Oprah Winfrey isn’t just a public figure—she’s the wealthiest woman in the entertainment industry and the first African-American woman billionaire. But how did she rise from a daytime talk show host to a media mogul? What leadership skills did she develop along the way? In this episode, Harvard Business School executive fellow Bill George explores the challenges Oprah faced on her path to success and how she overcame them. He explains how she shifted away from people-pleasing, found her unique voice, and embraced vulnerability as a key leadership strength.