Chris Bentley comes from a long line of pioneers.
There’s his mother, who was chair of the math and computer science department at Cheyney University, at a time when women were still the minority in both academia and math and science fields.
She’d always been a role model to young Bentley, and not just because he loved visiting campus, where John Chaney was coaching basketball (before he went on to Temple); he also admired how she’d spend her summers in West Philly, helping soon-to-be freshmen get up-to-speed on their math skills.
Before mom, there was Bentley’s grandfather, an entrepreneur who immigrated to the U.S. at age 19, a refugee from the Armenian Genocide who found his way to run businesses in the Boston area. Bentley’s dad is an engineer, his older sisters are an engineer and an actuary.
“I’m very leery of anyone who thinks either philanthropy or capitalism or nonprofits are the answer. I really think all three need to work in concert together,” Bentley says.
So it probably surprised no one when the youngest Bentley pursued engineering at Northeastern University, and got a totally reputable job in the field.
Still, that’s all it felt like to Bentley: a perfectly fine job. Not a mission. Not a calling.
A few years into his tenure, as the startup scene began taking off, Bentley felt a pull to get his MBA, at Temple. And good thing, too, because as a grad student, he started consulting for a Philly-based company called Murex Investments. Unlike any other place he’d worked, Murex is a community development venture fund, focused on job creation: The company invested in companies located in low- and moderate-income areas where employment was a critical issue.
“That was my first insight into, Oh, wow, there’s this sort of model of finance that also has this impact piece associated with it,” Bentley says.
That insight—in 2006, mind you, before “mission” was a buzzword, and B Corps were even on people’s radars—changed Bentley’s trajectory. Now, he’s the founder and Managing Director of De-Carceration Fund, which invests in businesses working to meaningfully dismantle the criminal justice system and its devastating impact on individuals, families, and communities. His team plans on raising $15 to $20 million to invest in 12 to 14 businesses, with institutional investors and high net worth individuals.
Bentley can now say—humbly, and only with enough nudging—that, yes, he’s proud of his work. That, yes, there are quicker ways to make a dollar, but that his job has meaning in a way he hadn’t found previously.
Because with De-Carceration Fund, Bentley’s goal is multifold: Not only is the intent of De-Carceration Fund to help his companies grow and be profitable, but it is also to create a return on investment whose impact is measured in lives, not dollars. This rethinking of the usual way of doing business—and the usual way of doing social activism—is what makes Bentley a natural fit for Generation Change Philly, The Citizen’s new series in partnership with Keepers of the Commons to highlight leaders in Philadelphia who are planting seeds now to impact the future of our city.
Collaboration is key
Quick to credit others, Bentley says his journey was paved by many mentors along the way. While working with Murex, he wound up on a project that eventually evolved into what’s now Good Company Ventures, the Philly-based accelerator that nurtures mission-driven entrepreneurs.
His network expanded; one connection led to another, and by 2015, Bentley landed an opportunity to work for New York-based Serious Change Investments, which is run by philanthropist Josh Mailman, one of the trailblazers in the impact investing space.
“As I worked with Josh and [other groups], I was involved in a handful of companies that touched on issues related to the criminal justice system,” he says. One of them was Edovo, which does tablet-based educational programming in prison facilities. Another, Pigeonly, was founded by a returning citizen and focuses on making it less costly and less complex to stay connected to loved ones while incarcerated. In Philly, there was Wash Cycle Laundry, which handles industrial laundry in an eco-friendly way, while employing returning citizens.
“There are two halves to this,” Bentley says. “There’s the half of getting your money out of doing bad things, and then there’s the half of getting your money into doing good things. Both pieces are important.”
And that work, he felt, was just the tip of a behemoth iceberg.
Critical to Bentley’s worldview, forged by his family and molded by mentors along the way: He believes no single sector has the solution. “I’m very leery of anyone who thinks either philanthropy or capitalism or nonprofits are the answer. I really think all three need to work in concert together.”
That’s why, when he decided to launch De-Carceration Fund in January 2020, Bentley started by assembling an investment committee that included returning citizens and advisers from leading nonprofits in criminal justice reform. His team includes Elizabeth Gaines, who’s been working in the nonprofit space on criminal justice reform for more than 50 years and Arun S. Prabhakaran, a former chief of staff with DA Larry Krasner. And then there are returning citizens like El Sawyer, a filmmaker from Philly; Frederick Hudson, founder of Pigeonly; and Taylor Paul, from Virginia, who famously spoke at The Citizen’s Ideas We Should Steal Festival and left the audience at once in tears, and catalyzed to make a difference. (You can watch his full talk here.)
