The Breakfast Club INTERVIEW: Harry O Speaks On Calculated Communication, Reputation, New Book + More
Jun 10, 2025
Harold Wilkerson, known as Harry O, is an accomplished entertainment executive and author of 'It's Beyond Words'. He discusses the significance of calculated communication and reputation management in shaping careers. Harry shares his journey from rapper to industry executive, emphasizing trust and authenticity. He touches on media's role in shaping hip-hop identities, the impact of strong female role models, and the need for modernized curriculums in education. Throughout, he offers practical insights drawn from personal experiences and his new book.
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Harry O's Career Evolution
- Harry O started as a rapper signed to Uptown and worked with Puff Daddy and Murder Inc. before transitioning to an executive role.
- He built lasting relationships with artists like Ja Rule, evolving from artist to influential business figure.
Build Trust Before Business
- Build relationships strategically by connecting personally before making business proposals.
- Gain trust through genuine communication, letting relationships grow naturally before discussing deals.
Avoid Purely Transactional Talk
- Avoid making all communications purely transactional to maintain strong connections.
- Invest in genuine conversations that foster lasting relationships beyond just business deals.
