E65 | Davy Rolando’s Dynamic Dual Careers: From Radio Stardom to Tattoo Entrepreneurship, Nightclub Innovations, and Iconic Music Moments
Davy’s story begins with his unexpected entry into the world of radio—a world he never imagined himself in. A chance encounter with a girl he met at Prana led him to a pivotal decision: pursue an unpaid internship at 94.1 or stay in his comfort zone. Choosing the former, Davy’s dedication saw him rise from street team intern to a beloved on-air personality on the Freak Show, captivating Tampa Bay listeners with his authentic, unfiltered voice for over a decade. His journey in radio wasn’t without its challenges, though. Davy shares candidly about the struggles of being the “fill-in guy,” always waiting for a permanent spot, and the patience it took to finally land a full-time position after years of grinding.
The Transition to Entrepreneurship
But radio was never Davy’s endgame. He always saw it as a stepping stone to something he could truly call his own. This episode dives deep into his transition from the airwaves to the tattoo business, where he co-founded Emphasis Tattoo in Tampa. Davy shares the calculated risks he took, starting the business two years before leaving radio and navigating the challenges of opening just before the COVID-19 pandemic shut everything down. His foresight in having six months of operating costs saved up ensured that Emphasis Tattoo survived and eventually thrived, even expanding its operations thanks to the good graces of a landlord impressed by Davy’s business acumen.
