The Dre London Invasion: How An Upstart Manager & Emerging Power Agent Helped Create Next Gen Superstar Post Malone

Cheryl Paglierani, Post Malone, Dre London
Photo by Adam DeGross
– Cheryl Paglierani, Post Malone, Dre London

It was a grand entrance like no other. The first power panel of June 2021’s Pollstar Live! Conference, entitled “Golden Era 2.0: How The Concert Business Comes Back & What It Looks Like,” which filled the Beverly Hilton’s Grand Ballroom, featured a murderer’s row of legendary live execs: Wasserman Music’s Marty Diamond, (Coldplay, Ed Sheeran, Janelle Monáe), Live Nation’s Arthur Fogel (Madonna, U2, Beyoncé and Jay-Z, Lady Gaga), Patriot Management’s Ron Laffitte (Pharrell Williams, OneRepublic, Backstreet Boys, Usher) and CAA’s Jenna Adler (Green Day, Jennifer Lopez, Doja Cat, Charli XCX), along with moderator Ray Waddell, President of Oak View Group’s Media & Conferences division. Also onstage for the first 20 minutes: a starkly empty chair.

With all eyes on Adler, sitting on the far right of the stage discussing the “Hella Mega Tour” with Green Day, Weezer and Fall Out Boy, just as Waddell asked if 2022 could be the busiest touring year in the history of live, a relatively unknown figure on the scene, who could help answer that question, quietly made his way stage right. 

He furtively slid into the vacant chair with little notice from the panel and there was a momentary tension between the audience who saw the late arrival, and the panel that hadn’t. Suddenly, with a look of surprise, Waddell looked over, saw him, stopped mid-sentence and said, “Hey Dre, what’s happening!?” The ballroom erupted into applause and laughter. 

Dre London
– The Grand Entrance:
Post Malone manager Dre London speaking at Pollstar Live! June 16. The panel also featured Ron Laffitte, Arthur Fogel, Marty Diamond, moderator Ray Waddell and Jenna Adler.

For many, showing up late for a packed panel would be their worst nightmare, but for Dre London it was an opportunity. Rather than obsequiously beg forgiveness or make excuses, he took the mic and ran with it. Much like one of his artists whose career he steers, the dynamo manager with the 1,000-megawatt smile and Cockney- tinged British accent (a tinge of Ali G), extemporaneously told the audience to “give ourselves a round of applause because we’re back outside!” The audience abided. It was, after all, June 16, the day after California dropped its indoor mask mandate. For many, this was the first time in 15 months they’d been around this many people, let alone so many in the live industry.

“He has no fear,” says United Talent Agency’s Cheryl Paglierani, who has worked with London and his client Post Malone as the artist’s responsible agent since 2015, when Malone was just 19. “Sometimes what holds a lot of people back from success is fear of failure, and you never see that in Dre. You could tell him something’s not going to work, but if he believes it’s going to work, he’s going to go full steam ahead until it works and find a solution because that’s just who he is.”

“It’s special because you can’t teach that,” says Jay Santiago, London Entertainment’s Director of Operations who has known Dre since he moved to the States in 2008. “That can’t be coached. Dre doesn’t have any fear. He’s not scared to say what’s on his mind. If there’s a moment that he can seize, he’s going to go after it, especially if it’s something that he’s been contemplating for a while. He’s going to go after it, 110 percent.”

That drive, especially in the case of Post Malone, 26, has yielded astonishing results. Posty’s $1.8 million average gross and 16,148 average tickets sold over the last 36 months, over 89 headlining shows, according to Pollstar box office reports, are undeniable. His “Runaway Tour,” which launched on Sept. 14, 2019, a week after the release of his Grammy-nominated third studio album Hollywood’s Bleeding, included five two-night arena stands, including New York’s Madison Square Garden, where he grossed $4.2 million and drew 30,486 on Oct. 14-15. Pollstar’s box office database shows that overall numbers stretching back to his first performance on May 30, 2015 at New York’s Webster Hall – which grossed $5,635 and sold 274 tickets – totaling $158.9 million in revenue from 1,628,415 total tickets at 145 headlining performances.

