|Before starting this mission, make sure you have a very fast car, as you will need it for this mission.|
After finishing up Extra Commission, Josh will tell you to meet him at a motel in Rancho, which is where you go to start this mission. Do the little bouncy bouncy and then Josh will tell you he wants to threaten Lenny a little bit. As you head to the marker, Josh will tell you that he drives a green Comet.
When you get to the marker, you see it disappear, but Lenny will be close (he's in the driveway of one of the houses). Lenny will see you as you get near and speed off, and since he's in a Comet, his car is very fast. Chase him down, damaging his car enough so he stops. Once he does, punch or hit him one time to scare him enough and finish the mission.