Cole Bennett and Elliot Montanez in the offices of Haight Brand, where Montanez works his day job Credit: Carolina Sanchez

On the evening of Friday, July 28, while the temperature outside hung in the low 70s, the Portage Theater was an enormous steam bath. When I got there just before ten, a thick layer of haze hovered above the roughly 1,400 fans packed into the hall—in retrospect I’m sure it was mostly weed smoke, but my first thought was that the humidity in the room had literally formed a cloud. I’m just 31, but I looked to be one of the oldest people there—many of the dozen rappers who performed that night have audiences who on average are barely past voting age. Headliner Ugly God has parlayed his millions of Soundcloud plays into mainstream visibility, and in June the Houston rapper became one of ten MCs selected for XXL‘s annual “freshman class” issue. Some of the openers have built similarly impressive online followings (Famous Dex), while others are local cult favorites (Big Body Fiji). And they’d all been brought together by a scrappy Chicago hip-hop site called Lyrical Lemonade for its second annual Summer Bash.

Lyrical Lemonade, which launched in fall 2013, began with a mission to spotlight Chicago rappers who were getting zero or very little coverage elsewhere. It found a gap between what was attracting media attention and what local hip-hop heads wanted to hear, and it made that space its niche. The Chicago scene responded with enthusiasm, and in short order Lyrical Lemonade grew into a brand, adding events such as the Summer Bash, a clothing line (often emblazoned with the site’s lemonade-carton logo), and sidelines in music-­video production and artist management. The site continues to write about local rappers with two-digit Soundcloud followings, but it’s also become a sort of hub for the newest wave of rising stars—the hip-hop community, not just in Chicago but around the country, is so rich in talent and evolves so quickly that in less than four years Chance the Rapper has become part of the old guard.

Videographer and manager Cole Bennett, 21, launched Lyrical Lemonade as a senior at Plano High School, an hour southwest of Chicago. For more than a year now, his splashy, colorful aesthetic has been attracting rappers from farther and farther afield—at this point, about half the people who pay him to make music videos are from somewhere besides Chicago. He’s worked with grimy underground hit makers whose successes have done almost as much for him (and for Lyrical Lemonade) as they have for the MCs themselves. A video he made for Florida rapper Lil Pump, “Flex Like Ouu,” has accumulated more than 26 million YouTube views since it was posted in April; Pump’s “D Rose” video, also Bennett’s doing, has racked up 42 million since January.

Those jobs are the main reason Bennett is the only person who makes money through Lyrical Lemonade. The site doesn’t sell ads (though he plans to change that within a year), and the clothing line isn’t enough of a profit engine to pay anybody. “Almost all of the revenue collected from clothes is invested back into the brand,” he says.

Bennett hasn’t written anything for Lyrical Lemonade in more than a year. The enterprise’s other principal, Elliot Montanez, who came aboard in early 2015, now edits the blog and oversees its small team of volunteer writers. The two of them hope to pay their contributors once they monetize the site, but they figure this approach will guarantee the writers are part of the team first and foremost to share music they love. “It’s a hobby,” Bennett says. “We want to know everyone’s really in it for the right reasons.”

Montanez pays his bills working full-time for entertainment-management company Haight Brand, which his older brother Eric cofounded with Michael Ahern and Chance’s manager, Pat Corcoran; based in Logan Square, it provides website design, merchandise support, and other services. He and Bennett also manage a couple rappers apiece, though they don’t take a cut of their clients’ earnings.

At the Summer Bash, I saw Bennett—a slim white guy in a camo-green T-shirt and orange shorts—seemingly everywhere I turned. He was at the entrance hustling people inside, ducking into doors that led who knows where, and addressing the crowd on mike between acts. But his demeanor at our interview seems relaxed, despite his businesslike attentiveness. He and Montanez are both single-mindedly focused, and apparently always on the clock. Montanez has just spent several hours editing Lyrical Lemonade after putting in a full shift at Haight that started at 6:30 AM. And Bennett’s relentlessness has impressed Chicago rapper Femdot, one of Montanez’s clients: “That man Cole, he never sleeps,” he says. “I don’t sleep, and I know he’s the only other person I can call at 4 AM who’s gonna answer the phone.”

Bennett and MontanezCredit: Carolina Sanchez

His mother, Susan Bennett, says her son has had that kind of determination since he was a kid. At age five or so, he joined a youth tackle football team, and in no time he was rattling off facts about the pros and dreaming of a sports career of his own. “He swore he was gonna be in the NFL—went to practice and practiced really hard, and he never really achieved greatness,” Susan says. When Bennett was ten, he saw the writing on the wall and sat his mom down for a serious discussion about his future. “He’s like, ‘Mom, let’s face it, I’m never gonna make it in the NFL,'” she says. “‘I’m gonna have to figure something else out with my life.'”

In his junior year of high school, Bennett got hooked on shooting and editing video. That spring, Chance the Rapper dropped his Acid Rap mixtape, which rocketed him to international fame, and his work with videographer Austin Vesely inspired Bennett as he tried to figure out how to contribute to Chicago’s hip-hop scene from an hour away. He’d drive to the city to see shows with his friend Bernie Niyonzima, a childhood friend of Vic Mensa‘s who now raps as Duffle Bag Buru.

Buru also helped Bennett film in Chicago, and in June 2013 he conducted an interview with South Holland rapper Kembe X that became the first video on Bennett’s YouTube channel. At around the same time, Bennett convinced his friend to try his hand at rapping. “He’d be like, ‘Yo, man, we should make videos, you should rap—you could be the best rapper in the town,'” Buru says.

Even then, Bennett had grand ambitions. “I was like, ‘I wanna do something more—I wanna be more involved, I wanna be able to help people have a voice, and build a platform,’ because I saw an opportunity,” he says. “There was definitely blogs around, but there weren’t nearly as many as there are now. You had Fake Shore Drive, Elevator, and stuff like that. I was like, ‘You know what, I think it would be cool to make my own music platform.'” He started bouncing ideas for site names off his mom.

“I don’t even know where it came from,” Susan says. “But I just said, ‘Lyrical Lemonade.’ He’s like, ‘That’s it!'”

Bennett wrote blog posts after school, covering obscure up-and-comers as well as the occasional established local such as Vic Mensa. Some of his first posts were about Sunnie Storm, Max Bouvagnet, and Carl, who’d eventually join Hurt Everybody (he now records and performs as Qari). In February 2014, he threw his first Lyrical Lemonade showcase, a free concert at the Music Garage’s modest performance space with more than a dozen acts, among them Treated Crew member Saint Millie, pop-forward rapper-producer Supa Bwe, and hip-hop group Supreme Regime (whose members included Carl).

“I got to meet a lot of cool people for the first time, ’cause it was all Internet relationships prior to that,” Bennett says. Alex Wiley of Chicago collective the Village showed up, and Bennett asked if he wanted to do an impromptu performance. “He came out and performed a song, and that was the craziest thing ever,” Bennett says.

In fall 2014 Bennett started classes at DePaul, which brought him closer to the scene he’d loved from afar. But at least at first, he concentrated on school, where he studied digital cinema and later communications. He wanted to prove to himself that he could do well. “I had nearly a 4.0 my freshman year—in high school I was a standard student, so that was a big deal for me,” he says.

Bennett shortly realized that his college workload would make it impossible for him to handle Lyrical Lemonade by himself, so in early 2015 he put out a call for writers on Twitter. He wound up adding two people to the team: One was Bryan Snow, aka aspiring rapper Space Snow, who died in a car accident last fall. The other was Elliot Montanez.

A native of downstate Coal City, Montanez had already crossed paths with Bennett, though he didn’t remember it—they’d played on competing high school football teams. Montanez had heard of Lyrical Lemonade before he came aboard, but he wouldn’t have known enough to want to answer Bennett’s call if it hadn’t been for a chance meeting at Vic Mensa’s Chop Shop show in March 2015.

Montanez was selling merchandise for Mensa, and after he got to talking with an overzealous teenager who’d sneaked into the venue, he invited the kid to help out. The teenager’s name was Luis Rodriguez, and he was a friend of Bennett’s. He also had a lot to say about Lyrical Lemonade. “He talked about Cole for about ten minutes,” Montanez says. “The way he spoke about him . . . it made me want to meet him.”

Montanez had some experience writing about music—he’d occasionally contributed to his older brother’s blog, See Beyond Genre—and within a couple weeks he had his first byline at Lyrical Lemonade. Rodriguez died in a car accident about a month later. “It’s like when you meet an angel—you meet someone and they point you in the right direction,” Montanez says. “Only time I ever met that kid, he put me on to Cole.”

In summer 2016, after a little more than a year with Lyrical Lemonade, Montanez took over as the site’s editor and administrator. After a day of work at Haight Brand, he’ll use a computer in the company’s headquarters to edit and approve blog posts for a few hours.

The site had 15 or 16 regular contributors when Montanez took over—”If you had two arms and could write sentences, you could write for Lyrical Lemonade,” he says—but he and Bennett soon whittled that down to seven or eight. Among the busiest these days are Vancouver resident Jake Lusted, whose early enthusiasm nearly alienated Montanez (“This kid was seriously e-mailing me every day for like a month”), and Lane Cowherd, a friend of Montanez’s from high school.

Montanez insists that his buddies don’t get special treatment (“I’ve cut my homies, I’ve cut my roommate—I don’t play that shit,” he says), but friendship is nonetheless a crucial part of Lyrical Lemonade’s success. “My main thing with anything—with Cole, with any of my friends, with anybody I manage, anybody I work with—if I don’t feel the friendship before anything, it just doesn’t work for me,” Montanez says. He manages Isaiah G and Femdot, and he says he spent about a year hanging out with Femdot before taking him on as a client.

Femdot definitely noticed that Montanez was putting in the time. “It just shows that it’s not something he’s trying to do just to get something—in terms of monetary gain or status,” the rapper says. “He genuinely believes in what I’m doing, and wants to be a part of it in any facet. There’s been many times where [he’d be] like, ‘Even if I don’t manage you, I’m still gonna rock with you—you’re my friend. That’s solid.'”

Montanez also put Femdot’s three 2016 EPs on Lyrical Lemonade’s list of the top 50 local projects of the year—at number ten, between Jamila Woods’s Heavn and Mick Jenkins’s The Healing Component. This might look like a conflict of interest, but given that the blog has no revenue and Montanez doesn’t get paid to manage Femdot, it’s tough to persuade yourself that anything really sinister is happening. “We don’t charge for posts or promotion or anything like that,” says Bennett.

Bennett manages a couple rappers too, including his friend Duffle Bag Buru. Buru had put music on the back burner after graduating from high school, but in October 2016 Bennett convinced him to return to the mike. “[Bennett] was bigger than any rappers that we even knew in the city—he had more of a name for himself,” Buru says. “The Lyrical Lemonade platform just made it easy. I didn’t have to worry about if people were gonna hear the music—I just had to worry if it was gonna be good.”

Bennett has helped Buru network by bringing him along on video jobs in LA and New York. This summer he landed his friend a featured verse from up-and-coming Atlanta rapper Pollari (on Buru’s track “New Bag”), and in February he booked him to open for irreverent Atlanta hit maker Playboi Carti at a Lyrical Lemonade show. “Cole’s place in the scene, his credibility—people are way more willing to accept the music,” Buru says.

Last winter Bennett decided to teach himself how to add animation to live-action videos, a skill that would shortly boost his profile hugely. Though he was still swimming against a torrent of homework (by then he was a sophomore at DePaul), he watched online tutorials to get the basics, drinking too much coffee and staying up even later than usual. A few weeks later he collaborated with Chicago videographer Laka Films to add animated flair—mostly bright white lines flashing from or outlining peoples’ bodies—to the video for Soulja Boy‘s “Workin’ It.” The clip features a cameo from Chicago sensation Famous Dex, and Dex called Bennett and asked him to make a video for his own “Hit Em Wit It.”

In early March 2016, Bennett ran a no-frills shoot in Dex’s Englewood basement. Up till then Dex’s videos had been quick and dirty, edited and uploaded within an hour, so he didn’t have much patience for Bennett’s process—editing and animating the clip took him about two days. “I’m coming home from class—he’s blowing up my phone,” Bennett says. “I was like, ‘Fuck it, I’m gonna FaceTime him—I’m gonna show him what I’ve got.’ I remember he had his hand over his mouth, like he’d never seen anything like that.”

