The following conversation with Verbal Kent took place over the phone back in May of 2020. Despite the odds, the year ended up being a fairly prolific release year for the seasoned Chicago emcee born Dan Weiss. He dropped two albums with Recognize Ali and Lord Beatjitzu as Dueling Experts, a collaborative full-length called Your Birthday’s Cancelled with Vic Spencer and Sonnyjim as Iron Wigs, and a solo LP The Blade Of The Short Cut produced entirely by Washington D.C.’s The Other Guys. All the while, he’s been steering the ship at Dollop Coffee, the Chicago-based coffee shop chain and roasting facility brand he’s owned and operated for about a decade now. During our call, we discussed the opportunities and challenges of being both a multi-location business owner and a touring rapper simultaneously, as well as the struggle to be creative in a pandemic. (FYI: This conversation was originally intended to appear in Forbes, albeit in a different form, in case the entrepreneurial tone throws you for a loop.)
I think it'd be helpful to get a bit of background on Dollop Coffee, from the beginnings to where you have multiple stores.
I grew up writing songs, scripts, and whatever else I wanted to plot out, in coffee shops, as a young person in high school and into the college years. I didn't graduate from college, because I was too busy at coffee shops, messing around and playing chess and smoking cigarettes, being like a hyper productive coffee shop bum. And back in the day if you were into coffee shops and coffee culture—I'm 41, so this is when I was like 16, 17, 18—coffee wasn't what it is today. Meaning, there was no pretension. The transformation of coffee into the wine realm of notes, the culture behind what makes coffee super delicious and artisanal, really wasn't that prominent in the mid-to-late ‘90s and into the early 2000s. It was really about the atmosphere. It was a place where I could be alone in a room with people, so like alone, but not alone, and alone inside, and outside I wasn't. I found that conducive for writing and for thinking. I basically spent all of my time soaking up energy of neighborhoods in coffee shops, trying to be a rapper when I was younger—and then I became a rapper.
I was on my own. There were a few local labels that I worked with a long time ago, Gravel Records and Molemen Records in Chicago. But primarily I was on my own. I met what was going to be my soon-to-be wife, and so I was a basically a full time musician. At that time, I was going to Europe, doing shows. I was putting out my own albums. I was making $30,000 a year or something, which was amazing for me to make that off of music. But I started thinking like, I gotta do something else too. I wanted to start a family. I started to kind of grow up. I had been able to travel, through music, which is really lucky. I had never left the country before music. My first time in Europe was because I was on tour. So I got some like life exposure out of the way. Now we're in the mid-to-late 2000s.
A few friends of mine had opened this coffee shop in uptown in Chicago. They were messing around. It was a neighborhood coffee shop. I’d introduced them to open it and they became business partners opened up this coffee shop. By 2010, they were not getting along and struggling and they were basically like, are you interested in this? From all my experience sitting around as a bum in coffee shops, I knew what they were doing wrong.I didn't have much “business experience” in hospitality. However, I felt like my life experience was enough to be qualified. I made a little plan, borrowed some money from a buddy, and bought them out. In 2011, we’d had our first kid, in November, and then October 15th of 2011, I bought Dollop, a one location company.
So you weren't busy enough with a newborn that you're like, let me also open a coffee shop.
That's right. [laughs] I needed more. It wasn't quite enough to be a musician and to have one kid. At the time, again, it wasn't like it is now. You didn't see a coffee shop on every block. I looked at it and I said, if you do this right, this is actually a really good time for this. I kind of just got lucky, in terms of my timing. I really do attribute a lot of it to luck. I wanted to focus on something that keeps me home, that could be like a good compliment to music, something I could set up and then be able to leave whenever I needed to, to tour or whatever. It was the right sort of fit for me. The first year, I doubled the revenue, went from like $200K to $400K a year annually. So right away I was like, okay, I've got something here. The neighborhood was really appreciative of everything. They acknowledged the changes I had made. We took care of people. We fixed the coffee shop…
It took about a year to really regain and reestablish all that trust. People would see that you all that and they'd say, this guy gives a shit, his staff give a shit, they're making an effort, I'm going to give it another try. And it just worked. But also, again—I'm joking, but I'm not—in 2011 there was like 12 coffee shops total. Now there's 1,200 or whatever in the city. So that's why I say like the timing was just flawless, to accidentally fall into it.
So it sounds like this hospitality business that you opened, you were able to balance that with the artistic business of a rapper, in a way. It's perhaps harder for others who own businesses to be able to pursue their creative side.
