If you think starting a company is hard, try doing it from prison

6 min read Original article ↗

Last Thursday, I had the great pleasure of being a volunteer judge for Defy Ventures’ Business Pitch Competition. Twenty five incarcerated men at Solano State Prison got a chance to pitch their business ideas to entrepreneurs for feedback, while 40+ others received one-on-one business coaching.

Overall, my expectations were shattered in the best way possible.

A few notes:

  • Defy Ventures is “an entrepreneurship, employment, and character training blended online program for people with criminal histories.” Basically, they help currently and formerly incarcerated individuals learn how to start their own businesses so they can reintegrate with society more successfully.
  • I use “EITs” below to stand for “Entrepreneur in Training”, meaning they’re participating in Defy’s program either pre- or post-release (pre- for this article).
  • This event took place at California State Prison, Solano. It’s a male-only medium security institution. It has capacity for 2,610 but had 5,050 inmates as of early 2011 (193%) and 4,123 as of late 2012 (158%).

Here are some lessons that I personally took away from it — particularly related to the SF tech scene.

1. We’re too entitled

The prison doesn’t allow visitors to wear blue colored clothing or denim for safety reasons, since this is the color the inmates wear. One individual emailed Defy the night before saying that he was a tech founder, so didn’t own anything other than jeans. Defy responded that they’re sure he could be scrappy like the other entrepreneurs and figure out a solution. He wrote back that he had figured out a way — that he wasn’t coming.

It’s quite sad given all our innovative thinking and make-it-work attitudes that people can become so close-minded when it comes to helping others.

2. We think on too short a time scale

One EIT had been in jail for 42 years. I’m 27. He has spent 1.5x my entire lifetime in prison. But he was still working hard in the EIT program, was still high in spirits, and had some rocking dance moves. Next time you think 1–2 years at a company is a lifetime, imagine spending 42 years anywhere. Big changes can take time.

3. We aren’t the only ones who hustle

One EIT said he regularly spent 8 hours each day of the weekend watching Defy training videos, because he didn’t have time during the week due to his prison job. His prison job, by the way, was one he chose so that he could build up the skills necessary to have a job as an installer/handyman after he gets released. “Working a 10 hour work day” 5 days a week when you spend 4 hours of it on Reddit is not hustling.

And despite severely restricted access to the internet and outside world, they’ve still figured out how to do research for their businesses. This often entails asking a friend or family member to do specific internet research and then mail it to them. One even asked my opinion on whether or not I thought Wikipedia was a reliable enough source for him to be basing business decisions on.

4. We don’t appreciate our upbringings enough

During the first part of the day, there was an exercise called “step to the line” — basically, EITs on one side, volunteers on the other, and anyone step to the line if the statement just read aloud is true for them. It started out light (“step up if you’re 18 or older”), increased in intensity from there (“step up if you didn’t know your biological father”), and got pretty emotional by the end (“when you were 18, step up if you thought you’d be dead by 21”).

The resounding discrepancy between the EITs and volunteers was related to family life in their early years. Most of the EITs grew up in a neighborhood where they listened to gunshots at night. Most had an abusive mother or father, or didn’t have one at all. This comes down to luck of the draw in the genetic lottery. And it’s really hard to break the cycle once you’re on it.

5. We think in grossly inflated numbers

One EIT broke down in tears after winning a $300 IOU in the final round (money granted to him to start his business once he’s released). He estimated only needing a few thousand dollars to get his own plumbing business up and running, and even wanted to hire other EITs once it was off the ground. Compare this to startups that raise millions of dollars with zero plan for monetization.

6. We’re f***ing lucky

I got to drive home in my car, change into the clothes I wanted in my apartment where I have my own room, and write this post on my Macbook Pro. Many of these individuals haven’t been outside the fences in over a decade; imagine being confined to solely your SF city block for 10 years. Imagine not being able to use a toilet without being watched. Appreciate the basic freedoms that you take for granted.

7. We’re all human

The EIT who won the $300 after getting 3rd place almost didn’t pitch at all — because he was nervous and felt like he wouldn’t be good enough. But multiple other EITs encouraged him to pitch, and helped keep his spirits up. After winning, he explained in tears that before today, he had felt worthless…and today he didn’t.

My experience with Defy was amazing, and I’ll be back to help out. What can you do?

  • If you have the financial capacity: send a donation to help sponsor the materials for an EIT. $360 funds the entire scholarship for one EIT. If you’re still struggling to figure out what to get people for the holidays, donate to Defy on their behalf instead of Prime’ing something that will just sit on the shelf anyway.
  • If you can donate time but not money: volunteer at an event. Solano is only an hour from SF via car, and the perspective alone is well worth the travel time. If you don’t have the time to do that, write an encouraging letter to the EITs and see if Defy can have it sent it to them. Just telling them you’re proud can be all it takes to change their life.