Saying "understand that you are here through very little of your own merit" is a recipe for causing already overly stressed students to do something rash, like jumping out of a building: http://web.mit.edu/~sdavies/www/mit-suicides/ (this list isn't even up to date).
Motivating people to work hard to feel like they've earned their place is a completely different thing than reinforcing the doubts and insecurities almost all of them have anyway.
The pressure at this place (and it's the same at any top-tier place) has been almost too much for me to handle sometimes, and that's without foolish words from foolish people designed to increase it.
MIT alum here. I know what you mean; the pressure can be tough. But also, they've got a lot of resources on campus to help.
I'm going to be on campus tomorrow and Thursday if you're interested in meeting up and talking about the stress. My email address is in my profile.
Maybe a more useful rephrasing is that your presence at the institution is a blessing, a gift, given whether you currently deserve it or not. Enjoy the gift and grow into it.
However, for some students attending Harvard, Stanford, Oxford or Cambridge can be an expectation and a realistic one at that if they have been given every opportunity to increase their chances of entry thanks to their parents influence and wealth. I understood the Author to be addressing these students. Perhaps they're a minority, but looking at the ranks of politicians and World leaders (from wealthy families I might add) coming from these institutions, it looks like more than just coincidence to me.
But who is going to address the underlying sense of entitlement of the guy delivering the "go fuck yourself" speech? Spiteful turtles all the way down?
It's designed to address the underlying sense of entitlement students at the World's best universities can have. As these places can be so hard to get into, successful applicants can adopt a defensive "I'm here because I'm the cleverest and deserve it" mentality. For somewhere like Stanford, having a lot of (daddy's) money is, for most students, also a pre-requisite to attending. The Author is exactly right, being born into a family with money does not mean you deserve to be there, even if you did work really hard during grade school and college. The Freshman's are enormously lucky to have been given the chance to study at Stanford and it is up to them to earn their place, retrospectively. Society will be the judge based on their future work.
The message is not so much "don't get comfortable because 50% will be gone by the end of the year" but rather more of "Welcome to Stanford. Understand that you are here though very little of your own merit. You have the opportunity to change that if you work hard and focus on the bigger picture of society and not just furthering your own wealth".