What is Jim's definiton of being rich.

You can find the answer to this in Chapter 8.

In this chapter, Jim says he used to be rich.  He says that he was once rich because he had $14.  But he was not able to hold on to his wealth.  Instead, he "speculated in stock."  In his case, what that meant was that he bought a cow.

He bought the cow for $10 but it died.  Then he took the remaining $4 (plus $1 of the $1.10 he got for the dead cow) and tried to invest it with a swindler.  He lost his money that way.