The over-the-top streaming industry has been a promising frontier for many creators in Hollywood. Companies both new and old have been able to strike it rich in the burgeoning industry. However, as time has passed, the competition gets tougher, and audiences get spread thinner and thinner. Even the most well-funded projects are at risk to fail without good execution. Enter Quibi: the streaming service designed by Jeffrey Katzenberg to enter into an increasingly mobile entertainment space. Through miscalculations and a global pandemic, Quibi met a swift end within nine months on the market. This paper provides a historical recount of Quibi’s development, reception, destruction, and offers insight into what went wrong to cause Quibi’s accelerated downfall. It is a cautionary post-mortem of how the volatile entertainment market can execute even a multi-billion-dollar project backed by the biggest names in Hollywood.