Annie, a twenty-eight-year-old architect finds out that she lost yet another competition she had high hopes for. As she considers options to save her business in crisis, her straight-laced boyfriend, Greg, suggests that she abandon her entrepreneurial dreams and settle for a stable job. On the other hand, Billy, a charismatic venture capitalist and old flame of Annie’s best friend, Adele, steps in to give Annie’s company a shot. What seems like a mentor-mentee relationship takes a startling turn when Billy clarifies that he expects more from Annie in exchange for his investment.