I'm willing to pay $5 for a Pumpkin Spice Latte because I know what I'm going to get. I'm going to get a tasty coffee and possible use of space and WiFi for a few hours if I want it. I have no idea what I'm going to get for an app. I may get something that is going to give me a few minutes of mindshare every day, or I may end up getting something which is completely useless. I have no way of knowing.
Starbucks also has no free alternatives. If I want to get a coffee when I'm in town I know I'm going to have to pay a certain price. There's no one handing out free coffee - or coffee that is free if I agree to read a few ads. That's not true of apps. Many apps have perfectly good free alternatives. The fact is, most of what Medium offers, I can get elsewhere. If what this amounts to is asking me to pay for Wait But Why, The Awl or the Ringer - I can get better elsewhere for free. There may be a price I'll pay for fuzzy thinkpieces that talk about how 'problematic' everything is, but it isn't very high.
If you want to get into non-free, $9.99 a month gets me either the entire history of recorded music, a selection of essential 'water-cooler' TV watching that I am going to be able to talk to other people about, or access to the entire archive of the Washington Post. I happily pay those and would probably pay 50% as much again, but it does mean that the bar for a glorified blog is very very high. I also have to say as far as Yipgo goes, then it had better be a damn good to-do list.