What about Paper? Not only did they charge from the start, they charged a rather high price, and entered a market full of existing competitors, some free.
Unless you are talking about a different Paper, Paper was a free app with an in-app purchase of tools (different brushes) available.
I know this because I downloaded it because it was free and then bought the tools. I wouldn't have tried it if they wanted the (I think) $4.99 up-front.
Good example definitely. I wonder what kind of money they're making. I also wonder if they would be able to do the same thing in 2014 that they did a few years back when they launched. I perceive the landscape as far more competitive, but I could be wrong.
Sometimes ... just sometimes, a fantastic product, and good lifestyle-type marketing (at least, from the videos on their site) can make all the difference. Paper is just leaps and bounds better than any other similar app ;)
I know this because I downloaded it because it was free and then bought the tools. I wouldn't have tried it if they wanted the (I think) $4.99 up-front.