Start a multiplayer game by selecting "Create Friends Game" from the Easy Drive menu. Then, select "Speedlists" from Easy Drive and edit 5 events into a custom speedlist. Next, invite a friend as custom speedlists can only be played in friend games.
Once you have someone in your game, start the custom speedlist you just created. You'll first be required to go to a meetup point, and once everyone is there, the event will start. Winning doesn't matter, so just play through to the end of all 5 events where the achievement will unlock.
A quick method is to create a custom Speedlist and selecting the "Arch Angels" challenge 5 times. It's a Park Up event, and it takes place the same place as the meetup. Because of this, you can sit in one spot the entire Speedlist and complete all 5 events without any effort. The event takes about 30 seconds each time.