Dre London and Post Malone
Kevin Mazur AMA2019 / Getty Images / dcp
Dre London (left) and client Post Malone appear at the American Music Award in Los Angeles in November 2019.

It’s that success that’s helped fuel the rapid expansion of London Entertainment Group, which now includes management clients Tyga and Tyla Yaweh; Maison No. 9, a rosé launched by London and Malone (with Global Brand Equities); a film and TV production division; and most recently AUX Live, a live music streaming service launched in June. And there’s plans afoot for far more.
Ask London, 40, how his climb began, and you’ll hear a British Horatio Alger rag-to-riches story fueled by his entrepreneurial spirt and by-hook-or-by-crook determination, deeply informed by growing up in the rough South London neighborhood of Brixton.

Dre London
(Courtesy London Ent.)

Dre London

“It’s one of the toughest areas in London,” he says. “It had some of the toughest [public] housing estates in the whole of London. It was a Jamaican community. It was very tough. And growing up there, taught me all I know today. I was a young hustler, I did it all. I dropped out of school at 15, tried to work one week for a company and said, ‘No way.’ I walked into the elevator leaving the company and said, ‘I’m never going to work for anyone again.’”

For the next several years, Dre had a number of hustles: in his teens he bought, refurbished and sold wrecked cars, later co-owned a clothing boutique, then flipped real estate. “When I was 21, I bought my first house and my first car, an Audi TT,” he says. “No one from my neighborhood had done stuff like this. By the time I was 22, I put down a deposit for my mother’s house. She still lives in it today, I finished paying for that house two years ago.”

London would also come to manage British rapper Cerose. “In the UK then it was more grime and drill music than hip-hop,” he says. “There was only a few UK rappers at the time making noise. I started going to New York, the Mecca of hip-hop, and felt like I was going to be able to break on the scene with my artist.” Making his way to New York in 2008, London references Malcolm Gladwell’s “Outliers” when discussing that time period.

“I started going to studios and working, mixing, spending all nights in studios and putting in my 10,000 hours,” he says. “I was making mistakes, learning and networking. I was in New York and the money I earned flipping houses was going down.”

Amidst all his networking, Dre met a rapper who would help him understand what the next level looked like. “I bumped into a guy called French Montana, who then was an underground street rapper,” says London, who helped put together Montana’s single “New York Minute,” with Jadakiss and producer Harry Fraud, and a subsequent track “Shot Caller.”

“I learned big lessons,” London says, “because I didn’t earn no money from none of this, I call it the hand smack moment. But that woke me up. I needed my hand smacked then rather than later. That was the first sign of like, ‘Aha! You actually know what you’re doing. People will listen to you and look at what’s happening next.’ So I started to build on it.”

Dre London, Post Malone, Jay Santiago
Photo By Eric Jcui Courtesy London Ent.

Rosébongs & Benteys: Post Malone, Dre London and Jay Santiago at an event for their Maison No. 9 Rosé.

Jay Santiago, who had met London early on in NYC, became a friend and then business partner. “At the time, Dre was doing a lot of networking in New York,” he says. “I would meet him in the Meatpacking District. Already at that time, we would be bumping into Rihanna, French Montana or Lil Wayne. He already knew people in the industry way before he even blew up, because he had that energy.”

But it wasn’t all champagne, caviar and Rihanna. Santiago vividly recalls a failed entrepreneurial foray that steeled Dre’s resolve to work in the music business.

“Our first venture was a beverage truck company called Kings of Queens Beverage,” Santiago says. “At that time, he had a storage facility, two vans and a 16-foot box truck.”

It was going well, Santiago says, until it wasn’t.

“There was one day in wintertime, it was probably negative 16 degrees with the wind, and we were counting up a load to put on the truck, and Dre’s nose wouldn’t stop running and he kept wiping it and wiping it,” Santiago says. “He’s like, ‘Man, fuck this, I’m moving to California. And I’m working full time on music. I’m not doing this.’ That’s the moment he shifted gears and said, ‘Yo, just sell everything. We’ll figure it out.’ And he left for L.A.” London’s first trip to L.A. came in 2013 and he returned the following year for another life-changing milestone.

