This is an unfortunate by-product of the "Google" economy (better say, "VC" economy). Pricing, for the most part, is a psychological thing. When 99.9% of the web products are "free", a $9.99/mo product requires a lot of explanations. If every bar out there would give coffee away for free (to sell you ads in the bar), would you still justify/buy the $5.99 vanilla latte? Possible, but the market would significantly shrink. It also does not help that most of the SV "businesses" do not operate according to business metrics, but following vanity metrics - like monthly recurring active users per square feet (or, worse, by how much they have raised - i.e. debts)