I thought about this one as well - it was a bit confusing as I thought the author was confusing cash flow with revenue at first, but then I realized - I think -

I thought about this one as well - it was a bit confusing as I thought the author was confusing cash flow with revenue at first, but then I realized - I think - he’s referring to the fact that an annual subscription has the hassle of “the annual renewal”, which is to say that you have to go through the whole pitch and hope and pray (and negotiation) so you get that annual subscriber to do it again each year. This, as opposed to simply billing monthly, continuously providing value, and reducing the headache.