Can a Company Recover from a Lack of Business Model?

There's a lot of chatter about decentralizing Twitter, claiming it's now too valuable to rely on an often flaky service with an API so open that it's destroying the service. What no one seems to want to examine is that giant elephant in the corner: if Twitter is so valuable why isn't anyone willing to pay for it?

Regardless of whether or not Twitter will ever become mainstream, for early adopters, the 250, and the majority of the Web 2.0-addicted populace rely on Twitter. Even a brief outage sparks a bitchmeme and panicked IMs and emails to others asking if Twitter is down. If Twitter ever decides to monetize via subscription, they should offer a free bottle of Xanax as a sign-up bonus judging by the panic that ensues during an outage.

The biggest problem Twitter has right now isn't whether or not they should migrate to another platform from Rails, which is usually the scapegoat for their outages, but how Twitter can start making money without losing the userbase that has brought them this far.

I've pointed out before that one of the major problems with Web 2.0 apps is that they don't seem interested in figuring out how to make money. The modus operandi for achieving viral success has become "Make it free. Get people there. Figure out the money later." How, then, can a company go from offering services for free to charging their users for the services without creating a riot or losing those customers? Whether it's via subscription or the ubiquitous ad revenue model, the user is still being asked to give something up to continue using a service.

You can argue that many of these free apps and services have achieved the popularity they currently enjoy primarily because they were offered for free. A critical mass can be reached more easily this way, because it requires no investment on the part of the user to start using the app, and they can easily get their friends to join in as well. But how does a company come back from that? How can you subscribe to the "build something cool and worry about monetizing it later" idea without eventually tanking your company? How do you convince your users that they are devoted enough to stick with you even when you shift how things work?