* Create quality service, prioritizing user experience over money
* Grow site to significant user base
* Start running out of money, because hosting and running a site does cost money
* Try to monetize service
* Get out-competed by another service still at step 1
The presence of VC money that's all about capturing market share now, and monetizing later does not help.
In the end, we have become accustomed to a world where things that cost money are given to us for free. When there are attempts to charge us so things remain sustainable, we get angry! It's a tough problem, and I don't know the solution.
All these platforms rake in millions of VC money to get market share (that is fine btw) but if you do not know how to monetize it, what is the point? And of course always being free and then moving to a paid model doesn't make your users really happy.
I believe it's hard, but not impossible, to refrain from abusive monetization and stay afloat longer.
Users expect these services to be free, because they are used to services being sold under-cost. The alternatives for 'platforms' that I know of are:
1) accept 10% of paying customers and 90% leaving, bad plan if you rely on the mass of present users
2) go for a tiered system, where certain features are gated by a pay-wall. This is very tricky, and asking for essential features will see free competitors come up. This can work if your sheer user-base is enough of a moat. (Reddit is still trying to make this one work)
3) sell user-data
3 is definitely seen as 'user-abusing' 2 tends to be as-well and 1 is not an option for any platform.
I can't think of a single platform that started of as 'free' and got profitable without being widely condemned for 'selling out users' except for YouTube (and I guess PornHub). The moat there is massive infrastructure needed for video and a huge, hard-to-move catalogue of content. That is, it is too expensive for some start-up to grow and capture the market.
I'd love to hear of any other success stories. Especially one that could work for a medium / reddit / flicker kind of site.