I think I had a natural lucky advantage, as far as some of the “risks” that are stereotypical about starting a business that involves any creativity, some of the intrinsic natural problems that people describe as like, nine out of ten businesses are going to close, that whole thing. Like, I'm a fucking rapper. Do you know how ridiculous it is that I’m semi-successful? Even though, obviously, it's relative in terms of what I set out to do, I was able to an independent musician and hip hop artist. To me, that's way more challenging and weird than running a coffee shop. So motivationally, it was easy for me. I had a confidence and a belief that this was definitely possible and, no matter what happened, as long as I wasn't broke I could get through it and figure out the system and fit in in this community. Some of the relationship building and the networking, putting yourself out there and always having to prove yourself to people, the music background trained me for that, you know?
Yeah, and I'm sorry if it sounds crass to refer to both as businesses, but both businesses are customer facing—
Yeah, they are. That's true.
—which puts you in a position where it's like you have to be on, in that respect, whether it's your fanbase or your customer base. In what you do, how you comport yourself and how you run your business matters.
They're both super social. I mean, not that you have to be social to be a successful artist, but in the business of music, it definitely helps to be able to interact with people unabashedly and be able to find what you need to find and promote something in a certain way. They're definitely connected.
How did you get from one shop to 20? How do you get that level of growth?
Well, I got confident. I decided that I wanted to make it a chain and do multiple, Dollop locations rather than starting new ones or different brands. I said I'm going to grow those brands. The cool brands. At the time, we didn't even roast our own coffee. And so that was on my mind, that roasting my own coffee could really establish a brand identity and then I could grow retail. I kind of saw the future, that I could grow retail and turn this into a wholesale business as well.
The quick version is that I was aggressive and looking for locations. I aggressively fundraised through my network—hustlers, friends, family, anybody I could find who wanted to invest in the concept. The one thing I did that was smart was I didn't sell a piece of the brand; I sold locations. People bought into the locations. So if you wanted invest, you invest in the restaurant, you invest in the cafe, you don't invest in the brand. I basically did that. The model was raise money, open a location, and then pay out profits from locations that made money. Then eventually, I unwound it all by buying investors out. Now I'm in a position where I consolidated it and have limited investors in a much larger company, one big company rather than 15 different companies. The early investors either were bought out or are a part of the big picture.
There's always lessons you learn in business, no matter what. I didn't go to school for it, but here we are. And now today, we have a coffee roasting operation and a bakery. We supply all of our own stuff and we sell coffee wholesale. So, if you're a coffee shop that needs coffee, you can buy from us. So, it definitely worked, but now we are at a very interesting crossroads.
With the pandemic, I know you had to close stores in March. When did you realize that was something that was going to have to happen? Were you anticipating the shutdown?
We planned on a shutdown almost the same day that Governor Pritzker announced there was going to be a shutdown after that Sunday. Before this whole shutdown happened, it was Sunday the 15th. I was in a kind of war room planning this all out. What are we going to do? How are we going to tell our staff? Are they going to support the decision to close? We were planning before we were told to close, because we didn't feel comfortable being open anymore. We didn't feel like it was the right choice for the community. Again, we're such a community place. It was terribly risky to be open. We were going through this entire plan of how we were going to shut down, how we were going to approach our staff, the landlord, our vendors. It was pretty, pretty intense. And then it was almost like this, I'll never forget it. It's like this fax came through on the wire that Pritzker came and said to everyone, the city is shutting down. And we were just like, okay, well that helps our messaging a little bit. I had a three hour headstart where we had already been planning for this, running the numbers and everything on the situation. We made a decision to shut down and then we were told to shut down…
You've had the music side of things in addition to the hospitality business for nearly a decade now, both of them going in concurrently. But that's also a business where the revenue-generating part has been curtailed by the pandemic. You couldn’t go on tour event if you wanted to go on tour right now.
That's right. And so musically, I just put out this Dueling Experts project with Recognize Ali as a group. We didn't sell a million copies, but what we did do is we really made some subculture noise as being a group that people want to hear with the sound people want. More importantly, we love doing it. We were about to plan a tour, and it would have been my first tour since Ugly Heroes. Me and Ali were both really excited about it. Mello Music was excited about it, building a new brand essentially—which is not going to stop. But the point is, we had some momentum and we felt it.
And Ali was just here. Ali lives in Ghana. He just came in town. It was the first time we met in person. He stayed here, we shot a video, we hung out. We're working on a second album. We have all this momentum. It's hard, by the way, I mean, as someone at my level of music, where I have respect and I've been doing it forever, but I'm also not like a famous person. I definitely am a part of history, but it's not as if I could just make a phone call and be like, tour’s booked, got three weeks here! For an artist at my level, and I don't know what people know about this shit or not, it takes a lot to get on tour and to make it work economically, to have that kind of draw. For us to be offered a spot where we can go tour in Europe for a month is a big deal. We had that opportunity and it was just, again, totally wiped out. Again, I'm not complaining, I'm alive, everything's fine. But you know, we had this momentum and energy built. Like you said, touring is done for the foreseeable future for everybody.