“To tell you the truth, the Grammys was the most boring thing,” he says. “I just sat there the whole time. It was just great for the experience because we’d never seen nothing like it, but what I didn’t know at that time was that I wasn’t there for the Grammys – I was there to meet this new kid named Austin Richard Post.”

His first meeting with Post Malone, London says, was “really relaxed.” It took place at the “White House” in Encino where Malone lived with a friend from Dallas, Jason Probst, a professional gamer, and some music producers.

Dre London and Tyga
(Dylan Bridgewater/Courtesy London Ent.)

Dre London with Tyga.

“We was just hanging out, chilling,” London recalls. “He was just 18 years old. I’ve never seen anyone change their clothes three times a day in the same house. Everything was happy-go-lucky. He had this one pair of velvet Versace shoes, the same shoes Trinidad James would wear. He spent all his wages before he left Dallas – I think he worked for two months – for these $900 shoes. I’m like, ‘Damn. This kid is smooth!’

“Our energy hit it off from the beginning,” London continues, “but I didn’t know how talented he was until a couple of nights later when he took out his guitar at night and sang a Sublime song. He would rap in the day and sing at night. I was just like, ‘I have to get this guy.’ It’s so crazy, we talk about it now but all that was on my mind was to take him to the top of the world. I didn’t know how I was going to do it, but I knew I had the experience.”

It took Malone several months to finally say six magic words: “So I guess you’re my manager,” London recalls. “Post isn’t the kind of guy that just jumps up and trusts people. He’s very humble, very quiet. I was like ‘OK,’ and it all started there.”

The impact Malone’s first major single, uploaded to SoundCloud in 2015, had on his career cannot be overstated. “White Iverson,” which has since been certified eight times platinum by the RIAA and streamed tens of millions of times more, catapulted him from bedroom musician to international superstar, yielded a label deal with Republic Records and started what would become an illustrious live career.

“When we first started going out live, there was no Cheryl Paglierani,” Dre says. “There was me, Jay, who is my right-hand man and Post’s road manager who takes care of too many things – I just call him Director of Operations in the office – and Bobby Greenleaf who’s our creative director was there. On the road it was really just me and Post, and Jay, who was doing four jobs, whatever was needed, playing security or driving while I was doing seven jobs and being the manager and doing what I do while Jay was standing next to Post, protecting the gold.”

One of the “big shows” London remembers was in Orlando.

“We sold 130 tickets,” he says. “By the time we got there, the place was packed wall-to-wall. I couldn’t believe it. It wasn’t our first show, but it was special because it let me know how very powerful the internet is. He was selling out 400-cap rooms off one song. I was telling Post, ‘You’re going to have to stretch the show out.’ We was going to have first a DJ play a couple of songs, and then he was going to do three songs, have a long DJ stretch, and then he was going to sing the same song twice. And it worked. And we just started building like that across the country.”

Post Malone
(Photo by Nicky Digital/Corbis via Getty Images)

Wunderkind: An early Post Malone show at Webster Hall in New York City on April 30, 2015 when he was 19 years old.

Another live milestone: 2015’s SXSW. “When we went to South by Southwest, we only had 4 shows,” London says. “I turned that into 14 shows in four days.”

This not only included shows with Chance The Rapper and Travis Scott, but a chance meeting that would have a huge impact on Team Malone.

“I had gone down to SXSW because I heard ‘White Iverson,’” says UTA’s Paglierani, 36. “I thought it was great, but I didn’t know what Post looked like. I was coming out of a show and someone stopped one of the people I was with. I didn’t really know what to make of the guy with the braids, gold teeth, wearing a jersey. He turned around and I realized on the back it said Malone. I was like, ‘Wait a minute, are you Post Malone?’ And he was like, ‘Yeah.’ And I was like, ‘Holy shit. I’ve been looking for you.’ And I said, ‘Where’s Dre?’ Dre and I had been texting and he was standing right next to him. And that was how we first met.”

