He would have got Musicmatch software with the iPod.
He would be better served downloading the iTunes software which is now available for the PC.
This will search his computer for all mp3 and automatically download it to the iPod.
I bought my wife one at Xmas and it is absolutley brilliant.
click here for the free download.
I should have said that Musicmatch can also tranfer to the iPod but it is useless compared to the iTunes.