I struggle to think of the occupation for which a $500 pencil sharpening is a good value, but if you just want to give loads of money to someone interesting, hey, why not?
The guy who runs it is a humorist, so there's that.
Oddly enough, it's the same guy who used to write the brilliant "Get Your War On" comic (and the more surreal "My New Fighting/Filing Technique"), for anyone who remembers those.
It's worth noting that the person behind it is a humorist and cartoonist, and while I expect that he'll actually sharpen a pencil if you pay him, it is almost certainly not meant to be taken as a serious method of pencil sharpening. I expect the significant increases in price after the service's inception—over an order of magnitude—reflect this.
The service is connected with a book that a New Yorker review suggests is classified as humor by its publisher out of a lack of "avant-garde reference" sections in bookstores.
I can see your point there. I remember my friend suggested some mechanical pencils to me a while ago (don't remember which brand) but I bought them because he said they were sturdy and the lead was stronger on normal paper so it wouldn't break as often. Yeah my 6th grade self bought into it and they felt like any other cheaper alternative brand