We bootstrapped our company as well and did not get (couldn't afford) health insurance for the founders until about 1.5 years in. By that time I was too embarrassed to go to the dentist and put it off for another 2 years. Worst decision ever. By the time I did go last year, it had been over 5 years since my last dental visit. I needed a root canal and I'm still getting my cavities I piled up in that time period filled (though I'm almost done).

Our insurance plan is not cheap, (we live in Hawaii and pay about $500/month each) but its essential. You worry about so many things when choosing the startup life, your health shouldn't be another thing on your mind.