Impact Series

How entrepreneurship and coding coaching applications construct a path from jail to employment

Leo Novsky, Defy Ventures Washington founder and executive director, leading incarcerated individuals, referred to as Entrepreneurs-In-Training (EITs), and executive volunteers through an exercise called “Step To The Line.” The experience, which took place at the Monroe Correctional Complex, is designed to highlight similarities between the two groups. (Candace Frank / Defy Washington Photo)

Incarcerated people and entrepreneurs, generally speaking, share some key traits. Both are willing to embrace big risks and to work the angles to put together a deal.

“You’ve gotta know how to hustle in prison, or you get nowhere,” said Leo Novsky.

So Novsky is tapping that entrepreneurial spirit to teach incarcerated people how to plan for launching startups after release, while also helping them redefine and reimagine who they are as members of society, as fathers and mothers, as friends and as employees.

“Entrepreneurship goes well beyond the ability to make a business,” said Novsky, who is the executive director of Defy Ventures Washington, a nonprofit providing training and mentoring for people in prison. “It does help people dream. It does give people abilities.”

Defy Washington is one of a handful of Northwest programs offering educational options for incarcerated people. The program, which is a local chapter of a national organization, launched last year and recently celebrated its first graduating class. Other efforts include Unloop, which teaches people who are currently incarcerated or recently released how to do software engineering, and Prison Scholar Fund, an organization providing financing for college courses and working to develop more degree programs for people behind bars.

Don, a Defy Washington participant, speaking at his graduation at the Monroe Correctional Complex. (Candace Frank / Defy Washington Photo)

There is a growing concern that America’s “tough on crime” policies of the past have failed in many regards. The U.S. has the highest incarceration rate in the world; some 2.3 million Americans are locked up, according to the Prison Policy Initiative, and 70 percent of convictions result in confinement. Washington state alone spends close to $700 million a year to incarcerate people.

One of the big challenges to curbing those numbers is the rate of recidivism: 34 percent of people released from prison in Washington become incarcerated again within three years, according to the state Department of Corrections. Educational programs chip away at those stats. Research from the RAND Corporation shows that recidivism is 43 percent lower among incarcerated people who participated in programs including high school instruction, vocational training and college courses.

But it’s tough to bring education to people in prison. Tight limits on technology mean that students learn to code without online access, sometimes practicing coding by writing it out longhand. Prison overcrowding can result in shuffling people between facilities, disrupting access to programs, advocates said. Fundraising for the efforts can be a hard sell — the Northwest programs rely primarily on private and corporate donations but some programs are taking hold.

Finding hope

“When we think about education, what pops into our heads are children. They’re full of hope, they’re easy to like, they’re easy to support, they’re easy to fund,” said Judge Marsha Pechman, who serves on the U.S. District Court for the Western District of Washington.

“What’s not easy are those we’ve locked up because they have offended our laws. It’s not easy to see the hope or promise, yet many of those same felons will be released someday,” said Pechman, in a recent address to the Washington Women’s Foundation, of which she is a member.

An Unloop event at the Washington Corrections Center for Women. (Unloop Photo)

The grant-making foundation this month announced a $100,000 award to Unloop, a Seattle organization helping the formerly incarcerated transition into tech careers. The nonprofit offers instruction in coding for people still serving their sentences, then supports them after release through Unloop Studio. The program has a bootcamp for those needing more engineering practice, and a studio that does contract work, building products and web apps for paying customers.

Unloop began teaching students three years ago, and 84 people have completed the program, with five of those now participating in the studio. There are 36 students in prison currently enrolled in classes. Unloop is free to participants, and after release, they can receive stipends or salaries for their work. The nonprofit is funded by private donations, corporate support and through partnerships with local community colleges.

Unloop’s creators realized that they needed to offer more support for people post-prison, which led to the creation of the studio.

“You have some folks who did grow up with the digital age, but even if that’s the case, a lot of the individuals were still marginalized from technology,” said Gina Castillo, Unloop’s executive director. The program provides tech training after people leave prison, including how to communicate by email and tips on using the internet.

Through partnerships with local community colleges, Unloop offers instruction at Washington Corrections Center for Women, north of Tacoma, and Monroe Correctional Complex, a men’s facility. The students learn full-stack web development. Tech companies including Amazon, Moz and Formidable have employees on Unloop’s board of directors.

There are many hurdles to finding employment post release, but Castillo hopes Unloop can help clear some of the barriers.

“The stigma-reducing factor of saying ‘I’m a woman in tech’ really bumps up against that incarceration narrative,” she said.

