Starting in Chapter 12, the story’s focus switches to Henry (Harry) Brierly and Philip Sterling, who live in New York City. Harry has his own office downtown and is considered a “man of affairs” (61). The mysterious affairs referred to sound important to his friends, but nobody ever sees them actualized. Philip is intelligent and well-educated. He wants wealth but is averse to the work of getting it. He also wants fame but can’t decide between the various worthy ways of achieving it. He tries studying law, but finds it not to his liking, and decides to make a career in literature. His insistence on starting out at the top of the ladder doesn’t pan out, so he’s unemployed.

The two friends decide to join a business venture with Harry’s uncle in Missouri, which they see as the wild frontier. All they know about the venture is that it has to do with a land and railroad operation. They’ll go in the role of engineers, though they have no knowledge of engineering.

Harry and Philip arrive in St. Louis, where they’re surprised to see everybody smoking in the street, openly drinking alcohol, and socializing on their doorsteps. Harry devotes much of his time to his appearance, with fancy clothes and excessive beauty routines.