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Rolling Loud’s penchant for hospitality and evolution helped shepherd its 2021 return

·5 min read

The key to the success of Rolling Loud — an international festival that boasts hip-hop’s biggest names — is absurdly simple: relationships.

Rewind to 2014. Travis $cott has “Owl Pharoah,” “Days Before Rodeo” and a string of singles to his name. Rolling Loud co-founders Matt Zingler and Tariq Cherif book him for their first festival, treat him like the superstar he would soon become and, just like that, a bond is born. Fast forward seven years, with a tumultuous 2020 behind them, the duo managed to keep the now internationally known, eight-time Grammy nominee — who has now dropped the dollar sign from his name — as the headliner for their first live music festival since 2019.

“When [smaller artists] get their own greenroom, they feel like a real artist, not just some kid online rapping who got booked for a show,” Zingler told the Miami Herald. “We’re just more attentive than other events have been to them, which sets us apart, which makes them want to play at our show.”

The fruits of Cherif and Zingler’s hospitality will be on full display this weekend with the return of Rolling Loud Miami. Scott, along with Lil Baby, Megan Thee Stallion and Lil Uzi Vert, are just a few of the hip-hop superstars scheduled to perform. Offstage, the co-founders upgraded the site experience with more art activation and amusement rides, as well as a bigger skate park and basketball court.

“We challenged our sponsors to really elevate when they activate something really cool for our attendees,” Cherif said in early July. Less than a week later, Rolling Loud announced two WWE Smackdown matches will be held on-site.

Execution and Evolution

Whether with the WWE or Scott, Cherif and Zingler’s knack for fostering new relationships also highlights a fundamental element of the Rolling Loud brand: evolution.

As the various sounds of hip-hop’s blogging era gave way to SoundCloud Rap (a term that Cherif hates; “I’ve never heard of another genre that’s named after the platform or medium that the music was released on. You don’t have cassette rap.”), the duo stood as a middle child of sorts. They showcase acts associated with the former, like A$AP Rocky and Curren$y, as well as the latter, like Playboi Carti and the now-deceased XXXTentacion.

Their Simone Biles-like ability to straddle that difficult line is one reason why their festivals have grown from one-day concerts in Wynwood to three-day bangers at Hard Rock Stadium and Citi Field that attract more than 200,000 people individually.

“They built the company based off of delivering and execution of what they promised people — fans specifically but also the artists too,” said Alex Castaldi, Rolling Loud’s director of brand partnerships.

Delivering, however, got a lot more difficult in 2020. With Rolling Loud Miami one of three festivals canceled due to COVID-19, calls for refunds soon flooded their social media pages. The brand obliged — even if most of the money had been spent on building the very lineup that attracted fans in the first place.

“We didn’t know when the festival was going to come back, if at all, that year,” Castaldi said. “But what we did know is that people are going to need music.”

A community of their own

Enter Twitch.

Known primarily for streaming video gameplay, Twitch partnered with Rolling Loud to produce content in the form of shows and virtual festivals. More than 4 million viewers tuned into the first Loud Stream festival, which featured performances by Swae Lee, Ski Mask The Slump God and NLE Choppa, in September 2020. Livestreaming has long been a way to enjoy Rolling Loud — Zingler professed the love for the medium in a 2018 Forbes piece — but the Twitch partnership pushed it to new heights.

“When you remove the capacity from the event and you add that livestream, you can have millions and millions and millions of people watching the show,” said Zingler. “It helps the artist because they’re getting exposure. It helps the event because the event is getting exposure. It’s something really cool we can offer the world for free.”

Cherif added: “Miami 2019 did like 12 million viewers. That’s more than the MTV Awards.”

As Rolling Loud has grown in size, so has its responsibility to the Black and brown communities driving hip-hop. The September Loud Stream occurred about four months after the murder of George Floyd, whose killing at the hands of a now-convicted Minneapolis police officer became a flashpoint for worldwide demonstrations on racial inequality. A Black Lives Matter backdrop is clearly visible in the show, but Rolling Loud’s support goes beyond signage.

Recording artist Kaash Paige poses in front of a back drop at Rolling Loud’s two-day virtual Loud Stream festival in Miami, Florida, on Saturday, September 12, 2020. Paige is scheduled to perform on day 2 of  Rolling Loud Miami.
Recording artist Kaash Paige poses in front of a back drop at Rolling Loud’s two-day virtual Loud Stream festival in Miami, Florida, on Saturday, September 12, 2020. Paige is scheduled to perform on day 2 of Rolling Loud Miami.

In addition to raising money for the Equal Justice Initiative, Rolling Loud will host organizations like Headcount and the Florida Rights Restoration Coalition on-site to educate festival goers about the importance of voting. Desmond Meade, the president and executive director of FRRC, which focuses on helping formerly incarcerated citizens reintegrate into society, says the partnership presents an “amazing opportunity” to encourage participation in democracy.

“What we’ve seen, especially in the hip-hop community, is that a lot of the fan base are those exact same people who’ve been impacted by those issues” restricting the rights of people who have served time, said Meade, who has worked with Rolling Loud since 2019. “… We have the power to change the conditions in our communities and one of the biggest megaphones to spread that message is through the hip-hop community.”

With Rolling Loud, Cherif and Zingler set out to create a community of their own amid a broadening hip-hop fan base. That goal has underscored nearly everything the two have done since; from their relationships with artists, to their pandemic pivot, to their promotion of social awareness. So when the very first fan walks through the gates on Friday, they’ll be entering not just another festival but a carefully curated experience comparable to another attraction roughly 200 miles north.

“We see ourselves as hip-hop Disney,” Cherif said. “We’re a world you can come experience and we’ve also branched out into content, lifestyle, merch and everything.”

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