Teaching entrepreneurship in prison: Learning how to run a business from behind bars
Today’s class is about failure.
Sonja Skvarla, who teaches the basics of entrepreneurship in this small classroom twice a week, spends the first hour talking with her students about how they define success and failure. She challenges them to think about their priorities, and how those may shape results.
Students split into groups for the latter half of the session to work on business plans. One team is mapping out the most effective way to run a tattoo parlor. Another sketches a revenue model for a fitness training company. Two others are in the final stages of planning a UFC gym built specifically for at-risk youth.
While this subject may sound ordinary, the setting for this class is certainly far from it. This is not high school; it’s not college; it’s not some one-off business seminar.
In fact, we’re probably in the last place you’d expect people to be learning about what it takes to be an entrepreneur.
We’re in jail.
After exiting Interstate 5 just north of Portland, Ore., I drive a few miles east, passing by a plush private golf club before pulling into a parking lot. I’m instructed to leave my phone in the car, and soon enough I’m walking past security and into the prison as barbed wire gates clank shut behind me.
Inmates, dressed in navy crew sweatshirts and blue jeans, pass by as I enter the Columbia River Correctional Institution, a 26-acre, minimum-security prison that houses more than 500 convicts.
Skvarla, founder of A Social Ignition, a Portland startup that helps inmates learn about business and prepare for employment after they are released, leads the way as we settle inside a beige-colored room.
Minutes later, I’m sitting in a circle with six others. Eyes closed and exhaling deeply through our noses, Skvarla tells us to be mindful.
Five minutes pass and we return to reality.
I introduce myself as Skvarla’s guest — she brings a mentor from the local community to each class — and explain that I want to learn why the students are thinking about entrepreneurship.
“I’m here for the same thing,” says Cody Connel, who was sentenced to nearly six years in 2012 for an armed residential robbery. “I want to gain knowledge and understand more about the business side of life. I’m happy that you’re here.”
Skvarla starts class with a fun exercise. She places a garage bin on one end of the classroom, then sticks ten pieces of tape to the floor, each a foot apart from the other. The closest piece to the bin is numbered with a “10 points,” the next with “20 points,” then 30, 40, 50, and so on until the tape at the other end of the room is labeled with “100 points.”
We break into teams of three. I’m with Cody and Jamal Gardner, who’s taking Skvarla’s class for the fifth time because he enjoys it so much. Jamal was convicted in 2005 on five assault-related counts and other charges.
“You get two shots with a paper ball from anywhere you’d like,” Skvarla explains. “If you make the first shot, you can move anywhere for the second. If you miss, you can stay at the same spot or move to a lower number.”
After two rounds, my teammates and I are losing by a wide margin. The opposing team played it safe, making a few shots in the 40-to-50 range. My squad gambled from deep range, and by the time it was my turn, we needed 130 points to tie it up. Jamal tells me to go big.
“Go for the gusto, my brotha!” he says emphatically.
I line it up from the 100-point tape, but miss badly. Our team loses, with a final score of 170-40.
Skvarla brings us together for a post-match talk. The discussion centers around why our team took big risks, and how the other team played it safe — and won.
Jamal says his first priority was selfish. Not only did he want to beat the other team, but he wanted to “maximize the win” by having the satisfaction of making a long shot.
“I’m not that great of a team player,” he admits. “That’s why I’ve taken this class four times.”
For this game, one team won and the other lost. Or, put another way, one team succeeded and the other failed. Skvarla spends a few minutes talking about what success means to each person, and more specifically, “defining the win.”
“What does it mean to win this game?” she asks. “Do I get something out of it? Do I want to have the most points? Do I just want to be a good teammate? Once you’re determined to win, your priorities come into play — are you a team player, or are you doing it for yourself?”
She also talks about how past experiences affected each person’s risk assessment when deciding to shoot close or far from the garbage bin. The stakes for this particular game, of course, were fairly low.
Quandrell Dumas, another inmate who was sentenced seven-and-a-half years in 2010 for drunken driving, second-degree manslaughter and hit-and-run driving, says something his peers in the room certainly agree with.
“But if they let us go home based on this game,” Dumas says, “I guarantee everyone would shoot from the 10.”
What started as a simple, fun game has turned into a tense conversation. It’s not surprising — today’s curriculum has a lot of meaning for the guys in this room given their past.
“Failure for me is to just do nothing at all and accept life on its terms,” says Quandrell, who goes by ‘Q.’ “Before I came to prison, I was an alcoholic gang member. Going back to that lifestyle for me is a failure.”
Jamal agrees, but noted that there’s a difference between failing and losing. He says that while failure is inevitable, losing is something you have control over.
“None of us will get it right and walk out and immediately become Carl Icahn or Richard Branson or anything like that,” explains Jamal, who’s been reading books like The Energy Busand The Art of the Start as assigned by Skvarla. “There will be failures along the way. The question is, am I strong enough to pick myself back up and say, ‘OK, this didn’t work out like I planned, maybe I want to do something a little different.’”
So what does this all have to do with entrepreneurship?
Skvarla stresses the importance of defining success and failure, and why doing so helps an entrepreneur make better decisions that can lead to a preferred outcome.
“The point of this whole conversation was not to come up with a right or wrong answer, but to bring you guys some more thoughts on your own personal risk-versus-reward, what success looks like, defining the win, all of that,” she tells her students. “There is no right answer because each of you has to figure it out for yourself. Sometimes classes like to wrap something up with a bow and say, ‘here’s the right answer, go off and conquer.’ Unfortunately, it’s not that easy. In entrepreneurship or life, there aren’t any right answers — you have to figure that out yourself.”
