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This case discusses the leadership and entrepreneurial styles of two of the most ''unusual'' business personalities the global corporate world has ever seen, Southwest Airlines'' Herbert D Kelleher and Virgin Group''s Richard Branson. The two leaders, though extremely different in their approach towards business, had a few traits in common. They both believed in having fun and paying attention to employees. The case explores the entrepreneurial and leadership attributes of both these leaders and attempts to bring out the similarities between them. After reading the case, students are expected to: (1) understand the various aspects of Herbert D Kelleher and Richard Branson''s entrepreneurial abilities; (2) understand the leadership styles of Herbert D Kelleher and Richard Branson and how their leadership abilities made their respective companies successful; (3) understand common attributes of leadership and entrepreneurship; (4) have an idea of the ethical dimensions of leadership and entrepreneurship; and (5) be aware of the various strategies adopted by Branson and Kelleher for creating a work environment and culture that helped Virgin and Southwest gain full employee support for all their ventures. The case is intended for MBA/PGDBM level students as part of the leadership and entrepreneurship curriculum.