By accepting Cawley’s money, Robert accepted a certain unspoken obligation to Cawley: he effectively promised to use his Yale education to succeed. Now, Robert is very aware that he’s not making the best use of his degree, and this contributes to the awkwardness of his interaction with Cawley. On the other hand, Cawley’s behavior seems remarkably callous and tone-deaf. To think of a student as an “investment,” good or bad, is dehumanizing and insulting. Like the businessman he is, Cawley expects immediate results, and for this reason he can’t understand what Robert is going through.