Photo by Kayla Bensing.

On a clear afternoon that looks warmer than it feels, Vincent Bolton surveys his potential customers walking up and down 16th Street and proclaims, “It’s prime time.”

He picks up his black shoulder bag with dozens of recently burned CDs and movies and begins his day. The songs on the CDs are a combination of commercial artists and tracks put together by local DJs, who look to Bolton and others to start to develop buzz around their work. Some discs also feature songs he has developed and recorded himself.

Movies go for $5 a disc, and music for less than that.

After a few steps, Bolton nods at a man he recognizes at the corner of 16th Street and Pulaski Road before heading south.

Although Bolton’s face looks younger than his 29 years, he walks like a man twice his age–”slightly bent over, with a little limp and just a hint of swagger as his weight shifts from side to side.

A few blocks later, Bolton gives a handshake to a teenager perched outside a convenience store.

The interactions are all a part of his business, he explains. “You’ve got to be out and among the people,” said Bolton, who often speaks in such a low murmur that you have to strain to hear what he is saying. “I’ve got to network with the people to have those relationships.”

Sometimes, there are long stretches where he sells nothing. Today is one of them.

It’s hard to make his $500 monthly rent, so Bolton has taught himself to install software, write code and repair broken hard drives to supplement his income.

He is determined not to return to the drug dealing that led to two convictions and snared so many of his friends.

In his neighborhood, Bolton is far from unusual in having a criminal record, no work and no connection to the city’s workforce development system.

But his solution to dealing with the space he inhabits between illegal and traditional full-time work is.

Bolton uses his considerable intelligence and entrepreneurial zeal to eke out an off-the-books living at the same time that he works toward his dream of owning his own business and producing music and rap videos. He plans to use his profits to help what he calls “The Holy City,” the only neighborhood he has ever known except for the two times he was incarcerated. “I think it will bring more jobs and hope into the community so that kids can look up to somebody they see everyday,” Bolton said.

As a child growing up in North Lawndale, Bolton earned high grades in his earlier years at William Penn Elementary School, but started to lose focus in middle school. “I’d study 30 minutes when the other kids weren’t studying at all, so it was like I had studied for an hour,” he said. “But I really should have studied for an hour.”

In addition to his academic troubles, Bolton saw the pillars of his world start to come undone shortly before he entered adolescence.

In the early ’90s, his father, singer Milton Wright, was killed during a drinking argument with a friend. Although Bolton did not live with his father, the loss hit him hard.

But not nearly as hard as his mother’s death. While talking on the phone, his mother, Darlene Bolton, had a heart attack and died. In the next room, Bolton never heard the woman who had given him life take her last breath.

He ended up living with his older sister, but she was too young to care for him. Desiring material comfort and not having someone to guide him, he started working the streets shortly after graduating from alternative high school Chicago Christian Academy in 1999. “I didn’t have someone in my ear telling me to keep going,” he said ruefully. “I’m underachieving.”

He’s working hard to change that. He has taken computer programming classes at area colleges, but his real passion is making videos.

He has made close to a dozen so far and uploaded them on YouTube. Mckinley “Bolo” Woods, a bright and muscular 20-year-old who gets by fixing cars, is his chief videographer, while Thomas “T Easy” is the main rapper. Bolton also works with varying levels of frequency with five or six other young men in the community.

One video shows Bolo bench pressing 225 pounds and staring straight into the camera as he does sets of bicep curls. Another has Bolo’s uncle Ollie Woods staring into the camera and unleashing a torrent of lyrics that return over and over again to the chorus, “Where I’m from.” A third is shot in black-andwhite and has dozens of men from the community marching angrily down the street in preparation for a fight with rivals from another neighborhood that turns out to be a rap battle.

Bolton gets his studio time, at $25 to $30 per hour, at Papermill Studio, owned by Maurice “Reese M.A.C.” Kilo, a North Lawndale native who has worked with Ludacris.

Kilo says Bolton’s timing is fortuitous. In the past, recording costs would be prohibitive for many aspiring artists who had to have deals with record labels to have any hope of making substantial amounts of money. But now, sites like YouTube have made it possible for comparative unknowns to make their mark.

Becoming a successful video producer can be a hard climb, but Kilo believes that Bolton and Bolo possess the ability and discipline necessary to succeed. “Success in this industry doesn’t come right away,” he said. “You have to have patience and talent, and these guys have it.”

Bolton may also get a boost in the form of his cousin, DJ Bobby Skillz, a tall, sturdy man with braids and eyes that brighten with enthusiasm when he talks about the cooperative of West Side DJs who are working to increase the amount of love, peace and respect in the community.

For Bolton, Skillz is a source for music to add to his discs and a connection through the DJs cooperative to outlets for his projects. For Skillz, Bolton is an important connection to the workings of the street and people’s current musical taste. “It’s like a triangle,” Skillz said.

It’s late afternoon, and the sun is just beginning its slow arc downward. Bolton makes a stop at a transportation company, emerging four discs lighter and $10 richer. “It’s hard to get by,” he said.

For an instant, he stands on Ogden Street, where the city’s skyscrapers and business district loom in the distance. Were he born in another, more affluent community, perhaps, someone with Bolton’s skills, intelligence and motivation could be working in one of those buildings, rather than scraping by.

If the thought bothered Bolton, he didn’t show it for long. There was still time before nightfall, and he knew that people were gathering on a nearby street. He squared his shoulders, took a breath and kept on walking his distinctive walk. He had work to do in The Holy City.

Contributing: Kayla Bensing

Jeff is the founder and executive director of the Center for Collaborative Investigative Journalism (CCIJ) and the Padnos/Sarosik Endowed Professor of Civil Discourse at Grand Valley State University....