As Trevor you'll eventually meet a woman named Maude as a Strangers & Freaks mission, shown as a question mark, ?, on the map. She wants you to bring her escaped convicts, for cash. She sends you regular emails with photos and last known locations.
The first one, Ralph Ostrowski, is down in the quarry where the big quarry truck is. DO NOT kill him, simply chase him in a car, stop him by shooting his tyres or trashing his car. I was lucky enough for him to get stuck behind a U section of barrier. Drag him out of the car, a cutscene starts, he surrenders and gets in your car as a passenger, take him back to Maude, the achievement will pop!
WARNING: If you use guns too much you can end up getting a wanted level, this will make it harder, try to shoot his tyres when you're still in the quarry area, or use a weapon with suppressor that you can shoot out of a car, like the pistol.
The location of Ralph is in the image below, courtesy of GamePressure.com: