Explore the evolution of cybersecurity strategies in this 20-minute talk by a16z general partner Martin Casado. Delve into the changing landscape of security threats, from medieval-style defenses to modern aerial warfare analogies. Examine the current misalignment between evolving threats and existing security measures, particularly due to cloud computing and increased system complexity. Learn how CEOs and CSOs should approach security planning, and discover the potential roles of AI and automation in addressing these challenges. Gain insights from Casado's first-hand experience navigating these shifts in the cybersecurity landscape.