In this conversation, Derek Sprau shares his extensive experience in the running community, particularly focusing on the production side of major marathons like the Chicago Marathon. He discusses the immense logistics involved in organizing such events, the role of charity runners, and the emotional impact of finishing a marathon. Derek also reflects on the challenges faced during the COVID-19 pandemic and his transition from full-time production work to consulting. The conversation highlights the dedication and passion of those involved in the running community and the complexities of race day operations. In this conversation, the speakers delve into the complexities of organizing large-scale races like the Chicago Marathon, discussing the intricate relationship between race directors and city politics. They explore the contrasting appeals of road marathons versus trail running, emphasizing the accessibility of road races for urban dwellers. The discussion also touches on personal aspirations in ultra running and concludes with a philosophical question about risk and personal values.