That support, coupled with a newfound community, set her on a path of entrepreneurship and social impact. This journey has culminated in ReImagine Freedom.

In 1993, Young Women’s Freedom Center was established, creating employment for girls from the streets. In 2017, under Nowlan’s leadership, they founded the Sister Warriors Freedom Coalition to build broader community power across California. And in 2021, they launched Beloved Village to provide housing solutions and economic support.

Nowlan was hired by the Young Women’s Freedom Center in 1996, out of Juvenile Hall. Though she left to try her hand at entrepreneurship, she came back decades later, in 2015 to help the organization grow from 3 to 75 people, opened 5 more centers across California, and increased the budget from $500k to $10 million to launch Sister Warriors and Beloved Village.

As the organization delivered on its goals, a few early funders recognized the promise of its vision and invested deeply. “These were not small, restricted grants,” Nowlan notes. “These were bold, multi-year, general operating investments rooted in trust. That kind of trust is still rare in the nonprofit sector.”

Learning on the Job

Nowlan didn’t have a traditional business background, but she had grit and a drive to succeed. Her first foray into the business world was a commission-only job selling merchant services, “getting like a fraction of a cent per transaction,” she recalls. It was far from the tech boom happening around her, but it sparked something in her.

“I started a couple businesses,” Nowlan says, “and along the way I met some amazing mentors who still mentor me today.”

One of her early ventures was Hope Solutions Merchant Services, an Oakland based service that helped local businesses navigate payment platforms. In talking with so many small business owners, she learned the ins and outs of operating a local community-focused business. In addition to running Hope Solutions, Nowlan became a consultant and launched a “shop local” program in Oakland.

Even then, the challenges were immense. “I was in public housing. I was a single mom. My only income was welfare,” she recalls. Going to business meetings with “my stomach growling,” Nowlan says, she was navigating a complex world.

Despite the obstacles, she landed a contract with the city of Oakland for her shop local program, beating out even Citibank, she recalls. “I undersold my contract,” she admits, “but I won because I was like for $5,000, I will build this program.” While she learned a lot, she internalized a feeling of failure when the business didn’t take off as planned.

After her first business venture, Nowlan got involved with Defy Ventures, a program for formerly incarcerated people. A national nonprofit organization, founded in 2010, it works to give people with criminal histories their best shot at a second chance by providing entrepreneurship, career readiness, and personal development training programs—both in prison and in the community

It was there that she met David Hornick, a venture capitalist and investor. “I did not know what a venture capitalist was. I did not know who he was,” Nowlan laughs. But Hornick saw something in her and agreed to mentor her.

“It’s been transformative to be able to have access to people that have been trained, who have networks, who can make connections,” Nowlan says. The mentorship helped her gain access to knowledge and resources that she didn’t even know existed.

Nowlan’s next business was Create Shop, a DIY gift kit company. She launched a Kickstarter campaign, but faced a new set of challenges. “I didn’t have family and friends around,” she explains. “I was unbanked and so were my friends.” Even with a successful Kickstarter, the barriers to bootstrapping a business were clear.

“I could have been more successful in my other business ventures,” she admits. “But I was lacking the passion required for that level of success. When I came upon the opportunity to scale ReImagine Freedom, I had an unwavering belief that the world needed this and that we would be successful. I would not give up, no matter what.

Early on, I met the founder of Pandora who told me he got 76 no’s before he got a yes. And we know that data consistently shows that female-led companies are told no more frequently and receive a significantly smaller share of VC funding than male counterparts. So I embraced the belief that every no was one step closer to my next yes.”

Ultimately, Nowlan made a pivotal decision: to return to the Young Women’s Freedom Center. “There’s not a lot of organizations, companies, and people who are taking bets on me, or people like us,” she says.

She took the skills she’d learned in business to scale the organization, expanding its reach across California and increasing its budget up to $10 million.

Young AF: Investing in the Untapped Potential of Women

Nowlan’s experiences have shaped her vision for Young AF (Young And Free), a new initiative within ReImagine Freedom. Young AF is designed to incubate businesses and provide mentorship, resources, and support to women entrepreneurs who have been system involved. The initiative has assembled an impressive advisory board, including serial entrepreneurs and venture capital titans like David Hornik, Joe Marchese, and Nyakio Greico.

“Our goal is to incubate this business…we’ll work with a couple of folks over a year to help them launch a brand,” Nowlan explains. The program is about more than just business skills; it’s about creating opportunities for women to realize their full potential. The organization just made its first $200,000 investment in Young AF, signaling the beginning of a much larger investment strategy.

But who are the young women benefitting from this new fund?

Nowlan points to Jade Hudson, a former client of the Young Women’s Freedom Center who is now a successful lifestyle influencer. “She’s somebody that we will work with through the incubation of Young AF to both launch this larger lifestyle brand, but also support these up and coming entrepreneurs who have all the ideas, all the brilliance, all the skills, but again, not the resources and support to make it happen.”

The initial focus is on the beauty space, because the women and girls they work with often go into these industries but they don’t see the returns that match their talent.

With Young AF, Jessica Nowlan is not just hoping to build a business – but a movement.