In early 2023, Jenn Hyman, the founder of Rent the Runway, announced her decision to step down as CEO of the company she has been leading for almost two decades. Throughout this time, she has dedicated her life to building the business, describing the experience as her most important contribution to the world. The company, known for its innovative rental model for fashion, experienced significant fluctuations, including a sharp decline in stock prices after its IPO in 2021 when it became the first IPO in history led by a female CEO, COO, and CFO. Hyman reflected on the highs and lows of her journey, acknowledging the challenges that came with taking the company public. Despite the negative attention surrounding the stock’s performance, she noted the milestone of being one of the few women to have founded and led a company to an IPO. However, she also expressed concern over the low number of female founders who have managed to retain leadership positions in their companies over significant periods. As she prepares to leave, Hyman emphasizes the importance of knowing when the right time is to step aside as a founder, suggesting that her departure is aimed at allowing new leadership to take the helm. She will not retain a position on the Rent the Runway board, signaling a clean break that allows her to explore new opportunities while also stepping back from the intense demands of managing the business. In the context of female entrepreneurship, Hyman's experience serves as an important case study in the landscape for female-led startups, particularly within the fashion rental space. Her departure is significant not just for Rent the Runway, but also for the broader discourse on female leadership in technology and business.