The Journey From Inmate To Entrepreneur

Is entrepreneurship an answer to America’s high recidivism rate? Fast Company explores one man’s path from prison to self-sufficiency.


Guys like us just want a chance to work and better ourselves, but that’s not so easy when you’ve served time. Your record is public information; it’s on Google. I have a lot of accomplishments to my name, but the first thing that people see when they look me up is my time in prison. You look around you at people who have no hope for a better life and it starts to wash off on you.

Angel LaCourt, 28

The Unmarked Building

In the heart of Kendall Square, the tech hub between Boston and Cambridge, there is a small unmarked building in an office park.


It could be mistaken for the service entrance to one of the startups or software companies on the premises. But behind the nondescript doors is a small gym filled with tech-industry professionals working out with former convicts and gang members who are in the process of attaining certification as personal trainers. The gym’s obscurity is intentional: It prevents former rival gang members from dropping by to finish off an old vendetta.

On a sunny May afternoon, a firm called InsightSquared is having a group workout session for a dozen employees. It is a sea of Lululemon yoga pants and trendy sneakers. Electronic dance music fills the air, with occasional interludes of Pharrell Williams and Rihanna. The sweaty group is hard at work doing rope training, using their upper bodies to swing heavy cords in wavelike motions. They then move into a drill, doing squats, push-ups, and burpees. They are led by young men shouting out the next activity, helping to correct people’s form, and keeping energy levels high.

One of these trainers is Angel LaCourt, a 28-year-old African American with a football player’s build, who commutes to the gym every day from his home in Roxbury, a gang-ridden neighborhood with one of the highest homicide rates in Boston. He’s been training groups like this for two years, ever since he was released from a three-and-a-half year stint in federal prison. While gaining valuable personal training experience, LaCourt has been forging bonds with clients from the tech community whose lives are worlds apart from his.


“We now have relationships with them,” he says. “They want to know how we grew up, where we’re from. They think, ‘You are the same guys we’re reading about in the newspapers and you’re actually good guys, just going through different circumstances.'”

The fact that LaCourt has been out of prison for this long makes him an anomaly among former inmates in America. Three quarters of released prisoners are eventually recincarcerated, over half within their first year of freedom. One of their biggest hurdles to reintegrating into society is finding a way to earn a living. Employers are hesitant to hire people with criminal records; former convicts are 50% less likely to get callbacks or job offers after an interview, even if they are well qualified. Without a source of income, many quickly return to a life of drugs and violence.

This is something LaCourt understands well. He was first arrested in his late teens. After his release from the state penitentiary, he found it so impossible to find work that he ended up selling drugs to get by. He was back behind bars within a year, this time in a federal facility. Today, he’s working hard to avoid repeating that mistake.


What’s clear to him is that traditional employment channels are unfavorable to men like him, so his survival will depend on being entrepreneurial enough to create a legitimate income stream for himself. He will need to deliberately seek people outside his crime-infested neighborhood to connect him to career opportunities or hire him as a trainer.

He’s begun to see new possibilities as he’s spent time in the Kendall Square gym, here in the heart of tech country, where innovation and entrepreneurship are upheld as important social values. These days, he has a packed schedule: He works with a full roster of clients and uses every spare minute to prepare for his personal training certification from the American College of Sports Medicine. After over a year of intense study, he will be able to graduate from a student to a bona fide personal trainer, which will allow him to start making around $100 a session—enough to be able to finally support his family. “I’m counting down the days,” he says.

A Path Back Into Society

Jon Feinman, a 32-year-old who spent his twenties in one of the most dangerous neighborhoods in Boston, launched this gym program, InnerCity Weightlifting (or ICW), five years ago. He hoped to create a place for young men with criminal records to develop personal training skills in order to find decent-paying work and a reasonable pathway back into society. Since the organization opened, it has helped over 250 young men and currently has 159 enrolled students.

Jon Feinman

ICW is an elaborate experiment in bringing people from different socioeconomic backgrounds into each other’s lives on a regular and meaningful basis. Feinman grew up a few hours outside of Boston, in Amherst, Mass., with parents who were psychologists and an older brother, Josh, who now works at ICW as a program director. After college, Feinman became an AmeriCorps coach in an East Boston middle school, where he saw how many young people grow up in hopeless circumstances, surrounded by poverty, drugs, and violence, with parents, cousins, and friends who have served time in prison. “They’re facing very real segregation and isolation,” Feinman tells Fast Company. “Sometimes this occurs in very obvious ways such as when people cross the street to avoid them. But frequently, it occurs more subtly, like not having the access to opportunities that I, for one, took for granted growing up.”

