This is the real meta-lesson, and particularly that "speak to your potential customers first" doesn't mean just asking sponsors[1], it means asking the entire community that the company hopes to serve.
Before making a significant change in business models, best case, publish a blog post explaining the changes (or a few possible scenarios and their perceived pros and cons) and ask for comments. Not being confident enough to do that is probably a sign that the change is higher-risk than is being acknowledged. And even in that case, pick, say, 100 random users and email them for their opinions.
[1]: Caddy stated that they asked sponsors, but that they incorrectly interpreted silence as support or at least neutrality.
We asked our sponsors about the header, not the pricing. And we did ask people for information about how they used Caddy but virtually none of the commercial use cases came up. For some reason people were reluctant to talk about it, even in private. I'm glad that at least some of them came out of the woodwork this last month. We look forward to more established business relationships in the future.
Before making a significant change in business models, best case, publish a blog post explaining the changes (or a few possible scenarios and their perceived pros and cons) and ask for comments. Not being confident enough to do that is probably a sign that the change is higher-risk than is being acknowledged. And even in that case, pick, say, 100 random users and email them for their opinions.
[1]: Caddy stated that they asked sponsors, but that they incorrectly interpreted silence as support or at least neutrality.