While at EA I worked on numerous paid products, as an entrepreneur I've built mostly free products. MEETorDIE, Commonred, and Startup Grind for a very long time was completely free. The pain of development cost with no income channel to support it have helped me learn a difficult lesson: build something that your customers will pay for. Thanks David Heinemeier Hansson.
RingCentral, which almost ten years since being founded, and boats tens of thousands of customers, had a free trail from their first day. Interestingly though they have always required a real credit card to sign up for a free 30-day account. As CEO Vlad Shmunis points out, this has helped them avoid a lot of the issues with fraud. He didn't say it, but I'm convinced it's also made them a lot more money. Here's why.
First they don't have the overhead of servicing bogus accounts that will likely never pay in the first place, and if customers are satisfied with the experience it's much easier to carry on with it having done the majority of the work up front.
I don't know where it originated from, but 'beta test your business model' rings in my ears on the subject. Don't put off beta testing a business model or you'll likely never get to it. I speak from lots of painful experience on the subject. When we launched Commonred last year we had hundreds of thousands of page views, but we put off our goals for introducing a business model, instead putting more time and energy into 'the product'. So dumb.
I'm convinced that had we introduced something right from the beginning, we would have made some money and that would have led us into a more fruitful and positive path for the product.