"I can't sync more than one folder? It syncs everything to every device? (not anymore). It doesn't use WebDAV? Oh well, at least it's simple. I'll just use it until something better comes along."
And they win.
Of course they have plenty of features, an API and much more flexibility that before if you want it, but none of that complicate the core function - a directory that syncs.
I dreamed about something like Dropbox before Dropbox existed; I always have had many different machines that needed to be "synchronized" by hand. I carried around hard drives, and Iomega disks and whatnot, and used "Beyond compare" to sync all of those and it was a nightmare.
The recommendation model of Dropox had nothing to do with me adopting it -- I didn't receive a recommendation and didn't send any. But I was very excited when I was first able to use it, and still find it amazing.
Before I used it DropBox was just another file sharing/syncing software. One of a whole stack of 'em that all seemed to suck in one way or another.
I'm sure that they all promised that they would be bringing cloud file storage to the masses as part of the initial pitch.... and I tried them all because, like you, I wanted this service before any of 'em existed.
Why did DropBox win and all of those others failed (or, at least, didn't succeed so wildly)? Why was it obvious to investors that DropBox was going to win, and the others "fail"?
Dropbox is not another file sharing software; the application form to YC doesn't even mention file sharing:
http://dl.dropbox.com/u/27532820/app.html
Dropbox isn't even about cloud storage.
Dropbox synchronizes your files between your different computers -- silently, automatically, without you doing anything except turn those machines on.
Nobody did this before Dropbox and still nobody is doing it now (except maybe AeroFS, which is much more difficult to setup and use -- but certainly not iCloud or any other "solution" that is restricted to one OS or company, and certainly no backup solution either).
That's why it was a fantastic idea... which has since been coupled with a brilliant execution, yes. But the idea itself was amazing.
That isn't to say Dropbox didn't blow them out of the water in regards to execution, but it wasn't an idea that was completely without precedent. Ideas rarely are, even if they seem like that in retrospect due to one company out executing everyone to an insane degree.
This part is important. The Microsoft service only synced to your other Microsoft things. iCloud only syncs to your Apple things. Dropbox syncs everywhere.
I don't think so. My first encounter with DropBox was very similar to my first encounter with Google... but it was "Oh look - another way to share files" rather than "Oh look - another search engine".
Or indeed many, many people's reaction to the release of the first iPod ("Oh look - another mp3 player").
Predicting their current level of success from the point of initial investment - pretty close to impossible without the benefit of 20/20 hindsight. Their success depending so much on how well they executed and the smart changes of direction that those companies made along the way.
(with, maybe, the exception of the iPod which was a bit more obvious for those that paid attention to iTunes)
E.g. Would DropBox be anywhere close to their current position if they hadn't figured out their freemium / recommendation based model for customer acquisition?