As a frequent non-paying user of the service (as well as a heavy user of Dropbox), I think it would be enlightening to see (or start building) an analysis of the company from a customer validation/startup building perspective. What lessons were learned in creating it/what can it teach current startup founders?
My business frequently used Drop.io when we needed to do a quick presentation or even to get a throwaway email. I was at the NY Tech Meetup when they presented. I wasn't blown away but I did tell myself "that's an easy tool to use".<p>So why at times did we use Drop.io vs Skype/Office/dropbox etc... it's because it was a single button click. Simple. No need to have to do multiple email verification. It was as easy using Google or doing a status update.<p>I do think they didn't receive a lot of traction was because their premium services was that they didn't develop the tools that weren't 100% small enterprise aimed but trying to do a consumer play.