Bob and Alice are posing as private investigators who are hired by someone to find out if their teenage son was at a specific liquor store location and show up on camera. Alice and Bob debate the morality of getting more information than necessary for their client.
A mother shares the story of how her daughter got a ticket on her first day of driving and how she ended up paying for damages to her daughter's car and another person's car after revealing a situation involving stoned friends and reckless behavior in a parking lot.
Comedian Bill Burr discusses the advantage of flying private as a comedian, specifically for doing one-night shows during the week. He also mentions the importance of money for private jets, but notes that it has helped with managing his busy schedule.
Comedian Louie Anderson helped this individual get into the comedy club and taught him how to perform without using curse words.
Former professional basketball player, Antoine Walker, shares a story about gambling with Michael Jordan where they almost lost $900,000, but ended up winning back all the money except $20,000 because Jordan got too tired to continue playing.
The speaker reflects on how they had a hard time justifying spending money on themselves until they reached a certain level of success in the entertainment industry where it became industry standard, all while experiencing the dark side of ticket-scalping.