Grandpa Simpson decided that it was time for him to hand out his life's savings to his family, which turned out to be fifty dollars to each family member. This episode primarily focused on Lisa and Homer's spending. Homer, after watching Marge return an expensive purse that she enjoyed, was inspired to abuse of return policies. This led to him purchasing goods that he had no intention on keeping. His only intention was to borrow the goods, use them, and then to return it to the store. Homer, in his infinite wisdom, took this to a level of shameless excess, and this behaviour eventually caught up to him.
Lisa, on the other hand, decided to use her money for a good purpose. Wanting to help cure the world of poverty, she put the money towards a bank that lent the money to help the financially underprivileged to help create a brighter future. After doing some searching on the bank's website, she noticed that Nelson Muntz was trying to start a bicycle repair shop, and she decided that he was deserving of the loan. Seeing Nelson succeed with his business, and want to drop out of school to focus on his work, led to Lisa taking Nelson to meet some successful people in an attempt to convince him to stay in school. To Lisa's surprise, these successful people all had one thing in common: they dropped out of school. At the conclusion of the episode, Lisa's dilemma was resolved, as Nelson realized the burdens of running his own business, and decided that staying in school was the better option.