Let me tell you about the very rich. They are different from you and me. They possess and enjoy early, and it does something to them, makes them soft where we are hard, and cynical where we are trustful, in a way that, unless you were born rich, it is very difficult to understand. They think, deep in their hearts, that they are better than we are because we had to discover the compensations and refuges of life for ourselves. Even when they enter deep into our world or sink below us, they still think that they are better than we are. They are different.

Framing the short story, this quote makes clear Fitzgerald's key thoughts on the rich: that they are too soft, too cynical, and that they think they're better than everyone else (despite clear evidence to the contrary). This quote also suggests that Fitzgerald views hard work and suffering as crucial components of personal growth. Without experiencing these things, a person will struggle to build meaningful relationships with others and live a satisfying life.

Nevertheless, his very superiority kept him from being a success in college—the independence was mistaken for egotism, and the refusal to accept Yale standards with the proper awe seemed to belittle all those who had.

At a basic level, this quote simply suggests that Anson failed to respect Yale and this attitude prevented him from being successful. Broadly, however, we can see that the problem was actually that Anson is too much like Yale. While Yale (as an elite institution) demanded he respect its standards, he (considering himself to be an elite person) demanded it accommodate him. It was specifically the attitude of superiority that Anson embodied that prevented him from fully succeeding in university. As the story progresses, readers are confronted with more and more evidence that the attitudes of the elite depend on asymmetry: Anson can only demand respect when others are willing to give it to him, and the same goes for Yale. In the same way, Anson can only toy with his lovers if they aren't doing the same with him. When there is no one willing to accommodate the wealthy, their attitudes are unsustainable.

Begin with an individual, and before you know it you find that you have created a type; begin with a type, and you find that you have created—nothing.

Anson is a rich boy, as the title of the story suggests. And over the course of the story we see that he is nothing more than this—a type without any substance. The world of the rich—to which Anson belongs—is void of any real meaning beyond superficial glamour and facades, and Anson's character fully exemplifies this. He has no interests, no meaningful relationships, and no real emotional connections to anyone or anything. His wealth allows him to remain aloof and avoid hardships, and a life of detachment has left him thoroughly uninteresting, incapable of finding love, and unable to experience true satisfaction.