Am I the only one who found the whole thing extremely patronising? "A homeless man who could teach me something, who would've thought. I went to MIT!"
About his username, it is absurd that you cannot admit to going to a good school without being pretentious. The classic example is how Harvard students say where they go to school, "in Boston". Hiding information about your successes because they might impress people is much more pretentious than making a username "MIT_Hacker".
Think before you attack people.