I've worked at a pretty wide range of tech companies throughout my 15+ year career. When I was young I would ask myself "what is leadership thinking!?", my realization later in my career was simply: "oh, they're not thinking"

14 year old and younger tech companies have only existed during a tech boom period, when money flowed easy from both investors and customers. There has been zero market pressure to put thought into building products.

In the case of dropbox in particular, any long term customers (such as myself) can confirm that there has clearly not been a coherent product strategy for at least the last few years.