This chapter follows the short, troubled history of Uber’s corporate culture and how a leader’s behavior can permeate an entire organization, turning the workplace environment toxic and hostile to underrepresented groups of employees. A deeper look at role modeling via the classic Bobo doll study demonstrates how simply observing someone else’s behavior can lead to either socially beneficial or harmful outcomes. On a subtler level, expectations held by others, and particularly those in power, can result in their fulfillment through unconscious words and action, termed the Pygmalion effect, as demonstrated with a study of teacher expectations and student IQ. Imitation, through either role modeling or conforming to expectations, lies at the heart of a culture’s establishment and rigidity.