Editor’s Note: This is part of our Good on the Ground series, profiling entrepreneurial women who are addressing social issues in innovative and inspiring ways.

Fif Ghobadian, a San Francisco entrepreneur, wants you to understand this: Life can go from good to bad, very quickly.

Born in Iran, she enjoyed a comfortable, affluent lifestyle until the eve of the Iranian Revolution, which led to the brutal death of her parents’ friends. Then a teenager, she fled with her family to London, finally landing in Northern California in 1979. “The concept of all of a sudden not having money was shocking,” she recalls. Her father, unfamiliar with the language and American culture, couldn’t find work. “There’s not a single door that opens.”

Second Chances

Listen to our podcast episode for more of our interview with Fif Ghobadian.

Despite the struggles, Ghobadian managed to attend Claremont Colleges in Los Angeles and ultimately built a successful career as a mortgage broker. But a few years ago, while reading “Orange is the New Black,” she was struck by the book’s central plot line: A person who goes to prison, even for a minor offense, can lose everything. “What scared me is that once you cross that line and you’re incarcerated, it’s almost impossible to come back into society,” she says. The desperation in that, she says, resonated.

In 2013, Ghobadian came up with the idea for Road Twenty-Two, a luxury T-shirt brand (think $76 for a classic crew) that would hire women who had served time in prison to box, trim and package its products. The name comes from the highway out of the Central California Women’s Facility in Chowchilla, Calif., the largest female prison in the U.S.

While her background is in finance, Ghobadian had worked early in her career for a number of big retailers, including Levi’s and the Gap. “I always thought it’d be great to create clothes that… can make you look edgy and fun,” she says. “I married the two ideas” — producing fashion and helping formerly incarcerated women — and sought a business partner. A friend suggested she contact Alice Larkin Cahan, a San Francisco socialite with a design background.

Together, the two launched Road Twenty-Two as a for-profit social enterprise in 2014. “We jumped into it,” Ghobadian says. They found a warehouse space, a sewing factory and poured resources into marketing and branding. Ghobadian, a single mom, sold an investment property that had been earmarked for her teenage children’s education, putting $300,000 into the business while Cahan added $100,000. Friends and family contributed another $80,000.

Working With Women

Next came hiring former female prisoners — simultaneously the toughest but most rewarding part of running Road Twenty-Two, Ghobadian says. It’s no secret that few companies employ people with criminal records, a big reason why recidivism rates are so high. (More than half of state prisoners wind up back in prison within 5 years of release, according to Bureau of Justice Statistics.)

The formerly incarcerated are sometimes homeless, and many struggle with addiction problems. “It’s a tricky population to work with,” Ghobadian says. “There are a lot of self-esteem issues. Just the idea of them showing up for work is in and of itself a challenge.”

To date, Road Twenty-Two has hired eight formerly incarcerated women. All have to be willing to earn minimum-wage pay. “Sometimes, in the world of crime, it’s much more enticing to make more money,” Ghobadian says. The women must also have the confidence to work for a startup, “where you do all sorts of different things and there’s a lack of consistency,” she says. It’s more typical for people returning to society from prison to take jobs in predictable fields like, say, construction — if they can get work at all.

One woman whom Road Twenty-Two has helped is Rachael Dunne, who manages the company’s customer care. In a video on the company’s site, she talks about the difficulty finding a job after getting hooked on drugs and landing in the county jail. Background checks would sink her chances. “I’d always have great interviews and never get that call back,” Dunne says. By contrast, Ghobadian and Cahan were “warm and welcoming.” While they asked tough questions about her criminal background, “they were interested in how those skills might be transferrable,” Dunne says.

Ghobadian says she’s been struck by Dunne’s improved self-esteem since joining Road Twenty-Two. “She is driven, more focused. She’s being held accountable, so she’s not going down a bad path,” Ghobadian says. “She can stand up with her head high and say ‘I matter.’”

Dunne agrees: “I am doing things I never thought I was good at doing and doing them well.”

More to Come

Looking ahead, Ghobadian says she hopes to hire more former female prisoners as soon as Road Twenty-Two expands. Finding the women has been surprisingly difficult, she says. While she had originally hoped to work with prisons on funnelling parolees over to Road Twenty-Two, “the bureaucracy’s insane,” she says. Instead, the company has worked with agencies like America Works and Glide, which help ex-prisoners get jobs.

Growth is coming slowly, although Road Twenty-Two is now sold in about 200 stores and broke even last year. This year, Ghobadian and Cahan plan to devote more resources to social media and hire commission-based sales representatives, which they hope will push Road Twenty-Two to $1 million in revenue by year’s end. They recently expanded their product offerings to include sweatpants, and are creating a lower-priced custom line for corporate marketing events. “The more money we make, the more people we can hire,” Ghobadian says.

Meanwhile, Ghobadian still works as a mortgage broker — a job she hopes to quit once Road Twenty-Two truly takes off. Juggling both roles is “pretty fast-paced,” she admits. But it’s worth it to build a startup that gives women a second chance.

She is still haunted by the memory of her father, who declared bankruptcy while she was in college. He eventually returned to Iran, and died this past September.  “I vividly remember him looking in the paper, circling phone numbers, calling for those jobs,” she says. “And I think that is actually what planted the seed of what money can do for you in your life, and what privileges it gives you.”

More from “Good on the Ground”: Meet the Women Who Teach Financial Skills to the Homeless

Read Full Transcript

Fif Ghobadian – CEO + Co-Founder – Road 22

FIF: There are a lot of socially responsible companies, however there aren’t
that many, that focus on the formerly incarcerated.

SOT: That burgundy looks pretty bloody good on you.
-I know, thank you. I’ve been asking Sheri can I have one. I’m going to represent Road 22.
-You already represent Road 22.

FIF: Road 22 is a fashion brand with a social mission to employ women who’ve been formerly incarcerated. We came up with the name Road 22 because it’s the road out of Chowchilla Prison, and it’s the road out of that system.

TEXT: Fif Ghobadian – CEO and Co-Founder – Road 22, San Francisco, CA USA

FIF: There are 2.4 million incarcerated in the U.S. 70% of the people who get incarcerated end up back in the system. When doors are shut and life gives you a bad card how do you undo that? How do you reverse the hands of fate and go back on track?

TEXT: Fif was born in Iran. Her parents fled the 1979 revolution.

FIF: We grew up really affluent in Iran so it was a pretty comfortable life and then the reality hit that assets were frozen in Iran. My dad couldn’t go back and my parents had to claim bankruptcy.

TEXT: Fif and her family moved to the U.S. and settled north of San Francisco.

TEXT: Her mother and father struggled to support the family.

FIF: I’ve seen in my life what life is like when you have everything plus more. And then at a very young age I saw the extreme opposite.

TEXT: Her mother sold her wedding ring so Fif could attend Claremont McKenna College.

TEXT: In 1984 she graduated in Economics and Accounting and began a career in corporate finance.

FIF: I worked for Levis, I worked for the Gap and then went through the whole corporate world in accounting. When I was about 32, 33 I decided, “You know what, I really wanna have kids.”

TEXT: To have the flexibility to be a single mother, Fif changed careers and went into the mortgage industry.

TEXT: As her children grew, she got restless.

FIF: I was reading Orange Is The New Black. This woman goes to jail after ten years for something really minor, and what scared me is that once you cross that line and you’re incarcerated it’s almost impossible to come back into society.

FIF: And I thought, “You know what, I wanna kind of do something to make, that makes a difference.” I always thought it’d be great to create clothes that competes with like the Gap but it’s cool, like T-shirts, sweatshirts that really felt good, that look good, and then I married the two ideas.

TEXT: In 2013 Fif asked her friend, and now domestic partner, Alice Larkin Cahan to design the shirts.

FIF: We had never ever thought about how to even make a shirt, didn’t know anything about it. And so, you know, we went, interviewed people. It took us 6 months to create our first shirt. And we launched the company within a year of the idea.

TEXT: Fif sold an investment property to fund Road 22. The shirts are sewn in a factory in downtown San Francisco. Fif hires women returning from prison to trim, fold and package the shirts.

FIF: The number one issue we battle with is self-esteem. They feel like they’re not worth anything so trust is a huge factor. They have had no concept of working, and it’s difficult for the people to come and work for 13 bucks an hour because guess what? They make more money if they’re hustling in the streets.

TEXT: Road 22 has hired 8 formerly incarcerated women to date. The shirts retail for $65 to $85 online and in dozens of stores nationwide.

FIF: One reason the shirts are higher priced is because it’s to bring awareness to a segment of the population that can make a difference. If you take it to someone who normally buys a designer shirt for like $115 and now you bring this message across maybe eventually people will realize this is a problem.

TEXT: To reach more people and provide more support to her staff, Fif is expanding the product line.

FIF: We wanna have the fashion brand continue and we want to create a lower-priced line, a little less detail in the shirts that we can use for corporate marketing, corporate branding because that’s more volume generated, a higher revenue stream.

TEXT: Fif still works as a mortgage broker.

FIF: It’s tough, definitely tough. The goal is that Road 22 will grow to the point where I don’t have to be a mortgage broker and work on Road 22.

SOT: All she need is a social worker or case manager.

-And that still takes six month to a year?

-It, it might take less than that because she’s homeless. It depends on her

FIF: I love seeing people wear the clothes. That’s fantastic. But the most gratifying is the change in the women’s lives. You know, just even if we change four people’s lives, right, that’s a big change.