AI, Adversaries & Adaptation with Jennifer Ewbank

The Entropy Podcast

In this episode, Francis Gorman sits down with Jennifer Ewbank, former CIA Deputy Director for Digital Innovation, to explore what it means to lead with purpose in a world shaped by geopolitical risk, digital disruption, and information warfare.

Jennifer shares stories from her extraordinary career in intelligence — from espionage during the Cold War to launching the CIA’s first AI office — and offers deeply human reflections on risk-taking, resilience, and transition. From the digital battlefield to the Camino de Santiago, this conversation ranges from high-stakes decision-making to how we build trust in an age of deepfakes and AI manipulation.

Takeaways

• Purpose Under Pressure: A clear sense of mission is what sustains leadership in complex, high-risk roles.
• You’ll Never Have All the Information: Good decisions often require boldness, not certainty — a lesson from field operations that applies to enterprise leadership.
• The Real Threats Are Already Inside: Critical infrastructure is increasingly compromised by cyber actors who may lie dormant for years before striking.
• Transition Is a Process: Jennifer’s solo Camino de Santiago pilgrimage was both a mental and physical journey into a post-CIA identity.
• Trust Is the New Battlefield: Generative AI, deepfakes, and algorithmic manipulation are eroding public trust at scale — and rebuilding it starts with education and digital literacy.
• Operational Mindset for Innovation: Solving complex problems quickly with limited resources isn’t just for the CIA — it’s the new model for digital transformation.

Soundbytes

• “Sometimes the greatest risk is not taking the risk.”
• “You never have all the information — expecting it is a recipe for paralysis.”
• “Absent a deep connection to purpose, you lose the urgency to solve real problems.”
• “The battlefield isn’t just physical anymore — it’s informational, algorithmic, and real-time.”
• “Trust is under attack. And the worst part is, most people don’t realize it.”
• “You think the algorithm is adapting to you. But really, you’re adapting to it.”