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Music Executives Are Dominating the Industry Again

Kevin Liles of 300 Entertainment is CEO, adviser, therapist, and life coach. It pays.
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Photographer: Heather Sten for Bloomberg Businessweek

Since the pandemic began, Kevin Liles has been running his New York record label, 300 Entertainment, from the patio by the swimming pool at his home in suburban Cresskill, N.J. Early one afternoon in January he’s there, smoking a cigar and conducting a staff meeting on Zoom. He doesn’t seem to notice that it’s started to snow. Sitting at a table near a blazing open-air fireplace, clad in a red hoodie and a green beanie with a pompom, Liles pelts his employees with questions about the performance of a potential hit, Play w/ me, by Bailey Bryan, a country singer turned edgy pop chanteuse. She’s scheduled to perform it on The Late Show with Stephen Colbert’s YouTube channel. Liles wants his promotions people to flog the tune harder to keep the streams coming.

Then Liles has what he later describes as a moment of divine inspiration. He tells his people that during this time of Covid‑19, protests against police brutality, and the storming of the Capitol by Trump-inspired goons, they should reach out to one another and make sure nobody is having mental health issues. Ending on that note, he hurries upstairs to grab something in his home office, a large space with pictures of himself with Oprah Winfrey, Bill Gates, and Barack Obama. As he walks he starts another call, with his chief financial officer. “When God talks to me, I gotta say something!” Liles tells his CFO.