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1) Set any landvehicle (bicycles excluded) race to Rally
2) Set the friend as the driver and just start right away
3) start the race
4) For precautions direct once or twice using the left and right on d-pad and let your friend drive through some checkpoints
5) Have the driver quit the session, making you be the only person on the "Job"
6) Achievement will unlock when it says "WINNER"