defy the odds: my humbling & humanizing day in prison

On March 9th, I spent the day at Valley State Prison helping budding EITs (entrepreneurs-in-training) graduate from a 6-month training program. I didn’t know what to expect — I’ve never been to prison, or known anyone who’s incarcerated. What I found there blew my mind — and broke my heart wide open.

The day began with a meet-and-greet where we connected with the entrepreneurs and started to get to know them. I discovered a group of diverse, determined and hopeful men — each a complex human being with a story to tell and big dreams for a better future

We broke into groups, and listened to business pitches from the EITs. Our task was to support & encourage the men, give them useful and authentic feedback, and choose the best pitches to go on to the finals.

In the middle of the day, we did a powerful empathy-building exercise called “Step to the Line” where we lined up facing each other — Silicon Valley coaches on one side, EITs on the other.

The organizer called out different statements, and each of us would “Step to the Line” if we recognized ourself in that statement. For example: “Step to the line if…”

  • Your parent kissed you goodnight and tucked you in
  • Your parent tried to kill or harm you before age 10
  • You did not feel physically or emotionally safe as a child
  • You graduated from a 4-year college
  • You thought you’d be dead before reaching adulthood

It was incredibly moving to see how many people related to these statements on BOTH sides of the line. This exercise made it crystal-clear that we are ALL human beings who make mistakes. And some of us — due to lack of money, privilege or early support — get imprisoned for our mistakes. And some do not.

Some exercises were stark: 100% of the Silicon Valley crowd graduated from a 4-year college, and NONE of the EITs did. Others were mixed: people on both sides of the line stepped forward to show that they didn’t feel safe or loved as a child, and many tears were shed.

At the end of the day, the EITs emerged in full graduation regalia, ready to celebrate their epic win and commemorate 6 months of hard, grueling work. The program started with 75 inmates — and 46 of them made it through to graduation. A very, very proud moment.

Seeing these men with their blue robes and gold tasseled hats — hopeful, smiling, proud —celebrating each other’s accomplishment and defying the odds that most prisoners face — was a profoundly beautiful moment to be part of. Several of them had family in the audience, there to witness the transformation of their beloved son or brother.

At the end of the day, I was invited up to the stage to share my thoughts with the crowd. I could barely talk through my tears — but I managed to tell them how much the experience meant to me, and how impressed I was by the brilliance, tenacity and sheer grit that it took for these men to complete their training program.

Afterwards, on the long bus ride home, we chatted briefly, then settled into our own thoughts and feeling about this profoundly moving day.

Brilliant entrepreneurs are everyone — but opportunity is unevenly distributed. I’m so grateful to Defy Ventures for giving me to opportunity to make a difference and have my heart and mind blown wide open. I’ll never look at prisoners the same way again — and I’m going to continue to support the incredible, life-changing work that Defy Ventures is engaged in.

If you have a chance to go to prison, DO IT — you will never be the same, and you will KNOW deep in your bones that you are making a difference.

Game designer, startup coach, author, entrepreneur