Two weeks later, the trio met up again in New York, says Paglierani, who had recently left CAA for The Agency Group (which UTA acquired later that year) and was just starting her own roster.

“They went to every agency,” she says. “I was the last meeting. Dre called me and was like, ‘He doesn’t feel like going to an office again. Can you come to the studio tonight?’ I was like, ‘Yeah, sure. No problem. What time do you want me there?’ He said, ‘Come at 10 p.m.’ I get there at 10 on the dot, Post doesn’t show up til 1 a.m. Dre was there the whole time, and he and I were talking about everything. We hit it off instantly. Post gets there at 1 a.m., we went out on a back stoop and he’s smoking a cig, and we talked for maybe 20 to 30 minutes. And I just remember he looked up at me and he said, ‘I like you. Let’s do it.’ And they hired me on the spot.”

“A couple of other big agencies wanted to sign us,” Dre says, “I wanted Cheryl who was fresh and had worked with one of the best agents [Cara Lewis]. She’s hip and female and instead of just going with all the guys that were in my ear telling me what they could do and what their previous artists were doing, I went for the underdog. Everyone thought I should’ve taken the biggest agent right there.” It proved to be the best move, Dre says.

“To make that decision at 2 a.m. in the morning on the studio stairs, smoking a cigarette when Cheryl was meant to be going to work next morning, and she was still out at 2 a.m. closing that deal in the studio – that’s what made me like her,” he says. “I just knew if someone was there with me at the studio with Post amidst life’s hustle and bustle, I could see it working.”

Dre London Cheryl Paglierani
(Photo: Dylan Bridgewater Courtesy London Ent)

Manager-Agent In The Sky: Dre London with Cheryl Paglierani en route to the Hive Festival Aug. 6-7, 2021 in Utah where Post Malone performed.

“From that day, we just clicked,” London continues. “We got along straight away. We fight for the same things. We’re so alike that even if we butt heads, we’re both fighting for the same thing. It jelled into a great relationship. Post loved her at the same time because she let him know like, ‘I’m here for you.’ That was her first client and she had everything to prove, and this was my first artist in America where I felt like I had more to prove. The three of us, we all had it to prove, as a team. So we set upon this journey of proving everyone wrong and building what we thought it would take, maybe, seven, eight years that turned into five years and an arena act with great music, great touring, great planning, smart teamwork, and we just built it.”

In early 2016, Post opened for Fetty Wap, and that spring he landed an opening spot for one of the year’s biggest tours.

“We was friends with Bieber,” London says. “He asked, ‘What about you guys coming on tour with me?’ And I was like, ‘What?’ I only had to hear a piece of that and the hustler in me came out. I went through hills and valleys to make it happen talking to [Bieber’s manager] Scooter [Braun]. He went up from doing 31 dates straight up to 59 shows.”

“There were so many moments on that tour when you just realized he was the real deal,” Paglierani says. “It’s not often you see artists get up on stage in an arena who have one song and be able to carry the building. He did it every single night. And that’s how he won over so many fans on that tour because he was so great and so authentic. He tells stories and he shows who he is during the show. That’s what makes him so special. And he still does that to this day.”

When asked for tentpoles in Malone’s live career, Paglierani can’t narrow it down.

Post Malonw
(Courtesy Cheryl Paglierani)

Post Malone and Cheryl Paglierani in the dressing room after the last show of the Beerbongs and Bentley’s tour at the Hollywood Bowl.