That’s when a lightbulb went off in Jamal’s head.
“I didn’t truly understand this until now: If I define my priorities, define what the win is for me, define if failure means quitting or just losing … you can create a path of least resistance just by defining it for yourself,” he says.
Toward the end of a mid-class break and before the students work on their business plans, Skvarla chats with a few inmates. The 36-year-old comes here twice a week on a volunteer-basis as part of her role at A Social Ignition, the startup she founded three years ago to help inmates prepare for a successful return to the local community.
“This is really energizing to me,” she tells Cody and Jamal. “Coming in here, having a fresh perspective, talking to new people about stuff — that is really inspiring to me. One of our board members asked me today what job I would want if A Social Ignition keeps growing. I said I still need to keep going to class. That’s the point of this whole thing.”
“That’s a humble approach,” Cody responds. “That’s cool.”
It’s clear that the inmates here respect Skvarla and appreciate what she’s trying to do.
Many of them, like Juan Tenorio — who’s been in and out of prison for committing crimes like robbery and possession of methamphetamine — only have a few months until they are released and her class has helped them with perspective and preparation.
After all, inside prison, there is no Internet access and inmates are rarely exposed to today’s trends in workplace culture, business strategy, emotional intelligence, and other related topics that are important for any entrepreneur.
“In here, they don’t have anything different — it’s the same stuff over and over,” Tenorio, who goes by ‘JT,’ says of the other classes offered in prison. “But her class, it helps me refocus my skills to do something else. This is what I should have been taught a long time ago.”
That’s something Jamal can speak to as well — after all, he’s paid to take this class five times now. He calls his time in this classroom “invaluable” and says he wants to become a venture capitalist one day that helps other startups.
The conversation carries on and Jamal notes how he’s an “all-or-nothing person.” Skvarla sees another teaching moment.
“I challenge you to correct yourself and say, ‘I have been an all or nothing person’ — it leaves you the option to be something else in the future,” she says. “It recognizes what you have done, but doesn’t define yourself as so final. You’ve been interacting with the world from a place of an all-or-nothing space, but that doesn’t mean that has to be who you are.”
Over the past year, Skvarla has helped 29 inmates graduate from her 12-session entrepreneurship class, which culminates with business pitch presentation days attended by leaders in the community like Portland Mayor Charlie Hales — it’s like TechStars Demo Day, only with aspiring entrepreneurs behind bars.
Her company also offers “The Long Haul,” a separate program meant to help inmates land jobs and see their startup ideas come to fruition when they are released.
“The program is very popular with adults in custody at the Columbia River Correctional Institution and they seem to really enjoy what she teaches,” said Dawnell Meyer, an administrator with the Oregon Department of Corrections. “It seems to really focus on practical skills for working, regardless of whether you want to own your a business or work for someone else. We like that.”
As we ride back to her office in Northeast Portland, I ask Skvarla why she does this.
“To prove that we need to invest in people with criminal records,” she responds.
Skvarla explains that with the way the prison system is set up in the U.S., 95 percent of people eventually are released. But the problem, she said, is that they aren’t prepared to stay away from activities that got them in prison in the first place. The fact that they have a criminal record doesn’t help, either.
“If we don’t help them prepare to somehow be better at life, then all the coping mechanisms they used before, they’re going to kick in again,” she said. “There’s no logic to that — it’s like, oh, you did bad things, you went away, you come out, and now we’ll give you fewer tools to do better things. That makes no sense whatsoever — logically, emotionally, socially, whatever.”
A Social Ignition, funded by private donations, is meant to be the support system that helps inmates gain the skills necessary to build a positive, productive lifestyle. It’s different than other classes offered inside prisons, most of which are based off traditional education models.
“The problem is, for most of these guys, traditional education didn’t work for them,” Skvarla said. “We’re not banking knowledge to them, saying that I know all the things and now you will know all the things. That’s not what this is about. It’s about finding our own answers to stuff.”
A Social Ignition also isn’t about second chances, nor is it something like The Innocence Project, Skvarla explains.
Instead, it’s a program that looks at life as a cumulative process — and one that focuses on a better future.
“I’m not going to judge why you did something illegal and whether or not that makes you a good person,” Skvarla said. “The point is, where are we going from here? And what can you take from that experience to propel you forward? Whether or not what we did in our experiences landed us in prison or not, we are all building on our experiences to take us to the next thing.”
Part of her company’s mission is to change the thinking outside of the prison gates, too. Skvarla brings in mentors each week — CEOs, entrepreneurs, people who have been incarcerated before — to help shift the stereotype and stigma that people assume exists among the inmates living behind bars.
It’s been a year since Skvarla first began teaching this class, and there are a few success stories already. Take, for example, Jason Buckley, who opened up a hot dog stand in Portland after leaving prison and graduating from A Social Ignition.
Skvarla said there’s a culture building around the class, one that’s somewhat of a counter-culture to playing poker, watching TV, or other activities available to inmates.
She admits that “it might take a few times” for some of the inmates to embrace what her class tries to provide. But it’s clearly already having an effect on many hopeful entrepreneurs.
“I’ve been an entrepreneur, but in the wrong way,” said JT, who enrolled in Skvarla’s class twice and was just released last month. “I have the hustle, I have the mentality. And now this class takes someone like me who was on the wrong road and helps us refocus. What she’s doing is a huge help to people like me.”