From Mall Heap to Microphone: Building a Music Career Between Two Worlds

Da Jamaican Boy’s music career started on a Caribbean mall heap with a stick as a microphone. Love letters became his first songs. After moving to Ontario, Canada, he recorded his debut solo track “Deep Ocean” in 2000 following a chance encounter at a Niagara Falls restaurant. He’s now featured on 20+ coast-to-coast mixtapes, blending Caribbean roots with Canadian influences.

How to Turn Musical Passion Into an Artistic Career:

Start where you are. Your childhood performances, no matter how humble, build the foundation for future success.

Transform personal expression into art. Love letters, journals, and daily writing become original songs when you’re honest.

Solo work requires different skills than collaboration. You need patience, hard work, and humbleness to create alone.



Blend your cultural worlds. Caribbean roots combined with new environments create unique artistic identity.

Your audience exists right now. Fans and supporters are waiting for your authentic voice.

What Were Da Jamaican Boy’s Early Musical Influences?

I can still see it clearly. Me and my friends standing on top of a mall heap in the Caribbean, using sticks as microphones, performing songs from our favorite artists. We weren’t singing. We were living in that moment, feeding off the energy, feeling the joy of music in our bones.

That mall heap was my first stage. Music was always my first love.

Growing up surrounded by Reggae and R&B greats shaped everything. I absorbed the rhythms, the emotion, the storytelling. Those performances on the mall heap weren’t practice. They were pure joy with my friends, using a piece of stick as the mic.

Bottom Line: Early musical immersion in Caribbean Reggae culture planted the seeds of passion that later grew into a professional career.

How Did Love Letters Become Original Songs?

I didn’t start creating my own music through traditional means.

I wrote love letters.

As a young boy, I wrote love letters to express connection and feeling. Those letters eventually transformed into songs because love songs were always my first passion. The inspiration from Reggae and R&B legends gave me the foundation, but the words were mine.

This shift happened naturally. When you listen to love songs from the greats, you learn how to express emotion. You learn how to tell stories. Then you take your own experiences and turn them into lyrics.

Bottom Line: Original songwriting often starts with personal expression in other forms. Love letters and written emotions evolve into lyrics when paired with musical influence.

What Happened After Moving to Ontario, Canada?

Moving to Ontario changed everything.

In high school, those mall heap performances evolved into backyard singing battles. My friends and I would perform for our classmates right after lunch. Different environment, different audience, same passion.

The audience loved the voice and the vibes. These Ontario schoolyard performances showed me what was possible. I wasn’t in the Caribbean anymore, but music still connected me to people.

After high school, I dove into the underground music world. I collaborated with other artists, learning the craft, finding my rhythm. I did a few collaborations before I ever recorded my first song.

But collaboration is different from standing alone with pen, paper, a mic, and a killer beat.

Bottom Line: Relocating to a new environment creates challenges but accelerates artistic development through exposure to different audiences and musical communities.

How Did “Deep Ocean” Get Recorded?

I was working in a restaurant in Niagara Falls, singing to myself. Someone approached me out of nowhere: “You got a good voice. I got a studio if you’re interested in recording.”

A few days later, I walked into that studio and recorded my first solo song. I wrote it on the spot. No preparation, no safety net. Just me and my truth.

“Deep Ocean” was about being a lover boy. Love songs were always my first passion, and that’s what poured out when I had to create something completely my own.

Recording a full song is not the same as a collaboration. No backup. No hiding behind another artist’s energy. Doing a solo track requires patience, hard work, and humbleness.

That first solo recording taught me something. You’re exposed and vulnerable when you stand alone. The process takes character, not talent or inspiration.

Bottom Line: The transition from collaboration to solo work reveals what you’re made of. Writing and recording alone requires patience, humility, and willingness to be vulnerable.

How Do You Blend Caribbean Roots with Canadian Influences?

I blend both worlds together now. What I learned in the Caribbean and what I learned in Ontario elevate me in the best way possible.

