Health insurance.
Health insurance.
Health care is mostly not insurance, is tied to employment for a purely historical reason, and is precisely the largest issue preventing people from ditching safe but boring jobs and going after something new.
(And YC clearly understands this: look at the age of YC founders. Young, healthy, able to depend on someone else's healthcare or none at all for a year or so. Oh, and no mortgage.)
Furthermore once you or your family member develops a "preexisting medical conditions", you may not be approved next time you decide to to from corporate plan to individual. My wife was denied by one carrier for having chronic migraine for which she was taking prescription drugs and not seeing a doctor more than once a year.
With a current state of healthcare/insurance, I will only be able to leave my current employer and start a startup for as long as COBRA and CAL-COBRA allows. After that I will be forced to either join a larger company or have my family be without healthcare if a carrier decided to deny us coverage for preexisting conditions.
THIS. Although in many states there is a high risk pool that you can sign up for, when insurers deny you. I know someone who's done this in California and while there was a 6-9 month waiting list, and the coverage wasn't great, it was much much better than no coverage at all.
States with high risk pools: