James Chapman’s Detroit Journey

James Chapman’s Detroit Journey: A Vision, A Bet, and A City That Believes

James Chapman came to Detroit in 2016 to work for the Family of Companies. That same year the Cavaliers won the NBA Championship. Three months into his new role, he found himself on a championship parade float, tossing beads into the cheering crowd. “I remember thinking, this is the best job ever,” Chapman says with a laugh. Soon, he would be helping to lead Detroit Demo Day.

Chapman was charged with leading entrepreneurship efforts in Detroit for Dan Gilbert and the Rock Family of Companies. Chapman came to Detroit to connect with entrepreneurs, build community and create opportunities. What he found was a city where big bets yield big rewards—a place where innovation meets grit, and where people rally together with a willingness to roll up their sleeves and do the hard jobs.

Detroit Demo Day: A City That Believes in Entrepreneurs

Chapman came in with a fresh perspective. He had built a successful mobile oil change business in Chattanooga, Tennessee, and launched a grassroots movement called Workaholics, bringing together night owls who were grinding to build something bigger. His experience as both an entrepreneur and a connector caught Gilbert’s attention. “Dan was looking for someone who could bridge the worlds of grassroots entrepreneurship and a high-powered business ecosystem,” Chapman explains. “Dan values entrepreneurship, he know how powerful it is and he loves Detroit. That is why he brought me in to help facilitate that community in Detroit.”

His first step was getting to know the community. “When I got here, I lived on the West Side,” he says. “I met with entrepreneurs, asked them what they needed, and built something based on their input.” Chapman knew that success would require understanding the landscape, not just imposing solutions. “That is why Detroit Demo Day worked—it was their idea,” he adds.

This mindset aligns with one of the core ISMs of the Rock Family of Companies: Always Raising Our Level of Awareness. Detroit Demo Day, a groundbreaking event where the Rock Family of Companies gave away $1 million annually to Detroit-based and Detroit-bound businesses. “We were probably the first private company or group to give away that much capital in one night,” Chapman says. “And when you do that, you are not just funding businesses—you are inspiring the entire ecosystem. People in the audience are thinking, ‘Next year, that is going to be me.’”

A Leader Who Listens

Chapman saw how much Dan cared about the city how he approached Detroit Demo Day. “Dan was not just putting up capital—he was putting in time. He was meticulous about the event, the impact and how it was rolled out and how it helps the community.” Chapman says. “That level of attention from someone managing billion-dollar enterprises? It tells you everything about his love for Detroit.”

It was about more than writing checks; it was about bringing Detroit together. Entrepreneurs, corporate leaders and communities. People who might not otherwise cross paths all sat under one roof, cheering for the city’s next generation of business leaders. “That was what I was most proud of,” Chapman says. “Creating those uncommon collisions.”

From Detroit to the World, But Always Home

Chapman eventually launched his own business, Plain Sight, a platform that helps corporate sponsors and event-goers make data-driven purchasing decisions so they get more out of events than what they put in. The first version of the product launched just months before the pandemic, presenting a significant challenge. But like Detroit, Chapman adapted. Today, Plain Sight is expanding into multiple cities across the U.S. and even crossing boarders by helping groups like Microsoft sponsor AI events in Canada and LATAM.

Yet, Detroit remains home. “My company is still headquartered in Detroit, and I am back all the time,” he says. “I tell people everywhere: there is no place like it. If you have never been, go. You will leave with a different impression.”

And perhaps, like Chapman, you will see what Dan Gilbert saw all along: Detroit is a city where people bet big, work hard and do well by doing good.