Louis Messina talks with George Strait, Taylor Swift and “Magical” Chappell Roan at the Billboard Live Music Summit

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

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

“I've worked with a lot of really ridiculous people in my career,” Messina said. “All the acts I'm working on right now, there's nobody that's a jackass, there really isn't.”

Messina credits Strait with launching his own career, saying that “if it weren't for George Strait, there wouldn't be a Messina Touring Group.” He also talked about helping develop Kenny Chesney, starting his work with Taylor Swift when he was 17, his impressions of Chapell Roan and more from his storied and flourishing career.

Below, find highlights from the conversation.

On George StraitWho “Connects with everyone in the audience”

Messina's first client, George Strait, recently made history by selling 110,905 tickets to a June show in College Park, Texas, for what was the largest 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, wherever you sit, you feel like George is singing to you. His eyes are his show, apart from his voice and music. But he connects with everyone in the audience and that, to me, is the secret of every artist… Every star artist knows how to connect with the audience, and the audience then connects with the artist. For me that's the key, and that's what I always pay attention to: how do the artist and the audience connect and how do they fall in love with each other? This is George. Every superstar artist knows how to do it.”

On working with Taylor Swift Since he was 17

Newman noted that Swift's Era tour, which wraps up in a few weeks in Vancouver, has grossed well over a billion dollars, then asked Messina what she saw in the superstar from the start. “He's better for everybody,” Messina said. I have never seen anyone have a work ethic like Taylor Swift. I met her when she just turned 17… She had a song on the radio… On the third night [of seeing her on tour] I just knew. I saw the sparkle in her eye, I saw her work ethic, and here's a 17-year-old girl singing for her high school friends and she just had the audience in the palm of her hand. And then every morning, he was the first person in the production office, after visiting the radio stations, and signing notes to everyone. Fans, DJs playing her music… She would be the first in the building and the last in the building. That's what's special about Taylor Swift, because she's one of a kind and she's going to outshine everyone. I was blessed to be there and see that relationship he had with everyone.”

In the “Magical” Roan Chapel

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

In the sphere

Reflecting on the differences between the venues, Messina reflected that ultimately “It's the artist's name on the ticket, not the building, except for the Sphere. That's a whole other ball game.” Newman then asked if any of Messina's artists could play the boundary-pushing venue, to which Messina said, “Yeah, I've got a few artists that could possibly play there.” Newman astutely noted that since Messina has 11 artists on the roster, there's 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 opened for George Strait. “He was third or second down,” Messina said of the lineup he had Chesney in, “and once I saw him, I saw his merchandise numbers, and he came back the next year, and everybody was in the stands early. and he was selling out his merch more than anyone… I just saw this magic 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 are completely crazy. I will play on the grass every night. I will play until the seats.” I said “No, you're not. You have to trust me.” And he did. This year was my 25th anniversary with Kenny. Kenny believed in me, I made him believe in himself, and then we made the world believe in him.”