Why don't you grandfather in your current free users and shut off the plan? That seems totally fair.
At present, it seems like bait and switch. You say it yourself in the post:
"One of the most prominent details we emphasized to everyone we spoke to in the early days of Trak.io was that we would offer a super generous Free plan."
So you got people to try and test your product based on this attractive premise, and now the ones who are perhaps too early stage to switch to a paid plan are stuck. With an analytics app, switching costs are pretty high.
Of course you have the ability to iterate, increase prices, etc.--and you should--I just think it should be done with a little more tact.
At present, it seems like bait and switch. You say it yourself in the post:
"One of the most prominent details we emphasized to everyone we spoke to in the early days of Trak.io was that we would offer a super generous Free plan."
So you got people to try and test your product based on this attractive premise, and now the ones who are perhaps too early stage to switch to a paid plan are stuck. With an analytics app, switching costs are pretty high.
Of course you have the ability to iterate, increase prices, etc.--and you should--I just think it should be done with a little more tact.