Almost all the student personal trainers at ICW come from homes much like the ones Feinman saw during his AmeriCorps years. Most come from families with incomes of less than $10,000 a year, which is nearly half the federal poverty level. Yet in Boston, pockets of poverty are not so far from pockets of wealth; the poorest neighborhoods—Roxbury, Mattapan, and Dorchester—are only about five miles away from Kendall Square, where tech workers often make six- and seven-figure salaries.

Feinman still sees a small proportion of his students get rearrested. Several have been shot: Feinman has discovered that attending students’ funerals is now a tragic, but invariable, part of his everyday life. “I hate seeing our students get back into trouble,” Feinman says. “But I take these isolated cases as evidence that we’re serving the right population. We have a screening process to ensure we’re targeting people within the highest risk category. If they’re not, we refer them somewhere else: There are many other programs out there that are better than ours at dealing with general at-risk released prisoners.”


With the help of donors who believed in his mission, Feinman raised $75,000 in 2010 to set up the first ICW gym in Dorchester, a low-income part of Boston. By last year, his fundraising efforts brought in over $1 million, allowing him to open the Kendall Square location in May 2015. Four student trainers and two coaches who supervise came over to help kick-start training sessions in the new gym. Feinman has enlisted local companies like Microsoft, Deloitte, and a slew of smaller startups to support ICW by encouraging their employees to use the gym or by bringing ICW personal trainers to their offices to lead staff workouts.


Adam von Reyn, InsightSquared’s marketing director and a fitness enthusiast, was thrilled when he saw industrial gym equipment being delivered to a space so close to his office. One day, he stopped by the construction site that would eventually become ICW’s Kendall Square gym and struck up a conversation with Feinman. When von Reyn learned about ICW’s mission, he managed to convince his CEO to sponsor staff workouts twice a week as a benefit and a way to build morale at the company.

Clients who come to this gym pay very reduced rates for their personal training sessions, since their trainers are still students in the process of being certified. One hour of personal training costs $25, significantly less than the $100 to $150 you might pay at another gym. Feinman tells me that this money goes directly to the student trainers, who can make up to $30,000 a year by working with clients. ICW also receives donations from companies like State Street and BNY Mellon, as well as several foundations, to cover the organization’s annual operating budget of $1.3 million.

An Army Of Self-Made Entrepreneurs

The wealth gap in the United States is bigger today than any time since the Great Depression. Some scholars, like Erik Brynjolfsson, a management professor at MIT’s Sloan School, believe that the technology sector is a main driver of this inequality. “It’s the biggest factor,” he told MIT Technology Review. He thinks the tech-based economy favors a small group to use their talents and make large amounts of money.


By opening a gym in Kendall Square, Feinman is deliberately tapping into the wealth of tech workers. “The Kendall Square tech community is full of high-net-worth individuals and often, our clients end up becoming our donors,” he says. And he’s found that the Boston’s tech community has been welcoming of ICW and excited about contributing to its work. In fact, many people who come to the gym say they have been searching for opportunities to give back to their community, but have struggled to make sense of what the most pressing needs are.

This can be a high-profile problem for tech philanthropists. Tech entrepreneurs donate significantly more than people in other industries, representing 49% of the $10.2 billion contributed by the 50 biggest donors in 2014. But where they choose to spend that money can and does generate controversy. Take Google, for example. The company is known for donating billions to charitable causes, but it has also been called out for focusing on problems in developing countries rather than improving the conditions in its own backyard, with Bay Area residents struggling with housing and transportation problems.

Given how segregated tech workers are from the poor and underserved, they sometimes fail to understand the nuanced and deep-seated problems these communities face. Mark Zuckerberg notably made a $100 million donation in 2010 to turn around the Newark, N.J., school system, one that has failed students for decades. Four years after the donation was made, the effort has been largely unsuccessful. When it came down to it, critics thought that Zuckerberg’s well-meaning plans didn’t consider the complex realities on the ground and failed to engage the community.


In contrast, Feinman believes that his program is effective precisely because it is community-based. “What really motivates me is the idea of social inclusion,” he says. “I’m excited about what happens when people from Kendall Square get to know our students and our students get to know them. Our students suddenly become part of an inclusive network and are suddenly put in touch with all kinds of new opportunities in the tech world.”

ICW’s philosophy of social inclusion is supported by the most current research on reducing recidivism. The Justice Center, a nonprofit organization, released a report last year about the most effective strategies states have deployed to cut down on reincarceration rates. Time and again, states found that bringing former prisoners into a community that offered supervision and support was critical to helping them succeed.

