This one is pretty straightforward, but a few things I learned (the hard way along the way). When you create your character, you want to select an established show such as RAW or Smackdown. I originally selected WCW and it seemed to take me nowhere. One thing to note also is that you will compete, and even though you are winning, won't be invited to the pay per views to wrestle. Don't mind this, as your chances will come. Also, keep an eye on the rankings - once you get your #1 contender match, the achievement is as simple as getting #1 contender and beating the champ. For me, I popped the achievement at Champion of Champions. One last thought is that the achievement doesn't pop right after getting the title, but did pop before going back to WWE universe, so be patient.
I also noticed that without losing any matches, that I was in the World Heavyweight title chase, but not the US Title chase. Might be difficult to go back and pop that achievement. Any ideas out there?