Castle/Second Castle was introduced when the crew were playing Family Feud 2010 Edition during the November 18, 2013 NLSS. To answer "Name something you're starting to think you'll never be able to afford," Josh replied with "House", resulting in the top answer of "House/2nd Home."
After guessing 6/7 of all the entries on the board, the NLSS crew came up short unable to guess the 6th and final entry. The bot family then stole the board by guessing "Castle." Ryan went into a rant due to the absurdity of the answer.
"We surveyed 100 13th century Barons..." - Ryab 2013
Twitch chat user "pelicanpubs" followed this up by writing "Castle/Second Castle."
Ryan was amused by this and declared it a "first world problem" in a tongue-in-cheek manner. The phrase was used in various forms for several NLSS broadcasts over the next few months. Since then it has died down in popularity among common NLSS conversation. Other variations of this meme still exist.