Joel is annoying and his success is annoying to some people because the software he sells is crappy and/or written by summer interns yet he manages to, apparently, rake in the dough. The jobs board thing is a case of meta-money-making (like Donald Trump converting the high profile he built up in real estate into a second revenue stream via a television show) and that also ... is annoying to some folks.
Anyway... Joel is annoying. Creepy? Not so much.
This guy has turned sort of creepy, though: