Bruce has a lot of data on a bunch of hard drives and he's looking for a way to catalog or collate the data, getting rid of duplicate files. Leo says there are de-duping tools that are designed to analyze and get rid of duplicates, but he'll run a risk of deleting something that only looks like a duplicate.
Lance upgraded to macOS Sierra and now his Time Machine isn't working. Apple Care hasn't been able to solve the problem either. He's even reinstalled the OS and Time Machine. It just hangs about 2/3 of the way through the backup. Leo says that nobody really likes Time Machine, especially when it doesn't work. No one really knows how it works, either. If Apple can't figure it out, it's a lost cause.
Daryl wants to know how long Carbonite will take to backup his hard drive. Leo says to take 740kbps x 60 then divide by 10. 10 KB per minute. If he does the math, it takes quite a bit of time. Carbonite knows this and as such, Daryl can request to have a hard drive sent to him and then he can back up his system and sent it back.
Dave is using Western Digital's backup software with his WD External drive. How can he be sure he's backing up all his data? Leo says that he can't since WD uses a protocol that backs up all files into one big master file (or what Leo calls a big ball of stuff).