I liked you have the guts to make this public.

I'd suggest you read the How To Apply guide, particularly the section on Matter of Fact answers: http://www.ycombinator.com/howtoapply/#matteroffact

I have trouble understanding what you plan on making by reading your answer to the first question. Write web software that records benefits? Make phone calls to insurance companies to figure out the best plans?

If the answer is you'll make a web-based payment system that aggregates and automatically invests premiums, I would put that in the first or second sentence.