Urban Grind TV Season 33 continues with an episode rooted in Chicago media, hip-hop history, entrepreneurship, and longevity as Lisa E. and Swing are featured in Season 33, Episode 11.
This episode brings together two guests who have experienced the entertainment business from very different sides — one through decades of radio and media production, the other through Chicago hip-hop history, major industry connections, and a career built through music and culture.
Lisa E.: Building a Career Behind the Microphone and Behind the Scenes
Lisa E. has built her career in radio and entertainment from the ground up.
Her journey began as an intern before expanding into work as an executive producer, on-air personality, podcast host, educator, entrepreneur, and entertainment professional.
Today, she continues to work across multiple areas of media through Lisa E. Entertainment, while using her experience to help others understand what it actually takes to build a sustainable career in radio, podcasting, production, and entertainment.
Her work extends beyond being in front of a microphone.
Lisa’s experience includes production, media relations, event hosting, public relations, voiceover work, artist management, celebrity and charity events, and education designed to help aspiring media professionals learn how to structure shows, book guests, secure sponsors, and approach the business professionally.
Her Urban Grind TV conversation gives viewers a look at the work behind a successful media career — including the discipline, relationships, preparation, and consistency required to remain relevant in an industry that continues to change.
Swing: A Living Piece of Chicago Hip-Hop History
The episode also features Swing, a veteran of Chicago hip-hop whose story stretches back to an era that helped shape the city’s musical identity.
Coming from Chicago’s North Pole side, Swing’s journey includes an early-2000s chapter connected to Bad Boy, along with experiences involving artists and movements tied to The Notorious B.I.G., The LOX, Do or Die, Crucial Conflict, and more.
Swing is also part of one of Chicago’s memorable records, “On My Momma,” appearing on the second verse and representing a period when the city’s hip-hop scene was developing its own unmistakable voice.
His story is not only about where he has been.
Swing is now working to preserve that history through his upcoming music and docuseries project, I WAS THERE.
The project revisits the artists, moments, relationships, performances, music, and culture surrounding Chicago hip-hop and the broader industry during the 1990s and beyond.
For Swing, documenting that history is about making sure the people who actually lived those moments have an opportunity to tell the story themselves.
Media Legacy Meets Hip-Hop History
What makes this episode unique is the way two different careers intersect around one common theme: longevity.
Lisa E. represents the behind-the-scenes discipline necessary to build a lasting career in media.
Swing represents an artist who experienced major chapters of Chicago hip-hop firsthand and continues finding ways to preserve, document, and contribute to the culture.
Together, their conversations highlight the importance of experience, relationships, reinvention, ownership, and making sure important stories are not lost.
Watch Urban Grind TV Season 33, Episode 11
Lisa E. + Swing
Urban Grind TV — Season 33, Episode 11
📺 Wednesdays at 11 PM CST
📡 Xfinity & Astound Channel 25 Chicago
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Urban Grind TV continues its mission of documenting artists, entrepreneurs, media professionals, and cultural figures whose stories deserve to be seen and heard.
Real people. Real stories. Real culture.