I was sitting in a chapel, in a crowd, and I was in prison -- the notorious San Quentin Penitentiary.
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.
2. Bootstrapping. As if prison riots, unfathomable living conditions and the absence of the Internet weren’t bad enough, an average prisoner gets a rationed state meal of less than 1,200 calories per day (an In-N-Out double-double has more calories).
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.
Consequently, each inmate becomes their own startup, an entrepreneur by circumstance rather than choice, and has to figure out a way to amass more resources. Inmates have to be relentlessly creative and forced to bootstrap their limited assets. Hustle can be anything from running the sports book, card sharking, winning weightlifting contests (where there’s often a buy in and payout to the winner), drawing portraits, tattooing and even selling pics of your ex.
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.
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.