If this is a correct translation, YC would be using it as a no-invest signal more than anything else, given how much the two original founders have talked about the importance of good character and decency in being a successful founder:
http://foundersatwork.posthaven.com/the-social-radar-what-i-...
I'm not trying to criticize YC here, not by much at least. I like YC and we even interviewed with them once. I don't know what kinds of answers they get or expect to that question, but I suspect that "hacking a non-computer system to your advantage" has only two categories of good answers, one being hacking a bureaucracy (which, let's admit it, is more like hacking a computer than anything else). The one is hacking people which feels a little bit psychopathic to me no matter how you put it.
I've done YC. I've met and closely observed many of the founders of the most successful companies, including the ones who are most revered for their ability to hack non-computer systems to their advantage.
Their behaviour is not remotely psychopathic, which very specifically means to act without any concern about causing harm to others.
To the contrary, these people stand out for their willingness to help others and create outcomes of mutual benefit.
I think this is where you're getting it wrong: you're taking a zero-sum-game approach, in which for someone to gain, someone else has to lose.
But good business (and good social hacking) doesn't work this way; it is all about creating win-win outcomes, by identifying and removing inefficiency and waste, or creating new opportunities for people to live more productive and enjoyable lives.
If you're interested in understanding this more deeply, I strongly recommend listening to this EconTalk podcast episode [1], particularly the story of the Padre.
For what it's worth, when I reflect on my own stint at running a YC-funded startup (which had a moderately successful outcome but not any kind of home run), I can recognise that one of my biggest failings was being too narcissistic. Since recognising this and spending several years working this tendency out of my character, my career success has improved dramatically.
I can also look back on a time in my life when I looked at some people who were more successful than me and assessed them as being a "psychopath", but it's clear to me now that I was just avoiding doing the self-scrutiny I should have been doing in order to become a successful (and good) person myself.
None of this is to defend the Browserling guy's conduct, which does seem rather ugly to me.
But psychopathic?
I'd really urge you to use terms like that with great caution and some self-reflection.
[1] http://www.econtalk.org/archives/2011/12/munger_on_profi.htm...
I appreciate your comment and I think you're right.