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Ep 14. The Music Industry Taught Him Power. The Classroom Taught Him Purpose.
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He was signed to Uptown Records as a teen.
He went on world tour with Diddy.
He worked behind the scenes of some of the biggest moments in music.
And then—he walked away.
Today, Harold Wilkerson (@uptownharry0) is a college professor, communication strategist, and founder of @chase.republic, where he teaches high-level professionals how to lead with clarity, confidence, and calculated communication.
In this episode of Success Unscripted, Harold shares the transformation that took him from the studio to the boardroom—and why he’s done playing the background.
We dive into:
- Why working with Sean “Diddy” Combs changed his path—and his mindset
- How media distorts identity, especially for men of color, and how to take it back
- The four types of self: open, blind, hidden, unknown—and why most leaders crash into their blind spots
- What it means to communicate with purpose, not performance
- Why he’s stepping into the spotlight—for good
Harold’s book, It’s Beyond Words: The Art of Calculated Communication, is available now on Amazon:
https://www.amazon.com/dp/B0F732MQS6
This episode is for the leaders who know they were never meant to stay silent.
In this episode, Harold shares his personal experiences working with Sean “Diddy” Combs. These are personal reflections, not endorsements. At Success Unscripted, we believe in making space for complex truths, integrity, and honest conversation.
Enjoyed this episode? or want me to cover a specific topic? let me know! message me @jessicarivera.co or check out my website JessicaRivera.co
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