“I feel like every album cycle, there’s a couple of those,” she says. “On the Bieber tour, just seeing him on stage in an arena was always a big thing. And then coming into his own headline shows when we blew out the ‘Stoney Tour.’ When he played The Bomb Factory in Dallas, his hometown, that was a huge moment. I also represent 21 Savage, so when we put up the ‘Beerbongs & Bentleys Tour’ with the two of them, that just went crazy out of the gate. To play two nights at the Hollywood Bowl felt like, ‘Oh my God! Now, we’ve really made it!’ And then going into the ‘Runaway Tour’ with two nights at Madison Square Garden was a huge moment. It’s like every time we’re elevating, there’s always that moment that’s like they’re still constantly reaching new heights. To go into Posty Fest last year at AT&T Stadium in his hometown and selling out, that was huge. I feel like those moments just constantly keep coming every time you think, ‘Wow! This is really it, this is huge,’ something new happens.”

Paglierani also credits the Malone team’s relationship with Live Nation, the tour’s promoter, and Colin Lewis, its VP of Global Touring.

“It’s such a good team,” she says, “because the second we’re putting something on sale, we’re watching what it’s doing. And if there’s room to tweak or use platinum ticketing to elevate those grosses where we can, we’re watching it in real time from the second it goes on sale until the show to make sure we’re maximizing the potential for him.”

Lewis agrees wholeheartedly. “I truly admire the deep connectivity Cheryl’s formed with Dre and Post,” he said. “Being there from the beginning and seeing Dre’s vision come to life creates a trust and unity that’s very powerful. We all admire the journey they’ve been on together.”

Back at Pollstar Live!, Dre went into excruciating detail about having to halt Malone’s gangbuster 2019-2020 “Runaway Tour” during COVID.

“It’s been very hard because we had to stop while we was on the second leg of a 55-date tour,” he said. “We was in full flow and we was moving and everything just seemed pretty normal. All of a sudden, I was getting calls, like, why am I still having Post go to the next show? People started talking about this virus, it wasn’t even called a pandemic yet, and everybody had to stop touring. I had trucks on the way to Denver and I was trying to explain to everybody like, ‘Do you know how much money it costs to get 75 to 80 trucks from one state to another state for a show and tell everybody the show’s off?’ It was crazy.”

The year was filled with pivots for Malone which UTA helped facilitate. Paglierani credits Toni Wallace and the UTA team as instrumental on the brand and film side, getting deals with JAEGER and Monster Energy, movie roles, sponsorship deals for Posty Fest – “We had over 20 partners last year,” Paglierani says – and his lauded Nirvana tribute livestream with Travis Barker, which was backed by YouTube and raised more than $500K for the World Health Organization.

London’s team has weekly calls with UTA team where the agency helps execute Dre and Malone’s visions. And the manager doesn’t hesitate to call the agency’s CEO.

“He’ll call Jeremy Zimmer and tell him whatever it is he needs,” Paglierani says. “And Jeremy will hop right in and help him, which has been great. To have a CEO who is so supportive of the music department and everything we’re doing and is open 24/7 to your managers, it’s a game changer.”

“Dre is one of the best in the business,” Zimmer told Pollstar. “His creativity is unmatched and he brings vision, determination and ingenuity to everything he does. He inspires everyone around him to strive for greatness, and I always enjoy working on tours with him.”

(Photo: Jason Koerner/Getty Images)

Stadium Bound? Post Malone headlining Rolling Loud on July 25, 2021 at Miami’s Hard Rock Stadium in front of 75K. “The first Rolling Loud, I had no idea who he was,” said Rolling Loud co-founder Tariq Cherif who saw Malone play the first festival in 2015. “Since then, we have great relations with Post, we go see him on tour. He beat me two games in a row on beer pong….” (Photo: Jason Koerner/Getty Images)

Post Malone, for now, is back on the festival circuit, playing headlining sets at Miami’s Rolling Loud (his spiritual festival home of sorts he’s played since its inception) and Lollapalooza. Upcoming stops include Reading and Leeds in the UK later this month, an appearance at New York’s Governors Ball in September and Posty Fest once again in Arlington, Texas, slated for October.
The multi-million-dollar question is what lies ahead now that Malone’s done multiple- night arena plays, headlined innumerable festival and seen his star steadily rise. Could stadiums be on the horizon?

“That’s been the dream from the beginning, and I’ve got some crazy ideas,” London says. “That’s all I’m going to say to you.”