He’s grateful to have a partner at De-Carceration Fund in Philly native Lawrence Williams. After graduating from Howard, Williams worked in FinTech in Atlanta and NY; he came back to Philadelphia after Covid-19, and was working for Social Venture Circle, where Bentley connected with him early in 2021, and convinced him to come on board.
Paul, for one, does not suffer fools, does not take his role as an advisor lightly. “I’ve learned in a short amount of time that a lot of organizations are predatorial on returning citizens,” he says. “They try to use our circumstances to get money, to get data, to get funding for the wrong reasons.”
Bentley, he says, is different. “Here’s a guy who could be doing pretty much anything—his resume is impressive, his background, his education—but he decided to invest in people like myself,” Paul says. “And when a guy like that comes into the fight and gets into the foxhole with you—a guy who’s never been in jail, never been in prison, but just understands that there are disparities and that the playing ground is just not level—it was a no-brainer to get involved.”
To date, De-Carceration Fund has five companies in its portfolio, the first four of which Bentley led investments for while he was still at SustainVC and Serious Change Investments: Pigeonly, Edovo, Wash Cycle Laundry, and Social Imprints, a San Francisco-based company that produces printed marketing materials and employs at-risk individuals.
The first company to be solely funded by De-Carceration Fund is UpTrust, an interactive online tool that makes it easier for a defendant to communicate with public defenders and parole and probation officers.
“It’s a communication tool to help remind individuals about upcoming appointments, requirements, check-ins,” Bentley explains.
“I always thought that Philadelphia had the opportunity to be a major nexus in the impact investing space,” Bentley says. “I really think the mechanics are all here in Philadelphia.”
Company policy prohibits Bentley from disclosing too much about the financials of any companies in the portfolio, beyond saying that all are doing well. Whether they will reach one of the many desirable outcomes of all startups—becoming cash-flow positive, landing an IPO, getting a buyout, and so on—remains to be seen.
“There are two halves to this,” Bentley says. “There’s the half of getting your money out of doing bad things, and then there’s the half of getting your money into doing good things. Both pieces are important.”
And Philly, he says, is at the forefront in many ways of the movement to do both. As The Citizen reported in July, this year and next will see at least 10 new venture funds offering over $350 million in socially-good investments that are actually doing something to make a fairer Philly.
“I always thought that Philadelphia had the opportunity to be a major nexus in the impact investing space,” he says, pointing to the fact that Philly has the most active chapter in the Social Venture Circle network, and that our business schools continue to churn out grads focused on impact. “I really think the mechanics are all here.”
Unlocking change
Now, if it sounds like Bentley is drinking his own Kool-Aid, he realizes this. “Having worked in this impact space for so long, you get to be a little bit in your own echo chamber,” he concedes. “You start to think [impact investing] is mainstream, when it’s really not yet.” But he believes that bringing an impact investing lens to the criminal justice space is absolutely essential, and possible.
“Pennsylvania has the second-highest per capita rate of individuals under supervision in the country,” he says. “And that’s not actually because of the number of people locked up—it’s because of the number of people on probation and parole, with unusually long probation and parole sentences.”
Anyone who thinks criminal justice is removed from their lives is mistaken: Today in the U.S, there are as many individuals who have been incarcerated as there are individuals with college degrees. And then there are the children: 10 million kids in the U.S. have had either one or both parents incarcerated. Mass incarceration, he goes on, is a public health issue. “There are studies showing that mass incarceration has resulted in a two-year reduction in life expectancy in the United States.”
Most importantly to Bentley, though, it’s a moral issue. “Any time you can get to know individuals better and see their humanity, suddenly it changes your outlook,” he says.
For all of our problems, locally and at the national level, he believes we have so much potential, so much room for improvement. “If you’re an innovator and you’re trying to figure out what your next opportunity is, [criminal justice reform] is a space where you can really come up with some interesting solutions to solve problems,” he says. “And if you’re a funder and you’re trying to figure out where is the place to make a truly catalytic investment, this is a space that should get consideration.”
The Philadelphia Citizen is partnering with the nonprofit Keepers of the Commons on the “Generation Change Philly” series to provide educational and networking opportunities to the city’s most dynamic change-makers.
