Louis Messina Talks George Strait, Taylor Swift & ‘Magical’ Chappell Roan at Billboard Live Music Summit

Louis Messina reflected on his storied career in touring on Thursday (Nov. 14) at the Billboard Live Music Summit in Los Angeles.

Speaking with Melinda Newman, Billboard‘s executive editor, West Coast and Nashville, Messina spoke about the working with some of the biggest names in music, with the 11-artist roster of his Messina Touring Company including Taylor Swift, George Strait, Kenny Chesney, Ed Sheeran, Old Dominion and recent signee Zach Bryan.

“I’ve worked with a lot of really goofball acts in my career,” said Messina. “All the acts I work for right now, there is not one that’s an asshole, there really isn’t.”

Messina credited Strait with launching his own career, saying that “if there were no George Strait, there would be no Messina Touring Group.” He also spoke about helping develop Kenny Chesney, starting his work with Taylor Swift when she was 17-years-old, his impressions of Chapell Roan and much more from his historic and thriving career.

Below, find highlights from the conversation.

On George Strait, Who “Connects With Everybody In the Audience”

Messina’s first client, George Strait, recently made history by selling 110,905 tickets at a June show in College Park, Texas, for what was the biggest ticket event anywhere in the United States in history.

Messina reflected on Strait’s special (and massive) appeal, saying that “When you’re at a George Strait concert, no matter where you’re sitting, you feel like George is singing to you. His eyes are his show, besides his voice and his music. But he connects with everybody in the audience and that, to me, is the secret of every artist… Every star artist, they know how to connect with the audience, and the audience then connects to the artist. To me that’s the key thing, and that’s what I always look out for: how does the artist and audience connect, and how do they fall in love with each other? That’s George. Every superstar artist, they know how to do that.”

On Working With Taylor Swift Since She Was 17

Newman noted that Swift’s Era’s tour, which wraps up in a few weeks in Vancouver, has grossed well over a billion dollars, then asking Messina what he’s saw in the superstar from the start. “She’s outworks everybody,” said Messina. There’s no one I’ve seen with a work ethic like Taylor Swift. I met her when she just turned 17… She had one song on the radio… By the third night [of seeing her on tour] I just knew. I saw the twinkle in her eye, I saw her work ethic, and here’s a 17-year-old girl singing about high school boyfriends and just had the audience in the palm of her hands. And then every morning, she was the first person in the production office, after she visited radio stations, and she signed notes to everybody. Fans, DJs that played her music… She would be the first one in the building and the last one in the building. That’s what’s special about Taylor Swift, because she’s one-of-a-kind and she will outwork everybody. I was just blessed to happen to be there and see that connection that she had to everybody.”

On The “Magical” Chapell Roan

Newman closed the conversation by asking Messina which artists he hasn’t worked with that he’d like to. He said he’d love to work with Beyoncé and Bruno Mars, adding “and who doesn’t want to work with Chappell Roan, though? What a superstar; what a unique artist. I haven’t seen anybody like her since — she reminds me of when Madonna first started. That attitude; she’s unique. I saw her at ACL and she blew me away… she’s one of a kind. She’s magical.”

On Sphere

While reflecting on the differences between venues, Messina reflected that ultimately “It’s the artist’s name on the ticket, not the building, except the Sphere. That’s a whole other ballgame.” Newman then asked if any of Messina’s artists might play the boundary-pushing venue, to which Messina said, “Yes I have a couple of artists that are potentially playing there.” Newman deftly observed that given that Messina has 11 artists on the roster, there are only a certain number of acts it could be.

On Guiding the Rise Kenny Chesney

Messina has been working with Chesney since the country superstar was opening for George Strait. “He was third or second from the bottom,” Messina said of the lineup he had Chesney on, “and I just saw him, and I saw his merchandise numbers, and he came back the next year, and everybody was in the stands early and he was outselling merchandise more than anybody… I just saw this magic that he had and the connection… We put Kenny on Tim [McGraw’s] tour, and then I said ‘It’s time to headline now.’ He looked at me and said ‘You’re absolutely crazy. I’m going to be playing to grass every night. I’m going to be playing to seats.’ I said ‘No you’re not. You’ve gotta trust me.’ And he did. This year was my 25th anniversary with Kenny. Kenny believed in me, and I got him to believe in himself, and then we got people to believe him.”