This Achievement is unlocked the first time you retrieve a Jiggy from the Jigg-o-Vend and deposit it in the bank in the center of Showdown Town.
Each time you complete a challenge, you earn a Jiggy. You can retrieve it from the appropriate level's vending machine (using the X button to lock on with the wrench and rotating the L-stick to release it). Use the wrench with the R-trigger to pick up the Jiggy, or load it into the trolley, and carry it over the big yellow bank platform in the center of Showdown Town to place it in the bank.