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Success Unscripted with Jessica Rivera
Ever feel like success comes with a script—one that doesn’t quite fit you? Welcome to Success Unscripted, the podcast where we break the mold, rewrite the rules, and redefine what it means to truly thrive. Forget the traditional rules and cookie-cutter blueprints; this is where we dive deep into the power of your words, your presence, and your influence to help you create lasting impact.
Whether through solo episodes packed with actionable strategies or raw, unfiltered conversations with industry leaders and unconventional success stories, this podcast delivers more than just inspiration—it’s a roadmap for transformation. From navigating leadership and building belonging to stepping into your authentic power, Success Unscripted is here to help you thrive.
Hosted by Jessica Rivera, an executive coach and business consultant who has led a $4 billion division and coached Fortune 100 and Fortune 500 leaders, this podcast combines real-world expertise with a fresh perspective.
Tune in to unlock your potential and redefine success for every season of your life.
Success Unscripted with Jessica Rivera
Ep 14. The Music Industry Taught Him Power. The Classroom Taught Him Purpose.
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
