In this thoughtful and inspiring episode of The Skittle Squad Podcast, we sit down with Shane McCabe, a storyteller, hospitality veteran, and creator of the podcast Necessary Pursuit. Together, they explore how creativity, community, and curiosity can shape an unexpected and deeply meaningful career.

Shane takes listeners through his journey from writing about influential women during quarantine to launching Necessary Pursuit, a show dedicated to amplifying powerful personal stories from across Tampa Bay and beyond. Drawing from more than 20 years in the hospitality industry, he reflects on the art of connection, the importance of asking the right questions, and how storytelling can bring people together in surprising ways.

The conversation also touches on Shane’s creative side hustle (yes, bedazzled flasks make an appearance), the challenges of building a podcast, and what makes Tampa Bay such a special place to create, collaborate, and build community.

This episode explores:
- How quarantine sparked a passion for podcasting
- The power of storytelling to build community
- Why Tampa Bay is a hub for creative connection
- Shane’s hospitality career and creative side hustle
- Lessons on curiosity, interviewing, and personal growth

In this bold, emotional, and unforgettable episode of The Skittle Squad Podcast, David brings listeners inside You’ll Be Gagged, a high-energy drag fundraiser celebrating community, creativity, and courage — and marking the first-ever drag performance of Holly Day.

The episode kicks off with chaotic color commentary, playful banter, and mounting anticipation as Paul Piper transforms into Holly Day, stepping into drag and onto the stage for the very first time. What begins with nerves and self-doubt quickly turns into a jaw-dropping performance that has the crowd cheering, dollars flying, and hearts wide open — all in support of Winter Pride St. Pete.

As the night unfolds, David and the Skittle Squad capture the magic on and off the stage: fabulous performances, gag-worthy moments, and a room full of people showing up for their community. The celebration continues with the crowning of the “You’ll Be Gagged” Queen, heartfelt gratitude for the performers and organizers, and the incredible announcement that over $15,000 was raised — at zero cost to the organization.

The episode also features powerful conversations with Winter Pride leaders Rob Hall and Dave Alvarez, who break down what Winter Pride means for St. Petersburg, why visibility matters more than ever, and how inclusive events create joy, safety, and belonging for everyone. From drag races and circuit parties to free community events, this episode showcases the heart behind the glitter.

This episode explores:
-Holly Day’s first-ever drag performance and on-stage debut
- Transformation, nerves, and the reality of performing for the first time
- Fundraising for Winter Pride and the power of community-driven events
- Gag-worthy performances, crowning moments, and pure drag chaos
- Visibility, joy, and creating safe spaces in St. Petersburg
-How local venues and organizers uplift LGBTQ+ culture and community

In this festive and fierce episode of The Skittle Squad Podcast, David takes listeners behind the scenes at the Drag Queen event at Cocktail in St. Petersburg, where rain, glitter, and drag collide in an unforgettable spectacle.

The episode opens with Holly Day (Paul Pfeiffer) preparing for the stage, giving listeners an intimate look at the nerves, excitement, and sheer determination that go into a high-stakes drag performance. From wardrobe chaos to DJ mishaps, this episode captures all the drama, laughs, and triumphs of performing under pressure.

As the day unfolds, David chats with performers like Joshua Beadle & Adriana Sparkle, community leaders including Pastor Andy, and local organizers supporting Winter Pride, highlighting the incredible people who make queer events and safe spaces possible in St. Pete. From spontaneous cannonballs to last-minute costume tweaks, listeners get a full immersion into the energy, dedication, and joy of drag culture.

More than just a show recap, this episode celebrates the creativity, resilience, and solidarity of the LGBTQ+ community — proving that even when things go wrong, queens always find a way to slay.

This episode explores:
- First-time and high-stakes drag performances in the rain
- Backstage chaos, costume prep, and performance realness
- The power of queer community support and visibility
- Fundraising for Winter Pride and the impact of community events
- How local venues like Cocktail, The Wet Spot, and The Ball uplift LGBTQ+ spaces
- Fierce performances, unexpected mishaps, and unforgettable moments