The Monk and the Riddle

The Monk and the Riddle is a business leadership book by American entrepreneur Randy Komisar. Drawing its arguments from Komisar’s (often humorous) lived experience, rather than didactic lists and frameworks, the book seeks to teach its audience how high-stakes business dealings, particularly those of Silicon Valley, actually go down. The book is structured as a series of dialogues between Komisar and two aspiring entrepreneurs whom he names Allison and Lenny. The dialogue touches on many topics in the startup life cycle and Silicon Valley’s dynamic, often problematic, social world. Komisar also imparts knowledge from the perspective of a venture capitalist at the top of the startup food chain, showing how startup plans are pitched, and often fail. The book is a departure from many business leadership texts, promoting a philosophy of work-life balance in which the self-proclaimed entrepreneur must perpetually ask the question of whether his work brings joy.

Short essays break up The Monk and the Riddle’s dialogue in Komisar’s distinctly reflective voice, as he looks back on his career. Without much explicit criticism of Silicon Valley, he weaves it into his descriptions of its culture. He also provides a number of tips for wannabe startup owners to navigate the tech space. These range from insights into the emotions of higher-ups, such as the fact that venture capitalists are usually reluctant to reject funding requests, to helpful tweaks for startups’ business models. He calls one of his favorite business leader archetypes the “Virtual CEO.” He argues that countless managers and C-level executives forego having a mentor or advisor, following a misguided belief that business is best learned by throwing oneself into the fray and sorting it out from there. He argues that managers are essential to running an effective business, especially when the business owners in question are young novices in their target industries. Startups, in particular, Komisar observes, are rife with inexperienced youngsters.

Komisar also argues that pitches about potential profits are not the most effective kind of pitches. The ones that stand out in the end manage to get potential investors excited about their core ideas, rather than their profit models. Komisar exhorts his readers to look for that flicker of genius in each of their business proposals. The converse business model consists of clever individuals who only want to get rich, and ironically, forego any chance of actually succeeding.



In his conclusion, Komisar concedes that his business strategy is more philosophical than practical. He asserts that the technical components of business models are better found in textbooks and business school lectures. At the same time, he makes a case for seeing the existential in the commercial. Most “laws” about business, if there are any, can be derived from empirical study, and need not be found in trite airport literature. Given that business success is more about personality and creativity than the rote memorization of academic content, Komisar concludes that business leaders should invest in individuals whom they find interesting and dynamic, rather than inert forms of capital. The Monk and the Riddle casts “success” in the business world as a metric that can only be evaluated by asking oneself whether he or she is happy doing his or her job.