I use my Caribbean upbringing for rhythm, emotion, and cultural authenticity. I use my Canadian experiences for diverse collaboration, new audiences, and broader musical exposure.

I educate myself every day. Learning never stops. I try to learn as I go along each day because the music world keeps evolving.

After “Deep Ocean” in 2000, I released my first mixtape, “Hard Life,” to the world. I kept making music, kept releasing, kept growing. I’ve been featured on more than 20 coast-to-coast mixtapes alongside hundreds of other artists, both independent and major.

Bottom Line: Blending cultural influences creates a unique artistic identity. Caribbean roots provide authenticity while Canadian experiences offer growth opportunities.

What Does It Take to Start a Music Career?

Here’s what I know now that I wish I could tell that boy on the mall heap:

You have to start somewhere to make it somewhere. Nothing happens without giving life a try. Fail and try again if that’s the case.

Your daily life is music. Write what you feel. Love what you do. Sing from the heart. Build for tomorrow, not just today. Be honest to yourself and your art.

Music is art.

Never tell yourself you don’t have what it takes. We all have our own fans and supporters waiting. They’re out there right now, looking for the voice that speaks to them.

That voice might be yours.

Bottom Line: Starting is more important than perfection. Your authentic voice will find its audience if you’re honest, persistent, and willing to learn.

Frequently Asked Questions

How did Da Jamaican Boy get into music?

Da Jamaican Boy grew up in the Caribbean surrounded by Reggae music, performing on a mall heap with friends using sticks as microphones. This early exposure to Caribbean rhythms and culture planted his lifelong passion for music.

What was Da Jamaican Boy’s first recorded song?

His first recorded solo song was “Deep Ocean,” recorded in Niagara Falls in 2000. He wrote and recorded it on the spot in the studio after being approached by someone who heard him singing at a restaurant.

How did love letters become songs?

As a young boy, Da Jamaican Boy wrote love letters to express emotion and connection. Growing up listening to Reggae and R&B love songs inspired him to transform these personal letters into original song lyrics.

What’s the difference between collaboration and solo recording?

Solo recording requires different skills than collaboration. You stand alone with pen, paper, a mic, and a beat. There’s no backup, no hiding behind another artist’s energy. Solo work demands patience, hard work, and humbleness.

How did moving to Ontario impact his music career?

Moving to Ontario, Canada exposed Da Jamaican Boy to new audiences through high school singing battles and backyard performances. After high school, he entered the underground music scene, collaborating with other artists before recording his first solo track.

How many mixtapes has Da Jamaican Boy been featured on?

He’s been featured on more than 20 coast-to-coast mixtapes alongside hundreds of other artists, both independent and major. His first mixtape, “Hard Life,” was released in 2008.

How does Da Jamaican Boy blend Caribbean and Canadian influences?

He uses what he learned in the Caribbean (Reggae rhythms, emotional storytelling) combined with what he learned in Ontario (diverse collaboration, new musical styles) to create his unique artistic identity.

What advice does Da Jamaican Boy have for aspiring musicians?

Start somewhere to make it somewhere. Write what you feel, love what you do, sing from the heart. Build for tomorrow, not today. Be honest to yourself and your art. Your fans and supporters are already waiting for your authentic voice.

Key Takeaways

Early musical exposure shapes your foundation. Growing up surrounded by Caribbean Reggae culture created the passion that fueled Da Jamaican Boy’s entire career.



Personal expression evolves into art. Love letters became original songs when combined with musical influence and honest emotion.



Environment changes accelerate growth. Moving from Caribbean mall heaps to Ontario schoolyards exposed him to new audiences and opportunities.



Solo work demands different character traits. Recording “Deep Ocean” alone taught patience, humbleness, and vulnerability that collaboration never revealed.



Cultural blending creates authenticity. Combining Caribbean roots with Canadian experiences produces a unique artistic voice that stands out.



Starting matters more than perfection. You have to start somewhere to make it somewhere. Your audience is already waiting for your authentic voice.



Continuous learning drives longevity. Educating yourself daily and building for tomorrow, not today, creates sustainable career growth in music.