In order to do this achievement, you'll need to progress through the game enough to complete the "FMX Training Program" level. Now, go to the garage and make sure to equip your rider in a "Excavator" Outift which requires a helmet, a top and a bottom piece. Any combination of items under this category of clothing will work for this achievement, you are free to purchase the cheapest 3 items to save money.
Now that your rider is equipped, go to the "Daredevil Showdown" event. Proceed slowly off the first ramp, and hold the "Proud Hero" pose until your rider crashes into the side of the building or ground floor. To hold a Proud Hero, make sure your bike and rider and balanced while in mid-air, and then hold down on the right stick. Give your rider a second to step up on the bike, and the trick is started.