Sometimes I see comments on HN about how that person would gladly pay for an ad free version of the service but experiences have shown over and over that it just doesn't work.
I don't think this was as obvious in 2012.
Their approach, however, by building a paid Twitter clone as the "killer app" of their platform, which isn't a very useful use case when you have free Twitter, awfully reminds me of what Dennis Ritchie wrote in Anti-Foreword of Unix Haters Handbook[1]:
"Your sense of the possible is in no sense pure: sometimes you want the same thing you have, but wish you had done it yourselves; other times you want something different, but can't seem to get people to use it"
They really wished they owned Twitter, and they did it their way, although if they really were Twitter owners, they too would have likely opted for the proven, lucrative, and more straightforward ad business over the protocol business at that point.
Criticism aside, it was probably worth trying anyway, and the fact that they raised funds in their initial campaign ($5/user if I remember correctly) was not easy to pull off and surprising.
It came with a block of cloud storage, an ad free social network, an API for devs to build on top of... those three ingredients alone were fertile ground for developers to make some very engaging, unique apps. It also felt much more communal.
I was a fan and definitely miss App.net
I like the riches in niches but even there it's increasingly more challenging getting a share of wallet because consumers are getting incredible value from services like Netflix/Spotify/Office/etc. They've been programmed for free or subsidized.
It's impossible to determine but as a thought experiment imagine if the only way to subscribe to Facebook after the .edu phase was to pay $1 / £1 / €1 per year.
Overall revenue would be lower but they wouldn't have to maintain enormous sales and ad-tech teams.
app.net flunked IMHO because noone understood what it was, not because it required payment.