Young musician and entrepreneur Silas Caldwell balances high school, a guitar shop, songwriting, recording and touring, and still has energy to spare.
Written by Leslie Criss | Photographed by Joe Worthem
Music, in one form or another, has created the framework of Silas Caldwell’s young life.
Tupelo-born, he lived his first seven years in the birthplace of the rock ’n’ roll king. When he turned 8, his family moved to Oxford, often cited as a center of hill country blues. At age 12, he moved about 250 miles north to Nashville, known by many as Music City.
He was born to music-loving parents, Missy and Tony Caldwell who surrounded their young son with their own favorite sounds, an eclectic musical mix. Silas grew up watching his dad play with hill country artists; his mom grew up on classic country and singer/songwriters like Bob Dylan. And his great-grandfather on his mom’s side, I.A. Turner from Skuna Bottom, Mississippi, played guitar for Western swing artist Sonny James. Silas never met his great-grandfather, who played a Gibson ES-335 Walnut TD, but he searched the United States for a guitar like Turner’s made in the same year in the same factory. He found one, and it is now Silas’ primary guitar.
Silas, now 17, is thriving as a young entrepreneur and a singer/songwriter/musician who’s making quite a name for himself in Nashville and beyond.
His first formal foray into learning to play music was at age 4, with Dr. Christopher Thompson and a Suzuki violin. He’s also an alum of Oxford’s Roxford University that offers lessons in guitar, bass, vocals, drums and more, and gives young musicians the opportunity to perform in groups.
At age 14, Silas and three other teens formed a cover band, Derailed. They had a large following and played multiple venues around Nashville, but when two members moved to Florida, the band ceased to be.
“When Derailed ended after two years, there was a real void,” Silas said. “I was at a loss as to what to do with all the time and energy I’d spent on that.”
That was when a longtime interest in owning a business reemerged. With support from his parents, and some of the money he’d made and saved while playing with Derailed, Silas and his dad became business partners in Caldwell Guitars of Nashville which opened in 2021.
“Silas has done most of the work on the business,” said his proud dad, a therapist with a full-time private practice in Nashville. “He did the tax paperwork, the website, all the front-end work that I had to sign off on. He is at the store every day.”
Silas, a high school senior, attends a hybrid home school that gives him time to work in the store, which is open by appointment. He’s met lots of cool guitar people, including a few famous folks.
In his spare time, Silas writes music.
“I started becoming serious about song writing when I was 14,” he said. “Typically, for me, the lyrics come first — something I’m feeling, getting something off my chest, heartbreak and desire are something we all go through. It’s like peeling back the layers on an onion.”
Heartbreak and desire? Silas laughed. “No girlfriends now,” he said. “No time and no money for girls.”
He does, however, find time for the music. In addition to song writing, Silas tours, sometimes solo, but more often with his band Silas Caldwell and The Magnolia Sound. Established in 2023, the band features Arthur Stover on drums; Dayton Swords, lead guitar; Tony Caldwell, bass guitar; and Silas on vocals and guitar.
A highlight for Silas was playing at The Bluebird Cafe, a famous Nashville venue. He wasn’t too nervous, but his dad was.
“I was nervous for him,” Tony said. “Everyone performing had either a Grammy or a No. 1 hit. And there was 15-year-old Silas, but he was great.”
These days, much of the music Silas plays is original.
“I would rather play original music for 10, than covers for hundreds,” he said.
His musical influences are diverse and include some Mississippians: Neil Young, Patti Smith, Lucinda Williams, REM, Bob Dylan, Tom Waits, R.L. Burnside, John Moreland, Andrew Bryant, Water Liars.
In August, Silas played a homecoming concert of sorts at the Link Centre in Tupelo. Back in Tupelo a few weeks later, he performed at Change Festival. And on Oct. 3, he’ll be in Oxford at the Powerhouse as a guest on Thacker Mountain Radio. Though he’s now a Nashville resident, Silas clearly loves the state of his birth.
“I wouldn’t rather be from anywhere else but Mississippi,” he said. “There’s blues, rock, mainstream music as we know it. It’s where it all came from.”
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