Rob Copeland, finance reporter for The New York Times and author of The Fund, discusses his book on Ray Dalio and Bridgewater Associates. Topics include the unusual workings of Bridgewater, the evolution of hedge funds, challenges in publishing a contentious book, the role of media in shaping the Bridgewater myth, and the ideological motivations of successful business leaders.

Investigative reporter Miles Johnson discusses his fascination with the mundane aspects of running criminal networks. He explores the Italian mafia's ties with real estate and healthcare corruption. Johnson shares the challenges of investigating transnational organized crime and highlights the risks faced by local reporters. He also talks about the difficulty of disconnecting from his work and the concern of becoming desensitized to the subject matter.

Hua Hsu, the staff writer for The New Yorker and winner of the 2023 Pulitzer Prize for memoir, discusses his book, the importance of capturing the texture and rhythm of the past, a deconstruction of selling out and friendship, the process of reconstructing memories, exploring obscure things and failed revolutions, and Asian American art and representation.

Roxanna Asgarian, author of We Were Once a Family, discusses trauma reporting, child welfare systems, and the emotional impact on birth families. The chapter also touches on the challenges faced by journalists and the power of therapy in processing trauma.

Daisy Alioto, journalist and CEO of Dirt Media, discusses her vision for creating a newsletter empire. They explore the content, writers, and business side of newsletters. They compare LVMH with the media industry and discuss the potential of centralized systems. They also talk about finding new writing talent and how their role as editors has changed their approach to writing. The podcast ends with thanks to listeners and a discussion about online scam protection.

Guest Ian Coss, journalist, audio producer, and composer, discusses the interesting topics of bureaucracy, the ambitious Big Dig project, interviewing for a historical narrative, the use of different podcast openings, the complexities of big infrastructure projects, creating an independent limited series podcast, and reflecting on the challenges and rewards of the Big Dig.

Mosi Secret, a writer for ProPublica, The New York Times Magazine, and GQ, discusses the need for a radical reimagining of human connection and responsibility. He explores the challenges of working on ambitious stories in journalism institutions and shares his experience writing about exceptional young Black men and desegregation efforts in a dangerous neighborhood.

Mary Roach, author of 'Fuzz: When Nature Breaks the Law,' discusses exploring taboo subjects, finding interesting material in lesser-known realms, and the importance of breaking through taboos to have healthy conversations.

Craig Mod, a writer and photographer, discusses his experiences with long walks in Japan and how it has influenced his writing. He also talks about the contemplative nature of his work and the process of writing his book. The guest reflects on friendship and the balance between themes in a book. Lastly, he explores the role of therapy in writing and emphasizes the importance of self-introspection.

Mona Chalabi, data editor at The Guardian and Pulitzer Prize winner, discusses the power of protest, the impact of journalism, and the importance of considering consequences. They explore balancing journalism and personal grief, the complexities of their relationship with institutions, and the role of funny illustrations in their work. The chapter also mentions their reflection on a story inspired by a Jewish prayer and their experience with racism and self-doubt.