This is a story based achievement. Once you do the opening bank heist mission with Trevor, you'll end up being Michael in a cutscene, sat on a bench. Lamar and Franklin walk past, Lamar asks you where a building is.
You then take control of Franklin, and you & Lamar walk to the back of a house, jump in two cars (you can choose to drive either of the two), and race them to Simeon's garage, part way through you get the cops on you. Lose the cops, get to Simeon's garage, and a cutscene kicks in showing Simeon having an argument with Michael's son Jimmy about him being racist.
Achievement will unlock during the cutscene!