I think you are short-changing the thoughtfulness of their long term investment partners (especially True Ventures - of which former Automattic CEO Toni is a partner). I also think you are thinking of Matt Mullenweg in the same light as many other startup founders, but he is quite different, especially in regard to his commitment to open source and publicly stated desire for Automattic to be a very long-term company, not reach a high valuation and have a big sale.

Now to your notes:

First, they don't have 20 sales people for VIP. They have less than ten for sure. Probably closer to five.

Second, VIP has more than a 100 customers, by far. And VIP business has grown ever since it was introduced, but simultaneously has become a smaller and smaller part of their overall revenues (I know this to be true). Which means other aspects of their business are growing faster than VIP.

I've followed Automattic closely for a long time. I don't at all see them as the type of company to just grab money in frothy markets. I think we'll see this money equip them to make some much bigger investments in the next couple years. They are certainly in better shape than any other CMS or blogging platform ever has been.