I'm usually a huge fan of pg, but in his essay about founders, there was one section which I wasn't very comfortable with:
http://www.paulgraham.com/founders.htmlSpecifically, when he talks about naughtiness, he says:
Morally, they care about getting the big questions right, but not about observing proprieties. That's why I'd use the word naughty rather than evil. They delight in breaking rules, but not rules that matter.
I have absolutely no interest in trying to play language games - and maybe I'm misunderstanding what pg is saying, but it has always seemed to me that the judgement of whether the rule that was broken was consequential or not is post-hoc. For example: had airbnb gotten in serious trouble and floundered in the aftermath of when they started scraping craigslist for listings, they wouldn't be clever and naughty, but reckless and foolish. Had zenefits managed to grow even more or hire some key lobbyists and get the law changed in time, their CEO would be hailed as a visionary genius that cut through pointless red tape.
Anyway: the reason I brought that up is that a lot of the ethically dubious things that Elizabeth Homes did are very similar to things which a lot of tech companies did at one time or another. Trying to push ambitious young men and women to look at rules and regulations as something they should take pride in hacking and bypassing is a dangerous game - even more so in fields that are highly regulated.
Addendum: part of the original hacker ethic was to ignore stupid rules. For example, we take delight in Feynmann cracking safes at Los Alamos, or finding some clever hack to bypass a pointless procedure. However: I think it's one thing to hack a system to make a point about how stupid it is, but it's completely different if you add a monetary incentive, and suddenly the rules that get broken are those that stand in the way of you making money. The two sets have a fairly small overlap.
Addendum two: in a complex society like the one we live in, we have a lot of dumb rules. I'm not trying to defend them - we should obviously get rid of them, even in healthcare. A lot of economists have written intelligently about how to make the approval process of the FDA more agile.