"I don't think it was ever the intention of the board to be malicious and cancel; I just think they were trying to make sure we were operating by the law. There are a lot of eyes on our event," Cherif tells Billboard. "I think maybe the city was trying to protect itself from anything bad happening."
The festival had been approved by Bayfront Park Management Trust executive director Timothy Schmand, only to draw the ire of board member Frank Carollo who said he first learned of the event from police and argued that Rolling Loud should have been approved by the full board of directors. Schmand resigned from his position after the dustup, stepping down after 25 years on the job and complaints that increased use of the Bayfront Park for events like Ultra Music Festival had brought new scrutiny from police and residents.
"We've done everything that you need to do to produce a good, clean, fun, safe event, and it was basically just a conversation, more than anything, about a few details of our agreement with the park," Cherif explains. "I think the city attorney and the commissioner caught wind of it and weren't aware how big the festival was going to be. They just didn't believe us when we said we were going to do that many people. Like we were crazy, because we are an independent company. We're not Live Nation, we're not AEG, we're not any of these established festival platforms. I think they look at two guys under 30 years old claiming that they're going to do 40,000 people and maybe they just didn't take us seriously, but we are very serious."
Dope Entertainment was founded in 2010 by Cherif and his partner
Matthew Zingler, Florida college students at the time: Cherif at Florida State and Zingler at the University of Florida.
"We actually lost our ass on our first show with Rick Ross," Cherif says. "We learned our lesson, and we went back to what we wanted to do, which was book this new wave of rap." Since then, Dope Entertainment has promoted for Curren$y, Wiz Khalifa, Mac Miller and Big Sean.
They launched Rolling Loud in 2015 as a one-day event at Miami's Soho Studios with ScHoolboy Q, Juicy J and A$AP Ferg headlining for 6,000 people. Cherif said Dope Entertainment didn't lock in a lineup until weeks before the event and got hit with "torrential downpour rain" at the beginning of the day. He estimates he lost about $100,000 on the first run, but made it up in 2016 with a 15,000-person event spread over two days with Future, Young Thug, Roy Woods, 2 Chainz and Ty Dolla $ign headlining.
"We were like, 'Well, I guess we proved the concept. Let's really go a lot bigger.'"
And he's feeling lucky, he said, especially after winning an approval from the Bayfront board on a vote he and his crew had been sweating.
"I was so stressed, but I had this weird moment," he explains. "I hadn't tied a tie in a long time, but I decided to wear a tie with my suit. As I tied it, I tied a double-Windsor knot first try. At that moment, I knew it was going to be a good day."
This year's Rolling Loud festival is divided into two main stages with the historic Biscayne Bay as a backdrop. A three-day GA ticket for the all-ages event is $249.99. Learn more at RollingLoud.com.