This was a huge struggle for me early on in my career--and it wasn't until our company had a group (3+ people) that would could affordable plans. Even then, we were paying over $1000/mo to insure 3 healthy 26-year-olds.
You can read more about my story here: http://thecreativecareer.com/2009/03/30/us-healthcare-system...
EDIT (In case the above is TL;DR):
"This means that many entrepreneurs and innovators—those of us paving the way on our own—are left with costly insurance or no insurance at all. Because of the limited choices for affordable healthcare, the decision to become an entrepreneur looks increasingly less attractive. Even if an individual is to secure an individual policy, the rates will be higher, and the coverage will be less than policies available through an employer."