How ‘Orange is the New Black’ inspired this luxury t-shirt company

Mural for the Netflix series 'Orange Is the New Black.'
Christophe Archambault | Getty Images
Mural for the Netflix series 'Orange Is the New Black.'

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."

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.

More from The Story Exchange:
This woman created the Uber of legal aid
Meet the women who teach financial skills to the homeless
The unusual item that inspired this science entrepreneur's career path

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.

Be Bold. Our Montgomery Star tshirt features a raw hem and sleeve for an edgy look. Grabs yours now on RoadTwentyTwo.com

A post shared by Road Twenty-Two (@roadtwentytwo) on

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."

Don't miss: The 11 highest-paying jobs for women

This article originally appeared on The Story Exchange.