Story related and cannot be missed.
Achieved near the start of chapter 3, Derek will learn you are friends with Joe, and task you with "collecting money for the barber" 2 will pay up, and 2 you will have to fight for the money. Usual combat applies, hold A to dodge and just after the opponent misses you hit Y for some heavy attacks, then B as he gets up to finish him off.
After returning to Derek, a short cutscene will play and then the achievement unlocks.