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S2 E43 | The Blase Network: Baltimore to Tampa Bay with Chris

What happens when a Baltimore podcaster visits Tampa Bay? A raw, hilarious culture clash that reveals surprising truths about American cities, sports fandom, and the entrepreneurial journey.

Chris from the Blase Network brings his Baltimore perspective to our studio, immediately diving into sports talk with passionate takes on the Ravens, Lamar Jackson, and the upcoming NFL season. But as the conversation unfolds, we explore something much deeper—the stark contrast between city experiences across America.

As a documentarian and podcaster born in what he calls “the ass crack of Baltimore,” Chris offers an unfiltered look at growing up in a city recently named America’s dirtiest for the third consecutive time. His stories about youth crime, political leadership failures, and the practical challenges of urban life paint a vivid picture rarely captured in mainstream media.

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S2 E42 | Ride with Alissa Hale: From Alabama to Florida, Alissa Hale’s Country Music Journey

Meet Alissa Hale, a rising country star who’s redefining what it means to be a modern artist. Born and raised in Alabama with a 12-year background in gymnastics and ballet, Alissa’s path to music came through an unexpected intersection of talent, determination, and a mother who believed in her enough to talk her up to a music producer.

During this candid conversation, Alissa gives listeners an exclusive world premiere of her upcoming single “Ride” – a bold, wild anthem for Southern girls who aren’t afraid to embrace their freedom and make no apologies for it. The track, releasing June 20th, perfectly captures her authentic country roots while bringing a fresh energy to the genre.

What makes Alissa truly unique is her innovative approach to building her brand. She’s created “Dirty Blonde,” a groundbreaking zombie video game that integrates her music into gameplay – something never before seen in country music. Players blast “deadheads” while experiencing her songs in an immersive environment, creating an entirely new way for fans to connect with her work. This creativity extends to her entrepreneurial ventures, including a hot sauce line featuring her signature blend and an upcoming ghost pepper version aptly named “Hot as Hell.”

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S2 E41 | Hard Money, Hard Lessons with Caleb Delgado

What happens when life knocks you down not once, but twice—and you find the strength to build something even better than before?

Caleb’s journey from Queens-born soccer player to mortgage mogul to nearly bankrupt and back again is a masterclass in resilience and entrepreneurial spirit. Growing up in Long Island with immigrant parents, he learned early lessons contrasting wealth and struggle that would prove invaluable later in life.

His soccer skills earned him a D1 college spot playing center midfield, but family financial troubles forced him to leave school and enter the mortgage industry at just 20. The timing couldn’t have been more dramatic—the early 2000s “Boiler Room” era of mortgage lending. Within months, Caleb was making hundreds of thousands, driving luxury cars, dropping $10,000 on dinner tabs, and living what seemed like the dream. Until 2008 hit.

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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!

E60 | Orlando Davis' Radio Revolution: From Gary Dreams to Tampa Triumphs, Celebrity Encounters, and Community Impact

From Small-Town Dreamer to Radio Legend: Orlando Davis on Happy Hour Holidaze

Welcome to another electrifying episode of Happy Hour Holidaze! In this episode, hosts Sean and Manny Febre sit down with Orlando Davis, the legendary radio personality from “Orlando and the Freak Show.” Orlando takes us on a journey from his humble beginnings in Gary, Indiana, to becoming a cornerstone of Tampa’s vibrant radio scene. Along the way, he shares invaluable insights into the radio industry, heartwarming community engagement stories, and hilarious anecdotes that will leave you in stitches. This blog post delves into the highlights of this fascinating conversation, offering a glimpse into the life and career of one of Tampa’s most influential radio figures.

Celebrating Milestones and Nominations

We kick off this special episode by celebrating a major milestone—our nomination for Creative Loafing’s Best in the Bay award! Orlando is quick to acknowledge the importance of this recognition, urging listeners to cast their votes starting August 1st. He dives into his inspiring journey, sharing how networking and seizing opportunities played pivotal roles in his career. Orlando’s story is a testament to the power of perseverance and the importance of authenticity in the radio industry.

The Wild Ride of the Radio Industry

Orlando and the Febre brothers recount jaw-dropping moments from Wild 98.7, including insane contests and unforgettable celebrity encounters. From interviewing Eminem to witnessing DJ Khaled’s rise in Florida, the stories shared are nothing short of captivating. One particularly memorable tale involves Orlando holding the studio hostage over technical issues—a testament to his dedication and passion for his craft. These anecdotes highlight the unpredictable and often wild nature of live radio.

