‘We Just Dream Big And Go After It’: How Khalid & Manager Courtney Stewart Built A Streaming-Age Juggernaut

Anthony Campusano – Khalid and Courtney Stewart
Khalid and Courtney Stewart in New York on April 4, 2019.

Khalid has never missed a show. Courtney Stewart likes to mention that simple fact when discussing his client, and it captures so much of what has defined the 21-year-old Texan’s speedy rise: his dedication to music, his reliable presence on the road and, most of all, his unwavering commitment to his fans.

“He’s been sick, like literally sick, and we had to take him to the doctor,” Stewart recalls, with a mix of amazement and skepticism. “When the doctor advised him not to perform, Khalid said, ‘I don’t care. I’m performing anyway.’ He loves his fans. That’s what drives him.”

The feeling is mutual. Three and a half years ago, Khalid Robinson uploaded his first music to SoundCloud from his hometown of El Paso; this summer, he’s headlining arenas, including Los Angeles’ Staples Center and New York’s Madison Square Garden, following an impressive 2018 where he secured a spot on Pollstar’s Year End Top 200 North American Tours chart with an $8.9 million gross.

Rick Kern / Getty Images – Fans First
Khalid connects with fans at South by Southwest in Austin on March 14.

Along the way, Khalid has already left an indelible imprint on contemporary pop music. His 2017 debut, American Teen, went double-platinum and catapulted two singles, “Young Dumb & Broke” and “Location,” to Nos. 1 and 2, respectively, on Billboard’s Hot R&B Songs chart. All told, Khalid has appeared on 20 songs that have cracked Billboard’s Hot 100, including Top 10 collaborations with Logic and Alessia Cara (“1-800-273-8255”), Benny Blanco and Halsey (“Eastside”) and Normani (“Love Lies”). Khalid was nominated for five Grammys in 2018, including Best New Artist and Song of the Year; as the year drew to a close, Barack Obama included “Love Lies” on his annual best-of list.

“It definitely surprised me,” Stewart says when reflecting on Khalid’s rapid ascent. “I’m not going to lie and say that I knew that things would happen the way they happened. I did have the faith that he would be at this level one day. But it takes artists years and multiple albums to get to where Khalid has gotten to, so it has really been a blessing. I’m grateful to be on this journey with him.”

An industry vet, Stewart has worked in the business since 2005. He earned his stripes managing R&B singer Bobby Valentino and, later, ran Ludacris’ publishing company and managed several in-demand hip-hop producers. (“I was just a sponge,” says Stewart of his early years in the biz.)

But seasoned as he was, when a former client passed Stewart a SoundCloud link to Khalid’s music in late 2015, it caught him off guard. “The songwriting is what impressed me the most,” he says. “Then, when I heard his voice, I was like, ‘Man, it’s so unique.’ It just really touched my soul.”

Stewart immediately arranged to meet Khalid, still in high school, and his mother, connecting with them in Atlanta in early 2016. His first impression? “This kid is a superstar.” And Khalid wasn’t just another promising talent with a stellar voice and some solid demos. He had a vision. “He knew exactly what he wanted to do,” says Stewart. “Everything that he’s accomplishing right now, he literally told me that when we met.”

Julia Lofstrand – Meteoric Rise
Khalid (center) and manager Courtney Stewart (right) in conversation with Billboard senior editor Gail Mitchell at Pollstar Live!

In a February keynote at Pollstar Live!, Khalid said he connected with Stewart from the outset as well. “I felt like he was super genuine and he cared not only about me, but began to become accustomed with my family and cared about my family,” he told the audience. “We look at each other as big brother, little brother more than anything. To have that relationship with your manager is a blessing.”

Still, even an immense talent like Khalid encounters certain obstacles when breaking into the industry. “The biggest challenge was trying to figure out where he fit,” says Stewart. “He’s such a unique artist. I feel like he’s one of one. When you’re unique, sometimes people will say, ‘You’re really talented, but I just don’t know what to do with you.’ People told him that – that’s what they literally said!”

Even worse were the executives who wanted Khalid to conform to cookie-cutter trends. “I walked into a couple of labels who told me they wanted to make me the next this and they wanted to make me the next that,” Khalid said at Pollstar Live! His response: “I’m not here to be the next anybody. I’m going to be the first me.”

Sensing reluctance among bigwigs, Khalid and Stewart appealed to the masses. “The cool part about it was that the people really gravitated toward it,” says Stewart. “That was our driving force, because we established a great touring fan base from the beginning.” Stewart would convert nonbelievers in the industry by inviting them to Khalid’s gigs. “They’d come out the show and they’d be like, ‘Wow, there were 1,000 kids out here standing in line for hours!’ They experienced what was going on firsthand and then some people stepped out and said, ‘We’re going to support this.’”

While many cautioned Stewart against booking a full-blown North American tour, often warning that Khalid hadn’t released enough music yet, the artist embarked on the “Location” tour, his first headlining trek, in January 2017. “Though the story was growing on the internet, I wanted to see what the fans looked like,” he says. “I want to see if we could really fill a room with 300 kids. To me, those are the real analytics – when you put a hard ticket for sale, they’re either going to come or they’re not going to come. Point blank, period.”

