Out of Office: I’m in Prison

Anyone who emailed me on November 15th received this auto-reply:

“I’m in prison.”

To be more specific, I brought a bus-load of my colleagues to spend the day inside a Level-4 maximum security prison in California, about an hour northeast of Los Angeles, as volunteers with Defy Ventures.

The purpose of the day in prison was a Business Coaching Day with people who had committed felonies, many for violent offenses, and to help them create businesses upon their release (or potential release) from prison. Defy refers to these people, who have opted into being a part of Defy’s program, as Entrepreneurs in Training (“EITs”).

Due to the prison’s rules, I entered the prison without my cell phone, watch, wallet, and anything except for the clothes I was wearing (which were color-specific per prison guidelines).

Despite any anxiety I had the morning leading up to the event, my day in prison was one my truest experiences in being human, in humility, and in humanity.

I can think of just a handful of times in my life when have I ever felt more present, inspired, and able to give and learn at the same time.

Through the the cheers, the tears, the high fives and hand pounds, and of course, the dancing, the experience of getting out of my comfort zone made me more comfortable than I’ve almost ever been. I felt safe, physically and emotionally.


Without more, it sounds like a pretty intense and potentially scary experience, so why did I do it?

And why do I encourage you to do the same and to bring your friends or colleagues?

Because of the need to get out of our own echo-chambers.

Because of the benefits of getting out of our comfort zones. Fear of what we don’t know is a big factor in derailing innovation and entrepreneurship — fear to continue, to push past our limits and to see things or do things differently than they have been done.

Because, as a driver of innovation, I believe in the need for people to share in the experience of digesting new and vulnerable experiences to evolve their world view and sharpen their strategic thinking.

Because, as a rule, we can’t dismiss people based on prejudice. And prisoners (during and post-release) are one of the largest class of those who are dismissed based on their background and our prejudice.

Because of the need to truly unplug and be present, and to inspire others to pause, to get off auto-pilot, to reflect, and to harness mindfulness and creativity.

Because agnostic of industry, it’s important for people to become even more self-aware and informed business leaders who see, think and feel.

And because I can think of no better business and life experience to share than a day in prison with Defy.

The day in prison included coaching and feedback to EITs on resume building, personal statement development and conception of business ideas.

More fundamentally, the day included breaking down barriers and preconceived notions between volunteers and EITs. The day was very much about connecting in the most authentic manner cutting to the core of humanity to transcend background, race, religion, gender, and any collective past wrongs that have been done by us or to us, with no judgment in that room. The EITs were humble, grateful, and could not have been warmer or more welcoming.

During an emotional exercise between the EITs and the volunteers, almost every single EIT shared that, while growing up, they had: experienced violence in their home, and often against them; had consistently heard gun-shots in their neighborhood; had a family member who had been to prison; didn’t think they would “make it” to 21 years old; one or both of their parents were not positive role models, and that their parents had not received college degrees. There were the circumstances that defined their “first chance.”

I stood toe-to-toe, locking eyes with an EIT named Hector, who shared that he had been thrown in the garbage before he was even five years old, to collect cans. As he spoke, I felt the tears well up in my eyes. I put my hand out to him and we locked our hands — I couldn’t help but wonder how many years it had been since someone held Hector’s hand. Hector…who lost his innocence when he was just a few years old, when his parents threw him into the dumpster. Hector didn’t want my pity — he wanted opportunity, he was there to learn, and he wanted someone to believe in him. I told him that I did. And I do.

It became clear that the circumstances of the EIT’s supposed “first chances” made it almost predestined that they would end up incarcerated. The deck was heavily stacked against them, from Day 1.

Enter, Defy Ventures.

Defy’s not-for-profit mission is to help America’s scrappiest underdogs transform their hustle and unlock their entrepreneurial potential in meaningful ways.

Defy encourages every member to create a business plan for a business that they can launch upon release that can be cash-flow positive in just 3 months. Post-release, Defy also supports EITs in the launch of their ventures by offering intensive hands-on entrepreneurship training, character development, mentoring, business incubation, financing opportunities and holistic personal development services.

I became involved with Defy Ventures early in 2016, when Defy was one of the first grant recipients of the Techstars Foundation. The mission of the Techstars Foundation is to support diversity in entrepreneurship, and Defy’s commitment to incarcerated and post-release EITs hits that mission in the numbers.

Led by tremendous founder and CEO Catherine (“Cat”) Hoke, Defy is one of the most powerful not-for-profit organizations I’ve ever encountered. And the results of Defy’s work are staggering: Defy Ventures graduates have a 3.2% recidivism rate (the rate at which they are re-incarcerated) compared to a national five-year average of 76.6%.

As it relates to “first chances” — Defy works to give the EITs a legitimate chance to succeed by equipping them with the knowledge to become profitable entrepreneurs, honorable employees, engaged parents, and committed role models and leaders in their communities.

Defy rightfully calls itself a “legacy breaker” — through its programs in and out of prison, it breaks the generational legacies of violence, poverty, and incarceration by equipping its EITs with the tools needed to have that true first chance.

How can you get involved?

You can participate in a prison visit — and better yet, you can arrange for a trip for your friends and/or colleagues. You can mentor and coach EITs who have been released and are participating in the program. You can make a financial donation. You can hire Defy’s graduates. You can support a business that has been started by a Defy graduate. All details on ways to be involved can be found here.

Of course, if you are an organization supporting diversity and inclusion in entrepreneurship, I also recommend that you check out the Techstars Foundation, here.

I’m rooting for all of the EITs, and I’m rooting for Defy.