I feel for the guy, for if you read between the lines of the latest news about Tumblr and one or two of his recent blog posts, he was obviously ousted by his board. So maybe it was a very difficult post to write.
However, I'm still astounded that this quality of writing could come from a company president.
And based on the recent decision to start selling advertising, it sounds like it's related to his inability to produce a top-line, or perhaps his aversion to the prevailing winds at the board about the timeline and methods to produce revenue.
My guess is that the missing periods at paragraph breaks indicate he wrote this on an iDevice. Space-space: period added. Enter-enter: no period added.
Quick test on a text field in chrome on my Galaxy Nexus shows the same behavior listed above: two spaces automatically ends the sentence with a period, but two carriage returns does not.
The inconsistent substitution of 'with' with 'w/' confuses me. Why do people even do that? On qwerty I know I find '/' to be much harder to strike than 'ith'.
However, I'm still astounded that this quality of writing could come from a company president.