I think the thing that makes me the craziest is the way this guy hopped on the current movement in our culture of sympathy toward students that is galvanizing a review of tuition and new policies. When our collective moral outrage on this issue doesn't even apply to him. Thirty years ago the proportion of tuition to earnings wasn't near what it is now. He could, actually, have paid off one degree. This guy reminds me of those people who make their kids sick so they can tell everyone they have cancer. He's lying about what his circumstances actually are to garner our sympathy and justify his abhorrent moral code.
His advice is absolutely relevant. The story he tells to support this advice is not relevant. It's not even complete and the parallels he draws between himself and the students of today are false. I find it crass to couple his choice to pursue three ivy league degrees thirty years ago with the impossible task of pursuing one degree today.