Inside Cole Bennett’s Lyrical Lemonade Empire

Years before it became a full-time job, Bennett launched Lyrical Lemonade when he was a high school student in the small Illinois town of Plano, looking in from the outside on a vibrant Chicago hip-hop community. As soon as he got his driver’s license, Bennett got in a routine of making the hour-long trip to the city every weekend. He brought his camera wherever he went and documented the scene, which included rising artists like Chance the Rapper, Vic Mensa, and Mick Jenkins.

“I remember the day 10 Day came out and Chance did his release party at Leaders,” he says, recalling the era that made him fall in love with Chicago rap. “You'd see Vic Mensa just walking down the street. Everything was right in front of you. It was all happening right in front of your eyes, and it was the craziest thing.”

In its early stages, Bennett’s YouTube channel was dedicated to Chicago show recaps, local cyphers, and documentaries about the city’s hip-hop scene. Then, in 2016 and 2017, he began working with artists like Famous Dex, Lil Pump, and Ski Mask the Slump God, and soon became the go-to video director for an entire subgenre that was exploding from SoundCloud pages into the mainstream.

Suddenly, Lyrical Lemonade’s scope was expanding far beyond the city of Chicago, but Bennett made a decision to stay in the city that inspired him to begin his career in the first place. He admits that it would have made a lot of things easier on him if he moved to Los Angeles or New York City when he started working with artists on a national scale, but he chose to set up the Lyrical Lemonade headquarters in Chicago instead. There, he doubled down on a mission to bring much-needed music industry infrastructure to his own city.

“I am in a position where I can help possibly make Chicago that next city, the next L.A., in terms of resources and hubs,” he says, “and really just make people more aware of the music culture here. For some people, it’s beneficial to move out of Chicago once you’re in a position to do so, but I think that there is also something to say about trying to give back to the city.”

Bennett explains that many of the city’s venues have grown wary of booking hip-hop acts in recent years because of a fear that violence will break out at shows, which has dampened the area’s once-vibrant live scene. 

“We need this city to open their arms and establishments to allow the scene to continue to thrive,” he says. “I tried to bring so many shows to Chicago, and venues would pass on them. I just couldn’t do the shows at a certain point because I had nowhere to throw them. Then I had to kind of build up my own structure and break through the wall.”

In the summer of 2018, Bennett took it upon himself to bring something new to the city and announced Lyrical Lemonade’s inaugural festival, Summer Smash, which drew 11,000 attendees in one day. The festival’s second year expanded to a full weekend, drawing 20,000 fans each day. By 2020, it will extend to three days, but one thing about Summer Smash will stay the same: it will always be a Chicago event.

“The festival will never travel elsewhere because we want to create a community in Chicago,” Bennett stresses. “We want Chicago to be the place everyone wants to be. As much violence as there is going on in the summer, there are just as many amazing things happening. Festival season is always such a highlight in all these kids’ lives in Chicago. It’s just a fun time to be around, so it was important for me to bring something like this to Chicago. It inspires people and gives them a fun, safe place to go and have a good time for a weekend. It’s something to look forward to. Something to take pride in, really.”

It’s 2 p.m. on a Thursday afternoon at the Lyrical Lemonade office in Chicago, and a wild game of basketball has broken out in the aging warehouse space. Weed smoke wafts through the air and Lil Tecca’s “Ransom” plays loudly through a stack of speakers in the corner as Bennett and his team swap stories about seeing DMX at Rolling Loud. 

To the untrained eye, it appears that absolutely no work is getting done. But as the chaos unfolds, Lyrical Lemonade’s A&R, who goes by Lil Jake, pops in with an update about DaBaby’s uncertain status as a performer at this year’s Summer Smash, before they all rally to come up with a solution to the potential crisis. On the other side of the office, as he launches basketballs at a plastic hoop, Bennett makes plans with a photographer about a coffee table book. The work environment at Lyrical Lemonade is far from traditional, but the small team finds a way to be extraordinarily productive.

“We just go with the flow,” Bennett says. “We’re all passionate about what we do, and we have a mission. We have things we need to get done, so we get it done, but we get it done in our own fashion. Some days, we might spend three hours having a dunk contest out there. And some days we might work a 20-hour day nonstop, and no one’s talking to each other. We’re just zoned in.”

Bennett has surrounded himself with a group of like-minded friends, many of whom he met in college, and he attributes much of the company’s success to the chemistry that exists within the team. “I’ve always been super selective with who we bring on because you never know who you can trust,” he says. “This is my baby, so I want to make sure other people treat it the same way. There is definitely a type of person I look for. It’s someone who’s selfless, has good intentions, has good energy, and wants to be a part of something special. They need to love it and be passionate about it. I really just like open-minded people, and good people.” 

He adds, “Success is putting people around you in a position to do great things. It’s about being able to pass the torch. I think being successful is being able to plant the seed that plants a tree that lives forever.”

Elliot Montanez, who runs the Lyrical Lemonade website, says Bennett has created a unique environment that inspires the rest of them to work their asses off without burning out. “It’s very fun,” he explains. “There's a lot of freedom. Everyone has worked jobs that they didn’t like and didn’t like going to. It doesn’t feel like that.”

Everyone on the team says Bennett leads by example. “I think his greatest leadership quality is his ability to present an idea and then execute it so well that anyone who witnesses that can buy into it and trust it,” notes JB, who handles design and development at Lyrical Lemonade. “He’s the hardest-working person I know, and I’ve met a lot of people who would probably claim that. People don’t understand that he might be on Instagram in the Dominican Republic, goofing around, but when he puts his phone down, he’s in the hotel room for 12 hours working on an edit.”

Bennett is the type of person who has a habit of saying he wants to change the world, but he manages to say it in a way that doesn’t sound corny. If you spend enough time around him, you’ll start to believe his wildest ideas, and it’s clear that everyone around him has bought into his vision. “We’re trying to change the world, and change the music industry,” Lyrical Lemonade’s executive producer Sal Tarantino promises, echoing his leader. “We are an independent company. We’re trying to do things super grassroots.”

There’s a genuine sense of joy and enthusiasm in the Lyrical Lemonade office that comes as a refreshing surprise to anyone who has spent considerable time in the music industry. “It's super cool because everyone's very passionate about what they're doing, and the music that we're involved with,” Tarantino affirms.

Bennett’s guiding principle at Lyrical Lemonade is that fun and happiness should be prioritized over everything. “I think that the No. 1 most important thing in the world is to be happy,” he explains. “I truly think that. I don’t ever really want to grow up. I just feel like a kid, and I’m happy. I'm living day by day, just having fun.”

He’s been able to operate the company like this because Lyrical Lemonade has remained independent, despite tempting offers. “We never got funding from any big company, and we never sold out,” Bennett says. “There have been some crazy offers there for a long time, and I just said, ‘No, no, no,’ because I wanted to do it how I wanted to do it. I wanted to be happy. I didn’t want to be controlled by anyone else. When I got to a point where I was making money off it, and I was able to make a living off it, I made a promise to myself that I’d always keep the passion first and I’d never prioritize the money aspect over the passion behind it.”

When the rest of the music industry took notice of his track record breaking future superstars, bids for the sale of Lyrical Lemonade increased, but Bennett’s answer remained the same.

“I was offered $30 million for Lyrical Lemonade around a year ago,” he reveals publicly for the first time. “It was the most refreshing feeling to decline that and stay true to myself. I didn’t even have to think about it, and I know that sounds crazy. I haven’t seen anywhere near that amount of money in my life at all.”

Lil Jake says this mentality is part of the reason Lyrical Lemonade has been successful and resonated with fans so deeply. “Cole genuinely cares so much about the music,” he says. “It’s never a money thing. Everything Cole does and everything Lyrical does is out of love. I think the most important thing that’s gotten us here is how much everybody genuinely cares about the music, cares about the art, and cares about putting on an experience.”

Analyzing his decision to turn down a series of offers, Bennett says, “I feel like I would’ve failed myself if I would’ve given up what I love for money, because I’m happy. More money can’t make me happier. It wouldn’t do anything for me. If anything, I’d probably be miserable, because I would eventually realize that I gave up what I love and I failed myself.” He adds, “I want to go to the grave and know that I did something I love my whole life and spread a message and stayed true to myself.”

Remaining independent hasn’t limited Lyrical Lemonade’s opportunities. Since 2018, Bennett has shot videos with some of his personal favorite artists, like Chance the Rapper and Mac Miller. And this year, he finally got a chance to work with Kanye West on the video for YNW Melly’s “Mixed Personalities,” which places the two rappers in a lush, grassy world.

Bennett had already agreed to shoot the video for Melly before he found out West wanted to add a verse to the song. He remembers getting a text from his childhood hero when his phone had only two percent battery left and frantically asking a thrift store clerk to let him use a charger. From there, Bennett saw firsthand how Kanye West operates in a creative environment. 

“He vocalized to me prior to shooting that he wanted to appear as a light from God,” Bennett recalls. “And just in a good, healthy place. So that was why I incorporated a lot of the grass, to make it feel very earthy."

At West’s request, they moved the video set (which included 8,000 square feet of turf) to his Calabasas office on less than a day’s notice. But otherwise, West was receptive to Bennett’s vision and let the young director call the shots, even when there were disagreements. 

“He kind of let me do my thing until the night before the video actually came out,” Bennett says. “Last minute, he wanted to make the video black and white. And I was like, ‘You know, I can’t really do that. This is really big for Melly. This is Melly’s moment, and blue and green is his color scheme. I told him he needed to trust me on this. So he just let me do what I needed to do. Working with him was cool. He was really respectful.”

Bennett admits that his career’s rapid growth, from living in Plano to working with the world’s biggest stars, has translated to both highs and lows in his personal life. 

“Everything happened so quickly for me,” he explains. “At first, I was so happy. I was like, ‘I’m living my dreams; God chose me.’ That’s how I literally felt when everything was happening [in 2017]. Then it became my life, and it became what I was doing day in and day out. I felt like I needed to uphold this idea of what people thought about me and my work. I would just pay too much attention to what other people thought of me,” He adds, “I was working so hard, and I forgot how to take care of myself and my friends. I forgot to be happy, because I was just working all the time.”

The death of Bennett’s newly acquainted close friend Mac Miller last September helped put things in perspective. “When Mac passed, it really affected me because he was such a positive person,” he says. “To see what happened with him, it made me appreciate things. He affected my life in such a way that it made me want to just show out for him because he’s looking down on me. I truly believe that.”

This year, Bennett was able to rediscover the enthusiasm that caused him to fall in love with the work in the first place. “One day I flipped a switch and I was like, ‘I’m here to make a change in the world, but, more importantly, I need to enjoy it while it’s happening,’” he remembers. “I realize I’m in a position where I control my own narrative. It’s like I’ve had the keys, but I was always sitting in the back seat. I finally hopped in the driver’s seat, and I’m just having fun now.”

Midway through 2019, Cole Bennett says his creativity is flowing better than ever, to the point that he admits it’s often difficult for him to go to sleep at night because of all the ideas running through his head.

Bennett’s latest creation is his most ambitious yet. After years of dreaming about it, he launched a lemonade company this summer. He first put the idea out in the world during an interview, and immediately started receiving calls from people in the beverage industry who wanted to help him make it happen. Now, following years of research and development, cans of his own lemonade will be available to the public for the first time at events like ComplexCon Chicago. By next year, he plans for them to be in stores across the country.

He admits he’s still “learning how to run a business,” but Bennett keeps tackling new ventures. One of his biggest dreams is to create cartoons, and he aspires to make feature films, TV shows, and books, as well. “I want to make everything,” he says. “I literally want to do everything. And I’m already working on a lot of those things right now.” Lyrical Lemonade is moving into a larger office space this year, which will expand its video production capabilities, but, perhaps more importantly, it will provide additional room for any other ideas he may cook up.

“I’m working on so many things outside of music videos because I don’t want to limit myself,” Bennett says. “I look to people like Steve Jobs, Rick Rubin, and Walt Disney. I look to artists like Tyler, the Creator and Kanye, who never limited themselves, always wanted to go above and beyond, and really try to change the world. They always do new things and try new things, and they never put a ceiling to themselves. That’s what I aspire to do. I want to leave an impact, and I want to create a structure and a blueprint for kids to come. Anyone can do it. You’ve just got to want it.”

Bennett says music videos will always be a part of his creative output, and hip-hop will remain the core of the Lyrical Lemonade universe. But he is beginning to think about his future more. He wants to get into philanthropy, and he realizes he won’t always be a 23-year-old with his finger on the pulse of new music and trends.

“Eventually I’ll be old and not in tune with things,” he points out. “I’ve actually been thinking about that a lot lately. One day I’m going to be old. I’m going to be an old dude who people aren’t going to look to for new music.”

Pausing for a moment, he adds, “But as long as I’m able to inspire and make change, I’m going to.”

ComplexCon is coming to Chicago on July 20-21, 2019. Experience the festival and exhibition at McCormick Place, featuring performances, panels, and more. For ticket info, click here.