How Kevin Liles & 300 Entertainment 'Move Our Culture Forward'

Kevin Liles executive of the year
Flo Ngala

Kevin Liles photographed on October 21, 2020 in New York. Grooming by Laura Costa at Exclusive Artists.

Whether supporting Megan Thee Stallion’s monster year, grooming artist entrepreneurs like Young Thug or showing up for social justice, the independent king is “a pillar” for his label and community.

This story is part of Billboard's annual R&B/Hip-Hop Power Players list, which spotlights the executives who continue to push the genres forward.

Midway through Megan Thee Stallion’s performance of her hit “Savage” on Saturday Night Live’s October season premiere, the sound of gunshots cut the music short. Audio clips of an iconic 1962 Malcolm X speech and of Black Lives Matter activist Tamika Mallory played, followed by an impassioned speech from Megan herself, calling for justice in the wake of Breonna Taylor’s death in March at the hands of Louisville, Ky., police — and for the protection of Black women and men in this country.

For Megan, 25, it was a powerful statement made on the biggest platform of her career, and the highlight of a year in which she topped the Billboard Hot 100 twice — with her “Savage” remix alongside Beyoncé, as well as the jaw-dropping Cardi B collaboration “WAP,” which also ruled the first-ever Billboard Global 200 chart in August. For Kevin Liles, the founder/CEO of Megan’s label, 300 Entertainment, it was further proof that nothing — not even a global pandemic — could slow down his newest superstar.

“She’s in there every day, going through it and having the conversations and working hard,” says Liles, 52, who co-founded 300 alongside Lyor Cohen (now YouTube’s head of global music), Todd Moscowitz (now Alamo Records’ CEO) and Roger Gold (Camila Cabello’s manager). “And her greatest time, right now, is during a pandemic. She’s still evolving and telling the story, and she hasn’t even put out an album yet.”

As Liles sees it, Megan’s banner year is also the epitome of 300 in peak form: generating hits, breaking artists and overcoming odds, while maintaining a social conscience and putting people — both artists and employees — first, even in difficult times. “We’ve all had a hell of a year,” says Liles with a self-deprecating laugh. “I might have just had a good business year, too.”

Flo Ngala
Kevin Liles photographed on October 21, 2020 in New York.

That year has certainly helped make 300 a hot commodity in a rights market where investors are streaming into the music industry. Liles plays down the possibility of a sale, but says the company never rules out potential acquisitions, mergers or strategic partnerships. “Two years ago, 300 had a campaign that we’re not for sale, and although we’ve had several companies and investors approach us, we’re interested in building a billion-dollar company and servicing our artists and partners to the best of our ability,” he says. “There is never an opportunity we won’t run down if it’s for the betterment of our artists.”

Megan’s success this past year — which also included a top 10 debut on the Billboard 200 for her Suga EP and top 30 Hot 100 hits with nonalbum singles “Girls in the Hood” and “Don’t Stop” with labelmate Young Thug — makes her the latest in a line of standout R&B/hip-hop artists that 300 has signed in its short history. Since launching as an independent in 2013, the company has scored No. 1 singles and/or albums from Fetty Wap (Fetty Wap), Migos (Culture, “Bad & Boujee” featuring Lil Uzi Vert) and Thug (So Much Fun, Cabello’s “Havana”).

By several measures, 2020 has been 300’s most successful year yet. Besides Megan’s ascendance to rap’s A-list, label artist Gunna (who is signed to Thug’s YSL imprint) landed his first Billboard 200 No. 1 with Wunna, as well as a Hot 100 top 10 (on Internet Money’s “Lemonade”), and Thug dominated the Hot 100 on 14 hits this year (including Travis Scott’s No. 1 “Franchise”), all of which were collaborations. “We do CEO business,” says Thug of working with Liles. “True partnership shit.”

Still, for Liles, 300’s strategy goes beyond hit music: Developing artist brands and powering individual empires within the company, like Thug’s YSL, are always priorities. “These are signs of building and providing an entrepreneurship inside our company,” he says. “I want us to be a wall socket: You plug in and power up.”

Liles has been honing this approach for over three decades since his time alongside Cohen as president of Def Jam Recordings in the late 1990s and early 2000s, and through his rise to Warner Music Group executive vp, a role that he held until 2009, when he left the label to launch the management company KWL Enterprises. “We always believed our job was a marathon and not a sprint, and Kevin Liles has proven just that,” says Cohen (who remains an investor in 300). “It has been inspiring to watch his journey and continued success.”

2020 hasn’t been entirely smooth for 300: Megan weathered both an ongoing label dispute (with early imprint 1501; though it has not yet been resolved, she is able to release new music in the meantime) and a traumatic shooting this summer, allegedly by fellow MC Tory Lanez (who was only just charged with assault in October). “All I can tell you is that I’ve been doing it for 36 years. I’ve seen every situation you could see, heard everything you could hear, and this too shall pass,” says Liles of guiding Megan through these challenges.

“I am grateful for the support and love that Kevin Liles has given me,” says Megan. “I value our partnership, love being independent and can’t wait to show the world what’s next.”

Flo Ngala
Kevin Liles photographed on October 21, 2020 in New York.

Amid the reckoning with racial injustice sweeping both the nation and the industry since the Minneapolis police killing of George Floyd in May, Liles has kept 300 true to its mission: raising money for social justice organizations, donating to charities, joining protests. “I could go down the list,” he says. “I told my staff, ‘We are a socially responsible company. 300 was created that way.’ I didn’t need George Floyd — I lived Rodney King. And guess what? I’m Black. I don’t need these things to tell me that social [justice matters]. No. I believe people are human. We’re a safe place for people to come express themselves, to express their freedom to be themselves.”

That, says Liles, is ultimately why his small company of 55 employees keeps punching above its weight, competing with and raising the bar for major labels and indies alike. “I’m built to be a pillar, to be a solid foundation so that people can stand on my shoulders,” he says. “It’s a way of life. I’ve dedicated the last 36 years to finding culturally relevant partners to be with to help move our culture forward."

This article originally appeared in the Nov. 14, 2020, issue of Billboard.