Cole Bennett: From Small-Town Illinois to Modern Music Empire

September 20, 2021
How They Made Their Bread

There's no question that music, specifically hip-hop, has evolved over the past several decades.

It feels as if the rap scene has gone from feared to friendly with the rise of social media and community-building. One of the behind-the-scenes (or behind-the-camera) leaders in this new generation of music has been Cole Bennett.

At only the age of 23, he's built a multi-million dollar music brand and has collaborated with artists from Lil Uzi Vert to Soulja Boy to Eminem.

How He Started

Growing up in the cornfields of Plano, Illinois - a town with a population of 10,000 - Cole had dreams of attending Illinois State, Iowa, or Mizzou and becoming a sports broadcaster. Like a lot of kids who grew up in the early 2000s, he and his friends spent a lot of time together and would record Jackass-esque videos on a home camera for fun. 

However, it wasn’t until his junior year of high school that he began taking his creative efforts more seriously. He was taking a multimedia class and had latched on to rap music early in life. With this, he began filming music videos for free with his mom’s camera and chopped them up in iMovie. 

His hometown was about an hour and a half away from Chicago, a city where hip-hop was growing, so he began to immerse himself in the Chicago music scene. This was the same time that Chief Keef, Lil Durk, Mick Jenkins, Vic Mensa, and Chance the Rapper were all up and coming so there was a lot to be excited about just within one city. He didn’t see the need to listen to music coming from anywhere else. 

But the journey to where he’s at now with Lyrical Lemonade didn’t really start until his senior year of high school.

One day, he and his mom were working through ideas on what to name his blog. He wanted a catchy name that could tie in an element from music and something not related to music whatsoever. He was trying combinations of different foods, fruit, and then his mom suggested “Lyrical Lemonade”. 

At first he was hesitant.. then, he knew it was perfect.

Loving everything that was happening in Chicago, he started a blog on Wordpress and began writing about the music and artists coming out of the Windy City because now, he wanted to be a journalist. This decision became the foundation of his work and his brand.

via Complex


Now, he wanted to get the brand and logo on everything he could so he started drawing the logo in notebooks at school, got stickers, clothes, anything he could get his hands on. 

To start building the brand, since he lived fairly close to Chicago, he would drive back and forth on weekends to meet up with artists, build relationships, and attend local shows. After spending time in the Chicago scene, he would come home from school and write 10 articles a day about local music that wasn’t getting covered by larger media brands. 

Being in a small town, he reverted to Twitter for all of his networking. He’d write his blogs, post the link to Twitter, engage with the artists he was writing about, and that’s truly how Lyrical Lemonade was born.

Then, he started to get his first real traction when he graduated high school and moved to Chicago to attend DePaul University.

He began as a digital cinema major but quickly switched up after a professor told him it was going to take over 10 years to become a director, his dream at the time. That of course bothered him and in true go-getter fashion, he dropped the digital cinema major and switched to communications because he figured if he had to be in college, he was going to learn about people and how to communicate and he’ll learn the technical skills of directing and video production on his own.

Now officially in the city of his dreams, he had free rein to do what he was passionate about. Local artists would come to his dorm room to film videos with his green screen, record interviews, and collaborate.

Similar to how people work a side hustle outside of their 9-5, Cole viewed college as his “job” and building lyrical lemonade was his side hustle. He didn’t attend many parties and stayed head down with the music.

An interesting takeaway from this period of his creator journey is that he never viewed Lyrical Lemonade being bigger than Chicago. Writing about music and collaborating with the local artists was something he truly enjoyed and didn’t imagine it could be any bigger than that. 

With this mindset, his biggest goal at the time was to throw a show at Reggie’s Rock Club, a small bar and venue in Chicago that has a standing room capacity of 400 people. The Rock Club was a hometown staple and he accomplished his goal quicker than expected, hosting his first shows in 2014. 


