During the past few years, Taylor's Bennett's older brother, Chance the Rapper, has become one of the most successful independent acts in music. But as the 21-year-old Bennett will tell you, it's he, not Chance, who has been leading the charge in their native Chicago for years now. "I was one of the first people to do independent distribution in Chicago," Bennett, who released his second album, Restoration of an American Idol earlier this year, tells Rolling Stone. "I tried to sell music before my brother. I'm actually the reason Chance decided he was going to stream his music. And he also realized that if he streamed it he could get those Grammys. The funny thing about it is that even though Chance was touring [at my age]. I'm almost positive he wasn't making as much money as I am."
"Of course nowadays Chance is a baller," Taylor says with a laugh. "He's doing just fine."
Talking to the younger Bennett is not unlike consulting a music-industry textbook. The MC will gladly hold forth on everything from his knowledge of split sheets to royalty payments, master recordings and publishing. And he's certainly unafraid to voice his disdain for major record labels and their signing tactics.
"What record labels do is they say, 'When you sign to us you don't have to worry about anything else,'" Bennett explains. "'You want that watch? You get that watch. You want that car? You can get that car. You want to buy your mom a house? Why won't you buy your mom a house.' But a lot of artists don't know their advances are recoupments. Nobody gets paid a large sum of money and never has to pay it back. You pay it back through your record sales, your touring, your merchandise, features, agency deals, etc. Before you look up you've spent all this money. Now you owe all this money, and if you can't pay it back the label will drop you, shelf you, and they might even sue you.
"I'm friends with a lot of big artists and they're signed to labels and they have no idea what kind of deals they're in," he continues. "Everything is about percentages to these labels. Everything is about numbers. Everything is about commas. And they don't really give a fuck if you ever become the biggest artist in the world or if you're just another Joe what's-his-name."
Ultimately Bennett says it was a no-brainer then for him to remain independent. "Me, as well as my brother, we're really some do-it-yourself people," he says. "Don't chase the blogs. Let the blogs chase you. Don't chase the playlists. Let the playlists chase you. You be the best artist you can be and when you work hard independently eventually those opportunities will come."
It's why the rapper formed his own record label, Tay Bennett Entertainment, and recently signed his first artist, the Chicago-based singer-rapper Bianca Shaw. Today, Shaw debuts her soulful new Bennett-featuring single "So High" via Rolling Stone. Produced by Bennett's longtime collaborator, Ludlow, the track has an airy, guitar-anchored vibe, and according to the producer was based on a track he initially named "Pizza" because "it was so tasty." "The chemistry is undeniable," Shaw says of her and Bennett playing off one another on "So High." "As soon as we made it, we both looked at each other like, 'This is the one.'"
Raised in the West Chicago neighborhood of Lawndale, Shaw took in a diverse musical diet as a child, listening to everything from Nas, Eminem and Missy Elliott to Erykah Badu and Sam Cooke. She played in a "girl band" with her younger sisters and played drums in her church choir. Last year, when performing as a member of a band auditioning to back Taylor, the rapper's dad, Ken Bennett (who is now Shaw's manager), discovered her. "My dad called me and said, 'You need to listen to this girl. She's real good!'" Taylor recalls. "My dad has great taste in music so I took him seriously."
Taylor agreed. Since signing to TBE, Shaw and Bennett have grown close, as she works on a forthcoming EP and full-length album. "I feel like they've adopted me into their family," Shaw says. She'd long respected Taylor and Chance's independent streak, and to that end, she says, "I want to follow in those same footsteps. I feel like I'm in great hands."
"What a lot of artists need is a solid foundation," Taylor offers of his mantra as a label boss. "As big as I want my artists to be, I want them to be happy."