Five years ago, Chris Redlitz walked into San Quentin State Prison for the first time. He came out a changed man ... luckily, only three hours later. The serial entrepreneur and technology visionary visited to speak to inmates about entrepreneurship. He'd agreed to do it reluctantly--but the passion he witnessed in that room soon convinced him to start The Last Mile, a business and technology incubator inside San Quentin, the oldest prison in California.

On my podcast, Innovation Crush, Chris talked about his passion, his personal transformation, the differences between incarcerated entrepreneurs and free businessmen... oh and that one time he sailed from California to Hawaii. 

Here's what the experience taught Chris about executing big ideas.

1.)     It's ok--and expected--to be afraid.

Chris describes in intricate detail the dark and rainy night he was scheduled to speak behind bars. One by one, shadowy figures entered from the blackness that loomed outside the building (by the way, in my mind, this happens in slow motion with pulsing, epic synths and bass from an Avengers devastation-of-defeat scene). It doesn't take much for fear to show itself to us after we say "yes" to an idea, a thought, or a request. More often than not, the lesson learned from saying "yes" far outweighs your instinct to run.   

2.)     Always ask for help.

After witnessing the intelligence, passion and knowledge the inmates had for entrepreneurship, Chris got home and told his wife/business partner about his idea.  "No effing way...!" she exclaimed. After some careful deliberation and thinking through, they come up with a solid game plan. 

It's easy for us to go blindly into battle for an idea we have, but the wise man becomes even wiser when he seeks counsel. Especially from those who may not be on the same high as we are after an epiphany-inducing encounter.

3.)    Innovation comes from necessity.

We've all heard or seen documentary-worthy stories about the resourcefulness of prison inmates. You can make anything out of anything, and get anything in from anywhere. And the most ingenious do it without getting caught. In the case of The Last Mile, the program has navigated rules and federal regulations to find ways for its participants to participate in social media, write up business plans, get mentored by the likes of Guy Kawasaki and MC Hammer (yes, that MC Hammer), and pitch to investors. They say the best innovation comes from constraint. If you feel you're short on time, resources, experts, energy and the like ... that's usually when you have no choice but to think outside the cell. 

4.)    Make sure everyone involved has what they need.

Whether you're hiring a CEO or intern, no matter how good they look on paper, no one comes and starts working their magic on day one. Or year one, in some cases. The people you lead need to understand you, the world you've created, and how they will best fit into it. This takes time. Upon release, each participant in Chris' program is set up with an internship or mid-low level job in the Valley while they work on their own business plans. Give your team time and resources to get acclimated and blossom.

5.)    Discipline takes discipline.

Chris knows he's dealing in the world of con men, thieves, murderers, and all around criminals.  In the traditional business world, we get off with warnings and strongly worded emails. In Chris's world however, The Last Mile's zero-tolerance policy means one missed session, one bad behavior report, and you're out of the program. As leader's the last thing we want to do is deal (properly) with weak links. As innovators, our ideas are only as good as they are executed. Discipline--both in terms of accomplishing tasks and confronting poor performance--therefore means sometimes weighing your compassion for people against the love for your product and your team.

Published on: Jan 14, 2016
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