His next biggest goal was then to host a show at the Metro, another local Chicago venue. 

At the time, he was doing shows every 4 months or so, and taking money earned from the previous show and reinvesting in the next. 

He then locked in a show at the Metro for April 28, 2016. Given that he’d done several shows for local artists, he wanted to bring someone from the outside into Chicago. Being close to the underground scene, he’d heard about Lil Uzi Vert from time to time, and decided he was going to take a chance and bring him in to perform in Chicago for the first time.


At the time, no one knew who Uzi was - there was no XO Tour Llif3 and The Perfect Luv Tape was released 3 months after the show. Since Cole had never booked an artist outside the city, he simply Googled “how to book lil uzi vert”, found a website, contacted his manager, and found out that it was going to cost around $8,500. 

He sent in his $2,000 deposit 2 months in advance and having never booked an out of town act, he wasn’t prepared for the additional costs as he ended up having to pay for Uzi’s flight, hotel, etc. 

This was his biggest show at the time, he was in deep, and needed this to work. 

However, he didn’t know what was about to happen...

In the time between booking and the show actually happening, Uzi blew up. 

In February 2016, he released one of his biggest songs, Money Longer, on SoundCloud and 13 days before the show, on April 15th, he released his third mixtape and first commercial mixtape, Lil Uzi Vert vs. The World.

Cole initially had the tickets listed for $36 (his highest price ever) so that if he could sell the show out, he wouldn’t lose money. It did end up selling out and to his surprise, the tickets began reselling for $250+ because now, everyone wanted to see the hot new artist. 

With his biggest show ever under his belt and a knack for discovering new talent, he had a new long term goal: host a music festival.

This was a pipe dream to him and with that, he hoped it would happen sometime down the road, maybe in the next 10-15 years.

This was in 2016. 

By 2018, the first Lyrical Lemonade outdoor festival, Summer Smash, was held at Douglas Park in Chicago with headlining artists including Joey Badass, Trippie Redd, Lil Skies, and Vic Mensa.


Fast forward to 2021, he’s built a multi-million dollar brand with Lyrical Lemonade, worked with artists from Jack Harlow to the late JuiceWRLD, continued to grow Summer Smash, and has cemented his name as one of the best and most well-known music video directors in the world.


How He Made the Transition to Full Time Creator

Since he started at a young age, he didn’t have the typical struggles that come with the journey towards being a career creator. He was still in high school so his expenses were almost non-existent. He was just a kid being creative and figuring out what he loved doing - and that was blogging about music. 

However,  around the same time he started writing, he picked up a camera and began filming and producing music videos as well. This was a life changing decision and an impactful skill set because it presumably ended up being the thing that has brought in the most income & attention to Lyrical Lemonade as it was being built.

via XXL

His transition to a full time creator happened during college when Lyrical Lemonade began growing as more than just a local hip-hop blog. He was still dedicated to the blog and the brand, but he began putting on more shows and making Lyrical Lemonade bigger than just his writing.

One of my favorite parts of his come up story is how he utilized Twitter to build brand and interact with the artists he was writing about. For me, everything good that's happened since I started my own entrepreneurial journey in July of last year has stemmed from relationships that began on Twitter.

All of these efforts slowly compounded until he was earning enough money through the blog, doing videos, and selling merch that it could be his career and wasn’t forced to get a “real job” out of college.

A Look Inside His Creator Business

Today, Lyrical Lemonade is a modern, digital-first music media empire. What started as just a kid with a blog writing about what he loved, has turned into a music video production company, a platform to shine light on upcoming artists, a brand with over 20 million combined followers & subscribers, a YouTube channel that exclusively hosts some of the most popular music videos, a Supreme-esque merch line, and now, they even sell actual lemonade.

via Yard

Living out his not-so-distant dream, Lyrical Lemonade now hosts an annual music festival, Summer Smash. Launching in 2018, it started out as a one day show and they ended up selling 11,000 tickets. The following year, they extended it to a two-day festival and sold 20,000 tickets. 

