You know, looking back it's silly, but when Youtube came out and started getting attention (I was still in school, so this must've been 2004 or so), I remember thinking to myself "so what?" -- the idea that it was novel just never occurred to me.
Back in 2002-2003, I ran a little startup (at 14-15) that did online music streaming. Built around a little PHP (later C++) daemon, you could set up playlists on the site and then connect to an icecast stream to play that playlist from any device you wanted. The music was ripped from CDs that my friends and I had, and we even added advertisements every X songs or N minutes. It eventually failed due to not being able to raise money to get licensing rights (my dad was running the business side and simply had no clue, but neither did I at the time), but it was just... no big deal to me. I had no idea that it was supposed to be a hard thing to do until a few years later, when I ended up working for MP3tunes trying to build the first online music locker.
I always just assumed that the trend towards storage and bandwidth being "free" was going to move fast enough that anything I could come up with would Just Work (TM).