On: Customers won't give you money unless you ask

How about the google apps route as an alternative to freemium?

1. Give it away for free for a long period to build a user base, get feedback and iterate.

2. After a while, switch to paid only for all new users. The old users continue for free so no-one has a right to get annoyed.

Seems a pretty good option to me.

Its a great option, if you have millions and millions of dollars in the bank.