We were lucky to catch up with Tyquan Chislom recently and have shared our conversation below.

Alright, Tyquan thanks for taking the time to share your stories and insights with us today. When did you first know you wanted to pursue a creative/artistic path professionally?

I knew I wanted to pursue this path when my words started haunting me. Writing was the first outlet poems, stories, whatever I could get down and then music gave those words a rhythm. I’d loop beats off YouTube, freestyle, and fill my phone with notes until it became more than a hobby. The first time people leaned in and really felt what I wrote or rapped, I knew this was bigger than me. From then on, I treated it like purpose turning pain into art, whether on the page or on a track.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

I go by Jackboyskii — rapper, writer, author, and storyteller. I came up in environments where you had to find your own way to be heard, and for me that outlet was writing first. Journals, poems, raw thoughts in my phone I was documenting my world before I even knew it was art. Music came after, giving those words a rhythm, a heartbeat, a way to travel beyond me.

What I create lives at the intersection of rap and neo-soul gritty storytelling wrapped in soulful textures. My writing is unapologetic: I talk about pain, survival, healing, and chasing peace. My music carries that same energy it might hit hard with street grit, but it always holds soul, honesty, and reflection. That mix is what sets me apart. You don’t just hear it, you feel it.

Beyond music and writing, I also run _maskedtherapy_ on Instagram  a platform where we take off the masks, talk about trauma, laugh, cry, and heal through real stories. It’s therapy without the suit and tie: raw conversations, spoken word, and community. maskedtherapy bridges the gap between my art and my purpose, giving people space to process their own journeys while connecting with mine.

On the writing side, I’m an author and poet, turning lived experience into books that read like survival guides and confessionals. On the music side, I’m crafting a sound that blends street reality with soulful elevation. Together with maskedtherapy, it gives my supporters both a voice they can nod their head to, words they can sit with, and conversations that can help them heal.

What problem do I solve? I give people language for what they’re going through. A lot of us grow up holding in trauma, pain, confusion —
I put it on the page, in the booth, and on platforms like maskedtherapy so folks know they’re not alone. My work creates conversation, relatability, and in some cases, a roadmap to healing.

What I’m most proud of is that I’ve never watered it down. Whether in my books, my lyrics, or my storytelling on maskedtherapy, it’s always the real me. No masks, no gimmicks just raw honesty with craft behind it.

What I want people to know about my work is this: I’m building more than songs, books, or posts I’m building connection. If you tap into Jackboyskii, you’re tapping into a brand of truth-telling that doesn’t flinch from the dark but always searches for the light. I stand on being authentic, versatile, and impossible to box in because life is messy, layered, and worth telling in full color.

What do you find most rewarding about being a creative?

For me, the most rewarding part of being a creative is the connection. When somebody tells me a song got them through a rough night, or a piece of my writing put their own unspoken feelings into words, that’s everything. It reminds me that what I create isn’t just about me it’s about building bridges through honesty.

I love watching how raw truth can shift energy. A verse, a poem, a conversation on _maskedtherapy_ those moments turn pain into power, for me and for the people who hear it. That’s the reward: knowing my art has the ability to heal, inspire, and make somebody feel a little less alone.

Are there any books, videos, essays or other resources that have significantly impacted your management and entrepreneurial thinking and philosophy?

Yeah, for sure. A few resources really shifted how I think about building as an artist and entrepreneur. Books like The 48 Laws of Power and Rich Dad, Poor Dad opened my eyes to strategy, discipline, and financial literacy lessons I carry into both music and business. I also connected with Nipsey Hussle interviews and Jay-Z’s perspective on ownership; their words showed me how to move with intention and build something that lasts beyond the art itself.

But honestly, a lot of my “resources” came from lived experience being in the streets, running my own plays, and learning the hard way. I study the game by watching, listening, and applying. That mix of real-life lessons and the wisdom I picked up from books, podcasts, and videos is what shaped my philosophy: ownership, consistency, and authenticity over everything.

Contact Info:

• Instagram: Jackboyskii / _maskedtherapy_ / OTM.merch
• Other: Can find my music on Apple music and Spotify under the moniker @Jackboyskii

Image Credits

Luis Sanchez