E65 | Davy Rolando's Dynamic Dual Careers: From Radio Stardom to Tattoo Entrepreneurship, Nightclub Innovations, and Iconic Music Moments

Happy Hour Holidaze

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In this compelling episode of Happy Hour Holidaze, hosts Sean and Manny Febre welcome back a familiar face, Davy Rolando, who is no stranger to the spotlight. From a 16-year radio career at Tampa’s 94.1 to becoming a successful entrepreneur with Emphasis Tattoo, Davy’s journey is a masterclass in passion, resilience, and the art of reinvention.

From Intern to Radio Star

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.

Nightlife Hustle and Lessons Learned

The conversation also explores Davy’s ventures into the nightlife scene, where he hustled as a DJ in Tampa’s strip clubs and dive bars. Davy recounts the dynamics of working in strip clubs, where professionalism was key to maintaining lucrative relationships and maximizing earnings. He and his best friend Matthias even took on the challenge of transforming a slow Tuesday night at Gasoline Alley into a bustling event, leveraging their connections and strategic promotions to build a successful club night from the ground up. The episode highlights the importance of fun, security, and crowd management in the nightlife industry, offering listeners valuable insights into the world of promotions and event planning.

Embracing New Ventures

As the episode unfolds, Davy discusses the inception of Emphasis Tattoo and the lessons learned from earlier business ventures, like the short-lived but successful Tattoo Soap. His partnership with renowned tattoo artist Dollars Tattoo led to the opening of their shop in March 2020. Despite the pandemic’s impact, their commitment to good business practices and innovative marketing strategies, such as acquiring the 1-800-TATTOOS phone number, has positioned Emphasis Tattoo as a standout in the industry. Davy also hints at plans for expansion and shares his vision of turning Emphasis Tattoo into a multi-location franchise, with a focus on perfecting their systems and ensuring that each artist is booked out months in advance.

Reflecting on Success and Future Goals

Throughout the episode, Davy reflects on the lessons he’s learned from his diverse career path, from the discipline of radio to the creativity required in the tattoo business. He emphasizes the importance of becoming an expert in your field and leveraging that expertise to build a successful business. Davy’s story is not just about personal success but also about inspiring others to pursue their passions.

Luvut

1. Journey to Radio and Entrepreneurship (00:00:00)

2. Stripping and DJ Promotions (00:11:17)

3. Building a Successful Nightclub Business (00:18:36)

4. Radios, Clubs, and Tampa Bay Lightning (00:29:18)

5. Transition From Radio to Business (00:36:05)

6. Tattoo Soap and Business Growth (00:47:39)

7. Musicians, Interviews, and Nightclubs (00:56:30)

8. Memorable Concerts and International Investments (01:05:00)

9. Best of the Bay Podcast Promotion (01:13:12)