Tampa financial adviser unplugs on air

Executive

Kevin Caldwell, 42, is the co-owner of Golden Road Advisors, a registered investment advisory firm in Tampa he founded in 2021. Prior to Golden Road, Kevin was a financial adviser for wealth management companies throughout Tampa Bay, including Morgan Keegan and a decade with Raymond James. A University of Florida alum, Caldwell also helped launch the school’s wealth management studies program and is a guest lecturer for a class on finance.

Diversion

Disc Jockey. On select Saturdays, or whenever a fellow DJ calls in sick at WMNF 88.5 FM community radio station in Tampa, Caldwell gets the call to guest-host two-hour time slots, manning the board and broadcasting curated playlists of Americana, folk, hippie, psychedelic and classic rock music. 

Listen to the music: A sixth-generation Floridian, Caldwell grew up in Clermont and, though he never played instruments, always had a deep love of music old and new. He eventually moved to Gainesville to attend the University of Florida and met a roommate who had a turntable, prompting him to go hunting through his parents’ old vinyl records collections when he came home that Christmas break. He was out in the garage when he came across a box of records, each one with the name K. Angers scrawled across the top in marker. They belonged to his mother’s sister — Kevin’s  aunt — who was killed by a drunk driver in the 1970s, well before Kevin was ever born. As a tribute, Kevin’s parents gave him the middle name Angers, so the two would share initials. The two also shared tastes in music: her collection was a treasure trove of San Francisco psychedelic rock, each album labeled as if it already belonged to Kevin. “I feel like I have this super unique relationship with her that no one else has because her music just speaks to me in this incredible way, and it must have to her too,” Caldwell says. “It’s kind of like a cosmic connection, honestly, and she was my first introduction to the Grateful Dead. It just hit me right away.”

He's gone: Caldwell moved to Tampa in 2005. It was here that his sister introduced him to his second great musical awakening — a funky little community radio station called WMNF. Caldwell was an instant fan, and the station fueled his love for music so much that he began to seek out opportunities where he could be closer to the scene. He began volunteering for the Gasparilla Music Festival

The golden road (to unlimited devotion): He also joined a networking group, based in New York City, that was made up of Grateful Dead fans in the business sector. It’s called “Wall Street Dead Ahead.” Through that group, Caldwell befriended an artist who used to design show posters and backstage passes for the Grateful Dead, he says. As the years passed, and the time came for Caldwell to form his own investment advisory firm, he named it Golden Road after his favorite Dead song, and used the same artist to create illustrations for his firm. 

Light my fire: Over his many years as a WMNF fan, Caldwell eventually befriended several DJs, including longtime local legend Marcie Finkelstein. During the pandemic, the radio station held a fundraiser with a unique incentive — anyone who made a $500 donation got to guest host a show with Finkelstein. Eager for an excuse to get out of the house, Caldwell shelled out the cash, he says. It was Finkelstein who convinced him during that first show that he had a natural gift as a DJ. 

You're in the band: But with a company to run and two small children, Caldwell didn’t think he had the time. That’s when she offered him the chance to be a guest DJ, subbing in for her and others whenever they couldn’t make it to the studio for their show. Caldwell learned how to operate “the board” and, over the last two years, estimates he’s probably subbed in for six to eight shows. “It’s incredibly terrifying and nerve racking, but its also like this beautiful creative outlet for me,” Caldwell says. “Now I’m just constantly making playlists for a show I don’t have scheduled but may be coming some day.”

Can you guess my name: Caldwell says he doesn’t have a DJ name for himself just yet but he isn’t opposed to the idea of getting one — “I think it would be so cool,” he says. His friends are always coming up with suggestions: Stairway to Kevin? Kevin on Earth? Tampa Kev? Caldwell from Claremont? Maybe even K. Angers. “That one hits home,” he says. 

One hot minute: Working at the radio station has helped Caldwell grow both personally and professionally, he says. “It teaches you that a minute is a lot longer than you think it is,” he says. “You can get a lot done in a minute on the radio.” 

Let it be: Caldwell says DJing has also hammered home the importance of always being prepared — nothing is worse than a minute of dead air. But perhaps the biggest lesson he’s learned from his new hobby is to “detach the creative process from the audience love.” It’s tempting to try to tailor a show to what you think your audience wants to hear, but the best results always come from the moments when Caldwell trusts his own gut and plays what he thinks is cool. “I try to remember to trust my gut, whether it’s as a DJ or in my wealth management firm. The best results are always the ones that are purely you — the results of your own intuition and tastes and what you think is right. … Everything in your life should be a creative outlet, you just have to let it be.”