Complete all levels of Escort
In Escort, you will drive around a car while a hooker does her job in the backseat. If you are in co-op, one person will drive while the other one does the job. News Vans and the occasional Private Investigator will follow you, so keep out of their radius. It’s best to go on the highway, and drive at top speed on the wrong side. The oncoming traffic will take out most of your pursuers. On the later levels, you have to perform requests, so you may find yourself needing to get off the freeway so often it becomes inconvenient to use the freeway method.
Note: You can shoot the drivers of the cars to get rid of the radius, but this is impractical in most situations.
There are two Escort activities with 6 levels each. I recommend doing this in co-op so you can work towards the "Confidence Men" achievement as well as "Crime Lord".