Alright – so today we’ve got the honor of introducing you to Corey James Gray. We think you’ll enjoy our conversation, we’ve shared it below.

Corey James, thanks for taking the time to share your stories with us today What’s the best or worst investment you’ve made (either in terms of time or money)? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)

The best investment I’ve ever made, hands down, has been in myself. Whether that was funding my own tours, buying gear when I didn’t know how I’d pay rent, or taking time to build platforms like Freestyle Mondays and Soul Cypher from the ground up. I’ve always bet on me, and the return on that investment has been undeniable, not just financially, but in terms of impact, longevity, and alignment with who I am as an artist and human.

Early in my career, I passed up offers that didn’t align with my values because I believed I could build something more sustainable and real. Some off my friends and family thought I was crazy but my choices led to performing in over 29 countries, working with the US State Department as a Cultural Ambassador, and creating programs that help people find their voice through freestyle and mindfulness. I didn’t wait for permission. I reinvested every dollar and every lesson learned back into my craft, and into building community.
If there’s a ‘worst’ investment, it’s probably the times I hesitated or underestimated the value of what I had to offer. But even those moments taught me something. The lesson? Bet on yourself, fully. Not just when it’s convenient or safe but when it’s necessary.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I was born to do what I do. My mom sang in church, my pops played the drums, and my godmother saw my love for music early and gifted my first drum set when I was 3 years old. Family events were like mini talent shows, skits, songs, performances; the kids were invited to entertain, and I embraced it all. I’ve been performing for as long as I can remember. Even though I’m naturally introverted, I’ve built a career centered around expression and connection. Hip Hop became the bridge between my scared inner world and the unlimited possibilities I dreamt of. It honed my public speaking, built my confidence, and assisted in me finding community around the world. Music became my way of being seen and heard. I grew up in a household that celebrated children being quiet. You were a “good kid” if you kept your mouth shut.

From early on, I knew the stage was where I belonged. There’s always a moment of nerves before a show or presentation, but once I’m in it, everything else fades away. Time slows down, the world quiets, and I am able to show up and show out. That level of presence has always confirmed that I was built to do what I do, not just for the performance itself, but for the way performance connects us to something deeper within ourselves and with others.

A major part of my journey has been Freestyle Mondays NYC. Now in our 24th year, Freestyle Mondays is a live band Hip Hop event, home of NYC’s MC Gameshow Competition, and a thriving community where we network, build, and share our Art. I co-founded it and continue to serve as CEO, producer, and host. Centered around live improvisation, lyrical games, and community, it became the space where I sharpened my skills, explored vulnerability, and discovered how freestyle could be a tool for personal and collective transformation. That experience laid the foundation for what would eventually become Soul Cypher.

Soul Cypher is a somatic approach to creative coaching that uses the essence of Hip Hop to help you tap into your authentic self. Through this work, I’ve seen participants finish creative projects like books and albums, conquer public speaking fears, and shift life paths entirely – new jobs, new relationships, and major breakthroughs. One of the most profound things has been witnessing two participants with traumatic brain injuries share that Soul Cypher assisted them more than their prescribed cognitive therapy post-surgery. That speaks volumes about the power of voice, embodiment, and creative play. And truly, one of my favorite moments is when someone who’s struggled with confidence suddenly finds themselves commanding a room, whether it’s face-to-face, in a group, or on the mic in front of an audience. Watching people step into their voice and own it? There’s nothing like it.

Of all the roles I play, the one I’m most proud of is being a dad. Fatherhood has kept my curiosity alive, the part of me that loves to play, explore, and take creative risks. It’s also given me the opportunity to reflect on my own childhood and illuminate the dark parts. In many ways, it’s allowed me to rewrite the story, not just for myself, but for my bloodline. It’s about breaking cycles and building new ones, rooted in love, creativity, and intention.

I love working with high-performance individuals, people who push themselves and operate under pressure, because I know that world intimately. I have the ability to thrive in high-stake environments, but I also know the value of rest and recalibration. Leaving NYC seven years ago to live in the Caribbean shifted my relationship to time and productivity. It taught me how to create space, not just to think, but to feel, and to tap into deeper wells of my own creative energy…drip drip.

Soul Cypher is voice activation, throat chakra work, that creates a safe and playful environment for growth and self realization. While I work with people from all backgrounds, I prioritize uplifting the voices of the underserved, especially Black and Brown folks. I’m drawn to people who are ready to face themselves, to peel back the layers of identity they’ve built around their jobs, families, or trauma, and explore what’s really there beneath it all. The nervous/excited energy people get right before a breakthrough? That’s home for me.

Whether I’m hosting, DJing, performing, or leading a workshop, my goal is always the same: to connect to the energy of the room, meet people where they are, and take them on a journey. I am able to get every person in the space to feel like I’m speaking directly to them. That’s a gift I don’t take lightly. It crosses over from stage to classroom, especially in those moments when the energy dips when teaching. Being able to read the room, shift gears, crack a Dad joke, or introduce fresh engagement, that ability to reset the energy is everything. It’s the same with DJing. If you linger too long at one BPM or genre, people tune out. Knowing when to pivot keeps things rocking, and I pride myself on bringing that awareness into every space I enter.

As a creative coach, I work across disciplines: DJ coaching, voice activation, freestyle mentorship, creative consulting, even psychedelic integration work using psilocybin in micro and macro sessions. I’m currently launching creative retreats in Grenada, and I host both virtual one-on-one sessions and virtual quarterly group programs. All of it is built around helping people unlock their creative voice, face themselves with curiosity and courage, and take steps toward their most aligned life. If this tickles your soul peace then hit up www.soultocypher.com
I’m also working on my first self-produced album, which I hope to release later this year, a project that reflects everything I’ve lived, taught, and navigated through.

At the end of the day, my work is about freedom through creativity, voice, rhythm, and story. It’s about using art as a vehicle for truth-telling and transformation. Whether I’m rocking a stage, coaching a client, or sitting in silence with someone in ceremony, I’m always listening for the deeper rhythm, the one that brings us home to ourselves.

Can you share a story from your journey that illustrates your resilience?

When I moved to NYC, I had $3,000, a couple of suitcases, and a dream, all packed into my little Geo Storm. I grew up in Massachusetts, so “home” was about a 4 to 6 hour drive away. I ran through that money quickly and had a hard time finding steady work. One of the only things that kept me afloat in those early days was selling knives for a company called Cutco.
They recommend starting with people you know, but I didn’t have any connections in NYC. So I started driving back and forth to Massachusetts twice a week to sell knives to family members. Shoutout to them for believing in either me or the knives. That job helped me pay rent and stay focused on keeping my music dream alive.
Eventually, I met my then girlfriend, a B-girl, who brought me to Breaking Battles. A lot of them also had MC battles with a cash prize. That circuit kept me going until I found my footing and co-created Freestyle Mondays.

Any resources you can share with us that might be helpful to other creatives?

Honestly, the most powerful resources weren’t external. I wish I had known earlier about the value of quiet, stillness, meditation, and grace. Just learning to slow down and be with myself would have saved me from a lot of unnecessary struggle and I may have less gray hairs.

Understanding that everything has its seasons was a game changer. Once you shift your perspective and start to see that things happen for you, not to you, it reframes how you experience rejection, delays, or detours. What used to feel like failure now looks like redirection. That mindset alone has been one of the most invaluable tools for me.

Contact Info:

• Website: https://www.soultocypher.com
• Instagram: https://www.instagram.com/coreyjamesgray
• Other: www.coreyjamesgray.com
  www.freestylemondays.com