I'm continually impressed that Dropbox continues to exist, so long after their primary product offering was so thoroughly sherlocked by the big two B2C companies (Google and Apple) and the big two B2B companies (MS and Google). Especially because I've never worked anywhere that used Dropbox, so they don't have the long-tail life support legacy B2B money keeping them afloat like say, Lotus Notes did.

B2C was lost to them the minute Google Drive and iCloud Drive both got decent enough. Clearly with all their random acquisitions and stuff they were trying to become a #3 to MS and Google for corporate, but it's such a moat to penetrate, since they'd have to become at least a little better than at least one of them at most of the big productivity things (email, calendar, documents & drive, chat, meetings), or be a lot better at one specific thing, enough that businesses will have an appetite to keep paying for GOOG/MS's bundles and add-on additional cost to pay for Dropbox too. If I had to vote for a company least likely to succeed I'd pick Dropbox, and that's without any shade to the people running it. They're just in a terrible market position.