It is equally important to help ex-felons find work if they are to reintegrate into society. Between 60-75% of ex-offenders are unemployed a year after their release. The National Institute of Justice found that most employers are reluctant to hire applicants with criminal records, yet, researchers found that when applicants were able to speak directly with the hiring manager, their prospects improved dramatically. The Institute concluded that personal interaction between applicants and employers was a key factor in successful hiring.


Feinman also believes that the tech world, with its emphasis on entrepreneurship and meritocracy, is an inspiring model for ex-convicts who are trying to piece their lives back together. Rather than creating pre-determined career tracks for his student personal trainers, he wants them to use their skills and certifications to create their own path. Some, like LaCourt, might choose to work for themselves as personal trainers. Others might seek employment at other gyms or even come back to serve at ICW. Still others might try to leverage their connections and relationships with clients to try to get an entry-level job at a company or pursue some other career entirely.

Given how hard it is for convicted felons to find work through traditional channels, Feinman’s strategy is to create an army of self-made entrepreneurs. In his view, entrepreneurial resourcefulness is the best path forward for convicted felons.

Uncommon Connections

On a Monday evening, LaCourt holds a group training session with three clients. He has developed an individualized routine for each of them, and shuttles back and forth to check on the progress of each person, guiding them through their workouts.


One of the clients, Ben, a data scientist in his thirties, is running out of steam trying to complete single-leg squats. LaCourt notices him struggling. “My left leg is much weaker than my right one,” Ben says, grimacing. LaCourt places his hand lightly on Ben’s shoulder: They’ve been training together for a month now and have clearly developed a friendly familiarity with one another. LaCourt’s approach is encouraging. “Keep your arms out,” he says. “And come right back up once you lower yourself to the bench.”

The session wraps up. As Ben packs up his things, he asks LaCourt what he did over the weekend. LaCourt had just taken his 9-year-old son to sleep-away summer camp. “It was his first time at camp last year and he cried and cried when I dropped him off,” LaCourt says. “I was like, ‘Should I just drive back home and forget about the whole thing?’ But my boy stayed and toughed it out. At the end of the week he was so happy he didn’t want to come home. So this year, he’s staying for two weeks.”

Feinman has seen his students forge remarkable connections with clients. He’s observed a recently incarcerated drug dealer, still on parole, playing a game of pickup basketball with an MIT professor. He’s watched personal trainers covered in tattoos marking their gang affiliations asking startup entrepreneurs what it really means to “build an app.” Twice a week, he oversees a team of ICW personal trainers at Microsoft’s Cambridge headquarters; after the sessions, he overhears personal trainers and employees exchanging stories about the silly things their children do at the playground.


“People who used to cross the street to avoid each other are now crossing the street to say hello to each other,” Feinman says. “We’re seeing our student personal trainers benefit from a new network; they’re suddenly seeing possibilities for their life they couldn’t even imagine before.”

Angel’s Lost Scholarship

Angel LaCourt has a very clear memory of the moment when he was shackled and shipped to federal prison. It was his second prison term: He’d already done two years in a state penitentiary. This time, after being picked up for selling drugs, he was brought to a holding facility while his sentence was processed. In those days, sitting in a cell, all he could think about was how he was going to miss more formative moments in his son’s life. His boy was four at the time. “I wanted to be a better father than the one I had,” LaCourt says. “I wanted to be the greatest father in the world.”

In federal prison, LaCourt’s days were full of activity. Since he had graduated from high school, he was eligible to take some college courses. He had a plumbing certificate, so he did plumbing work and sewed canteen bags for the Army through a program called Unicor. He put away around $100 a month.


In his free time, LaCourt would lift weights at the gym. Throughout his childhood, he had been a keen athlete, playing basketball and football. It was a way to escape some of the troubles at home. His mother was addicted to crack cocaine, causing her to behave erratically, so LaCourt and his sister grew up fending for themselves. When Angel was 12, LaCourt’s father gained custody of his children, but he supported his family largely by dealing drugs. In his teens, LaCourt began selling marijuana himself.

In spite of all this, LaCourt maintained a B+ average in school. He fantasized about landing a football scholarship and to one day play in the NFL. A lot of children in inner city neighborhoods have the pipe dream of escaping poverty through sports, but LaCourt actually showed promise, catching the attention of his coaches and football scouts. “I came pretty damn close to making it happen,” LaCourt tells me with rare vulnerability in his voice. LaCourt received a slew of football scholarships to universities across the country, including one to Boston College, a school known for its strong academic standing and its Division One sports teams.

