In this episode, Jason Kikta and Rich Cassleberry discuss the challenges of IT security and how to make better risk decisions. They explore the difficulty of proving a negative in security and the lack of obvious metrics of success. They emphasize the importance of balancing risk and finding the right level of security for the organization. They also discuss the need for reputation management and building trust within the company. The conversation highlights the value of security tools that automatically take action and the need for ongoing evaluation and improvement in security practices. They conclude with advice for new security practitioners, encouraging them to find a path to yes and how to be a trusted partner within your organization.