The Conversation with D
Shortly after arriving in Charleston, Shepard is approached by a young man called D. Having been asked for money twice already, Shepard guesses that D wants a dollar as well and tells him that he does not have any money. D is offended and almost starts a fight, saying that he just wanted to start a conversation. Ironically, when the bus arrives and the two have to depart, D says "Make sure you bring some money next time!", indicating that he was indeed looking for a quick dollar.
The Shelter
When Shepard arrives at the shelter, he is at first impressed by the clean and immaculate appearance of the building. However, ironically, the state of the interior is the opposite, as it is filthy and smelly.
Living the Dream
Contemplating America's contemporary society, Shepard points out the irony of work to fulfill our dreams, which leads to our inability to actually live our dreams: "And we live in luxury homes and condos that we can’t even enjoy because we have to work overtime to cover the mortgage payment."
Phil's Advice
At the shelter, Shepard meets a Phil, whom many of his peers consider one of the "resident nutcases at the shelter that nobody really paid much attention to." Ironically, he is the one giving Shepard important advice on how to apply for a job effectively, which eventually leads to Shepard getting the job at Fast Company: "Yep, crazy Phil Coleman, a guy that most people ignored, had the secret. Be assertive. That’s it. Make the manager see it as a mistake not to hire you."
The Ultimate Irony
In the end, Shepard reports the "ultimate irony" of his project: After having worked hard to be able to support himself and save some money for his future endeavors, he is forced to come home and spend his money on his mother, who suffers from cancer: "With each of us working hard enough just to support ourselves, my brother Erik and I had to come together to provide financial support for our mom."
