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Mark Stewart Interview: Breaking Into Music & Staying Relevant — Then Vs 2019

A conversation with veteran music manager Mark Stewart about changing tides and the democratization of the recording industry.
Mark Stewart Interview: Breaking Into Music & Staying Relevant — Then Vs 2019

Mark Stewart’s managerial prowess cannot be understated. Working with his brother Tricky Stewart, The-Dream, and Frank Ocean, and famous for his work with Beyoncé, Rihanna, Usher, and more, Mark’s name is attached to massive, GRAMMY-winning and nominated records ("Single Ladies," "Umbrella"). 

As a businessman and executive, Stewart stands a cut above the rest, always willing to move with the changing tides of the industry. Mark Stewart has rightfully enjoyed a 30-year long career in a fickle and unforgiving game. 

Stewart was kind enough to sit with me for an interview about his beginnings, getting on and staying on, his views on the current industry, and more. 

Our conversation, lightly edited for content and clarity, follows below.

DJBooth: What was it like breaking into the industry with Tricky Stewart?

Mark Stewart: It was very different. For us, it was 1989. I was 19 years old, just barely out of high school. Trick was 15, still in high school. My older brother, Laney Stewart, was a producer as well and he started a jingle business. We're from Chicago and jingles were really big there in the ‘80s. He started doing his own jingles—the jingle business is nine-to-five. We would get the studio managers to let us use [the studio] after hours into the wee hours of the morning, and Laney would make records. We sat at his feet and just watched, we became studio rats.

We caught a break—and this is where it differs—when one of the ad agencies that Laney used to write for sent a blind tape to a publishing company in LA. They listened to an unsolicited tape and decided they wanted to sign Laney and this woman. Laney got a publishing deal in 1989, and that started everything for us. Tricky started apprenticing under him as a producer, and I thought I was gonna be an engineer.

We started catching breaks as early as 1989, 1990. Just getting on projects, and in those days, with all the labels, it was so many more opportunities to go and work. [Every label] was its own building. You could go to LA, do a series of meetings, and come out with cuts! At the time, we weren’t making hits, we were making album cuts, and Tricky caught his first break at 15, 16 just being a kid and hanging around all these other sessions. That’s how it started for us.

Now, you can connect with people through the internet, and those things freak me out. In those days, we had real gatekeepers, and you had to have someone walk you in and vouch for you to crack anything in the industry.


With the internet, has breaking out become democratized?

We sit around and discuss this. It’s a gift and a curse. The way we had to get in, you had to go through someone. Now, everyone has access, but there’s a lot more competition. When you see projects emerge off a meme, do you realize how good that has to be to make it through all the clutter out there to connect with fans? I think there’s a lot of dudes my age that see a downside to that. I don’t. If you are good enough and you have something that cuts through, regardless of quality level, that’s a win. I think things being open the way they are is a good thing. It’s open to what the people want, and what the people want is always what matters most.

In 2019, if you have a hit on your hands, you earned it. Especially with how fast everything is moving.

Absolutely, and I don’t have a problem with the meteoric rise of [songs] that take hold, even if it’s off Instagram. If you can convince people you have [a hit] in under 50 seconds of listening to your record, you’ve done something special. Technology moves in every industry, and you have to be willing to accept that. Particularly with musicians and producers, they don’t always embrace the changes, and I think they should.

Do you think it’s easier to break through and harder to stay on, or the inverse?

That’s a great question. I don’t wanna say it’s easier to breakthrough. I still think it’s hard to break through; there’s just more access. It’s harder to stay on because the consumer has so many choices and options. When you’re in high school, and you have to decide if you’re going to spend your money on pizza or buy that record or tape, that’s the era I came from. When I bought a tape, a record, it meant a lot. Now, if you’ve got seven bucks, you have access to everything. Everybody’s got everything, so staying on is a constant “What’s next?” I see these young artists, and they understand how to stay piped in with their audience. But if you don’t and you fall off, they will move on.



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With the advent of streaming, music fans have become more fickle.

