UPTOWN — For Dan Weiss, coffee shops and music were always entangled. The shops were where he wrote songs and met new musicians to collaborate with.
Despite spending most of his 20s writing music in cafes around Chicago, Weiss said he "didn’t even dream of being in the coffee business at the time — or in the music business."
Somehow he ended up tangled in both.
"I was just a kid soul searching — looking for something to be a part of," Weiss said during a brief break from his post behind the register of the original Dollop Coffee at 4181 N. Clarendon Ave. in Uptown.
Dan Weiss talks about the balance between his music and business lives.
Inside the shop, it's hard to imagine the 37-year-old father rocking indie crowds in foreign countries as Verbal Kent, but Weiss says he has become accustomed to walking the line between his two sometimes-clashing personas.
Weiss says he has matured from a 20-year-old slinging his CDs in record stores to an entrepreneur dominating the North Side with his brand of neighborhood coffee shops.
By the end of the year, Weiss will open his 10th coffee shop, and Verbal Kent will drop his 10th album.
"I sat in this room writing songs then I decided I wanted to own the room," he said of the revelation that led him to break into the coffee shop business. "The story is really organic. None of it was what I thought would happen, which is why I don’t take it for granted."
The Birth of Verbal Kent
Weiss' ambition was evident way before Verbal Kent ever existed.
In high school, "he thought he was going to the NBA. He was set on it happening," said Shaye Robeson, a friend that's been in Weiss' circle for his entire journey.
The two bonded immediately as freshmen in biology class because they were outcasts at their Evanston high school. Weiss was "developing an interest in hip-hop" and Robeson preferred early jazz "so we weren't surrounded by a lot of like-minded people," he said.
But Weiss didn't "just have a need to be different," said Robeson. "He was different."
Weiss said when he found himself "bored" while studying creative writing and advertising as a student at Columbia College, he grabbed a notebook and scribbled hip-hop lyrics, which planted the seed for his future alter ego, Verbal Kent.
The name is a nod to Roger "Verbal" Kint, a con man who creates a complex narrative based on his surroundings in the 1995 thriller "The Usual Suspects."
"I started writing in my spare time and I wasn’t very good at it, but it was just a hobby. I was just sort of looking for something to dive into. I wanted to apply myself [and] I didn’t really know how," he said.
As he honed his skills, rapping grew from a hobby to a passion. He began searching for artists to collaborate with and was surprised by the lack of like-minded artists at Columbia.
But he found his people in Chicago's coffee shops.
"I started to find people that were like me in cafes ... and I sort of networked through coffee shops," Weiss said.
While Weiss was spending what felt like a full work week in them, Robeson "wouldn't have hung out [in coffee shops] if it wasn't for Dan."
"Where hip hop all started for Dan was in coffee shops. As his skills improved and his career emerged coffee shops were his home base to do his writing and thinking," he said. "It's kind of funny. For any Verbal Kent fans, the last thing you expect is a poet in a coffee shop."
A Poet in a Coffee Shop
In 1999, Weiss dropped out of college and founded the band Organic Mind Unit, which included Robeson on the bass guitar.
Originally, Weiss wasn't imaging himself as the band's frontman, but its drummer — a skill he had been teaching himself. But "as he started putting [the band] together he ended up behind the microphone. I think that's where Dan started developing into a rapper more than a musician," Robeson said.
When others had doubts, Robeson remembers Weiss telling them: "We're going to become a unique voice in the hip-hop world."
"I shared that vision for a little bit too," Robeson said. Weiss was the driving force behind the group.
"I could say he was the leader, but he was more than that — he was what drove us forward. What kept the band together was Dan's vision."
"There was no where in the city I didn’t play, but the scene isn’t how it is now," he said. "There were a bunch of indie labels and the best we could do at that time was the Metro. If you were playing at the Metro, that was like huge for you. We didn’t want to be famous musicians... It was just about how can we get good at rap. And it was a blast."
In 2003, Weiss signed with the label Gravel Music and released his first solo single, "Alien Rock," which would appear on his debut album "What Box." At the time, there were just a few independent hip-hop labels forging a sustainable path, but those labels paved the way for a fresh wave of underground artists, Weiss said.
Labels like Gravel, Def Jux (later renamed Definitive Jux), which was founded by El-P, of Run the Jewels, and Rhymesayers Entertainment, which boasts artists such as Aesop Rock, Atmosphere, Brother Ali and MF Doom, "set the tone for how to be an independent touring artist. They were not majors they were underground," he said. "They toured the country and made friends wherever they went. They started small and all of a sudden were selling out shows."
Weiss wasn't selling out shows on tour. Sometimes he was performing for a hundred people, other times "I might get to open up for a bigger act... if the timing lined up," he said.
Weiss got to see the world as tours led him through Europe and says he learned a lot about music and about business. But one thing he didn't get from his years in the music scene? A healthy paycheck.
"[It] was try whatever you can to possibly make it, but really follow your own path. Money was not important to me," he said. "I really was that dumb."
Surviving On Music and Coffee
After years of "surviving" off a meager income from touring, selling records and doing features, Weiss said that familiar boredom began to set in. Though music was still his first love, Weiss says he knew he needed a steadier source of income soon as his energy for the touring life waned.
As he battled with that, his roommates Robeson and Phil Tadros were partnering to open the original Dollop in the retail space below their apartment. Tadros currently owns eight Bow Truss Coffee Roasters with plans to double by the end of the year.
"That lifestyle of not being able to save money and not being able to know what tomorrow might bring got a little tired for me," Weiss said.
His entrance to the coffee shop game presented itself in 2008, when Tadros approached him to help manage Noble Tree, one of his other coffee shops. Weiss didn't have money to invest in the shop, but was given "equity in the business and the property" in exchange for helping with the business, he said.
He ran the shop for about two years, but it eventually shuttered, and he walked away with enough confidence to partner with Tadros to open Kickstand, 824 W. Belmont Ave., in July 2010.
After opening Kickstand, the two would partner to open three coffee shops at Columbia College, where they both had dropped out years earlier.
Even though Noble Tree and Kickstand were just "breaking even or losing a little bit," Weiss said he stayed in the game in part because he truly loved the work.
But by the end of the year, "I think I was making less money than I was making before," he said.
Shaye Robeson, Dan Weiss, the drummer from Organic Mind Unit Anthony Reid and Phil Tadros in the early 2000s. [Provided by Dan Weiss]
From Beans to Beats and Back
As he battled the financial stresses of coffee shop ownership, Weiss says he found solace going back on tour — where it was never about money. But he couldn't escape the problem even as he hopped from venue to venue for shows around the globe.
"I was in South America and I remember looking at my bank account from the shops and being like 'you’ve got to be kidding me,'" he said.
In Santiago, he performed for a crowd of about 500 people, re-igniting his passion for hip-hop.
His interest in the coffee business waned.
"The hip hop scene in Santiago is really small. If you do it, you do it for the love only, so there wasn't a lot of attention around it because [rappers] were not superstars. It reminded me of when I started," he said.
Back in the states, Tadros and Weiss sold off their collection of coffee shops. Weiss took the time to focus on music and started the record company Rap Mechanics — but the vacation wouldn't last long.
A few months into the sale, the shops' new owner gave them an ultimatum: watch the coffee shops they build up from the ground close, or take them back.
After resuming control of the shops again, the two struck a deal that gave Tadros the bulk of the coffee shops and gave Weiss control of Kickstand, he said.
"Kickstand was my chance," he said, describing the pep talk he gave himself when he decided to go all in:
"It’s your coffee shop now. If you need money for it, you put it in. If it needs someone to come in because someone is sick, you’re coming in. And I did whatever I could to learn the industry from the inside out as opposed to the outside in."
Building A Brand
The passion Weiss developed for Kickstand inspired him to dig deeper into the café business. With the help of a silent partner, Weiss purchased the original Dollop. Soon after he "decided I wanted to grow more and started looking for locations," he said.
He was approached by a Streeterville broker looking to bring a neighborhood coffee shop to the area. When he opened the shop at 345 E. Ohio St. and rebranded Kickstand as a third Dollop outpost in April 2013, he began paving the way for the brand's rapid growth.
This year, Dollop will expand to 10 locations, adding outlets at 225 W. Washington St., 55 W. Monroe St. and on the University of Chicago campus.
"The music life has gone from me from dying to get put on, to being in the respected lane I’ve always wanted to be in," Weiss said.
Weiss says he's thrilled with the niche he's carved out for himself, and hopes to keep one foot in each world — the coffee and music scenes.
"What’s fun about my story is that with each new café there’s a new album," he said. "And it all came from the same place."
Verbal Kent, Red Pill and Apollo Brown combine to create the Mello Music Group Ugly Heroes. [Courtesy of Mello Music Group]
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