Gather initial thoughts and broad opinions about the book.

1. Before reading Business Adventures, what did you expect from a book about finance originally written in the 1960s? How did the actual stories surprise you or challenge those expectations?

2. Brooks’s style is often compared to that of modern financial storytellers like Michael Lewis. If you’ve read a book such as The Big Short (2010), how did Brooks’s narrative approach feel different or similar? How effective was his focus on character and drama in exploring these complex events?

3. Although Business Adventures was written decades ago, it continues to attract contemporary readers. After finishing it, which aspects of the book still felt relevant to you? Did any of the stories feel particularly dated?

Encourage readers to connect the book’s themes and characters with their personal experiences.

1. The GE scandal revealed a corporate culture of “winks,” coded language, and unwritten rules. Thinking about your own work experiences, have you ever encountered a situation where the official policy differed from what was implicitly expected of you? How does that kind of dynamic affect a workplace?

2. The story of the 1962 market crash shows how quickly fear and group behavior can influence individual decisions. Have you ever found yourself influenced by other people’s reactions during a high-pressure situation? How did that affect the way you responded?

3. David Lilienthal’s journey from public servant to private entrepreneur involved a major shift in his professional identity and worldview. Have you ever experienced or observed a significant career change that led someone to reconsider long-held beliefs or values?

4. As described in “The Fate of the Edsel,” Ford’s researchers focused heavily on creating a specific “car personality” to appeal to consumers. When you think about a major purchase you’ve made, how much were you influenced by the product’s brand image versus its practical features?

5. Have you ever had to decide what knowledge, skills, or information you could appropriately take from one workplace to another? How did you distinguish your own professional experience from information that belonged to your employer?

Examine the book’s relevance to societal issues, historical events, or cultural themes.

1. What does the GE price-fixing scandal suggest about corporate accountability? How have public expectations for executive responsibility changed since the 1960s, and in what ways have they remained the same?

2. Brooks portrays the 1960s tax code as a complex system in which the official progressive tax rates didn’t always reflect what different taxpayers ultimately paid. How do his observations connect with current debates about tax fairness and economic inequality?

3. The Texas Gulf Sulphur case was a landmark in defining the illegality of insider trading. Decades later, what new ethical challenges has the digital age, with its instant access to information, created around fair access to market-moving information?

Dive into the book’s structure, characters, themes, and symbolism.

1. What do you think is the effect of Brooks’s literary, character-driven approach to financial journalism? How does framing these events as human dramas, rather than as dry economic case studies, change your understanding of them?

2. Across several essays, Brooks explores how even experienced leaders and institutions struggle to predict or control events. Which story illustrated this idea most powerfully for you, and why? Was it the meticulously planned failure of the Edsel, the unpredictable 1962 market crash, or another event in the book?

3. How does Brooks use figures such as Clarence Saunders and Richard Krafve to explore broader ideas about American capitalism? What do these individual stories reveal about the systems they operated within?

4. Think about the book’s structure as a collection of separate essays. What common thread or overarching argument do you believe connects these 12 different “adventures” into a cohesive whole?

5. How does Brooks use Saunders’s unfinished Pink Palace to shape the reader’s understanding of his ambitions and legacy? Did you notice any other objects, places, or even phrases in the book that took on a deeper symbolic meaning?

Encourage imaginative and creative connections to the book.

1. If you were asked to write a new chapter for a modern edition of Business Adventures, which recent business story from the last decade would you choose to tell? How would you capture the essential human drama at its core, in Brooks’s style?

2. What challenges would a filmmaker face in adapting “The Impacted Philosophers,” with its focus on coded language and nonverbal cues like “winks,” into a compelling movie? Who would you cast in the key roles to convey the story’s tension and conflicting perspectives on responsibility?

3. How could you re-imagine Saunders’s battle with Wall Street from the perspective of one of the short sellers he tried to corner? What might their motivations and justifications have been?