On being nimble while riding out uncertainty

What does your work entail in the day-to-day?

Each day is completely different, because it’ll run the gamut from meetings with business partners, writing or recording feature verses, or just planning. One thing that popped up is that me and [actor and comedian] Baron Vaughn had this opportunity to do this show called Call & Response. It was a talk show that arose to have the conversations around racial injustice that were at the center of the public consciousness in [June 2020]. Suddenly we were doing a show every day for two weeks, so for two weeks, I was prepping to interview Roxane Gay, or Travon Free, or Roy Wood, Jr., the next day. But that was just two weeks. It’s wild how things can vary from day-to-day, while I’m trying to be nimble and ride out the uncertainty of the pandemic. It’s like trying to spend time working on things that I already have planned and trying to be open to new opportunities that have arisen in the midst of all of this.

How do you balance that time?

A lot of it for me is based on what’s most time-sensitive. If I have a livestream that next day, then I’m spending a lot of time prepping for that. If I owe somebody a feature verse, then they might have to wait. If there are certain production companies I’m working with to develop some TV ideas, that’s gone a little slower than it usually would, because things pop up that are a bit more pressing. I have a Patreon that I’ve been nurturing; I have to put a little bit of energy into that as often as I can. I just launched a podcast network, so on that tip, we have a show that drops every Wednesday. I’m constantly in a cycle of helping to edit an episode, describe the episode, post the episode, promote the episode when it comes out, and then do that whole cycle over again every week.

There’s merch items that I’ve created, and that’s about constantly being in a cycle of generating images, pricing things, getting mock-ups designed, setting dates for when those things would be available, promoting those things until they hopefully sell out, and starting that process over. So there’s some cyclical things in there, too. That’s in addition to the long-term stuff, TV and music that I’m working on, and the short-term things that pop up as opportunities to take advantage of in the immediate sense.

I’ve read that typically you would jot down ideas on tour and flesh them out after you returned. How has that process changed?

I would come up with a lot of ideas on tour, but I was never on tour more than two or three weeks at a time. I would say the majority of my ideas happened with me sitting at home, or going through life, or driving, or in whatever life situation I found myself in—a moment where I had some time to think.

Again, it’s a balancing thing, right? Because with the pandemic, with the lockdown, I’ve had, in some perspectives, more time to think. But it’s weird, because it’s been a little difficult to separate the thinking time and the doing time during quarantine—which, before, was a little bit more split up. You can plan your time better. I often feel like I have a million things to do. Sometimes I get a little restless, if I’m also sitting and trying to think of things. I haven’t quite found that balance yet.

How do you make sure that all these projects help and not hinder one another? You’ve said that the concepts for the upcoming Secret Skin and your next album play into each other, for example.

Well, it’s beyond just thematic. I actually try to make these things work together in a business sense too, right? Part of the deal behind the podcast is I’m going to make merch for the podcast that moves through my merch company. Same with music, right? It’s to make music, which generates merch, which again goes through my merch company. And the podcasts are all music-centric, which, in addition to celebrating the music that I want to talk about, gets my name out there even further into the music community, even if it’s not as a performer. Business-wise, I would like for all these things to work together.

Why else did you launch your own label and podcast network?

It’s all about ownership, you know? I’ve had a lot of experiences where I wanted to do things and I’ve had to try to sell it to people, and I’m over a lot of that. Not so much labels, because I guess I’ve had an easy time with labels, in terms of working with independent labels who got what I was doing and was able to do whatever I wanted to do. When it comes to the music part, ownership is more about needing more of the revenue than I get when I am working with a label.

On the podcast tip, I had a lot of what I considered to be good podcast ideas. I went through a lot in trying to sell my ideas to networks—a lot of piloting, a lot of writing, demoing things—and got told “no” a lot. I think part of it was because people don’t really understand the value of celebrating and talking about music that they aren’t familiar with. I’m kind of focused on hip hop that’s more like… What’s the word? I don’t know if there’s a clear word for what it is, but it tends to be more on the independent, alternative side of the spectrum. And in that, I often found myself trying to sell ideas that I thought were really good, to people who had no idea about this field I was operating in. They didn’t see the value. I got really tired of that. I wanted to put myself in a situation where I got to choose and execute things that I know are good ideas and that there is a market for. That brought me to start my own network.

Between the podcast and the TV stuff that I’m attempting to do, there’s a lot of trying to sell people on the merits of an idea. I find that process excruciating and often soul crushing, and I want to get away from that as much as I can.

This is a hell of a year to debut all these endeavors.

It’s been rough. I mean, even though it’s been triumphant in terms of actually seeing me get to a place where these things are real, it’s such a rough time to try to release and promote new products. PR is ridiculous right now, and that’s something that I’ve usually been able to lean on or at least have a fair understanding of. But between the pandemic and the racial injustice protests, and those emotions and that sensibility being at the front of everybody’s focus, it’s been really hard to figure out the best way to get attention on a new product. So it’s great that I have the platform built that I want to have. Now it’s figuring out how to let everybody know about it in this uncertain world that we live in right now.