But LaCourt was already deeply embedded in the gang scene. In the early 2000s, gang violence and shootings in Roxbury had reached new heights. LaCourt found security in a close group of friends in his neighborhood affiliated with H-Block, a Roxbury gang. They had guns and weren’t afraid to use them to protect one of their own. In the face of the constant threat of violence, LaCourt’s friends offered loyalty, protection, and moments of kindness. “They were like a family to me,” LaCourt says. “If one of us needed anything—money or a ride somewhere or whatever—they would do whatever was necessary to provide.”

Angel LaCourt, standing between Harold and Hollander streets.

Around graduation, LaCourt was arrested for shooting a man from a rival gang. He lost his scholarship to Boston College and spent what would have been his first two and a half years in college in a state prison. Right before getting locked up, he fathered a son with a girl from his neighborhood and desperately wanted to be part of his newborn child’s life. “At the time, I didn’t feel bad for what I did, because if I hadn’t tried to get the other guy, he would have shot me first,” he says. “But I regret it all now because if I just had a little guidance or someone to tell me, ‘Leave that all that alone, you have so much more ahead of you,’ I would probably be in a different place today.”

LaCourt left state prison at the age of 22, but found it impossible to earn a living. When a potential employer Googled his name, his criminal record would pop up before his athletic accomplishments. He did his best to stay away from gang activity, but in a fit of desperation—and an effort to try to earn a living for his son—he started selling drugs again. In less than a year, he got picked up on a federal sentence, landing him in a New York penitentiary. He was 26 when he got out. “By then, I had lost nearly five years of my son’s life,” LaCourt says.

This time, he needed to find another way to earn a living. At a halfway house, he heard an ICW representative give a talk about the Dorchester gym. LaCourt’s first thought was that he was tired of going to his local YMCA gym, which was dull and uninspiring, so it might be interesting to try out another facility—especially one that was free.

So he showed up at Dorchester one day and met Feinman while he was lifting weights. “As I was leaving, Jon said, ‘See you tomorrow!’” LaCourt remembers. “And I thought, this dude doesn’t even know me and he’s telling me I’m going to want to come back tomorrow.” But LaCourt did come back. That was two years ago.

The View At Microsoft

On a bright Tuesday in June, LaCourt and two other ICW trainers head to their twice-weekly workout at Microsoft’s R&D headquarters. The sixth floor has floor-to-ceiling windows that boast stunning views of the Charles River; sailboats and rowboats glide gently by. Beyond the water, the entire Boston skyline is visible.

LaCourt started coming here two years ago to help with the employee workouts. During his first visit, the view literally took his breath away. After the session, he bought a sandwich and sat in one of the lounge chairs overlooking the water.

Today, LaCourt is a regular at the Microsoft offices. The conference-room workout session is overseen by Josh Feinman, ICW’s program director and Jon Feinman’s brother, who has 10 years of personal training experience. The ICW trainers have moved aside chairs and set up mats and kettlebells. A group of five employees arrive; four are regulars who’ve shown up twice a week for months.

Aimee Sprung, a civic engagement manager at Microsoft, tells me she first met Jon Feinman when he entered ICW as a project in a nonprofit startup accelerator two and a half years ago. Sprung had been thinking about ways to improve the employee health benefits at the Cambridge offices, especially since the gym facilities at Microsoft’s headquarters in Redmond, Wash., were spectacular by comparison. She was the one who suggested bringing ICW trainers to Microsoft, and Feinman loved the idea.

“Besides the social good aspect, it’s been a really great way for employees from different divisions to get to know each other,” Sprung tells me. “Some people have seen pretty remarkable improvements to their fitness level. And mostly, it’s been good for morale.” The workout sessions at Microsoft have become the model for other on-site training programs: Deloitte has recently tapped ICW to bring student trainers to their Boston headquarters as a benefit.

ICW trainer Jarreau Pelote with clients in a group workout session

LaCourt is soft-spoken during the session and moves around the room to help clients with their form one-on-one. The day’s routine is on the board: five reps of burpees, seven reps of single-leg tap squats, 10 push-ups, then stay in a plank position for a minute.

Josh Feinman says that learning to communicate with clients is an important–and daunting–part of the training. Surrounded by wealthy employees who are mostly white and Asian, trainers at first can feel unmoored and unprepared. “When we ask our students what their greatest fears are, they don’t say prison or guns,” he says. “Those are things they are very familiar with. For some of them, it’s speaking confidently to their clients that scares them.”

For Microsoft’s employees, meanwhile, the sessions aren’t only about building bigger muscles–they also strengthen the community’s senses of empathy and social justice, says Sprung. “For those of us who live and work here in Kendall Square, it can be hard to imagine what life is like in other parts of town,” she says. “But coming to these sessions week after week, you really get to know your trainers and you learn about what everyday life is like for them.”

