There's a place for free, but I agree that those who start businesses and then have to come up with a plan to generate money are doing things completely backwards. It's one of the reasons I am annoyed at Twitter; they should be shunned for starting this thing with millions of dollars of other peoples' money and ultimately having no idea how they're ever going to make any of it back, but instead they get played up lik…
But I think under the talk of freemium, the important questions get lost. Freemium - it's so easy, you give part of it away for free, and part you charge for. Right?
But what do you give for free? What do you charge for? How do you convince people to pay?
Those questions typically go completely unaddressed because of the assumption that money will, magically, appear somehow, with enough viral growth.
People treat the free part of freemium as if you can just slap it on like Sriracha sauce, and improve everything. That's simply not how it works.
Freckle has an extremely limited free plan and we sort of hide it. It is freemium but it is so limited it irritates some people.
But, based on the way other SaaS entrepreneurs choke on their coffee and go "Monthly?!" when I tell them how much we earn per 1000 accounts (total), that extremely limited, fairly hidden account works extremely well for us. :)
And, for the record, I believe the best free-mium strategy is to give away related content, not the thing itself. Give away the occasional cheese stick or cup of cocoa -- not the milk, and not timeshare access to the cow.