FWIW, I remember him sounding quite dejected and sincerely questioning whether it was all worth it. It didn't seem like a "I failed big time and now I'm living on top of the world" kind of opening. I still feel sad when I think about it.

That's not to disagree with you, we often overlook the struggles and challenges of people in lower economic classes or less prestigious positions. More just to say I didn't get that humble brag vibe at all.

Oh, and I also don't know if he got paid, as I think he was an alumnus and it may have just been a volunteer speech. Again, I know there are other speeches in which people do get paid and follow the pattern you outlined, just saying I don't think this was one of them.