Rick Kern / Getty Images – Free Spirit
Khalid performs at South by Southwest in March.

To help guide Khalid’s touring career, Stewart connected the burgeoning artist with powerhouse agent Cara Lewis, who has a long professional history with Stewart, in 2016. “It was clear to me from the beginning of our meeting that Khalid was destined for a huge career,” says Lewis, who also represents artists including Eminem and Travis Scott. “He possessed amazing star power with so much passion about his music and the visions he had, not to mention the body of work he presented for me to hear.”

Lewis was instrumental in booking the “Location” tour and has worked with Khalid and Stewart ever since. “She just understood the vision of building the touring fan base organically from the ground up,” says Stewart. “She helped us to lay that out, to play the right markets, the right venues. And that tour was a success.” Adds Lewis: “At [age] 18, there was no reason to rush anything. We knew his talent and the music spoke for itself.”

Khalid, for his part, put in the work – and not only onstage. “I gotta meet everybody,” Khalid said at Pollstar Live!, explaining why he would linger outside venues for hours to chat with fans. “I want to make sure that my relationship with my fans is genuine, that they know that I genuinely care about them and that they can come to me and they can ask me questions and they can talk to me.”

The strategy worked. Mere months after playing to crowds of a few hundred at venues like New York’s SOB’s (450-person capacity) and Los Angeles’ The Roxy (500), Khalid was performing for crowds several times that size on his “American Teen” tour in summer 2017. And his explosion in popularity extended beyond the country’s metropolises. Take Sacramento. On Feb. 14, 2017, Khalid played to a sell-out crowd of 425 at the California capital’s Harlow’s Nightclub, grossing $6,375; on Aug. 31, 2017, he played less than a mile away to a sell-out crowd of 4,006 at the Sacramento Memorial Auditorium, grossing $138,207.

By May 2018 and his “Roxy” tour, Khalid had graduated yet again, this time selling out sheds including Colorado’s Red Rocks Amphitheater, where he grossed $496,706 on May 14, 2018, and Los Angeles’ Greek Theatre, where he drew 11,106 and grossed $762,820 over two sold-out May nights. “The plan from the beginning was to create touring platforms that would showcase Khalid as a headliner,” says Lewis. “We collectively agreed to play the right venues, offer fan-friendly ticket pricing and build his fan base without missing a step.”

Aside from a smattering of dates supporting Travis Scott and Lorde, in May and October 2017, respectively, Khalid has consistently headlined – something that Stewart says has, at times, required resisting temptation. “When you get a call from – I don’t want to disclose the artist, but from literally the biggest artist in the world – when you get a call from them personally saying, ‘I want you to join this tour [as my opener],’ that’s a tough ‘no,’” he says with a laugh. “But it was important for Khalid at that point in his career to stay the course.”

That mentality extended to Khalid’s second album Free Spirit, which arrived April 5. Naturally, A-listers inquired about teaming with Khalid in the studio, but the artist and his team knew that lining the album’s credits with stars wasn’t necessarily a recipe for success. “We wanted to keep our recording process in a space where Khalid could be himself,” says Stewart, who executive produced American Teen and Free Spirit. “Sometimes it’s intimidating if you’re getting in the studio with some of the biggest producers in the world.”

Amy Harris / Invision / AP – Festival Phenom
Khalid performs at New Orleans Jazz & Heritage Festival in 2018.

Free Spirit includes several prominent names – production whizzes Stargate and Disclosure appear, as does guitar virtuoso John Mayer – but it’s notably lighter on flashy features than the records many of Khalid’s peers release. Plus, as Khalid explained at Pollstar Live!, he kept his fans satiated between albums by releasing collaborations with artists from Billie Eilish to Shawn Mendes.

Khalid’s ascent continues apace. Free Spirit debuted at No. 1 on Billboard’s Top 200 Albums with 202,000 equivalent album units earned, making it the fourth-biggest week for an album this year. “my first number 1 album y’all I love u guys so much man holy fuckkk,” Khalid tweeted Sunday afternoon, hours before performing in the penultimate spot on Coachella’s main stage, ahead of Ariana Grande.

Just days after the “Free Spirit” tour went on sale, Lewis told Pollstar that she and Khalid’s team were adding second shows at Staples Center, Madison Square Garden and Toronto’s Scotiabank Arena due to high demand; more North American markets would’ve seen second dates were Khalid not taking the tour to Europe immediately afterward. Says Lewis: “Khalid’s fan base is unique, extremely passionate and always demonstrates an urgency when buying tickets.”

Khalid and Stewart’s partnership, meanwhile, remains strong. “Courtney and Khalid have a very trusting relationship, and with good reason,” Lewis says. “Their synergy is one of a kind and it is as close to family as you can get.”

“His family is honestly like my family now,” says Stewart, mentioning shared birthday parties and trips overseas. That partly stems from accepting personal and professional boundaries. “I love that [Khalid’s mother] has always, since day one, respected my position,” Stewart says. “They have a term for parents of young acts: momagers. A lot of artists that have been really talented have not broken because parents have gotten in the way and wanted to manage, but it’s not their skill set.”

Given her son’s talent and his manager’s commitment, Khalid’s mother has little reason to worry. As Stewart puts it, “We just dream big and go after it.”