In this episode, we're pulling back the curtain on one of the most controversial and inspiring figures in modern business - Sophia Amoruso, the self-proclaimed "Cinderella of Tech." We'll explore how her troubled youth and counterculture lifestyle unexpectedly prepared her for entrepreneurial success. Through Sophia's journey, we'll examine the dark side of rapid business growth, the challenges of maintaining company culture, and the pitfalls of overnight success. We'll also discuss the impact of the #GIRLBOSS movement on female entrepreneurship and debate its criticisms. From eBay to bankruptcy and beyond, we'll analyze the triumphs and tribulations of this polarizing figure, and what her story reveals about the American Dream in the digital age.