Years before his merch instantly sold out, Kanye West was ordering him to alter his videos or Quavo was sliding into his DMs, Bennett was just another highschool student scouring SoundCloud for the next big thing. Living in Plano, Illinois, Bennett felt a connection to the bustling local Chicago hip-hop scene, which he discovered after hearing Chance the Rapper’s debut mixtape, 10 Day. At that point, Bennett’s blog—Lyrical Lemonade—was covering hip-hop in general, but following 10 Day the site began to hone in on the Chicago scene specifically. As soon as he received his driver’s license, Bennett spent every weekend making the hour long commute between his hometown and Chicago where he recorded freestyles, show recaps, and the scene in general including Chance, Vic Mensa and Mick Jenkins—all of which wound up on the Lyrical Lemonade youtube channel. Between blogging and producing video content, Benton spent all his free time on the website and when a filmmaking degree at DePaul University felt too constraining, dropped out to focus on the site entirely. Within a few months his youtube channel was well recognized throughout the industry, boasting hundreds of thousands of subscribers.

Already notable for documenting the scene, Bennett wanted to be an active participant, which led to “Chicago’s Biggest Cypher, Ever”, inclusive sessions open to the public hosted by Lyrical Lemonade. The video—which included both emerging artists as well as normal individuals—quickly went viral, and established Bennett is not only a blogger, but a filmmaker and director. From there, requests came flooding in. First, there was Soulja Boy, who asked Bennett to animate his “Workin It” video. Then the management side of the business kicked in, when Bennett successfully booked Lil Uzi Vert to headline a sold out Lyrical Lemonade showcase—Vert’s first show in the Windy City. Finally, there was upstart Chicago talent Famous Dex, who hired Bennett to produce his videos and offered the 20-year-old full creative control. Suddenly, Bennett had cemented a link between one of the most prominent faces of the SoundCloud rap generation, and a true company was born.

Within months, the Youtube channel boasted millions of subscribers. Bennett rented an old warehouse space in Downtown Chicago and hired a string of employees—predominantly friends from college and those he had met through the scene. While the company quickly expanded, Bennett’s notoriety grew, the go-to director for the SoundCloud generation. Everyone from SmokePurpp to Warhol.ss (whom Bennett manages) were working with Bennett, producing free form videos which Bennett shot and animated himself. With a meager budget and almost no overhead, Bennett directed viral hit after hit, including SmokePurrp’s “Ski Mask” in Miami, where Bennett introduced the world to Lil Pump. Bennett’s trademark style—handycam, cartoonish illustrations and neon-tinted lighting—eventually transcended music videos and informed an entire brand aesthetic, including the website, office and logo, an animated lemonade carton that could be straight out of Nickelodeon.

With hundreds of videos under his belt—and already have expanded into management—Bennett wanted to push the brand to the next level, including a now 2-day festival, Summer Smash which draws 20,000 concert-goers each day and, of course merch. Apart from the limited drops only available on the Lyrical Lemonade website, the company launched a capsule alongside Chicago retail icon RSVP Gallery (which also instantly sold out as). While distribution is limited, Bennett’s more than 10 million Youtube subscribers are constantly itching for more, and willing to pay a significant markup to get it.

What distinguishes the company—apart from tapping the next generation of hip-hop at a fundamental level—is the ability to relate to Generation Z. Bennet—at just 23 years old—is a peer and his interests perfectly align with those of his audience. Whether it’s filming a video for YNW Melly or launching a beverage (lemonade, naturally) at ComplexCon, Lyrical Lemonade operates on the sort of gut instinct, intuition and care free attitude that defines the next generation.

Today, Bennett maintains sole ownership, and claims he has turned down numerous offers to sell the company—including one for more than $30 million. Clearly, he feels passionate about the brand he has built. While media conglomerate may be a bit of a stretch, few companies have the reach Lyrical Lemonade does in the space it occupies. Whatever Bennett does next—merch or otherwise—guarantee it will make an impact.