Annual subscriptions are a terrible thing for a bootstrapped business without a huge runway because a sales of annual subscription is a liability from the accou

Annual subscriptions are a terrible thing for a bootstrapped business without a huge runway because a sales of annual subscription is a liability from the accounting and legal perspective. Just because you got cash does not mean it is yours. In the first month only 1/12th of the money is yours. By spending more than 1/12th you are basically borrowing the money from the customer based on the terms ( whatever your service was ) at the moment of subscription sale. If you have a runway, already then it is great and optimizing for the cashflow is great. If you do not have a runway, the last thing that you want to do is commit to a long term delivery of something rather than charge the customer monthly.