I know I have to look in a tavern but I don't know which one. I've read that it starts in the closest tavern where you turned level 14, but that was weeks ago and I'm level 52. Anyone mind giving me some advice on what taverns to find him in? Or can it literally be any tavern?

Whiterun's tavern, right behind the old woman's market stall. When inside, talk to the dude who challenges you to a drinking game.

It can be any tavern.


I've encountered him at the tavern in Whiterun as well as the tavern in Ivarstead.

It can be in any tavern. Look for an NPC named Sam. I don't remember his last name.