The speaker shares their experience of pretending to be a high roller at casinos by dressing up and acting like they were busy with work. They would strike up conversations with floor men to seem familiar with the scene.
The speaker recounts a reckless road trip with his friend Adam and how they drank beer, smoked cigars and played Rod Stewart's music for hours until they ran out of beer and got refused service at a liquor store due to the speaker's age.
The speaker shares their experience of winning 100 dimes at the encore by letting someone else roll the dice and mentions a crazy night with their friend David Sachs.
The journalist is given access inside a prison cell to interview JJ, a man who is locked up in a housing unit with hundreds of other men and spends most of his time reading books and listening to the radio.
The speaker recounts a conversation with a neighbor from his apartment complex while he was living in Silicon Valley and working on his first company, which involved late night chats near a concrete pond.