This case illustrates how a leader’s lack of self-awareness can derail his or her career and sabotage the performance of a company. It features Shai Agassi, founder and CEO of Better Place, a charismatic, visionary leader who promises a solution to the world’s reliance on oil. His charisma and convincing rhetoric are initially very effective at attracting investor and policy maker support for his idea of a network of electric cars with rechargeable, swappable batteries. The case describes Agassi’s journey from visionary founder to capital raising as one of the most successful startups in history. Agassi’s charismatic personality is observed as he pitches his vision in a TED Talk video. The case explores Agassi’s drivers and strengths by describing his background, including his family life, cultural context, and career history as an entrepreneur and senior executive at SAP. The case then outlines the unraveling of Agassi’s business and how he becomes increasingly disconnected from his stakeholders’ interests and the changing context. Agassi’s meteoric rise in popularity among media, investors and potential consumers is subsequently derailed by signs of narcissistic behaviour, poor financial management and strategy execution and unbalanced stakeholder engagement. Agassi’s bravado and defensive behaviours contribute to the loss of interest and commitment by partners, colleagues and investors and the eventual bankruptcy of the company. Agassi’s blind spots in his relationships, neglect of specific sets of stakeholders, tendency towards over-conviction in the business model, and inability to adopt an agile mind set contribute to his career downfall.