Sure, the Dropbox comment will never stop being a meme.

But in a world where, for example, a competing product like Fantastical already exists, costs less and does more, it does seem valid to be wondering what is going on.

As others have said, investments in startups are based a lot more on the potential of the team behind them than their existing products.

"People were too cynical about one YC startup, therefore any future cynicism is invalid" doesn't really make a lot of sense.

I don't think it's fair to compare a way to seamlessly move data around with "We’re building a calendar app for the Mac menu bar."

I think the point was that Dropbox was not at the time viewed as "seamlessly moving data around". We see it in retrospect as revolutionary, but that was certainly not the view at the time since many of us had already seen online storage platforms come and go (xdrive, anyone?).

I will not comment on whether this calendar app is revolutionary, it might not be, but it's also possible it is something that will make an impact. There's lots of untapped potential in the calendar and event space, in my opinion.

Is there an opportunity to make a cheaper Dropbox? Their paid service is very expensive.

OneDrive?