While most teenagers make an extra buck mowing lawns or waiting tables, John Rich used his entrepreneurial skills to find a much more lucrative high school job. Granted, it may not have necessarily been legal.

"I went to a new high school my senior year, all the jobs in the little town where taken ... you couldn't flip a hamburger," the 'Celebrity Apprentice' winner tells Seattle radio station KMPS. "I found a way I could wax the old tractors on a tractor dealership, and I would take the money and give it to the older brother of a friend of mine. He would take it and buy beer, I would put the beer in the back of my '71 Dodge Dart Swinger, ice it down, and I would sell them at the lunch break for $10 a piece. You gotta do what you gotta do."

He wasn't the only member of the Big & Rich who bent the law a little bit back in the day. Big Kenny admits that their new single 'Fake ID' may not be entirely fictional. "I was definitely one of those kids who wanted to get into the bar to see my favorite bands," he says with a laugh. "I loved music. We did what we had to do to get into there."

While John's high school occupation wasn't entirely on the up-and-up, it did prepare him for his recent success. "I grew up working on used cars lots, working on hog farms, you name it," he explains. "'Celebrity Apprentice' was all about, can you come up with an idea on the spur of the moment and juke and jive with the curve balls the world's throwing at you? I kept smacking them. Somehow I pulled off that win at the end and we got $1.4 million for St. Jude ... This is shaping up to be probably the greatest year of my life."

The singer-songwriter's stint on the hit NBC show was so intense that his 2011 Xtreme Muzik tourmate Gretchen Wilson was intimidated. "I was afraid to call or text or talk to him," she admits. "I knew how focused he was. I knew how difficult this was going to be. I wouldn't have traded places with him for anything in the world ... The only time I spoke to him when he was doing that was was when he texted me for a little bit of money, and I said, 'I'm in.'"

Listen to the full KMPS interview with Gretchen, John and Big Kenny here.

The 2011 Xtreme Muzik tour with Big & Rich and Gretchen Wilson is currently on the road. Catch up with them next in Deadwood, S.D. July 8 and 9. Get a full list of their concert dates here.