This study analyzes the figurative language used by Lenny and Randy in The Monk and the Riddle by Randy Komisar. The study aims to identify the types of figurative language used by both characters in the novel, examine the similarities and differences between them, and understand how figurative language reflects their perspectives on entrepreneurship and success. This research applies Harris's (2018) theory of figurative language and uses a qualitative descriptive approach. The data consist of selected sentences containing figurative language spoken by Lenny and Randy about startup proposal in the novel. The data were collected through close reading, classified according to the types of figurative language, and analyzed based on their meanings and functions in context. The findings show that metaphor is the most frequently used figurative language by both characters. Lenny mainly uses metaphors to express ambition, competition, and financial success, while Randy uses metaphors and analogies to explain leadership, responsibility, risk, and personal fulfilment. Although both characters rely on metaphor, they use it for different purposes that reflect their contrasting personalities and values.