I can provide you a really great experience at ~$100/yr and a really great experience with VIP at 45k/yr. That is a huge gap (I know!) but at our core Automattic is a technology company, and very small given the market we’re addressing, and so it’s just as important what we choose not to do as what we do. I want to laser-focus our smartest folks on just a few areas, and do those areas better than anyone else in the world.
From a comment by Matt Mullenweg (WP CEO)