For his part, Bennett had never seen anything like the numbers Dex’s video racked up. His most-watched video at that point had about 100,000 views. “Hit Em Wit It” now has more than 15 million—though doors have been closing in Dex’s face since September 2016, when surveillance footage that leaked on Instagram apparently showed him beating his longtime girlfriend. XXL editor in chief Vanessa Satten has cited the video to explain why Dex didn’t make the cut for the magazine’s 2017 “freshman class” issue.

But at the time, that leak was still months away, and “Hit Em Wit It” opened the floodgates for Bennett. He began making videos for local stars such as King Louie and Lil Bibby, as well as for the Soundcloud rappers who began breaking out this year—his video for “Ski Mask,” by Miami MC Smokepurpp, hit the Web last July, four months after “Hit Em Wit It.” Not long after his work with Dex, in spring 2016, Lyrical Lemonade was demanding so much of Bennett’s time that he sat down with his mom and one of his older sisters to talk about the idea of taking time off from school.

“We all as parents think your child should go to college and get a job—you just envision that as normal,” Susan says. “It was a little frightening, but exciting at the same time, for Cole to make a decision like that. It was very well thought out, and I know that he considered everybody’s feelings along the way. I knew that he was making the best decision for him and his career.” Montanez had already left Robert Morris University, quitting in late 2015 to focus on his music-industry ambitions.

Both Bennett and Montanez seem to have made the right call. In just a few years, Lyrical Lemonade has gone from throwing small shows at the Music Garage and Jerry’s in Wicker Park to putting together big showcases with rising stars—including Lil Uzi Vert’s first Chicago gig, at the Metro last April, and Playboi Carti’s February concert at the Portage. Bennett says Carti’s road manager told him at the show that the rapper hadn’t planned to play any dates before releasing his self-titled mixtape in April—not until Lyric Lemonade came calling. “She’s like, ‘We did it because it’s a Lyrical Lemonade show—we’ve seen your work, we know what type of shows you guys do, we know that you guys have a good reputation in the music scene,'” Bennett says.

Bennett puts a lot into the Lyrical Lemonade concerts—if tickets sell better than he’d hoped, he plows the extra money back into the production, spending it on a light show or on T-shirts to toss out to fans. Now he’s booking a Lyrical Lemonade fall tour.

Today Bennett coud probably work exclusively with rising stars, but he still wants to invest in Chicago’s hip-hop scene on a grassroots level. Since 2015 he’s filmed free public cyphers in parks and on beaches, inviting anyone who feels like it to rap a cappella in front of his camera—he’s been uploading the series to his YouTube channel under the running title “Chicago’s Biggest Cypher, Ever.” The fifth installment will be this fall, but given the growth of Lyrical Lemonade’s following, Bennett expects a crowd so big that he’ll have to think carefully about a location.

Bennett and Montanez take pride in Lyrical Lemonade’s continued coverage of unknown artists—they get just as much attention as rappers name-checked in glossy magazines. For this reason, I’ve used Lyrical Lemonade as a resource myself: to learn about promising young local rapper Ausar Bradley, I read his Lyrical Lemonade Q&A.

Lyrical Lemonade doesn’t do top-tier numbers on its blog—Quantcast reports 27,708 unique visitors from within the U.S. for June 2017. But because that statistic doesn’t say anything about who those people are, it also doesn’t say much about the site’s influence or reach. Rather than discuss website stats, Bennett and Montanez prefer to talk about the person in Portugal who recently ordered a Lyrical Lemonade shirt.

Bennett continues to shoot videos for Chicago rappers, including Cdot Honcho, Roy French, and his management clients, Duffle Bag Buru and the rabble-rousing Warhol.SS. But he hopes to take on new ventures soon—among them creating a literal lemonade sharing the brand’s name (“We can print out and assemble the carton right now”) and opening a physical storefront to sell Lyrical Lemonade clothing.

The most recent Lyrical Lemonade clothing collection dropped Monday, August 14, and in less than 24 hours the swim trunks had sold out. For the past year, Lyrical Lemonade has contracted with Haight Brand to help with manufacturing, online sales, and shipping—Montanez’s day job sometimes involves fulfilling orders for his passion project.

“Lyrical Lemonade had the second most sales this month, behind Chance the Rapper, with over 30 clients on that list,” Montanez says.

“Did that happen?” Cole asks.

“Yeah,” Montanez says. “It’s cool.” v