He might be known for breezy, devil-may-care songs like ‘No Shirt, No Shoes, No Problem’ and ‘Summertime,’ but when it comes to business, Kenny Chesney takes things very seriously. In fact, as the New York Times discovered during a recent profile, he’s an extremely involved, hands-on boss.

And an extremely generous one, too.

As far as Chesney’s concerned, it’s all about clear 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 explained. “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.”

To illustrate that principle, Chesney’s been known to hold a lottery for the merchandise proceeds at the end of a show, putting every crew member’s name in a hat and giving the winner the night’s take. For a guy who can earn $300,000 in merchandise sales in a night, that’s no small gesture.

Another fringe benefit of working for the Chesney operation? Annual, week long, all-expense-paid trips to the Virgin Islands for the members of his crew — and their significant others. Like the man’s been known to sing, you’ve got to ‘Live a Little.’

So what does Kenny Chesney look for in 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]