He later had a job helping his father deliver Pepsi-Cola, but as a loyal Coca-Cola customer, he walked away because he felt as if he were deceiving the customers.
Now Waltrip is at another career crossroad, unsure if its time to climb out of his race car.
The two-time Daytona 500 winner said Thursday he will end his driving career at the end of 2009 if his results don't improve this season.
"I want to race for many more years," he said at media day for the Daytona 500. "I want to race the NAPA car in '10 and beyond, because I'm the best guy for it. But if I notice (teammate) David Reuitmann out in front of me and I'm not able to catch him, and if I don't see the results that I think can get the 55 car the results it deserves, then as an owner, I want to get somebody in there that can post those results."
The 45-year-old Waltrip is starting his third season in the dual role of driver and owner of Michael Waltrip Racing, an endeavor he said mentally drained him and affected his on-track performance. He's not won a race since 2003 when he still drove for Dale Earnhardt Inc., and he's had just four top-10 finishes since leaving DEI at the end of the 2005 season to start his own team.
But building from the ground up was an enormous undertaking, and Waltrip had plenty of bumps along the way. He embarrassed himself and new manufacturer Toyota with a cheating scandal during the 2007 Daytona 500, and was later involved in a bizarre incident where he wrecked his personal car and a neighbor saw him climb from the overturned vehicle before walking home through the woods in his socks.
His three-car team was struggling to qualify for races, and sponsorship woes took their toll on the budget. Waltrip eventually took on a partner, Robert Kauffman, a founder of the Fortress Investment Group.
That stabilized the organization, and there were small signs of progress in 2008.
"Because we were so bad, we were the most improved team," he joked. "It's sort of one of those awards you don't want to get."
Waltrip admits the stress was often overwhelming and he nearly snapped when, after an accident at Bristol, Clint Bowyer said over his radio: "Michael Waltrip is the worst driver in NASCAR, period."
Waltrip said he'd reached his breaking point long before that August wreck, but Bowyer's remarks were the final straw.
"The last three years, '06, '07, '08, probably have been the most difficult years ever for me," he said. "And maybe that came to where I wanted to beat somebody up when Clint Bowyer said what he said at Bristol because I didn't deserve that. It just made me mad. The fact that the whole world heard it was probably the hard part."
He and Bowyer have since patched things up, and, its possible the comment was the one thing that spurred Waltrip to turn things around.
A former marathoner, he's returned to running and working out, and thinks he's currently in the best physical shape of his career. He's also not harping on past personal issues, and declined to discuss Thursday the dissolution of his marriage.
But he knows he's in a better place as he prepares for his 25th season.
"I think mentally I am more stable then I've been in a long time," he said. "Mentally, I think I'm back, confident and enthusiastic. I want to do (drive) really bad, and if I don't, I'm going to do something else. That simple."
Waltrip said if he must relinquish his race car, he'll focus on owning MWR and his work as a NASCAR television analyst.
He's asked often if building his own race team was a bad idea, and Waltrip said the jury is still out.
"Stay tuned. I don't think I can answer that yet," he said. "But I will give you a hint: If you drive down to Cornelius, (N.C.) and there's a for sale sign in front of that big building we built in the next year or two, then yes, I will regret it.
"But if we're able to continue the progress that we made so far, and we're able to become one of the teams where people want to land and sponsors want to be, then the challenges and sacrifices will be well worth it."
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