This story has been updated.

André Swanston sold his company for nine figures and is now a serial investor who is behind an effort to bring a Major League Soccer team to Bridgeport — and he says none of that would have happened if he didn’t attend The Hotchkiss School in Connecticut.

Swanston, originally from the Bronx, enrolled at the prestigious Litchfield County boarding school in the late 1990s. His time at Hotchkiss was “the most formative years of my life,” he told The Connecticut Mirror’s State Policy Editor Erica Phillips, and it was where he built a lasting network integral to his career.

Phillips and Swanston, the co-founder of a data management platform for the entertainment industry, sat down at the Ferguson Library in Stamford for “This Could Work” on Tuesday, the first in a four-part CT Mirror event series with successful Connecticut entrepreneurs.

The origin stories of each interviewee will be a consistent topic of conversation in “This Could Work,” and Swanston’s centers around his Connecticut education: He met the co-founder of his start-up at Hotchkiss, and at the University of Connecticut, his entrepreneurial spirit took shape when he started promoting concerts and parties throughout Connecticut and western Massachusetts.

He spent years handing out flyers to advertise events, but over time, he noticed a shift in event promotion: more of it was happening on social media. Around that time, he also saw more people listening to the radio by streaming their favorite stations and anticipated a shift to streaming in movies and television as well.

Those observations led him to realize companies would want, and need, a way to monetize their streaming audiences. So he founded Tru Optik — a company that helped segment streaming audiences for targeted advertising. In 2020, the company was sold to TransUnion for nine figures.

But the journey to get there wasn’t easy.

Swanston said his co-founder found it harder than he expected to build the technology behind their product, and Swanston himself had a hard time getting meetings with venture capital firms, which historically have not invested in minority entrepreneurs at the same rate as their white counterparts.

“I could not even get a meeting with a lot of the firms to make the pitch,” Swanston said. “So there was no opportunity to show the merit of my ideas or intellectual property or stuff like that, because I couldn’t get into the room.”

So most of the capital for Tru Optik came from individuals, Swanston said — and to raise the funds, he turned once again to his Hotchkiss connections, as well as the Connecticut Innovation Fund, a pool of money run by the state Department of Economic and Community Development.

His first angel investor was Kristi Matus, a former CFO of Aetna whose daughter happened to be a Hotchkiss student. One day, Swanston said, Matus was chatting with a fellow parent on the sidelines of a Hotchkiss game and she told him about Tru Optik.

He happened to be a venture capitalist who specialized in the media and entertainment industry and ended up investing $500,000 into the company.

“I literally would have been out of business if I did not go to a specific prep school and have a specific network, because I couldn’t get into meetings on the merit of what I had actually done,” Swanston said. “So my network, frankly, saved me and gave me an opportunity.”

His experience struggling to raise capital has informed his post-Tru Optik work. He and his wife, Michelle, founded Swanston Organization, which invests in entrepreneurs — specifically women and minorities, whose pitches make up 70-80% of the organization’s investments.

The Swanstons have also started an endowed scholarship at Hotchkiss, and their newest venture is an effort to bring a soccer team to Bridgeport.

Swanston and representatives from Major League Soccer’s development league, MLS NEXT Pro, announced the Connecticut United Football Club in January 2024, with plans to play at a new waterfront stadium in Bridgeport. That stadium was slated to open in 2025, but its opening date has been pushed back to 2026.

The decision to bring a major soccer team to Bridgeport was in large part because, Swanston said, “Connecticut is the largest, most densely populated, most affluent market in America without any of the top five major sporting leagues.”

“We have no NFL, no NBA, no MLB, no NHL, no MLS. It’s absurd, right?” Swanston said, pointing out that Connecticut sports fans end up spending money at stadiums in Massachusetts, New York and New Jersey — but not in Connecticut itself.

Though building a professional sports team is a different venture than building a data management platform for streaming services, both reflect Swanston’s history of noticing, and seizing on, an opportunity.

“Sometimes you just have to, you have to do it for people.” Swanston said. “You have to be the solution.”

Correction: A previous version of this story incorrectly stated that Swanston moved to Connecticut to enroll at The Hotchkiss School, but during this time his family continued to live in the Bronx, where Swanston would return during school breaks.