In this powerful episode of The Skittle Squad Podcast, we take listeners on a journey that begins with nostalgic memories of MTV’s golden age and ends in one of the most meaningful conversations of the season about healthcare, HIV, and the life-changing impact of compassion.

As we reflect on early jobs, pop culture, and how those experiences shaped our work ethic, the conversation shifts toward the profound impact HIV has had on LGBTQ+ communities and the importance of accessible, judgment-free care. We are joined by Dr. Bob Wallace, founder of Love the Golden Rule, a nonprofit clinic built on the belief that every patient deserves dignity, respect, and love no matter their background.

Dr. Wallace shares how his mission grew out of personal transformation, the ongoing challenges in HIV care and gender-affirming services, and why the Golden Rule isn’t just a philosophy it’s a blueprint for better healthcare and stronger communities.

This episode explores:
- The cultural shift from MTV’s music video era to reality TV
- How early jobs shape resilience and purpose

- The lasting impact of HIV on LGBTQ+ communities
- The mission behind Love the Golden Rule & community-based healthcare
- Why compassion and dignity must be at the center of medicine
- How living by the Golden Rule can change lives

This is a moving, hopeful conversation about healing, humanity, and what it really means to show up for one another.

In this heartfelt and hilarious episode of The Skittle Squad Podcast, we are joined by author and writing coach Jillian Abby, whose memoir Perfectly Queer has been helping people find the courage to tell their stories. Together, they dive into the messy, funny, and deeply human world of social media, personal identity, and what it really means to live authentically. From poking fun at vague-booking and selfie culture to unpacking the emotional journey of coming out later in life, Jill opens up about leaving behind a career in accounting to follow her calling as a writer and ghostwriter.

This episode explores:

- The chaos, humor, and heart of social media

- Writing as a tool for healing and self-discovery

- Coming out later in life and finding your true self

- Mental health, identity, and personal growth

- How telling your story can create connection and understanding

Whether you’re a writer, a late bloomer, or someone still finding their voice, this conversation will leave you feeling seen, inspired, and a little more brave.

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

In this special behind-the-scenes episode of The Skittle Squad Podcast, David takes listeners inside one of St. Petersburg’s most vibrant LGBTQ+ events “Yule Be Gagged” at Cocktail for a festive, fast-paced look at drag, community, and holiday magic.

The episode kicks off outside the dressing room with Holly Day (Paul Fifer’s drag debut ), as nerves, excitement, and rhinestones collide ahead of his first-ever performance. Listeners get an unfiltered look at what it really feels like to step into drag for the first time.

As the day unfolds, David checks in with fans, performers, and local business owners who make events like these possible. From devoted podcast listeners like Ashley Walker to Nancy of Funshine Properties and Kevin from Cocktail, the episode highlights the people, passion, and partnerships that keep the St. Pete LGBTQ+ community thriving.

More than just a show recap, this episode captures the heart of the community celebrating visibility, supporting local businesses, and showing up for one another with joy, humor, and a little chaos.

This episode explores:
- A first-time drag performance (and all the nerves that come with it)

- What really happens behind the scenes at a Pride fundraiser
- Holiday glam, drag prep & performance realness
- The power of LGBTQ+ community support
- Local businesses uplifting queer spaces in St. Pete
- Why events like “Yule Be Gagged” matter more than ever

In this high-energy episode of The Skittle Squad Podcast, we sit down with the unstoppable Dioscar DeMilo, Mr. St. Pete 2025, creative powerhouse, and proof that sometimes a one-way ticket is all it takes to change your life.

Dioscar shares the raw, real, and often hilarious story of moving to NYC with $1,000, one suitcase, and zero plan, and how that leap of faith launched him into a journey of self-discovery, drag artistry, and pure resilience. From early performance mishaps to finding his style, embracing his body as art, and building the confidence to “be bad before you get good,” his story is packed with wisdom for performers and dreamers alike.

This episode explores:
- Turning accidents into artistry & building a drag identity
- Moving to NYC with nothing but courage and a carry-on
- What it really takes to become a fierce performer
- Celebrity encounters, crushes & unexpected inspirations
- Resilience, identity, and chasing big dreams
- The journey to becoming Mr. St. Pete 2025

A vulnerable, funny, and totally inspiring conversation for anyone who’s ever dreamed of performing or simply starting over.

In this honest, heartfelt episode of The Skittle Squad Podcast, we sit down with Vernon Vaden, general manager of Mister D’s, Creative Loafing “Best Bartender” winner, and one of the youngest leaders in Tampa’s nightlife scene. Vernon walks us through his wild, inspiring journey, from military life to go-go dancing, overcoming addiction, and rising through the ranks to lead one of Tampa Bay’s most beloved gay clubs.

We talk about the real stuff: the work behind bartending (yes, it’s part therapy), the grind of nightlife management, choosing sobriety to get your life back, and how community patrons, friends, and chosen family can save you when you need it most. Expect laughs, real talk about mental health, late-night bar confessions, and the kind of empathy that makes our scene feel like home.

This episode explores:
- Life behind the bar - bartending as care, craft, and connection
- Transitioning out of the military and reinventing yourself in queer spaces
- Addiction, recovery, and choosing sobriety to regain control
Winning Best Bartender — what that recognition felt like
-Go-go dancing, tips, and the unexpected ways performance pays the bills
- How nightlife builds chosen family and keeps community strong

Tune in for a conversation about resilience, accountability, and how showing up for each other keeps our community alive. If you or someone you love needs resources, Vernon and the hosts talk openly about where to turn.