Join us at the Winter Pride Street Festival in St. Petersburg, Florida as we connect with community members, local businesses, and LGBTQ+ organizations working to create inclusive spaces across Tampa Bay.

In this episode of the Skittle Squad Podcast, we explore how Pride events go beyond celebration. They help build community, support LGBTQ+ entrepreneurs, and create safe spaces where people can show up authentically.

From discovering new businesses like Dad’s Kitchen to meeting Ruben, owner of Bubba Bear Sweets, and learning about the work of the Tampa Bay LGBTQ Chamber, this episode highlights the people and organizations making a real impact in the local community.

 In this episode:
 - Highlights from the Winter Pride Street Festival
 - Community stories from local attendees and organizers
 - Local business spotlight: Dad’s Kitchen
 - Meeting Ruben, owner of Bubba Bear Sweets
 - How the Tampa Bay LGBTQ Chamber supports local entrepreneurs
- Where to stay connected with LGBTQ+ news and events

Events like Winter Pride are more than festivals. They are opportunities for connection, celebration, and building stronger, more inclusive communities.

We’re LIVE from Winter Pride in St. Petersburg, Florida and let’s just say… it started with chaos.

From wrestling an 8-foot step-and-repeat in the wind to launching interviews with local changemakers, this episode captures the real, unfiltered energy of Pride in action.

We bring the Skittle Squad booth to life with bubbles, laughter, and candid conversations with incredible members of the community including Dave from Tampa Bay Gay as well as Allison and Ilene from The Zest Zone.

But this episode also addresses something deeper.

After a surge of new followers and online hate comments, we talk openly about what it means to uplift the LGBTQ+ community in divisive times. Why Pride matters. Why safe spaces matter. And why love is louder.

 In this episode:
•  Behind-the-scenes booth setup chaos
•  Community shoutouts and returning guests
•  Drag Race excitement and local events
•  Supporting LGBTQ+ businesses and nonprofits
•  Handling online hate with resilience
•  Why Winter Pride in St. Pete is so important right now

This is what community looks like.
This is why we show up.
This is why Pride exists.

In this empowering episode of The Skittle Squad Podcast, we sit down with Samara Di’Angelo and Kendall Di’Angelo, the creative forces behind Coven of D’Angelo Entertainment, to talk about what it really takes to build independent drag spaces from the ground up.

From early online streaming days using OBS to producing full-scale in-person shows, Samara and Kendall share how resilience, reinvention, and relentless belief in themselves helped them grow from digital performers to community builders. What started as adapting during uncertain times evolved into a bold, artist-led platform that uplifts performers and creates opportunities where none existed before.

This conversation dives into the realities of drag entrepreneurship the hustle behind the glam, the challenges of event production, the power of social media marketing, and why the most important “yes” you’ll ever hear is the one you give yourself.

 This episode explores:
 The origins of Coven of D’Angelo Entertainment
 Transitioning from online drag shows to live performances
 Building independent, artist-first drag spaces
 Using social media & streaming to grow your audience
 Supporting new performers & strengthening LGBTQ+ community
 Why resilience is everything in creative entrepreneurship

In this powerful episode of The Skittle Squad Podcast, we sit down with Pastor Andy for a heartfelt and eye-opening conversation about faith, justice, and what it truly means to build inclusive community.

From breaking down silos between advocacy groups to opening church doors as free meeting space for justice-driven organizations, Pastor Andy shares how collaboration—not competition—is the key to lasting change. We explore the intersection of LGBTQ+ advocacy, support for the unhoused, immigrant justice, and why movements become unstoppable when we choose to stand together instead of apart.

This conversation challenges us to look beyond our own circles and ask a powerful question: Who’s missing from the table?

 In this episode, we explore:
-  Drag as liberation, joy, and protest
-  New Year’s Eve chaos & unforgettable stories
 - How Christian nationalism harms LGBTQ+ communities
 - Police relations & protecting the unhoused
 - Why allyship and bridge-building matter now more than ever
 - How humor can coexist with radical change

This episode is a moving reminder that the “edges” are often the true center of change—and that when we build bridges instead of walls, we create communities where everyone belongs.

If this conversation resonates with you, don’t forget to subscribe, follow, and share with someone who believes in building a more inclusive world. 

In this magical season finale of The Skittle Squad Podcast, we sit down with Chris and Ryan Zubrick, the creative minds behind the beloved Zubrick Magic Theater, for an unforgettable conversation about wonder, storytelling, and the power of live performance.

The Zubricks share how two independent magic journeys collided when they were double-booked for the same event, sparking a partnership that would grow into one of Tampa Bay’s most intimate and immersive theaters. From transforming a former call center into a thriving magic venue to designing shows that put the audience at the heart of every illusion, Chris and Ryan reveal how passion, persistence, and community made it all possible.

They also open up about weaving personal stories into their acts, adapting each show to the people in the room, and why keeping magic accessible for all ages has always been at the center of what they do.

 This season finale explores:

-  How two magicians built a theater from scratch
- The magic of intimate, audience-driven performances
- Turning a simple space into a home for wonder
- Using storytelling to make magic meaningful
- Why community support made all the difference
- How authenticity brings every illusion to life

This heartfelt finale is a celebration of creativity, connection, and the belief that magic truly is for everybody.

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