How did I get the "What does it mean?" achievement?
This sequence is triggered on an overlook with a tent in east of The Highlands. It's most accessible from the cliff at the end of the Hyperion base on the east side of the map. Jump straight down to the tented overlook. Either Handsome Jack or Claptrap will imitate the popular "Double Rainbow" clip and trigger the achievement. A "double rainbow" glows in the distance:
Video walkthrough by GameFront: