WHAT I LEARNED AT RIKERS (value hustle and stay humble)

I recently spent a morning at Rikers Island prison to kick off an entrepreneurship program for inmates as part of Defy Ventures. It blew my mind.

Twenty volunteers spent three hours with fifty soon-to-be-released prisoners, all of whom wanted to learn more about the training program being offered by Defy Ventures. Defy is an organization that offers ex-criminals education, funding and contacts so they can transform their lives through entrepreneurship.

We sat on one side of a large gym, and the prisoners sat on the other, with at least a dozen correctional officers lined up at the back. The atmosphere was moody and suspicious until a group of Defy graduates, themselves all ex-prisoners, stood up and shared how they had transformed their hustle from criminal to legitimate. Hearing real stories from relatable people loosened everyone up.

One of the speakers was David Lee*. David is a super-smart second generation Chinese guy who had spent three years behind bars before he was eighteen years old. He got mixed up in organized crime, used his considerable ability to steal and con, and was eventually convicted for aggravated armed robbery.

When he was released, David realized just how much he’d let down his parents and decided to become the first in his family to finish high school. He ended up getting a college degree, an MBA and recently got angel funding for his own tech start up. He was going on MSNBC the day after we met, and looks and talks like a Harvard grad.

What was striking to me about David was that the same skills that got him into trouble are getting him out of trouble. He’s charismatic, resourceful, resilient, creative and organized. These same characteristics that made him such an attractive gang recruit are now helping him become a powerful business leader. I heard similar stories from all the other Defy grads who spoke; stories about how they had managed to successfully reapply their hustling skills into business and entrepreneurship.

Unfortunately, I’ve found that hustle is often lacking in the corporate world. People are bright and do good work, but are generally too insulated and removed to need to be as hungry and ingenious and brave as the Defy graduates I was listening to. But in the fast-moving, low barrier, opportunity-filled world of today this presents a huge risk to large corporations as these skills are going to become more and more valuable as they try to fend off new competitors and entrepreneurs in general.

Catherine Hoke, the Defy founder and CEO, then blew my mind. Not because of her story though (which is by the way amazing), but with an exercise she ran called ‘Step to the Line’. It’s an empathy exercise designed to demonstrate how similar or different two groups of people are. A line of tape was stuck down the middle of the gym, with prisoners lined up one side, and volunteers on the other, facing each other. Catherine would shout out various ‘step to the line if…’ statements, and you would move forward and stand on the line if that statement was true for you.

These numbers are approximate but close enough…

‘Step to the Line if you like sports’. 15/20 volunteers stepped forward, 45/50 inmates. An easy one to get us started and identify some common ground. There were a few of these type of statements, ones that were designed to connect and keep it light. Then it got deeper and more intense.

‘Step to the Line if you have a college degree’. 19/20 volunteers stepped forward, 2/50 inmates. Unsurprising but sad. ‘Step to the Line if you were homeless before you were 18’. 0/20 volunteers stepped forward, 20/50 inmates. 20/50. I couldn’t believe it. That’s a lot of people. ‘Step to the Line if you were abused as a kid’. 2/20 volunteers stepped forward, 35/50 inmates. ‘Oh my god’ I thought. ‘Step to the Line if a family member has been murdered’. 1/20 volunteers stepped forward, 15/50 volunteers. It went on and on like this. Statement after statement revealing just how hard and unfair life had been for the people I was looking into the eyes of.

The message was obvious but important. I’m lucky and privileged and should be humble and not forget it. And, by the way, we should all avoid prison like the plague because Rikers didn’t look like a lot of fun.

* Name changed to respect confidentiality