A Walk In Roxbury

After the 4th of July weekend, LaCourt offers a tour of his neighborhood of Roxbury. I drive across town from my home in Cambridge into the heart of Boston, over the Charles River, by the Boston Symphony Orchestra past Fenway Park, and the residential neighborhoods are full of housing projects. The deeper into Roxbury you go, the fewer businesses there are on the streets; it’s hard to spot a single grocery store or bank. This is not Starbucks territory.

It’s 10 a.m. and LaCourt and Jon Feinman are on Humboldt Avenue, Roxbury’s main drag. LaCourt looks anxious, distracted by every car that passes, carefully glancing at each driver. Drive-by shootings, at any time during the day or night, are a regular occurrence.

LaCourt is willing to take us down the larger streets in his neighborhood, but thinks we should avoid side streets. Over the last few days, there have been flare-ups between rival gangs in these parts, with multiple reports of homicides.

Humboldt Avenue intersects with Hutchings, Homestead, Howland, and Harrishof. Parallel to Humboldt is Harold Street, which intersects with Hollander and Holworthy. This is the reason that the dominant gang here is called H-Block; it’s been at war with the Health Street Gang from nearby Jamaica Plain since the 1980s. Over the last four decades, hundreds of people have been killed: most have been affiliated with gangs, but many have been innocent bystanders caught in the crossfire. Last year, there were 213 shootings in Boston, mostly concentrated in the gang-held areas of Dorchester, Mattapan, and Roxbury.

“Many of my friends never made it past 18 or 21,” LaCourt says. He points to one street corner and then another and one more after that, where close friends of his have died. “I’m 28 and that makes me old, in these parts. I’ve outlived so many people.” We pause at a makeshift memorial attached to a street sign. “I sometimes come here and have a drink to my friend, remembering the good times we had,” LaCourt says. “His daughter is eight years old now. She didn’t get to spend much time with her father.”

LaCourt’s grandparents uprooted from Puerto Rico nearly a century ago. They quickly found their way to Boston, where their extended family had already begun to settle in Roxbury. From the 1940s onward, the black population in Boston grew exponentially as communities began to migrate from the South, but because of redlining and blockbusting practices, many lived in racially segregated neighborhoods like Roxbury and Dorchester that suffered from a lack of city services like proper trash disposal and public bus routes.

Until LaCourt was well into his teens, he never left the 24-block radius of Roxbury. He had never seen the landmarks that people associate with Boston: the Charles River, Faneuil Hall, Harvard and MIT, the Italian restaurants in the North End. There was no way to leave his neighborhood without a car. Only one bus route connects upper Roxbury to downtown Boston and because of gang violence, accidentally getting on a bus with the wrong person could get you shot. Several friends of LaCourt’s have been gunned down as they tried to leave the bus. “One reason to join a gang was just transportation,” he explains. “You had a safe way to get around.”

While Feinman has closely observed the devastation that gang violence has brought on individual lives and families of the young men who come to ICW, he also understands the reason for the gangs. “They are making decisions I don’t agree with, but these decisions are rooted in the logic of their circumstances,” Feinman says. “These gangs are based on love and support for one another that no one else is really willing to show them. People think that our personal training students don’t care about anything, which makes them easy to write off. But, in fact, they care so much about protecting what little they have and standing up for one another in the only way they know how that they’re willing to lose their life to a bullet or jail.”

As our tour comes to an end, LaCourt is asked if he plans on leaving Roxbury. “Of course,” he says. “But money is always an issue.” He’s doggedly working to get his personal training certification, so that he can begin to earn between $100 and $150 an hour for training clients.

Only five months into its existence, ICW’s Kendall Square location had a full roster of clients and more signing up by the week. Feinman’s beginning to think of the organization’s next move. He’d like to set up another location in Boston, perhaps on Tremont Street, a long road running between one of the most expensive downtown neighborhoods, full of boutiques and chic restaurants, and the projects of Roxbury. Feinman is convinced that the ICW model will work in other parts of the country where extreme poverty and fabulous wealth are within walking distance of one another. He’s beginning to plan for new ICW locations in Chicago, Los Angeles, and Philadelphia.

LaCourt, for one, says he’d be eager to help expand operations when they move outside of Boston. “I’d love to start over somewhere new, where no one knows me,” he says. “A place where I could bring my son to the park and not have to watch my back.”

About the author

Elizabeth Segran, Ph.D., is a senior staff writer at Fast Company. She lives in Cambridge, Massachusetts