Demonstratively, you are right, as you have shown with Stack Overflow and Trello. But, I think it will take a while for developer mindset to adapt to this new idea. While in reality it may be more difficult to execute on the "old-fashioned" model, in concept it seems much easier to approach. I build something, and then people pay me for it, simple. The new model of I build something, give it away for free, and then come up with a way to make money from a niche part of that seems like a huge risk to take, especially for someone who has not had the previous successes that you have had (using the old-fashioned model) and so doesn't have the same reputation, connections, and capital to support their new venture.
Right. It's not so easy to pull off for someone bootstrapping (but then again, rich players / people with audiences / people with social capital will always have an advantage, this is no different)
Agreed, it's completely unintuitive to a lot of software developers. I run a revenue API company for app developers to help them monetize free apps, and in three years, of all the paid app developers I've spoken with, exactly zero have initially believed me that free App Store apps can generate revenue to even approach the revenue they think they'll capture with a for-pay app. They don't realize that the avalanche of free apps is going to crush them like a Mack truck.
Common sense, creator's optimism, and B-school economics all suggest that paid beats free, I get it. But, sh-t's changed. Chris Anderson wrote Free: The Future of a Radical Price five YEARS ago, but I wish more creators and developers on HN took the ideas described there to heart.
