The achievement icon is almost identical to The Legend of the Star achievement icon except instead of wearing blue star glasses, Vault Boy wears red heart shaped ones and the red caps are now gold chips.
The chips for the achievement are cumulative, so even if you use some, they still count towards the achievement.
xbox360 Dropping chips on the floor and picking them back up will result in the cumulative figure of collected chips rising by that amount. For example: Dropping 100 chips, and picking them back up 5 times will result in the achievement unlocking.
Accumlating more than 250 chips before entering the Dead Money game space, will cause the game script to remove the chips, and re-add them upon entering the world. This will result in the achievement unlocking without reaching the full quota of 500.
pc When picking up the 500th chip the game will crash, when looting 500th chip from container you will no longer hear gunshots/footsteps/collar beeps/dialogue/etc. Also, the 'Esc' key will cause game to freeze/crash.