Drew Houston writes without capitalization. Would you say the same to him? Ideas are what matter, not apostrophes.
On your second point, I think there's a clear difference between consistent lack of capitalization that is obviously a stylistic quirk, and simply using a homophone because you don't know (or, I guess as it turns out, don't care) that you're doing so. This is a common mistake and not usually due to ESL/EAL.
But I won't do it again, as it evidently is not a net good in this medium. Sorry, folks.
Thank you for informing me. Now that I know this, I'll look more seriously at Dropbox alternatives. This degree of carelessness and disrespect for others is dangerous in the CEO of a company asking me to trust them with my data.