What’s unique about this is that typically, a lot of dollars have to be put towards marketing to have a successful festival. However, since he built his brand digital-first and grew an audience along the way, he could market the festivals organically through his own social media channels.

Outside of the music videos, blog, and shows, their merch line is one of their biggest revenue sources. They typically do seasonal drops, limited quantity, all online — mirroring the exclusivity and hype of Supreme and other streetwear brand releases. In an interview with Gary Vaynerchuk, Cole mentioned that they've sold 1,500 hoodies in 8 minutes on release at $60/piece.


Quotes & Creator Takeaways

"Be yourself and whether (that) works out or not, you're going to be happy and I think happiness is the most important thing."
"We're all on a path to somewhere, we don’t always know where that somewhere is. but that’s ok, because there will always be a destination."
"The day you give up on your dream could be the day before your dream comes true & changes your life forever. if you really want it, let the passion drive you through the finish line"
"These labels give me so much trouble. Probably because I turned down all of their offers last year. Lyrical lemonade is one of the last self funded companies in this shit. Never fell victim to the industry, and I’m so so proud of that"
"I’ll never understand why people have a problem with the Birkenstocks. I enjoy being comfortable and if we’re being honest, the shits are stylish"
"I’m changing the world in this next decade, some how, some way for the better"

Takeaway #1: Twitter is disgustingly underrated

Lyrical Lemonade was built in the trenches of Twitter. By writing articles and sharing them on Twitter, Cole was able to engage with artists he was writing about without having to be physically present, allowing him to reach more people and build more brand than if he was networking in person. Whatever business or brand you're trying to build, if you're not taking advantage of the unlimited reach and ease of starting conversation on Twitter, you're doing yourself a disservice. Even a decade after launching, out of all the social media platforms, I believe Twitter holds the most power for creators.

Takeaway #2: Not everything has to be profitable from Day One

When Lyrical Lemonade was just starting, Cole bought fairly expensive, high-quality hoodies to get the LL logo on them. But rather than selling them with high profit margins, he sold them at a loss to get his brand out there on something that people would want to wear. Now, they sell out thousands of hoodies in minutes after launch.


The Wrap Up

Cole's built a business of his dreams, collabed with artists that have defined our generation, and became a household name in the music industry, all before the age of 25. What started as a blog and has since evolved into something greater, he's living proof that by following what you're passionate about, there's a chance you can turn it into your career.

And to put this on the record, I have a feeling we'll see a Lyrical Lemonade or Lenny NFT coming soon - Cole's fairly close with Gary Vaynerchuk and with the development of VaynerNFT, I can't imagine that something doesn't come from that.

Overall, Cole's been an inspiration to many young creators and even though he came from a small town, nothing was going to stop him from living out his dreams and chasing his passions.

via ViralTrench


More Content From Cole

A Tour Of The Lyrical Lemonade Office (2019)

Mindset is Everything | Cole Bennett | TEDxUIUC

COLE BENNETT | Before They Were Famous | Lyrical Lemonade

Juice WRLD - Lucid Dreams (Directed by Cole Bennett)

Eminem - Godzilla ft. Juice WRLD (Directed by Cole Bennett)

Juice WRLD - Bandit ft. NBA Youngboy (Directed by Cole Bennett)


Featured on

The Cole Bennett Interview - No Jumper

The Origins of Lyrical Lemonade | Meeting with Cole Bennett

Social Media

Twitter: Cole Bennett, Lyrical Lemonade

Instagram: Cole Bennett, Lyrical Lemonade

YouTube: Lyrical Lemonade, Lyrical Lemonade 2

Treyton DeVore

Treyton is a creative entrepreneur, writer, and financial planner.

He's been featured in Morning Brew, NerdWallet, Marketwatch, and more.

treytondevore.com

Related Posts