Proponents of Unloop caution that while there are multiple organizations that work with this population, they take very different approaches and apply their own philosophies to empowering people who are currently or formerly incarcerated. Unloop said that people need more than a pep talk and a business plan to succeed — they need access to real education experiences and the formal economy.

Entrepreneurs-In-Training at the Monroe Correctional Complex pose with Leo Novsky, lower right. (Candace Frank / Defy Washington Photo)

Pitches for urban gardens and hot sauce

James Newell, a partner with the Seattle venture capital firm Voyager Capital, recently visited the Monroe complex to volunteer with Defy Washington’s participants, which the program refers to as Entrepreneurs-In-Training or EITs.

After shedding his electronics and passing through security, “you go through these gray walls and glass and all of a sudden you’re in a room where everyone is shouting,” said Newell. The men all want high-fives. They’re excited to engage with visitors, which on this day included a group of entrepreneurs, business owners and executives there to hear the EITs’ three-minute business pitches.

The rules for the business plans are as follows: it has to be a legal enterprise, it must require less than $20,000 in startup costs, and it has to generate revenue within 90 days. Defy Washington helps the EITs work out their plans including calculating direct and indirect costs, their sales projections and product-market fit. The training teaches participants how to prepare a resume, cover letter and LinkedIn page. It polishes their professional behavior including how to make and hold eye contact and bolstering interview skills.

Newell was impressed with many of the pitches — particularly given that the EITs are unable to do online research in preparation. One man had developed a green thumb gardening at the prison and proposed a business that designs, installs and maintains urban vegetable gardens. Another had a side hustle crafting his own “Hard-Time Hot Sauce” driven in part by the need to spice up otherwise bland prison food.

Entrepreneurs-In-Training at a Defy Washington event at the Monroe Correctional Complex. (Candace Frank / Defy Washington Photo)

“It has a very authentic story behind it, given its origin, which I think could resonate with consumers,” Newell said of the hot sauce. “That felt pretty viable to me.”

The program won recent praise from former Zillow CEO Spencer Rascoff, who attended a Defy Ventures event near Los Angeles.

“The visit gave me a new perspective on incarceration and empathy for incarcerated people and their families,” Rascoff posted on Facebook. “It also reminded me that although people do have free will, our outcomes are heavily influenced by factors which are beyond our control.”

Newell’s visit included exercises to explore the similarities between himself and the other mentors and the incarcerated men, as well as the differences — particularly in their backgrounds and access to opportunities. The experience revealed the shared humanity between the groups, and made Newell a believer in the necessity of providing education and training for incarcerated people.

“They’re doing their sentences, and then all of a sudden they’re on the outside,” said Newell, “and what sort of tools as a society are we providing them to make sure they don’t end up back there?”

Second chances

Of the original 46 students, 26 completed the inaugural Defy Washington training. Novsky is getting ready to select another class of 50 this October.

Washington has close to 20,000 incarcerated people, including those on work release, with roughly 8,000 people released each year. Novsky would like to expand other prisons statewide. He wants to launch a business incubator and other support for formerly incarcerated people. But the costs add up and the group is solely funded by individual donations.

Defy Ventures started in New York City in 2010 and is operating in six states at 18 prisons. The recidivism rate for graduates is 7 percent, and they’re also finding jobs at higher rates, with 82 percent employed within a year, compared to 15 percent for others released from prison.

“This program is about defying the odds and second chances,” Novsky said.

Dirk Van Velzen knows about second chances. He found one through his own startup and a college degree earned while locked up for a series of commercial burglaries.

Van Velzen created the Seattle-based Prison Scholar Fund while still behind bars. After his release in 2015, he won first place in the Social Venture Partners Fast Pitch Program. The fund helps incarcerated people nationwide pay for their education and offers mentoring and tutoring. The organization is working to make more degrees available through a hybrid program that allows students to study using both offline and online instruction.


In 1994, the government eliminated incarcerated peoples’ access to Pell Grants that cover college costs for low-income people, cutting off an important path to education. Only three years ago did the Obama administration launch a pilot program to bring back limited funding.

The Prison Scholar Fund has supported 129 students since 2006. Van Velzen was able to persuade his father to cover his tuition, but realizes many incarcerated people don’t have that sort of resource. He knows that he was lucky.

“I don’t think luck should have a strong role,” he said, “in people’s ability to reinvent themselves.”

Editor’s note: This story was updated on July 9 to replace references to “inmates” with the less pejorative phrase “incarcerated people.” A paragraph was also added regarding Unloop’s stance on prison education and training programs.

Editor’s Note: Funding for GeekWire’s Impact Series is provided by the Singh Family Foundation in support of public service journalism. GeekWire editors and reporters operate independently and maintain full editorial control over the content.

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