But since establishing his three-car Sprint Cup operation in 2007, the younger Waltrip's organization has steadily seen progress, to the point where when folks talk to Darrell, many are likely to say now, "Oh, you're Michael's brother, right?"
And that name and his company's reputation within the sport are going to continue to get bigger and better, particularly with both Michael Waltrip Racing drivers, Clint Bowyer and Martin Truex Jr. Not only did both drivers make last season's Chase for the Sprint Cup, Bowyer finished a career-best second place in the Sprint Cup standings, just 39 points behind eventual champion Brad Keselowski.
"Oh, by far," Waltrip said in an interview with Bleacher Report this week. "We didn't have the history to have a lot of confidence about where we were starting a season. And this season, we feel confident about our cars, we love our teams and drivers and we really feel good about who we are.
"All in all, we feel good about where we are with our team and the fact that we have the same guys turning the wrenches and driving the cars in 2013 that we had in 2012, that's a really important part of why we are confident about where we are as an organization."
No one feels better about it than the guy whose name is on the building, who pays the bills and who is now as comfortable as being called "boss" as he is by his first name.
"It's been a long road, no doubt," Waltrip said. "We started out (in 2007) with a new manufacturer (Toyota) and a new team, and we were racing against folks that had been around for many, many years. And we struggled mightily. We couldn't make races, weren't competitive.
We had told our sponsors and partners that joined us back in '07 that we would win, and that was not true. And so, luckily, I had a lot of equity built up with NAPA, Aarons, Best Western, Freightliner, the folks that were there back then, and that allowed us the chance to get it right.
"We finally got to the point where we were competing for wins every week with both the NAPA car and the 5 Hour Energy car in the Chase last year, so I'm just thankful that the partners and sponsors all stuck around long enough to let us have the success that we told them that we would have.
"It's real important to me to do what I say I'm going to do. It took longer than I hoped, obviously, but now we're competing for and doing the things we thought we could do when we started this organization."
Last year's March race saw Truex, Boyer and Brian Vickers (subbing for Mark Martin) finish third, fourth and fifth. In the August race, the three MWR drivers again finished in the top 11.
"Bristol was one of our strongest tracks last year, for sure," Waltrip said. "We came out and for the first time, finished all three cars in the top-five in the spring, and then (ran strong again) back in the fall.
"We have really fast cars, and we're really confident about this new Gen 6 car at Bristol. It's going to be fun to watch the new car; it's a little bit lighter this year, and that will help more at Bristol than anywhere we've raced so far. It's going to be fun."
As was the case last year, Mark Martin is running a part-time schedule of 24 races for MWR, with Vickers the designated fill-in for most of the others.
However, with Martin having such a strong start this season, and if he can win two races or more in the 17 pre-Chase events he's entered in, there's a possibility he could become the first part-time driver to make the Chase as a wild card (provided he's in the top 20 in the standings heading into the Chase).
That possibility is not lost on Waltrip, who would love to see Martin have one last shot at winning the Cup championship that has eluded him for three decades (although Martin has finished second in the standings five different seasons).
"Yeah, we've talked about it and just think that would be a great problem to try and figure out when that happens," Waltrip said of Martin potentially making the Chase. "We want everybody to wonder that, and we kind of wonder it, too. And if we have to figure it out, that would be a great problem to have."
Waltrip spoke with Bleacher Report as part of a telephone media tour to talk about one of the most unique promotions to hit NASCAR in many years, the Peak Stock Car Dream Challenge.
The program, sponsored by Peak Motor Oil and Antifreeze, runs through May 31 and bills itself as a "nationwide search for the next Michael Waltrip Racing stock car driving star."
Waltrip, Bowyer and Danica Patrick will all be involved in the promotion, which asks aspiring racers to submit video auditions of their personalities and driving ability to
The key for contest entrants is to try and convince judges that they should get a dream-come-true opportunity to showcase their natural ability behind the wheel of a race car. Videos will be judged on originality, racing enthusiasm, racing ability and experience, attention to the Peak brand and accumulating points on each contestant's online profile page.
Points will be acquired by uploading photos to Instagram from races and tagging @peakauto on Twitter and Facebook. Entrants' videos must also reach a minimum of 500 views.
An accompanying sweepstakes for race fans will include a number of prizes including a brand new 2013 Toyota Tundra, driving school experiences, a VIP trip to watch a race at Daytona International Speedway and more.
"The videos will be fun to watch," Waltrip said. "You upload them to the web site, and you get them liked on Facebook, Twitter, Instagram also gains you some momentum, and there's a sweepstakes that goes along with this as well, where you can win a Toyota Tundra pickup truck and other cool prizes.
"You go there and enter some videos of what you've accomplished, what you've done and what your goals are and it's a round of testing with our team," Waltrip said. "That's really exciting for me. I love to give people chances that otherwise wouldn't have them. And thanks to Peak and this challenge, they're going to get that opportunity."
The top 10 winners will compete in a three-day racing program in July at an as-yet unnamed short track with coaching and judging from Waltrip, Bowyer, Patrick and other key figures in NASCAR.
One overall winner will then be chosen for additional training, as well as the opportunity to earn their NASCAR competition license and then be put in a Peak-sponsored stock car in a sanctioned race to "prove that they have what it takes to become Michael Waltrip Racing's next stock car driver."
"There's a chance for someone with that same kind of drive and determination to show what they've got, and Danica, Clint and I are going to watch them, and hopefully, it'll be the next star one day," Waltrip said.
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