Class of 2024

Kenny Lumpkin

Owner, Dewey’s Jazz Lounge and All American Bar, Grill & Patio: Age 28

Like most people, Kenny Lumpkin found the pandemic to be a time of reflection and figuring out what’s really important.

And while doing that, he concluded that being a consultant for Big Pharma just wasn’t working for him, and he needed something else. After some research — and soul searching — he determined this something else should be a return to his roots in Springfield accompanied by an entrepreneurial gambit, an effort to replicate the kind of jazz establishment he found, and came to love, while living in the Boston area — Wally’s Café Jazz Club.

And he did, with Dewey’s Jazz Lounge on Worthington Street, an establishment he opened in 2021, when there were still many COVID after-effects and other challenges to overcome.

Three years later, Dewey’s has become a downtown staple, attracting visitors from Springfield, across the 413, and beyond. And in 2023, Lumpkin doubled down on his dream, opening a second venue — All American Bar, Grill & Patio, a sports bar on Dwight Street. The two sites complement each other well and have attracted different audiences.

“My biggest worry about opening two restaurants a block from each other is that they would cannibalize each other,” he said. “But we haven’t seen that; we’ve been able to hit both sides of the market. We have an older, more mature crowd at Dewey’s that will come to see live music, and we get a younger crowd at All-American that will get down with a DJ.”

Lumpkin, who is also active in the community, with a turkey drive at Thanksgiving and a Christmas clothing and toy drive, said being an entrepreneur is essentially what he thought he would be, a roller-coaster ride replete with challenges and rewards.

“Every day is a learning experience, and every day is something new,” he told BusinessWest. “That’s what I love about it.”

His philosophy, about life and business and their myriad challenges, is best summed up with a tattoo he wears proudly, reading ‘Find the Sun.’

“It means to find the bright side of things,” he explained. “I try to remain optimistic and see what good is coming from all the hard work you put in. And it’s amazing when people pull you aside and say, ‘you’re an inspiration to this community,’ or offer a simple ‘thank you’ for bringing this concept to Springfield.”

He’s heard a lot of that since that COVID-inspired reflection of four years ago, which helps explain why he’s a member of the Forty Under 40.

—George O’Brien