I think got this trophy earlier than the other solutions. I was able to do it on the mission "No Love Lost" (given to you by Faustin). It was the first time I got a bike in the game.
You will get a bike to follow Faustin's daughter's biker boyfriend. After getting on the bike, make a right onto the long east-west rode and pop a wheely (just pick up speed and hold back on the L-stick). You can hold back on the joystick longer than you would think before crashing the bike.
Note: 500 ft seems longer in this game than it would be in real life. Also, you will probably have to redo this mission unless you are REALLY good.