Today we’d like to introduce you to Fleetwood JR.
Fleetwood, we appreciate you taking the time to share your story with us today. Where does your story begin?
I’m Fleetwood Jr., a proud native of Orlando, Florida, and the co-founder of Da Underdawgs Podcast and Underdawgs Worldwide LLC. Our story begins in January 2022, with a simple yet powerful conversation between me and my co-host, Slie Lyfe. We were talking about the state of hip-hop culture and the overwhelming negativity that was being pushed into the algorithm. It was frustrating to see how much of the narrative surrounding the culture was focused on drama and conflict, overshadowing the real stories of growth, struggle, and triumph.
That’s when it hit us—we could do something about it. What started as an idea to change the narrative evolved into a platform where we could celebrate the journeys of people in all walks of life. We set out to create a space that would uplift others, where we could roll out the red carpet and give people their flowers while they were still here. The goal was simple: to promote positivity, foster connections, and showcase the diversity of experiences that make up our community.
We wanted to highlight that, although everyone’s journey is different, we’re all connected through shared struggles and triumphs. We believed that when people shared their stories of passion, hustle, and perseverance, they could inspire others. It became a platform where not only did we tell stories, but we also educated and motivated people by shedding light on the challenges and hurdles that come with the journey. It’s all about offering a full perspective—because success isn’t just about the wins, it’s about learning from the losses, too.
What began as a conversation in early 2022 has since evolved into Da Underdawgs Podcast, now in its ninth season. Each season features over 20 episodes and we are currently in our 9th season, and we’ve crossed the milestone of having over 100 episodes and 100 guests. Initially, we started by reaching out to people within our network, but we quickly realized that the internet was a powerful tool to broaden our reach. So, we set our sights beyond our local community, and began connecting with people from all over the world.
Over the course of the podcast, we’ve had the privilege of interviewing an incredibly diverse group of people—artists, entrepreneurs, actors, personal branding coaches, fitness experts, chefs, DJs, athletes, photographers, filmmakers, and so many more. Our conversations have ranged from discussing the intricacies of personal branding to the realities of being an independent artist. Each guest brings their unique perspective, and every story is a valuable lesson for our listeners.
One of the highlights of our journey was kicking off Season 9 with our first international guest— a music producer from Brazil. This episode marked a significant milestone for Da Underdawgs Podcast, as it opened the door for us to expand our global reach. It was a reminder of how interconnected we are, and how our platform has evolved into a space that connects cultures, industries, and perspectives from all corners of the world.
But Da Underdawgs Podcast is just one part of our vision. In December 2024, we launched Underdawgs Worldwide LLC, a music distribution label and sub-label under Empire /GT Digital. This was an exciting new chapter, one that allowed us to combine our passion for music with our drive to help other artists. With the blessing from DVD Global Empress the Queen Of South Beach, Florida, we signed and also have the ability to assist emerging artists in distributing their music through an established industry label.
We’ve also recently just partnered with a television network Xperience Television as a brand ambassador as well.
Today, we represent a growing roster of talented artists from Orlando and Atlanta, helping them navigate the complexities of the music business. For us, it’s about more than just distributing music it’s about supporting these artists, guiding them through the process, and ensuring their voices are heard in an industry that can sometimes feel overwhelming.
Looking back on the journey, it’s clear to me that everything we’ve done has been about connection. Whether it’s through the podcast or the music label, our mission has always been to plant seeds. We see ourselves as a space where artists, entrepreneurs, and creatives can come together to grow and learn from each other. Just as the podcast was built to share stories and wisdom, Underdawgs Worldwide is designed to help artists plant their seeds in fertile ground, so that they can cultivate their own success and inspire others along the way.
It’s been an incredible ride so far, and we’re just getting started. Our journey is a testament to the power of collaboration, positivity, and giving people the platform to share their stories. And as we continue to grow, I hope our story serves as a reminder that no matter where you come from or what challenges you face, you’re never alone and you have the power to change the narrative.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
There was a moment during our journey when things slowed down, and it was a moment I will never forget. Due to personal reasons involving family, we had to cease production on the podcast for about six months. It was a difficult decision, one I wasn’t prepared for. The weight of the situation left me feeling disconnected, and honestly, I didn’t feel like myself. I questioned whether we’d be able to continue, but we had so much content already in the pipeline that I knew we had enough to hold us over.
Despite the break, something incredible happened. The platform continued to grow even while we were on pause. People were still discovering the podcast, and the support from our audience never wavered. It became clear that the message we were sharing, the positivity and the stories of resilience, were resonating with people in a meaningful way. The podcast had a life of its own, and it was growing without us having to force it.
When I finally made the decision to pick the ball back up and get back in the game, it was almost as if we’d never left. The transition back into creating new episodes felt seamless, and it reminded me of how much this platform had become a part of me. The connection with our audience was still there, and the energy was even stronger than before. It was a testament to the power of consistency and the passion of the people who supported us, even when we were temporarily absent.
That experience taught me a valuable lesson about resilience and the importance of staying true to your purpose. No matter how hard things get or how many obstacles you face, if you’re doing something that aligns with your passion and purpose, it will find a way to thrive. I didn’t know it at the time, but that break was exactly what we needed to reset and refocus on our vision. It gave us the clarity to come back even stronger.
Looking back, the journey has been one of growth and reinvention. We’ve learned that every setback is an opportunity for a comeback, and that no matter the challenges, we have a platform that’s meant to change the narrative. Through it all, we’ve remained committed to uplifting others, planting seeds of wisdom, and inspiring those who follow us to keep pushing forward, no matter what obstacles come their way.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I’m Fleetwood Jr., originally from Orlando, Florida. I’m one of the founders of Da Underdawgs Podcast and a recording artist signed with Empire/GT Digital. First and foremost major shoutout to the Queen of south beach a legend in hiphop DVDGLOBALEMPRESS for recognizing my hard work and dedication providing me the opportunity to sign with empire as well as become apart of a roster of a talented roster of individuals such as Problema lirical , AlceF , lordmaji, BigKingDaGoat,
When it comes to my podcast, I’m incredibly proud of reaching Season 9, with over 100 episodes and more than 100 guests. We’ve gone global, and it’s humbling to see the impact we’ve had—especially when we hear from our audience about how we’ve inspired them. Consistency and authenticity have always been at the heart of what we do, and it’s amazing to see how that’s been recognized.
In music, my proudest moment has been signing with Empire, as well as aligning with 4DaCultureWorldwide, one of the biggest teams in South Florida. These milestones have been huge for me, both personally and professionally.
What sets me apart is my approach to music and content. As an artist, my wordplay is one of my defining traits. I take pride in wrapping my bars in layers that allow the listener to unravel and truly appreciate the depth of what I’m saying. I use heavy lingo and alternative ways of expressing myself, pulling in references that make my music more intriguing to me—and hopefully to my audience as well.
As for our podcast, what makes it unique is how organic and genuine it is. We didn’t come into the game chasing any specific goal; we just followed our instincts and let the content speak for itself. I believe both in music and as a content creator, it’s important to keep it less stressful by staying true to what feels right, and that’s exactly what we’ve done.
Can you talk to us a bit about happiness and what makes you happy?
What makes me happy is seeing the impact and growth of what we are doing. As I stated we are all connected and we are all servicing and helping each other as we continue to elevate
Contact Info:
- Website: https://Www.underdawgsww.com
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