Transform Your Hustle

“I’m running from nothing, no thoughts in my mind
Oh my heart was all black
But I saw something shine
Thought that part was yours, but it might just be mine
I could share it with you, if you gave me the time
I’m all bloody knuckles, longing for home
If it weren’t for second chances, we’d all be alone”
– Gregory Alan Isakov, from his song  Second Chances

I struggled to write the introduction to this podcast episode with Catherine Hoke, CEO of Defy Ventures, and our dear friend Brad Feld. I struggled because I have only a few ways to relate to and fathom a life lived by the prisoners that go through the entrepreneurship program that aims to transform their hustle – and ultimately, give them a second chance (or as Catherine, Brad and Jerry talk about in this episode, sometimes it’s a legitimate first chance).

I had a good chance in life, backed by privilege, good parents, and a safe midwestern town. My biggest run-in with the law is likely a toss up between that speeding ticket I got in college in Montana, or watching Shawshank Redemption. A penchant for the illegal wasn’t part of my menu of options in my life situation. I was too busy braiding my horse’s mane.

But I know that’s not the case for everyone. Some of us come into this world in situations with less privilege and more prejudice, with less safety and a necessity for the gritty hustle to survive. Some of us are born into families and lineages historically laden with the struggle to survive and thrive, where if we were to follow in the footsteps of our relatives, we’d find ourselves behind bars by default.

We all have a somewhat pre-wired set of options on our menu for life. If we have a limited set of choices, we may eventually run up against what seems to be like our only available options. It takes deep inner looking to increase the list of choices available on our menu. Otherwise, the world that is all we know can become the only world that we’ll ever know, repeatedly caught in whatever cycle that we find ourselves in. So often we stay close to those limited options because it keeps us closer to our kin and ushers in a sense of belonging, safety and love, even when the choices don’t seem that great.

Regardless of who we are, we all have different settings for our menu of choices in life. Until we take a closer look and expand our notion of what’s possible, what we can do, what we deserve, and what we’d like, these options can limit us and our growth and add to a general feeling of “stuckness.”

The program Catherine established at Defy Ventures aims to help prisoners defy the odds, the stereotypes, and perceptions. It is a bit of a startup redemption for the prisoners; they learn to move beyond the failure of a specific circumstance and situation that landed them in jail in the first place. For the ones that get to leave, they learn that moment doesn’t have to define them forever, or confine behind bars of self-loathing. And, they transform the skills of their old hustle and apply them to a new hustle, giving themselves as well as those they love more options, more choices, and freedom.

By breaking the cycle they move forward. By consciously choosing a different game, and a better life, these prisoners forge new opportunities for themselves,for their kids, and their communities. It allows them to work from a new structure of how to be and belong in the world.