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In this conversation, I sit down with Rashan Brown—spoken word poet, founder of Poetry Me Please, and someone who's masterfully building his creative vision alongside a full-time career. What started with heartbreak in high school and a fascination with battle rap has evolved into a platform that's bringing spoken word poetry to stages like Brooklyn's Kings Theatre. Rashan's journey is the perfect example of what's possible when you commit to your authentic path without sacrificing financial stability.
We dig into the real challenges of entrepreneurship—the events that profit, the ones that don't, and why he views every "loss" as an investment in Poetry Me Please's future. He shares how having a nine-to-five has actually given him the freedom to take creative risks without the pressure of needing every event to generate revenue. We also explore the deeper "why" behind Poetry Me Please—how it's become a vehicle for healing, community building, and creating spaces where artists can express themselves authentically. Rashan opens up about the internal work required to sustain this vision, the importance of conviction over certainty, and those early breadcrumb moments (like performing Maya Angelou at Virginia Tech with Nikki Giovanni) that pointed toward his future.
This conversation is for anyone who's ever felt torn between creative passion and practical reality. Rashan proves you don't have to choose—you can build both, one intentional step at a time.
Takeaways
By Justin Castelli5
1010 ratings
In this conversation, I sit down with Rashan Brown—spoken word poet, founder of Poetry Me Please, and someone who's masterfully building his creative vision alongside a full-time career. What started with heartbreak in high school and a fascination with battle rap has evolved into a platform that's bringing spoken word poetry to stages like Brooklyn's Kings Theatre. Rashan's journey is the perfect example of what's possible when you commit to your authentic path without sacrificing financial stability.
We dig into the real challenges of entrepreneurship—the events that profit, the ones that don't, and why he views every "loss" as an investment in Poetry Me Please's future. He shares how having a nine-to-five has actually given him the freedom to take creative risks without the pressure of needing every event to generate revenue. We also explore the deeper "why" behind Poetry Me Please—how it's become a vehicle for healing, community building, and creating spaces where artists can express themselves authentically. Rashan opens up about the internal work required to sustain this vision, the importance of conviction over certainty, and those early breadcrumb moments (like performing Maya Angelou at Virginia Tech with Nikki Giovanni) that pointed toward his future.
This conversation is for anyone who's ever felt torn between creative passion and practical reality. Rashan proves you don't have to choose—you can build both, one intentional step at a time.
Takeaways

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