Heroku was able to do it because it had a lot of funding in the beginning (and is now part of a public company). Very hard to bootstrap freemium, especially if there are per-user costs like with hosting.
(I run gondor.io so I understand :-)
(I run gondor.io so I understand :-)
Yes, bootstrapping freemium is hard. I would love to see discussions on how to do it right.
Don't get me wrong. I am revenue driven. I am not crazy about freemium. But I see way too many entrepreneurs not putting themselves into the mind of their target users.
I would trivial Gondor.io as a more specific Python oriented version of Heroku. The benefits are hopefully more obvious, and I would argue that freemium is not important for Gondor.io.
However, the problem I have had with micro-blogging platform is in the details, which often results in me not using it more than twice or thrice. I would easily pay $250/year if ThoughStreams worked for me, but I don't know that. Currently the site looks great and it makes me really want to try it, but I doubt that I will be able to make a decision in 30-days. I am willing to try though.
Best of luck!