They have choices! If you take a kid to an ice cream shop every single day and say here are all the flavors, they’re gonna keep trying stuff. They’re gonna try everything that’s out there, and that’s what it’s all about. How much can they sample? I remember when Chris Brown dropped [a 45-track album], and I was talking to my wife and kids, like, “Why is he doing this?” Everything I’ve been trained [to do], it just doesn’t make sense. But my kids were like, “Nah, it’s kinda cool because he’s dropping his hard drive off. Letting us look in his hard drive to see what we like.” I never thought of it that way. They thought it was cool; I thought, “What is he doing?”

To keep up with the shifting nature of the business, what is an example of something you had to unlearn?

Where do I begin? Almost everything! There’s a lot you have to unlearn and be open to. As a manager and dealmaker, there are some contexts when you’re devising a career. But something you have to unlearn is how much music to put out and the frequency. When I started, some artists would wait three, four, five years between albums. Beyoncé can’t even do that. Everybody’s gotta be coming with something, and it’s not even just music anymore. It’s something that connects the artist to the public.

One of the biggest things I’ve had to unlearn is there’s no manufacturing anything. I came from an era where you can go, “We need our uptempo smash, we need our ballad.” There was a way of crafting a record and a career. Now, if you do drugs and your audience does drugs, that’s the connection! You have to find the real, authentic connection and let it go. You can’t craft, build, and develop an artist in your light. It’s just not like that anymore; it’s all about authenticity.

Since fans have more choices, do you feel like the connections they build with their favorite artists are stronger?

I would think that people think it’s stronger now. Back then, it was stronger for the reasons I said earlier. The first concert I went to was Madonna in 1987. Lied to my parents, said I was going to sleepover at a friend’s house. We had to sleep outside for tickets. You couldn’t do it on your phone. When you went through those steps to connect with an artist, I think it meant more. Now, it’s "I’m connected until the next guy comes along on Spotify." You can buy the record, get a t-shirt, get a ticket, and you don’t have to leave your bedroom.


Pivoting to you, have you ever thought about leaving the music industry?

Wow. I think you have to think about that, just being honest. I’ve thought about not necessarily leaving the music industry—we all start as music fans—so I’ll always do something relative to the industry. But I don’t wanna be 75 years old, trying to figure out the mind and consumption patterns of a 13-year-old girl. In urban music, I believe it’s a young person’s sport, and you have to leave it to them at some point. I think about it all the time, like, “What’s next?” Because you can’t do youth culture music forever. I can always sign young talent, but even with that, there’s a gap of understanding. I keep a young team around me, but I don’t know how long that’s gonna sustain me.

Is there any fear there? It sounds like you’re mindful that there’s an expiration date on this era of your career.

I’m not fearful, no, because I think if you stay in the industry long enough and have enough contacts, there are things you can do to move. It’s a little different for me because I’m an executive. It’s a little harder for creatives. I have a more broad view, so it allows me to think of more stuff. You have to face it head-on, you can’t be fearful of change. Sometimes you can move ahead and reposition yourself. There’s no fear with that.

After 30 years in the industry, how has your relationship to music changed?

I think about ten years ago, I had to decide to say I’m gonna remain a music fan no matter what because that’s what drives me. Who I am as a consumer, what I like, what shows I go to, that has to remain unchanged. Who I am as an executive, that’s the work part, requires research. So I just separated the two. Because I’ve done that, I don’t have that sense of “Oh, man, my relationship to the industry has changed.” Sundays are for me being a fan, and I’m listening to an old record… That conversation ends on Sunday night. On Monday, we’re going to work talking about what’s happening in 2019, 2020, and 2021. I try to play today and win today, based on today, and not always reflect backward.

That’s admirable. I’ve spoken with artists who can’t hear music the same way anymore.

That’s rough, and I know some of those people, too. It’s easier for me because I don’t have 1,000 songs that I’ve written. I’ve been parts of things, so it’s easier for me to apply my intellectual thought. I do respect the fact creative people have a more difficult time making those adjustments.

I remember when streaming first started and so many old heads were against it. Everybody had a reason for why they were concerned. But I looked at it like you had the biggest record collection ever. As a music fan, whatever mood you’re in, you could go and access it. To me, that’s an advantage. The days where you wanna shut off the industry and go and listen to this old album because when I was 14, it made me feel this way and I wanna touch that nerve? Go back and do it! Indulge! Music is there for you to do so. When it’s time to come back, you come back and deal with the here and now.


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