What if I told you that cybersecurity strategy can be turned into a solvable math problem? Modern cyber strategy is based on security standards and frameworks, but these are not prescriptive. We then leverage vendor inputs, consultant opinions, and trend-of-the-day approaches right along with our own gut feelings and preferences. What is missing from all of these is a focus on outcomes. Very little attention is paid to what has worked well in the real world because such data is only available in narrow information silos. Imagine if we intentionally gather outcome information and create detailed models of outcomes vs. strategic approaches for organizations of various types and sizes. Imagine using open-source intelligence (OSINT) and AI capabilities to turn the immensity of security strategy into a computer-manageable math problem where correlation strength leads to cybersecurity success. This would enable practitioners to pursue the strategies that work, predict failure in an objective manner, and automatically adapt to changing threats and defenses. This talk presents an approach to such a solution, its potential strengths and weaknesses, and how the security community might benefit long-term from such a vision.