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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!

E35 | Damon Hart's Blueprint for Triumph: Real Estate Resilience, Wholesale Wisdom, and Surfing the Tampa Bay Market Waves

Unlocking the Secrets of Real Estate Resilience with Damon Hart on Happy Hour Holidaze

In the latest episode of “Happy Hour Holidaze,” hosts Sean and Manny Febre welcome Damon Hart, a renowned real estate investor and the visionary behind Foxy Home Buyers, to share his journey of resilience, strategic innovation, and the relentless pursuit of success in the real estate market. This episode is not merely a conversation; it’s an expedition through the trials and triumphs that have shaped one of Tampa Bay’s most influential real estate figures.

The Journey Begins with a Game of Monopoly

Damon’s tale starts in an unexpected place: the childhood board of Monopoly. This game, symbolic of his early fascination with real estate, became the cornerstone of his career. Damon reminisces about his initial steps, from playful banker roles to becoming a significant player in Tampa Bay’s real estate scene. His story is a testament to the idea that the seeds of our future successes are often sown in the playful endeavors of our past.

Navigating the Storms: The 2008 Housing Crisis and Beyond

The episode takes a deep dive into the tumultuous waters of the 2008 housing crisis, a defining moment for Damon. With candid vulnerability, he discusses the challenges he faced, including non-paying tenants and the daunting reality of becoming a “motivated seller.” This segment is particularly enlightening for listeners, offering a raw look at the hardships that can beset even the most ambitious entrepreneurs.

The Art of the Bounce Back

What sets Damon apart is not just his ability to face challenges but his unparalleled skill in turning setbacks into comebacks. The episode explores Damon’s strategic pivot from adversity to opportunity, emphasizing the importance of adaptability, continuous learning, and leveraging one’s network. Damon’s journey underscores the essential truth that resilience is not about avoiding failure but about how one responds to it.

A Masterclass in Real Estate Strategy

Sean and Manny skillfully steer the conversation to uncover the layers of expertise Damon employs to stay ahead. From wholesale real estate to asset management and innovative marketing tactics, Damon offers listeners a masterclass in the strategies that have enabled him to thrive in a competitive market. His insights into communication, market analysis, and creating value provide invaluable lessons for anyone looking to make their mark in real estate investing.

Beyond Business: The Human Side of Real Estate

Perhaps the most compelling aspect of this episode is the exploration of Damon’s philosophy on business and life. His approach to real estate investing goes beyond transactions; it’s about building genuine connections, creating win-win situations, and conducting business with integrity. Damon’s emphasis on mentorship, giving back, and building a legacy of positive impact adds a profound dimension to the conversation, inspiring listeners to consider not just the financial but the human side of business success.

Conclusion: Lessons for the Aspiring and the Seasoned

This episode of “Happy Hour Holidaze” is a beacon for anyone navigating the complex world of real estate or entrepreneurship. Damon Hart’s story is a powerful reminder of the resilience, strategic thinking, and human connection required to succeed. Whether you’re a budding entrepreneur, a seasoned investor, or simply someone in search of inspiration, this episode offers a treasure trove of wisdom, strategies, and personal reflections that transcend the realm of real estate.

As Sean and Manny wrap up this insightful episode, the takeaway is clear: success is not just about the deals you make but about the difference you make. Join us on “Happy Hour Holidaze” for more stories that inspire, educate, and entertain. Here’s to the journey of turning dreams into reality, one episode at a time.

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