Ask HN: Going Unemployed?

I'm currently employed at a large software corporation that treats me well but where I am incredibly bored by the things I do. The environment doesn't fit my personality. I have learned so much more on my own time reading and hacking than I have over the past couple years at the company. Ultimately, my eventual goal is to start a company or work at an early stage startup. I don't see my current path leading me there. I'm considering quitting my job so I can devote my time to learning new things and starting/joining a startup. My biggest worries are: 1. Resume gap 2. Healthcare

I've been good about saving money and living frugally so I can go at least a couple of years without a paycheck.

Should I make the move and just quit? How do you go from a corporate job to a startup? Am I right in thinking that I will be challenged and learn a great deal more about technology, management, and business at a startup?