To me it looks like the mistake it looks like you made wasn't offering a free product. It was offering ".. a super generous Free plan. A free plan so generous t

To me it looks like the mistake it looks like you made wasn't offering a free product. It was offering ".. a super generous Free plan. A free plan so generous that an average funded startup would very rarely outgrow it.". One reason for giving away free accounts is that lone hobby developers can very quickly become founders of rather bigger startups. These lone hobby developers are likely to only be interested in free - $9/month is a fairly big investment for someone just doing a hobby. The second it becomes a real business, on the other hand, that $9 is likely to look quite different. On a very note, I work for a pretty large organisation and have quite a lot of input in product choices. I also tinker around with stuff in my spare time. I definitely won't be paying you $9/month for my tinkering, and so I'll never get to know if it's something I'd want to recommend for consideration for my organisation. And I doubt I'm unique in this kind of position. The trick is to make the free stuff only good enough for those people who would never pay for it anyway (allowing people who could become customers in the future a chance to get used to your product), and make stuff that would be critical to any real user - such as access to support, ability to support multiple users or whatever - only available to your paying customers. Otherwise, you run the risk of chasing off a lot of potential future business.