Over the course of his still-young career, Taylor Bennett has built himself into a formidable businessman in his own right. The Chicago MC, whose music often extends beyond the traditional boundaries of hip-hop, has been independently releasing music since his 2013 debut project, The Taylor Bennett Show, and grown significantly as an artist through his latest release, February’s Restoration of an American Idol.
Along the way, he’s taken full advantage of the opportunities that have come his way through branding and marketing deals and a savvy understanding of the complexities and intricacies of the business side of the music industry, while managing to maintain control of his career and music.
Lately, that’s been paying off in a big way. Bennett just finished up his first headlining tour, a 15-date, month-long run across the United States booked by his agent Cara Lewis, and recently launched his own label and management company, Tay Bennett Entertainment, alongside his manager Joseph Cabey. Those topics were on his mind when he and Cabey spoke to a class of college students at New York University’s Clive Davis Institute of Recorded Music on Thursday night (April 27), in a class taught by MAC Presents founder/president Marcie Allen that also featured Forbes senior editor Zack O’Malley Greenburg, CAA head of music partnerships Tom Worcester and desirelist CEO Eric Sheinkop as guest speakers.
“When you’re young, a lot of people underestimate you,” Bennett said about building his early career in Chicago, relating his and Cabey’s difficulties in locking down studio time and booking shows in the city. “That’s something we faced constantly.”
It’s also something to which many in the class could relate, and Bennett and Cabey took several questions from students throughout their 30-plus minute talk on branding, collaborating with other artists and the tricks to maintaining independence within the music industry.
“We don’t like to force anything,” Cabey said when asked about vetting brands that he and Bennett want to work with, noting that they’ve mostly partnered with legacy brands like Diesel and Timberland, although not necessarily exclusively. “When it comes to new brands, we look at, what are their core values?”
Bennett added that maintaining loose, familial relationships, rather than business-centric or transactional ones, is important in creating mutually-beneficial situations. “It’s all about family vibes, not something that’s so suit-savvy. We want to create some type of longevity [in the relationship].”
Bennett, who has collaborated with the likes of King Louie, Lil Yachty, Jeremih and his older brother Chance the Rapper over the years, also explained what he looks for when working with other artists. “The first thing is, what sounds good? It’s always about that natural feel,” he said. “Because it’s about the product — that’s what you’re selling.”
He also explained that, while he doesn’t feel artists should be required to make positive music for their communities, his own material does have an overarching point: “My idea in making music has always been about bringing genres together, bringing people together.”
Cabey said that the two of them are working on initiatives to benefit homeless youth in Chicago, and are looking to create a space where homeless youth can come and express their creativity, referencing the work that Chance the Rapper — often with assistance from Taylor and Cabey — has done and continues to do with his Open Mic events for high school kids in the city. “There’s no judgment there,” Bennett said. “All you hear is applause.”
When one student asked about the key to being independent, both Bennett and Cabey had the same immediate response: “Distribute your own music.” On major streaming services — Spotify, Apple Music, Soundcloud and the like — placement is key, they said, whether that’s on a service’s landing page or a top playlist like Spotify’s Rap Caviar, with its 6.5 million followers, and that making relationships goes a long way. But, Cabey added, “The first step is to cater to your fans; the power really lies in your fans.” Streamers, brands and corporations, he said, will assess and measure, “How much will your fans buy into you?”
Bennett ended on one student’s query about why he started his own label and management company by relating an anecdote that he said taught him about the underside of the industry. A producer with whom he’d been crafting a full-length project with demanded that he sell the music when it was finished, while Bennett wanted to release it for free; an argument ensued and the producer suddenly charged Bennett and Cabey thousands of extra dollars for studio time.
And while they eventually worked out a deal, Bennett resented being put in a situation outside of his control, and set up a situation for himself that included a vehicle for him to help others as well. “Why would I be so selfish,” he said simply, “as to keep all this [industry knowledge] to myself?”