Originally Posted by Darth Maleval
You first have to be at least Level 14. Then he just randomly will show up in any local pub. It could be any one, so if you just keep visiting them...he should show up eventually.
It's whichever pub is closest to you when you hit level 14. So if you hit 14 fighting bandits outside of Whiterun, he would be found at the Bannered Mare. If you hit level 14 while in the Ratway in Riften, he'd appear at the Bee and Barb... etc, etc...