Ali is in Toronto right now; he has some family there. He's taking a step back right now and he wants to be focused on family, health, and safety. Our momentum is essentially paused. Energy-wise, we talk all the time. Everybody is looking at everything differently, and everything is different creatively for everybody now too. I mean, I'm sure people you talk to in interviews are saying the same kind of shit—and they're lying if they don't. But like, what do I write about right now? You know, what am I going to talk about? I'm not going to talk about fucking coronavirus. How many songs can there be about quarantines?
It's actually crazy what's happening. I end up talking to a lot of major label rappers for Forbes. I'm pivoting to more kind of Q&A style stuff there with artists who are putting out music, trying to find out from them how they're operating. Some folks have home studio set ups or have recently recorded surpluses of material. And then you have the folks who are dropping quarantine-themed mixtapes or their new album has bars about coronavirus just sort of tossed in. It’s a timestamp of when it was recorded.
The whole thing, it's thrown me off creatively. I don't know if it's just me or not, but I have a hard time. I guess I could just be honest [laughs], which is a great approach to music, I guess. My character, what I like to write about, I'm a lyricist. I grew up as a battle rapper, and it's all about creative ways to destroy enemies. And you know, I just don't want to fight anybody right now. [laughs] I just want to help everybody. It's just different. My whole mindset is different and I'm in this weird survival mode in a way that I've never, you know, that many people have never had to face. And so I'm at a creative crossroads right now. I almost wish, I almost wish I could do an Ugly Heroes album right now, because it's more the vibe.
You want the energy of other people to work with and play off, right?
Yeah. It's definitely a sad music time, for sure. At least for me it is. It's either like a really happy music time or like a really sad time. Just to be frank, I'm a little stuck and my focus is on surviving. It’s just weird, man. It's like, everyone, the whole world, if you have any common sense, you're in survival mode right now. It's a very bizarre time.
It's a curious thing because a lot of rap music is about survival. But it's about surviving the circumstances that you grew up in, about surviving the circumstances in which you've lived your life in—
—or like surviving your own demons, right? Whatever it is. It’s just so personal too. I don't know, man. Whatever happens, happens, in terms of what I write about next. I'm excited but, at the same time—I don't know about you—my creative spirit is being challenged. I'll admit that right now.
It's tricky for me because with the majority of what I do, my revenue-generating thing is also my artistic expression. And it blurs sometimes. I mean, I'm pretty proud of the majority of what I write, in the sense that I don't feel like I'm compromising or selling out or whatever bullshit someone wants to call it. But I can't turn off that creative thing because it is my sole means of earning a living right now. I don't know whether I'm producing good work right now, by my own standards, because I'm too in the weeds with it. I'm thinking project to project. I can't think about something that's big. Like, if someone said to you, we're going to send you the setup to make an album at home right now, you'd be like, what am I going to write about?
Yeah, I'd have to think about it and I'd have to really refocus and re-shift the kind of instinctual survival mode—protect my family, save my business, pay my mortgage, which is ironic. Because, aside from the fact that I didn't have a family, that was the basis and the fuel for me, being someone that didn't have money, it was music at all costs, back when I was starting. It's eerily similar, in a bizarre way, but yet here I am.
It's also tough. I am surrounded all day and all times. It would have to be like, everybody goes to bed, Dan writes songs at 10 o'clock ‘til two in the morning. But then Dan's got to get up at six in the morning or whatever. And again, I'm trying to save the business. So it’s an overwhelming time, I guess. Don't get me wrong, I'm still writing. I'm doing features and I'm actually collaborating with a lot of people who are in different countries right now, which is really interesting. You get to talk to people about what they're going through. But definitely right now, I'm more business focused probably than ever in my life. Easily, I can say that.
Your priorities have shifted and what your day looks like has shifted so much that to carve out that time is more of a challenge than ever. I would say that, ideally, you shouldn't feel pressured to create in a time like this.
I think you’re right. I think I'm probably scared. I probably have more fear about the future than I ever have. I'm doing everything I can to not confront that fear. And I find that, historically, my best writing comes from me being open about my feelings. To be honest, I'm probably harboring a lot of anxiety and fear about what could happen to my life if things don't pan out right because of all this. And I think maybe that's the core of it all, for me, to really get back to full on writing mode and album mode is being open and honest about how devastating this could be. But I don't want it to be like that, so I'll probably avoid that, you know?
Obviously, in your discography, there’s plenty of material that is personal, confessional, and narrative, in addition to the battle mode you’ve described. There's something about being faced with this decision and go, is this a part of my personal life, what's happening right now, that I feel like I want to create something from?
Very, very true. My friend. Very good point.
That's what it comes to. You gotta ask yourself, do I want to make a rap album about how all this is affecting me? Maybe, maybe not.
Right. No, you're right. And I don't know if I do. I'm not sure yet.
Purchase Verbal Kent’s music, including the newly released Dueling Experts album DE2: Sand The Floor, here.