Conversation With Mackwop

In this episode of No Ceilings , Glasses Malone sits down with Mackwop of Top Dawg Entertainment for a candid conversation about hip-hop, branding, and the realities of building a career in music. Mackwop reflects on “falling into” rap before realizing how much he still needed to learn about the business side of the culture—from understanding BPMs and hit records to marketing, branding, and artist development.

He shares stories about early mentorship, creating records like “200,” quitting his job to fully pursue music, and approaching early label deals with a hustler mentality instead of a long-term artistic vision. The discussion also explores the evolution of streaming, podcasting, and independent media following projects like Tupac Must Die , an iHeartMedia podcast deal, personal setbacks, and the release of Cancelled .

Mackwop and Glasses unpack how digital platforms have become more difficult yet more powerful for shaping identity, building community, and giving outsiders a fuller perspective on street culture. They also critique the rise of “hood vlogs,” the commercialization of street credibility, and the lack of accountability surrounding cultural exploitation—delivering a raw conversation on authenticity, survival, and protecting the integrity of hip-hop culture.

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