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entrepreneur.com/article/236764
I was sitting in a chapel, in a crowd, and I was in prison -- the notorious San Quentin
Penitentiary.
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I’m a volunteer with The Last Mile, which is designed to teach selected inmates how to
become tech entrepreneurs. The program consists of volunteer-driven, weekly classes
within a six-month semester. For the final project, each participant creates a business
plan they translate into a five-minute pitch. They pitch to a live audience of invited guests
from the outside world, during their own private demo day.
My participation with the charity has been infinitely rewarding and mind altering.
Through my interactions with participants in the program, I’ve learned three skills every
startup entrepreneur needs to learn from prison inmates.
1. Politics. Every business has them, even startups. It’s that invisible dance of jockeying
for position in the pecking order, subtly negotiating everything and ensuring each step is
methodical. It’s done by founders, investors, clients and employees alike.
In a startup, one misstep can mean diluted equity, missed investment opportunity or the
loss of a large client. In prison, one misstep can lead to social isolation, race riots and,
worst case, death.
Every inmate has to master the art of prison politics if they want to survive. We’ve all
watched an episode or two (or 10) of Orange is the New Black, but TV prison is nothing
like the real thing. Prison politics are no exception.
The bottom line is mastering prison politics for inmates can be the difference between life
and death, and entrepreneurs should treat startup politics just the same.
In fact, every prisoner gets the bare minimum issue of everything. Most institutions
provide these basic items: a 2-inch golf pencil, 2-inch toothbrush, state-issued toothpaste,
one roll of toilet paper, a pair of pants, a pair of boxers, two pairs of socks, an undershirt,
an over-shirt and a state penitentiary guidelines handbook.
The point is that an inmate is forced to operate at his or her most optimal efficiency,
leveraging their already-scarce resources. All newly-formed startups can learn from the
bootstrapped inmate.
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3. Hunger. When was the last time you were hungry? I’m not talking the latest fad-diet
hunger or “so-busy-I-skipped-lunch” hunger either. I’m talking about the emotionally-
wrenching, spiritual-awakening hunger that arises from deliberate starvation. Thanks to
rationed meals, all inmates experience that agony. Funny things happen when starved
though. Proximity to death brings clarity.
For the enlightened inmate, that literal, physical hunger can translate into an intangible
and powerful motivating force. When harnessed and used properly, it can lead to
unparalleled success in the system and upon release.
The conclusion is that often a startup doesn’t have the indispensable hunger it takes to
succeed until it’s just too late, and an inmate simply doesn’t have that luxury.
My experience with The Last Mile has enabled me to be a better leader, and although as a
volunteer I’m there to teach, I’ve found I’m the one learning a thing or two.
Written By
Andrew Medal
Entrepreneur Leadership Network VIP
Andrew Medal is the founder of The Paper Chase, which is a bi-weekly newsletter. He is
an entrepreneur and angel investor.
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