March 8, 2021

Corner Office: Kenny Chesney: Country Singer, Songwriter and C.E.O

Q. So, you’re the C.E.O., in effect, of Kenny Chesney Inc. How big is the business?

A. I have 120 employees on the road every day, and about 30 other employees off the road. I remember being on the bus a couple years ago, and I looked out the window of my bus and said to myself: Who’s paying for this? And it hit me: You are! I was in charge of making sure that we get from Point A to Point B, that we all do it seamlessly and that we all do it effectively, and we all do it on time.

Q. Tell me what’s important to you in setting a tone and a culture among your employees?

A. It’s important for me to be sure that everybody knows what everybody else is doing. I want there to be a level of respect between everybody. You get that many people out on the road at once, and all of a sudden agendas sometimes can become a part of that. And sometimes they’re not your own. There’s this idea that somebody’s job could be more important than somebody else’s, and to me, that’s not true.

Q. So how do you make that real — everybody should have respect for everyone else — rather than just a slogan?

A. I want all the people out there who work with me to feel as appreciated as possible, especially the people who are the first to get up in the morning and the last to go to bed — my crew guys. Sometimes we do a “merch” lottery. We put everybody’s name in a huge sombrero and whoever’s name I pull out gets all of the money from merchandise sales for that night.

Q. How much money could that be from the merchandise?

A. Probably the biggest check was three hundred grand. But do you know what those guys did? This is why I think this kind of thing works: They waited until the end of the year and I wrote one big check to the crew and they divided it up 13 ways. Doing things like that just motivates people.

Q. What else do you do?

A. At the end of each year, I take the band, crew, the merchandise people, catering people, my management team, their wives, girlfriends, whatever, down to the Virgin Islands for a week to thank them. I pay for everything, and we’ve done it every year since 2002.

Q. I imagine a lot of artists just focus on the music and let others worry about the business. Obviously, you’ve not done that.

A. I don’t have the computer chip to say, “O.K., I’m just going to write my songs and sing them and the business is up to you guys.” I’m so hands-on, from the color of my tour bus to what I eat for dinner at 5 or the way the lights are hung. I mean, you could only imagine what diesel fuel costs me as an overall expense for this year. It’s exhausting, but that’s me. And my name’s on everything.

Q. Over the course of your life, what do you consider as some important leadership lessons?

A. An important mentor for me, in terms of teaching me that there’s a right way and a wrong way to do things, was probably my football coach. And playing football was one of the first times in my life that I realized nothing is given to you. You have to work really hard. I was a very short, slow wide receiver on a very mediocre football team. And we had to work really hard to be as mediocre as we were.

Q. What made you decide to get so involved in managing and leading your business?

A. For the first five years on the road, I didn’t make any money at all, and I had no idea what I was doing — none. I was fresh out of college, and I didn’t really think that this was going to last. But there were moments when I thought: What if it does last this long? What if this is going to be my life? And if it is, how am I going to approach it? And I realized that I wasn’t saving any money. I couldn’t afford a house. I had no investments. I had nothing.

And I sat down with my manager, Dale Morris, and told him what I wanted to do and realized that I wanted this to be my life. He had been in the business a long time, and he had a great business mind. That’s when I realized I didn’t just want to be a singer-songwriter and let everybody else take care of everything. And from that moment on, I started really paying attention to a lot of detail and to what I was making every night.

Q. What are some of the more subtle points of leadership you’ve had to learn?

A. It can be hard to be everybody’s friend and still show them that this is the way it’s got to be. And I’ve gone both ways. I’ve been everybody’s buddy and then it was tough because you put yourself in a position that’s not the best when you have to let people go. That was tough for me. I’m still kind of everybody’s buddy, but they know I’m the boss. I think it is possible to be friends with employees, but there has to be a respect level where you’re not taken advantage of, either.

Q. When you’re on the road, you’re spending a lot of time with your employees.

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