http://valleywag.gawker.com/what-happens-when-a-healthcare-startup-leaves-you-with-1598186714
What kind of lessons can we learn and build upon to truly re-imagine this sensitive, regimented industry where UX == livelihood?
As much transparency as legally possible.
constantly blog about the behind the scenes, you need to be seen as a hero always - never be in the position where you need to publicly apologize - always do whats right for the customer, show how much money you lose doing the right thing (see https://www.thelevelup.com/interchange-zero) and the amount of cash you are sinking into protecting your customers and your reputation when you get it wrong.
TRUST is #1 here, medical bills are a huge pain point already, you REALLY don't want that anger aimed at you because of some small issue, or worse, CREATE the pain where there was none.
lesson from OSCAR: your customers are not your investors, their money is not something you can experiment with. So on't get bill estimates wrong, and eat the cost when you get it wrong. Earn the TRUST that you and your investors will do the right thing, you'll need backers to put up their reputation here as well.