Empowering Independence: Taylor Bennett Talks Indie Success

“I think that you have to fail in order to know how to succeed.”
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Success comes at the behest of consistency. At least, that’s how Chicago’s Taylor Bennett sees it. By all accounts, Taylor is an independent success story: he has his own label, he owns his own masters, and he can help other artists grow their careers. His career is the product of thoughtful trial and error, but also of hours of research and making the right decisions to put himself in the best possible position to control his creativity and his financials.

“It’s important that I’m an independent artist, so I can say ‘No,’” he tells me. “It’s about being able to say ‘No’ and learn from it. I think that you have to fail in order to know how to succeed. If you don’t succeed the first time, you gon’ try it again. It’s the same situation for a lot of artists, there’s a lot of things that they’re going to fail at before they’re going to do it. The worst thing that an artist can do is end up taking a contract that confines them. Then you don’t get to fail.”

With that, Bennett has had his fair share of hurdles, from growing up in Chicago (“I was an inner city kid in Chicago; you learn from a lot of different situations”) to just recently becoming a new father. Along the way, preserving his independence has allowed him to keep his creativity burgeoning in the face of adversity. Being the ultimate decision-maker in his career has made everything from his upbringing to fatherhood more manageable.

At the center of his independence is distribution, promotion and revenue platform, TuneCore. “When we found TuneCore, we instantly knew that it was the application that we needed to further my music career,” Taylor says. In 2014, he first used TuneCore and fell in love with the opportunity to stand alongside big-time acts like Drake on iTunes. “It was next to Drake. For me, as an independent artist, to be able to see my music next to Drake’s music, that’s when I fell in love with TuneCore.”

From there, Bennett pursued understanding the music business with a fervor. Not just for himself, but to help other artists understand everything from splits to royalties and mechanicals. He was the one who showed TuneCore to our beloved Chicago son, Chance The Rapper. “Something that’s very rewarding, for me, is building my career but also helping other artists build their careers through my label, Tay Bennett Entertainment,” he remarks.

With the help of TuneCore and his know-how, Taylor never thinks about a major label deal. His dreams are worth too much to give away a percentage so freely. While he is undoubtedly the picture of independent success, he stresses that it wasn’t for lack of trying.

“If you wanna be an independent artist, the real tactic is how independent and how much are you willing to get your hands dirty?” Taylor stresses. “How often are you willing to make business calls? Do you wanna go to the gym and work out, or do you wanna drink lean and smoke? Do you really do the background work?”

Our full conversation with Taylor Bennett, lightly edited for content and clarity, follows below.

DJBooth: Let’s start with: Why is being an independent artist important to you?

Taylor Bennett: It’s important that I’m an independent artist, so I can say “No.” It’s not about being able to say “No” to a show date or to a contract deal, but it’s about being able to say “No” and learn from it. I think that you have to fail in order to know how to succeed. If you don’t succeed the first time, you gon’ try it again. It’s the same situation for a lot of artists, there’s a lot of things that they’re going to fail at before they’re going to do it. The worst thing that an artist can do is end up taking a contract that confines them. Then you don’t get to fail. You lose control when you sign a deal, so that’s why it’s important for me to be independent.

What are some hurdles you’ve faced while building an indie career?

I’ve gone through various things. I was an inner city kid in Chicago; you learn from a lot of different situations. One of the things I can say, recently, is having a son. I just had my son, Charlie. That’s also why it’s important to be independent, to be able to have the time and to make the decisions to suit your lifestyle best and work in your favor. Be in control of who you are, and what you represent.

Another thing that was really big in my career was me coming out as openly bisexual. In the hip-hop community, that was a big thing. It let people see me in a different light, it let me see things in a different light. It let me view things from a standpoint, clearly, that I had never been able to see through.

Business wise, in the music industry, everything is a failure in order to make something perfect. All these corporations and businesses, if you see them and they’re successful, that’s because they’ve failed. They also know how to keep going and keep pursuing what you want. In the music industry, you know, it’s not having money at certain points to get into the studio. Once I had the money to get into the studio, not spending it on the right things… I can’t afford to give the quality to my fans. That happens to every artist. I went through that early on in my career. The problems never really stop, they just get bigger. Mo’ money mo’ problems [laughs].

I really appreciated you coming out, absolutely. What else has been rewarding in building your career?

Something that’s very rewarding, for me, is building my career but also helping other artists build their careers through my label, Tay Bennett Entertainment. We’ve been working with Bianca Shaw, who very early on, you all helped me and Bianca early on when we put out “Only Difference” produced by TGUT. That was the first song that she ever did that got over a million plays. Because of that song, we were able to go out and get Twista on the “So High” remix, which was the next song that would surpass millions of plays. That really helped build her career, and moving forward, just last week she headlined her listening party at the Apple Headquarters in Chicago. Almost the whole city came out. That’s really dope, to be able to see artists that I love, have their careers come to the light. And to be able to take away the sense of frustration that I definitely had trying to navigate the music industry early on. 

Going back to the financials, what makes TuneCore such a valuable resource for you?

In 2014, I decided that I wanted to put my music out on a distribution platform, but I didn’t want to sell my music or give away a percentage. At that point in time, everyone was putting their music out on SoundCloud. But the producer that I had made the project with was like, “Nah, I wanna sell this project. We put too much time and too much money into this project to let it go out for free.” Me and my manager at the time looked into what kind of platforms were out there where we didn’t have to sign a contract and we didn’t have to give away a percentage or take the advance that we would have to recoup.

When we found TuneCore, we instantly knew that it was the application that we needed to further my music career. The idea, at that point in time, of me being able to distribute my project… I distributed the project with TuneCore and on iTunes, it was one of the top five projects. It was next to Drake. For me, as an independent artist, to be able to see my music next to Drake’s music, that’s when I fell in love with TuneCore.

I also wanted to learn, further, how to keep distributing my music and also learn how to branch out and show other artists [how to distribute their music]. The first artist that I ended up showing TuneCore to distribute was Chance [The Rapper]. He decided to distribute with TuneCore for Coloring Book. It literally put a compound on the independent movement which Chance started, with touring and merchandise. Now, you could compete with label artists on Apple Music and on Spotify.

My journey after finding out about TuneCore was to continue on the same path but to start trying to educate people about distribution. Also, the method of doing splits, the understanding of publishing, mechanicals, royalties, and owning your masters.

I know you’ve got your label, but would you ever want to do a major label deal, or is the TuneCore situation so good you don’t need a deal?

Definitely never enters my mind. I’m good off of what I’ve done. Cole Bennett, the creator of Lyrical Lemonade, said this to me on time: everything that you see in the world was made by somebody. None of this stuff was always here. Whether we’re talking about Atlantic, Sony, RCA, it doesn’t matter who we’re talking about. All of those labels have built their success based on the hard work and putting that time in. Something that’s easily misunderstood is the idea of having an independent label with a parent company. 

Let’s say I’m like, “Yo, Donna, I’m gonna give you this 5,000 dollars to make your dreams come true. I don’t want you to pay me back the 5,000 dollars. I want you to give me 30 percent of whatever you make.” As soon as that decision is made, you have priced out your dream. And your dream is whatever you make it, as big as you think it could possibly be. I know my dreams are worth way too much money for anybody to put a dollar sign on it.

So it’s really about how you value yourself as an artist.

We really are speaking about people, because artists are people. When you sell your masters or your future intent, like what Kanye West is going through [with EMI], the reality is you’re selling something that you haven’t done yet. You’re selling future work, and technically, that is slavery, to me. So it really comes down to how you value yourself as a person. Through material values, we have lost the sense that money is not everything. My managers, we people run around all day trying to make money, trying to control stuff, and these people are trying to control us, because they know we’re the money. You know what I’m saying?

Pivoting, you’ve got your EP The American Reject coming in April. Can you tell me what goes into releasing a project as an indie artist running their own indie label?

A lot, yo! You gotta go out to New York and run around to these offices. I don’t think I’ve ever put at least a thousand dollars into marketing. Everything that we’ve done has been organic. These conversations, now I can do a SXSW conversation with the CEO of SoundCloud; I can call Steve Stout when I’m in New York—the head of United Masters. I could call my booking agent, which is one of the number one booking agents in the world. All those conversations happened through connections with people that were much, much smaller than them. We just kept putting in the effort. We kept putting in the work. We kept going. We kept digging deeper. Now I’ve done Jimmy Fallon; I’ve done Steven Colbert; I played Good Morning America.

If you wanna be an independent artist, the real tactic is how independent and how much are you willing to get your hands dirty? How often are you willing to make business calls? Do you wanna go to the gym and work out, or do you wanna drink lean and smoke? Do you really do the background work? 

From where I come from, music wise, I think it’s very much so looked at as a record deal is you getting rich. But if you really wanna be successful as an independent artist, that means you need to be better than the industry that’s here at hand. That’s what me and [Chance] do. We’re steps ahead. We’re looking at what labels can’t do and what we can. As long as I can keep that list way longer, then I know that we’re doing the right thing.

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