Kenny Chesney Is A Cool Boss

Kenny Chesney is known for breezy songs like ‘Summertime’ and ‘No Shoes, No Shirt, No Problems’, but when it comes to business, he takes things very seriously. As the New York Times discovered during a recent profile, he’s an extremely involved, hands-on boss. 

And an extremely generous one, too.

To Kenny Chesney, it’s all about understandable communication. “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,” he said. “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.”

Kenny has been known to hold a lottery for merchandise proceeds at the end of his shows, putting all crew member’s names in a hat, then giving the winner the night’s take. Sometimes he earns $300,000 in merchandise sales in a night, so that’s no small prize.

Another great benefit of working for Kenny Chesney? Annual, week long, all-expense-paid for the members of his crew — and their better halfs.

What does Kenny Chesney look for when he hires an employee? “I want to know about their family. I want to know what they do in their down time. I want to know what their dreams are. I want to know what they watch on TV. I don’t care about their religion or their political views. I don’t care about any of that,” he told the Times. “But I do have to know if, deep down, they’re a solid person, and that they’re not on drugs and don’t have those kinds of problems. I can’t have any of that stuff in my life. I’m too healthy, and I’m too focused. I want to know if these people are focused.”

[Taste of Country]