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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.

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E64 | Christian Pena’s DJ Domination: From Teen Passion to Music Industry Icon, Radio Innovations, and Club DJing Challenges

The Birth of a DJ: Christian takes us back to where it all began—his love for music sparked at age 16 when he discovered the art of DJing. He recounts his relentless pursuit to land a spot on WTMP’s urban radio lineup, battling challenges like performing live without modern tech aids and overcoming age-related setbacks in the club scene. His journey from mixing tapes in his room to becoming a sought-after DJ is a testament to the power of passion and perseverance.
Life on the Edge: Christian dives into the contrasting worlds of entrepreneurship and traditional jobs, exploring the leadership and sacrifices required to build a career from scratch. He shares his experiences of juggling the uncertainty of entrepreneurial life with the false security that often comes with a 9-to-5 job. Through his story, listeners gain a deeper understanding of what it takes to step out of the comfort zone and chase their dreams.

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E63 | CJ Holland’s Golfing Greatness: From Baseball Beginnings, Junior Tour Dominance, to College Aspirations

What does it take for a young athlete to transition seamlessly from one sport to another while becoming a dominant force in the world of junior golf? In this insightful and inspiring episode of *Happy Hour Holidaze*, hosts Sean and Manny Febre sit down with CJ Holland, a rising star who’s taking the junior golf scene by storm. At just 15 years old, CJ has already achieved remarkable success, ranking 31st on the Hurricane Junior Golf Tour and earning accolades as one of the top young golfers in his district.

CJ’s journey began at the age of two, when he first picked up a plastic club and started swinging away in his backyard. Supported by his family, particularly his father and grandfather, CJ’s passion for golf grew as he spent time on the putting greens and golf courses near his grandparents’ home. His story took a pivotal turn in eighth grade when he made the bold decision to leave baseball behind—despite excelling as a Little League All-Star—to focus entirely on golf. Since then, his game has evolved dramatically, earning him multiple top finishes in highly competitive tournaments.

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Send Your Question

Got burning questions about business, entrepreneurship, or anything in between? We want to hear from you! Send us your queries, and hosts Manny and Sean Febre will answer them on an upcoming episode of Happy Hour Holidaze. Don’t miss this opportunity to get expert insights while having a great time. Simply drop us a message with your questions, and let’s dive into the world of business together!

E45 | Cliff's Chronicle: Crafting Tampa's Digital Buzz, Foodie Fame, and the Pursuit of Social Media Mastery

Navigating Tampa’s Digital Currents: A Deep Dive with Cliff Carithers on Happy Hour Holidaze

Welcome to another enthralling episode of Happy Hour Holidaze, where hosts Sean and Manny Febre explore the fascinating world of digital entrepreneurship with Cliff Carithers, the visionary behind TampaLatest. Episode 45 offers a vibrant mix of insightful business strategies, personal growth tales, and an insider’s look at Tampa’s bustling digital scene. Join us as we decode the secrets behind building a successful online presence in one of Florida’s most dynamic cities.

From Humble Beginnings to Digital Maverick

Cliff Carithers didn’t start with a roadmap to digital success. His journey began as a fresh-faced high school graduate, whose curiosity and drive plunged him into the complex world of SEO and digital marketing. Early in the episode, Cliff shares how his initial experiences working for a local SEO firm laid the groundwork for what would eventually become a thriving personal venture.

As he navigated through the initial challenges, Cliff’s breakthrough came from recognizing a niche for TampaLatest—a platform dedicated not just to highlighting the glossy side of Tampa but to broadcasting a genuine narrative of the city through social media. This approach not only differentiated him from the crowd but also created a loyal community base eager for authentic content.

The Art and Science of Engagement

One of the episode’s highlights is Cliff’s detailed discussion on the art of engaging content creation. He delves into the mechanics of what makes content shareable and engaging, emphasizing the importance of authenticity and strategic planning. Whether it’s highlighting a local business, covering an event, or sharing a piece of city news, Cliff’s approach is meticulous and data-driven, aimed at maximizing reach and engagement on social media platforms.

Sean and Manny probe into the specifics of how Cliff manages to keep his content fresh and relevant. Cliff reveals his strategy of balancing educational and entertaining content, which has been crucial in building and maintaining his audience. He also touches on the tools and technologies that aid his content creation, from scheduling tools to analytics software that helps track performance and engagement metrics.

Navigating Brand Partnerships and Growth

A significant portion of the conversation is dedicated to exploring Cliff’s partnerships with major brands like Busch Gardens and Red Bull. Here, Cliff provides a playbook on how budding digital entrepreneurs can attract and maintain fruitful collaborations. He stresses the importance of alignment in brand values and audience demographics, which ensures that partnerships resonate well with existing followers while attracting new ones.

Cliff’s narrative is a testament to the power of strategic growth and networking. His ability to leverage relationships into opportunities has seen TampaLatest become a pivotal part of Tampa’s digital and real-life communities. This segment is particularly enlightening for listeners interested in understanding the dynamics of brand partnerships and influencer marketing.

Ethics and the Future of Digital Influence

In an increasingly digital world, the ethical considerations of influence and content creation are more relevant than ever. Cliff and the hosts discuss the responsibilities that come with a large online following, including the impact of their content on public opinion and individual behavior. This part of the episode shifts to a more reflective tone, where Cliff shares his philosophy on transparency and integrity in digital communications.

Looking ahead, Cliff expresses his ambitions for TampaLatest, revealing plans to expand into real estate and other sectors. His vision for the platform encompasses a broader service offering, aiming to match Tampa residents and newcomers with ideal living situations through engaging, informative content.

Conclusion: Lessons Learned and Glasses Raised

As the episode winds down, the hosts reflect on the key lessons from their discussion with Cliff. For aspiring digital marketers and entrepreneurs, Cliff’s story is a blueprint for thoughtful growth, resilience in the face of adversity, and the importance of staying true to one’s values.

Listeners are left with a mix of actionable business insights and a dose of inspiration, all served up in the convivial, relaxed atmosphere that Happy Hour Holidaze is known for. So, raise your glass to new learnings, a ripple of laughter, and the endless possibilities that await in the digital world.

Don’t forget to tune in next week for another episode of Happy Hour Holidaze, and in the meantime, follow us on all platforms for more episodes that blend business savvy with life’s lighter moments.

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