Deeper Impact of Radio

It’s not all glitz and glam in the world of radio. Orlando emphasizes the deeper impact of radio on the community. He reflects on the evolution of social media’s role in the industry and the responsibilities that come with being a public figure. Authentic communication, he argues, is crucial for building a loyal listener base. This episode touches on the transformative power of radio, from community outreach to shaping public opinion.

Memorable Moments and Hilarious Anecdotes

Orlando shares some of the wildest experiences from his radio career. From a contestant smearing feces on his face for front-row Prince tickets to the infamous “pigs in a blanket” challenge, these stories showcase the lengths people will go to for coveted prizes. Another standout moment involves a live on-air protest, where Orlando and his team refused to leave the studio until their technical issues were addressed. These anecdotes provide a glimpse into the high-stakes and often unpredictable world of live radio.

The Evolution of Wild 94.1

Learn about the strategic decisions behind the station’s evolution, including the frequency change from 98.7 to 94.1 for better reach across the Bay Area. Orlando discusses the business side of radio, including the challenges of tracking listeners through Nielsen ratings and adapting to market changes. The move to a more powerful signal was a game-changer, allowing Wild 94.1 to reach a broader audience and solidify its place as a leading station in Tampa.

Starstruck Moments and Celebrity Encounters

Orlando recounts his starstruck moments with celebrities like Eminem and Rihanna. He shares behind-the-scenes stories from the radio industry, including an unexpected encounter with Michael Jordan at the Hard Rock Casino. These anecdotes offer a fascinating glimpse into the world of celebrity interviews and interactions. Meeting Vida Guerra and Iggy Azalea are highlighted as particularly memorable experiences, showcasing Orlando’s ability to connect with stars on a personal level.

Philanthropy and Community Engagement

Orlando’s commitment to community service shines through as he talks about his annual toy drive, which has raised millions for local children over the years. He shares heartwarming stories of generosity and the impact of the drive on the community. The toy drive, which started as a small initiative, has grown into a major event, thanks to the support of the Tampa community and Orlando’s tireless efforts. He emphasizes the importance of giving back and how he uses his platform to make a difference in the lives of others.

Navigating the Challenges of Radio Management

As a program director, Orlando faces the tough task of managing a team and making difficult decisions. He shares insights into the challenges of leadership, including the emotional toll of hiring and firing staff. Orlando emphasizes the importance of being prepared and ready for opportunities, a lesson he learned from his mentor, Tom Rivers. His role as a program director requires a delicate balance of creativity, management, and strategic thinking.

Reflection on a Storied Career

With over 25 years in the radio industry, Orlando reflects on his journey and the lessons he’s learned along the way. He talks about the evolution of his career, from his early days in Gary, Indiana, to his rise to prominence in Tampa. Orlando’s story is one of resilience, adaptability, and passion for his craft. He shares his thoughts on the future of radio and the importance of staying true to oneself in an ever-changing industry.

Vote for Happy Hour Holidaze

Don’t forget to support us in the Creative Loafing’s Best in the Bay award by voting every day starting August 1st. Your support means the world to us!

Tune In and Subscribe

This episode of Happy Hour Holidaze is packed with thought-provoking discussions, entertaining stories, and a hearty dose of humor. Whether you’re a radio enthusiast, an aspiring broadcaster, or just someone who loves a good success story, this episode is a must-listen. Subscribe, rate, and review our podcast to stay updated on our latest episodes.

Key Takeaways

  • Orlando Davis’s inspiring journey from Gary, Indiana to Tampa’s radio scene.
  • The impact of strategic decisions on the success of Wild 94.1.
  • The role of community engagement and philanthropy in Orlando’s career.
  • Hilarious and unforgettable moments from Orlando’s time in radio.
  • The challenges and rewards of being a program director.
  • Insights into the evolution of the radio industry and the importance of authenticity in broadcasting.

Final Thoughts

Join us for this exciting episode of Happy Hour Holidaze and get an insider’s look into the world of radio with Orlando Davis! This episode is a testament to the power of perseverance, the importance of community, and the wild, unpredictable nature of live radio. Cheers to new learnings, a ripple of laughter, and insightful evenings!

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