Do you think everybody’s attention is on whatever disasters are happening?

It’s not so much about people’s attention. People are consuming entertainment just as much as they’re consuming news or consuming think pieces or anything else. I think it’s the outlets. I think it’s websites getting smaller. I think it’s writers getting laid off. I think it’s editors getting laid off. I think it’s podcasts trying to figure out how to get guests on when everybody’s remote and figuring out workflow. The things that you would usually do to let people know about something, the way you would engage in a campaign—all of that’s broken right now.

So it’s the systems of getting information out there that I find to be most challenging, more than consumer attention. It’s hard to get news out about what you’re doing to people who aren’t super dialed into you right now.

How has your workflow been affected?

I’ve been able to do the work, but motivation’s been a little harder than usual. The landscape is very dreary, and I don’t often feel super energized to do the work, even though I do execute. In times past, I would have been up for things more. I would have had more pep in my step when it comes to some of the projects I’ve been working on. I have noticed that my motivation drags so much.

I have to push myself a little harder. What that will sometimes mean is that I take longer doing things than I would like to. I still get them done, but it puts me in a situation where I’m apologizing to some people because they’re waiting on something from me. I don’t like that feeling. But I’m doing what I can do day-to-day, you know what I mean?

I think that there are a couple of people that I deal with that are probably at the end of their rope waiting for me to do stuff, but for the most part, people have been pretty understanding, yeah.

You met Baron back in, what, 2012?

2011.

So you’ve built off that working relationship for years, from The New Negroes to Call & Response. Meanwhile you released a wrestling documentary, and obviously you can’t predict a rapper-wrestler beef. [laughs] What’s the balance between planning these longer-term moves and acting on impulse?

The balance is between executing what you have already planned to do but also being open to new opportunities appearing on the landscape. It’s having a little bit of energy to be able to pour into things that pop up. Oftentimes what helps is that those pop-up opportunities tend to come with a little bit of money—or at least, the thought that there might be money.

My 2020 plans were heavily based on music and the continuing engine of music as we know it: putting out music, touring, that sort of thing. Because we don’t live in that world right now, I have to be very attuned to when revenue opportunities might pop up. I have to be very open, because me being flexible and having some energy for my brain to improvise in certain situations is what has helped me to pay my rent in the past few months.

Call & Response literally started from a phone call that I had with Funny or Die. I know the people who run that place pretty well. The murder of George Floyd happened. Everything kind of stopped. We had a conversation about ways that they could affect the situation, effective ways to bring light to the things that were occurring. And we started to come up, in this conversation, with the potential of doing a show that literally addressed these issues. We talked to comedians and thinkers. From that conversation, we had this opportunity to do Call & Response.

If my mind hadn’t been open to thinking about some solutions… I had a lot on my mind at the time, as you could imagine, with the world being on fire and specifically the way that it was/is. There’s a world where I don’t have the mental resources to be open to thinking of that as a particular solution. But luckily, fortunately, I was. And in that, something arose that helped me to pay my rent.

This has been a period of soul searching for a lot of people. This question might sound corny, but any tips for that soul searching? How can people approach or brainstorm opportunities that they might not have previously considered?

The answer to this is going to be a little corny as well. But one thing I often come back to—and this is something that’s reflected in Call & Response, reflected in the podcasts that I do, and even reflected somewhat in the music I make—is always making the kind of stuff that I want to see and staying attuned to the value of that. Like I was saying, I’ll talk to a podcast network and they don’t see the value in what I want to make. But I have to not internalize that and continue to see the value in it, because there is value in it.

Ultimately, that’s the bottom line question. What do I want to see here? If I were searching for a podcast to listen to, what would it be? If I was looking for an album to listen to, what would it be? If there was a livestream I wanted to tune into about the conversations of the day, what would it be? Those things always inform my ideas and how I go about doing things.

Compared to a major podcast network looking for “x” number of downloads, what are your metrics for success?

It still does depend on what industry you’re talking about. Just because my aim is more indie don’t mean that my podcast business isn’t ad-driven. It still is at the end of the day. These products, no matter how heady I think they are—they still have to be able to reach people. I have to do the things that I feel are necessary to make sure that it reaches that audience, because at the end of the day, it’s like any industry. The metrics are numbers. It’s consumers. It’s consumption. It’s audience. It’s all that. I choose a tough path for that sometimes, because the things I’m interested in do tend to be a little bit more specific. But at the end of the day, the metrics are still the metrics.

So your relationship with those numbers are, “OK, I have to work with you somehow.”

Absolutely. But that’s part of being realistic about the business and making money, too. Yes, we all want to make art, but we also have to sell art if we want to be an artist for a living. It’s on us unless we’re fortunate enough to be surrounded by people who have nothing else to do but to serve your whims and pick up the slack where you fall off. I know from just being in hip-hop, on the independent level, on the underground level. The more I can learn about how the business actually works, the better off I am in every sense of the word. The more I can learn about how the record business works, about how the touring business works, about how the merch business works—all of it puts me in a better position to actually live off the art.