2 weeks ago
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Chad Williams has worn many hats in the world of culture and entertainment, from sound system operator to entrepreneur and festival director. His career was sparked by bass lines and vinyl. As a teenager, he built a sound system that taught him how music could bring people together. That early lesson stayed with him even as he studied business abroad and began shaping a vision for entertainment back home.
He later moved into restaurants and lounges, places that celebrate culture and bring people together. In 2017, Streetz Festival became the next step, combining food, music, and culture on one stage. Now in its fifth year, the festival continues to be a space where communities connect and experiences come alive.
Drawing inspiration from a family steeped in entertainment, the energy of the streets, the resilience of the Jamaican people, and pride in local culture, Williams has built his career on creating spaces that feel alive. With Dragon Stout backing Streetz, he is ready to write another chapter in Jamaica’s festival story. In this edition of 5 Questions With..., Williams reflects on the beginnings of his career, the passion that drives him, and the lessons he carries into every new venture.
1. What drives you to continue bringing new experiences to Jamaica?
Potential! Jamaica has always been at the forefront of global culture; but I feel our people deserve to experience that same level of innovation at home. What drives me is seeing faces light up when we introduce something fresh – whether it’s a new concept at Streetz or in one of my businesses. It’s about pride, representation, and showing that Jamaica can host world-class experiences without losing its authenticity. I’ve been able to channel this through various experiences like parties; restaurants like The Porch, Oceano, and an exclusive membership lounge called The Republic.
2. How did the idea for the Streetz Festival first come to you, and what gap did you feel it could fill in Jamaica’s entertainment scene?
The idea was born between my partners and me. It came from recognising that there was a disconnect between our everyday street culture and the big entertainment platforms. Streetz Festival was designed to bridge that gap to take the raw energy of the streets and put it on a stage where it could be celebrated, respected, and enjoyed by everyone. I felt Jamaica needed a space where dancehall, fashion, food, and community could live side by side as one unified experience.
3. What does street culture mean to you personally, and how is that reflected in the festival’s vibe?
Street culture is Jamaica’s heartbeat. It’s the creativity, hustle, and unapologetic self-expression that you see every day. It reminds me of my own journey in a sense, starting from humble beginnings and building something bigger. At Streetz Festival, that vibe comes through in every detail: the music, the food stalls, the fashion, the art installations. It’s raw, real, and proud.
4. When people think of Chad Williams, what legacy do you hope they remember, both professionally and personally?
I want to be remembered as someone who created things that excited, elevated Jamaica’s culture, and inspired others to dream bigger.
5. What’s a piece of advice you would give to young creatives or entrepreneurs looking to build something impactful?
Don’t be afraid to start small; but start with purpose. Focus on building something authentic that represents who you are and what you believe in. Most importantly, be deliberate and don’t be afraid to go alone. Stay consistent, stay resilient, and never lose sight of why you started.
BRAWTA:
Outside of work, what is a hobby that you enjoy doing?
That’s a constant struggle, but I am working on balance. Outside of work, I try to travel and explore new food [and] cultures. It’s inspiring to see how different places celebrate food and music; it always sparks ideas that I can bring back to Jamaica. On a simpler level, I enjoy just kicking back with close friends and family.
English (US) ·