CHAMPIONS
FOR
CHANGE
Plain Sight CEO James Chapman Wants Everybody to Win
By: Kwasi Boadi
On the basketball court, James Chapman was a natural-born point guard. For him, team success was always the priority—making plays for himself wasn’t enough if he wasn’t setting others up to score, too.
His love for the sport paved his way out of the Chattanooga, Tennessee neighborhood that raised him, and dreams of one-day going pro led him to stints playing in college and Mexico before he ultimately landed at a tryout for the NBA Development League’s Texas Legends. The moment was a crucial turning point for Chapman, but not in the way he’d hoped.
Inactivity just wasn’t in his nature, in part, because he was raised by people who were always grinding.” I grew up around a lot of entrepreneurs by necessity. My cousins would work a job, but then they would also cut hair or do hair outside of the house,” he remembers. “Everybody had a hustle. Everybody was[always] doing something.”
For a brief stint, Chapman’s hustle landed him at FedEx unloading boxes during the 3 am shift. It was a drastic departure from the life he’d envisioned for himself, but he looks back on that period with gratitude for the lessons learned. “I had to learn that down doesn’t mean out,” he tells REVOLT. “Just because I’m down at this moment, it doesn’t mean that I can’t pick myself up from my bootstraps and just figure something else out.”
His big break finally came when a childhood friend told him about a government-funded workforce development program helping low-income workers cultivate corporate job skills.
Detroit Demo Day was Chapman’s opportunity to step into his calling. He was approached for the opportunity by Cleveland Cavaliers owner Dan Gilbert. His team was looking for an “entrepreneur helping entrepreneurs” to create a program that would give back to Detroit’s small business community.
After relocating to the Motor City, Chapman’s first order of business was to meet with the area’s local business owners so he could gauge their most pressing needs.
The annual showcase gave the city’s small business owners an opportunity to celebrate one another, connect with potential consumers and pitch their businesses for a much-needed capital infusion. The most rewarding part for James? Seeing Demo Day’s impact on other Black business owners like Nailah Ellis. As he recalls, the legacy Detroiter and owner of Ellis Isle Tea was the case study for just how impactful Demo Day could be. “She was at a point where she was doing well, but she needed that one thing to get her to that next level.
She showed up, she showed out, and she won $300,000 at Detroit Demo Day. And then, she used that money to grow and scale her business into even more cities.”
Spearheading the multi-year initiative was a testament to Chapman’s talent for developing mutually-beneficial connections between people. As he talks, it’s increasingly clear that his years on the basketball court planted those seeds. Playing ball taught him that you go further by going together. “I’m a community builder,” he says. “I’m somebody who wants everybody to win. And so, that shows up in everything that I do.”
One afternoon in 2019, while brainstorming in the attic of his Airbnb on the west side of Detroit, it occurred to Chapman that he would need a digital tool to take his community-centric mission a step further. His musings that day laid the groundwork for Plain Sight, an app that now seeks to reimagine how people network. “I was looking for a tool to help me be a better community builder,”he recalls. “With Plain Sight, I’m still providing access to capital, but it’s access to human capital if you are an attendee using our platform.”
Plain Sight’s methodology is all about connecting people at events and coworking spaces based on their mutual needs. Once someone joins, they’re not asked to upload a profile picture, an intentional move to combat unconscious bias. Instead, their profile centers on the help they’re seeking and the skills they can offer to support others. Now, a little over three years into its mission, the app has roughly 22,000 people in its network consisting of business professionals, event organizers, and brand sponsors with one thing in common: They’re all looking for a helping hand.
And with his sights now set on ushering more sponsors onto the platform and expanding beyond the US, Chapman knows that his work is just beginning. There’s still a deficit in the capital—both human and financial—that’s afforded to Black creators and business owners, and he hopes his team can contribute to closing that gap. “The country will only [reach] a shell of its potential if we don’t fund business owners, black business owners he explains. “The folks that aren’t allowing us to have access to this capital, they’re hurting themselves more than they know because our black innovation is being stifled.”
With this sentiment in mind, Chapman plans to keep fighting the good fight. Harnessing the power of human connections is his calling, and he now sees the purpose in his work more than ever. “I’ll [always be] an entrepreneur helping entrepreneurs and helping other people with their journey as go-getters. I think it’s just a part of my legacy, and I want it to be that way.”
He got cut from the team, and he had to reconsider his purpose outside of the gym for the first time in years. “When I had to transition into something else, to be honest, there was a moment [where] I didn’teven know who I was anymore,” he recalls. He had a choice in the face of that challenge: He could let that setback break him or use it to propel himself forward. Chapman chose the latter path.
His involvement was only supposed to last a summer, but after seeing his work ethic and willingness to help others, facilitators asked him to join their staff full-time. In just three years, he worked his way to the top of the organization, becoming one of its executive directors in the process.
Climbing the ranks gave Chapman the confidence to forge his own path, and entrepreneurship felt like the logical next step.
So, he left the development program and began pouring his time into a mobile oil change business that presented him with a new set of hurdles to clear. Those experiences sharpened his business acumen, and the more he learned, the more eager he was to share his insights with other local entrepreneurs facing the same challenges. “I felt like me doing business myself is cool, but I really felt called to help other people be successful with their business ventures and with their aspirations.”
That community immediately embraced him because he made it a point to listen more than he spoke. “What kept coming up is, they felt like they needed to be celebrated, and they felt like they needed more access to founder-friendly capital,” here members. Detroit Demo Day was birthed from those conversations.
James Chapman playing for his alma mater Bluefield College
James had an early love for basketball
James speaking at Chattanooga Startup Week
James relocated to the motor city to help start Detroit Demo Day
James speaking with Che Pope at Detroit Demo Day
James moderating a founders panel at Black Founders Demo at Miami Art Basel
James moderating a founder panel during Cadillac's Making Major Moves Brunch
Uncover the remarkable story of Nailah Ellis Brown, CEO and founder of Ellis Island Tea, and follow her path to success.
CEO Nailah Ellis Brown is Leveraging Her Success to Help Others Find Theirs
Click HERE for more stories of fearlessness and determination from Cadillac.
James Chapman on his passion for supporting others
James Chapman on the need to support Black business owners