We caught up with the brilliant and insightful Brandon Bishop a few weeks ago and have shared our conversation below.
Brandon, thanks for taking the time to share your stories with us today The first dollar you earn is always exciting – it’s like the start of a new chapter and so we’d love to hear about the first time you sold or generated revenue from your creative work?
The first time I earned money from my music was when I got a paid show in November of 2023. I was booked by Keisha Kautiouz of Ear Hustlin Entertainment, to headline her show on Black Friday. Very few words come to mind that do the feeling justice. I was so grateful to be seen as someone who was worth paying to perform. Having my name on the up in lights for first time made me feel like i had made it and signed a record deal. The show was dope and I received payment without issue. That moment means the world to me and I will honestly never forget it. I am so grateful to have had the opportunity to make money off doing what I love.

Brandon, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
Brandon Bishop, professionally known as Cyphersick, is a Chicago-based lyricist and independent recording artist. Known for his raw storytelling and authentic lyricism, Cyphersick has been a force in the Rap/Hip-Hop scene since his early teens. Growing up in Chicago’s “Low End” neighborhood shaped his artistry, infusing his music with the resilience and grit that come from life’s trials and tribulations.
Cyphersick began his journey at the age of 14, and by 16, he had an agent, Reginald Scott aka Quest. At 17, he signed with Chicago’s independent label D.U.B. L.I.F.E. Entertainment, where he honed his craft before returning to independent status. Over the years, he’s caught the attention of prominent industry names such as DJ SMALLZ, Coast 2 Coast Mixtapes, A&R Hits, and Slip N Slide Records.
His early career highlights include performing at open mic events across Illinois and Indiana, Columbia College, and the first two Midwest Rappers Balls in Chicago. A standout moment was his performance at the Sturgis Motorcycle Rally in South Dakota, earned through his music’s strong performance on Biz-Zar internet radio, where he charted in the Top 100 for nearly a year. Cyphersick has also shared the stage with notable artists like Project Pat, Stove God Cooks, Fuego Base, Bone Thugs-N-Harmony, Waka Flocka Flame, Shawnna, and Sasha Go Hard.
After years of grinding in the music scene, Cyphersick took a seven-year hiatus to focus on personal growth and building a career outside of music. His ventures in customer service and IT support provided him with new perspectives and resources, enabling him to travel the country and broaden his worldview. This journey of self-discovery is evident in his evolved sound and introspective lyrics.
In 2023, Cyphersick returned with a vengeance, releasing his single “$urvivor” on September 15th, featuring Henny Roxx and Ace G $M.I.E.$. The track, a powerful anthem of resilience, has been met with acclaim from fans and peers alike. His music continues to resonate deeply, telling stories of survival and triumph that reflect his experiences growing up in Chicago.
Cyphersick’s talent has taken him on tours to cities like Phoenix, Hartford, Houston, Atlanta, Gary, and Aurora. His music has also been featured on major radio platforms, including Shade 45, Power 92, and 90.7 FM. Beyond his performances, he’s built connections with East and West Coast artists, forming meaningful relationships with talents who have inspired him throughout his career.
In addition to his recent single, Cyphersick has released an official music video for his track “Plug Str8” featuring Fuego Base. The video showcases his signature style and further cements his place in the Hip-Hop scene. He has also released two installments of his highly anticipated trilogy of projects, My Time 1 and My Time 2, which are available now. The final installment, My Time 3, is set to drop in late 2025.
Now 34, Cyphersick is determined to cement his legacy as one of Chicago’s standout artists. With his unwavering passion and a fresh perspective, he’s proving that a hiatus doesn’t diminish greatness—it amplifies it. The comeback season is here, and Cyphersick is ready to leave an indelible mark on the music industry

In your view, what can society to do to best support artists, creatives and a thriving creative ecosystem?
The best thing society can do to support artists is to show underground/unsigned artist the same love they show their favorite major artists. Buy tickets to shows, buy their merch and wear it in pictures that you post on social media and tag the artist, pay for their music instead of getting it for free on streaming platforms, add them to your playlist on streaming platforms, subscribe to their Youtube channel and follow all their social media site. There are so many ways to support a thriving creative ecosystem when you care about the culture. People just have to do it.

What do you think is the goal or mission that drives your creative journey?
My mission is to inspire others to never give up on their dreams by me making mines a reality. People who come from nothing need something as proof of concept. They need to see someone else who looks like them win before they realize that they can too. That is the focal point of my journey as a creative right now. Music and art saved my life through people who inspired me. I am a firm believer in paying that forward.
Contact Info:
- Website: www. Cyphersick.com
- Instagram: @Cyphersick
- Facebook: Cyphersick
- Twitter: @RealCyphersick
- Youtube: Cyphersick

Image Credits
Photo Credit: @SkillzOnTheBeat

