These are old but the Ask YC Archive has good advice. Here are the threads on Health Care: <a href="http://www.gabrielweinberg.com/startupswiki/Ask_YC_Archive#toc6" rel="nofollow">http://www.gabrielweinberg.com/startupswiki/Ask_YC_Archive#t...</a>
As a freelancer I've used ehealthinsurance.com to buy my own health insurance in the past. But this depends a LOT where you live: It used to cost me around $75/month for decent coverage in the Philadelphia suburbs vs around $300/month for bare bones coverage in the NYC suburbs (North Jersey).
If you put some contact information in your profile (or contact me at my username at my username dot net) I can put you in touch with someone who can at least get you some quotes from a bunch of different carriers at no cost to you. (i.e. a broker)
HSA accounts with a high deductible plan are a great way to self insure and save money. We have the $5300 deductible plan for my family via Assurant and fund our HSAs to pay the costs. For a family of four, we pay about $320/month.<p>We do have health expenditures that we cover out of our own pocket but it generally adds to be less than what we would spend for a $500 deductible plan with all the amenities.
Used to get mine through the FreelancersUnion, but they screwed with their health insurance way too many times for it to be a viable option for me. As a result, I buy mine from ehealthinsurance.com and got a policy from United that fits my needs. Also, if your startup has more than one employee, you can form your own group, and get better group rates ... even if only one of you signs onto a policy.
I had COBRA for many months from my former employer (worked well, very expensive). Then I found an excellent broker in the Atlanta area and got a good HSA plan from Aetna. So far so good, much cheaper, provided we don't have claims.
I'm not a YC founder but I got an individual plan from Blue Cross Blue Shield (MN) through ehealthinsurance.com. It is an excellent plan (so far) and wasn't nearly what I was expecting to pay (<$150/mo).