From Juvenile Hall to leading a multimillion-dollar fund, Jessica Nowlan’s journey is anything but conventional.
By the age of 13, Jessica was on her own—navigating incarceration, homelessness, and systemic neglect. But it was the Young Women’s Freedom Center that changed the course of her life. “They didn’t see me as broken,” she recalls. “They said, ‘You shouldn’t have had to survive on your own all these years.’”
This moment of affirmation—and the community that followed—sparked her path into entrepreneurship and social impact, ultimately leading her to become the Executive Director of ReImagine Freedom, a women-centered nonprofit she scaled from $500,000 to over $15 million.
Building Power, Purpose, and Programs
Jessica returned to the Young Women’s Freedom Center in 2015 after having been hired there in 1996, straight out of Juvenile Hall. She didn’t come back empty-handed. Armed with business experience and bold ideas, she:
- Expanded the team from 3 to 75 members
- Opened 5 new centers across California
- Launched major initiatives like the Sister Warriors Freedom Coalition and Beloved Village
- Grew the budget from $500k to $10 million
Support from visionary funders—unrestricted, multi-year grants—helped bring this vision to life. “That kind of trust is rare in the nonprofit sector,” Nowlan emphasizes.
From Hustle to Hope: The Business Journey
Despite having no formal business training, Jessica dove into entrepreneurship with relentless grit:
- Hope Solutions Merchant Services helped local Oakland businesses manage payments.
- She consulted on “shop local” programs, even landing a contract with the City of Oakland—beating out Citibank.
- Later, she joined Defy Ventures, a program for formerly incarcerated individuals, where she met her mentor, VC David Hornick.
Jessica’s ventures didn’t always succeed—but each step revealed her deeper calling.
“I could’ve been more successful in earlier ventures,” she admits, “but I didn’t have the passion. With ReImagine Freedom, I had belief. I was never going to give up”
Introducing: Young AF (Young And Free)
Her latest initiative under ReImagine Freedom is Young AF—an impact investing fund and business incubator for women impacted by incarceration or systemic barriers.
The aim? Incubate real businesses for real women—with access to mentorship, funding, and real tools for success. Backed by an all-star advisory board including David Hornik, Joe Marchese, and Nyakio Greico, the program is already making waves with a $200,000 investment to kickstart its first cohort.
One of its first collaborators is Jade Hudson, a former client turned lifestyle influencer. Through Young AF, Jade will not only launch her own brand but mentor the next generation of women entrepreneurs.
“These women have the ideas, brilliance, and skills—but not the resources,” Nowlan says. “That’s what we’re here to change”
More Than a Business—A Movement
Nowlan knows the odds—and how to beat them. With Young AF, she’s rewriting the future for women who were never supposed to win. It’s about business, yes—but more than that, it’s about economic justice, freedom, and hope.
