I really like this, and I think you could even add some LLM features in there for more natural conversations.
The biggest issue I have is that it is a bit weird putting our startup ideas into someone else server. Is this open-source so we can self host? The central db for questions could still be curated by you in the repo, we would just pull to update the questions on our end. For new questions we would make PRs. You still decide which questions are good.