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.TakeawaysPurpose 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.”
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Love, Lies & Likes with Dr. Nicola Fox Hamilton
In this episode of the Entropy podcast, host Francis Gorman speaks with Dr. Nicola Fox Hamilton, a cyber psychologist, about the complexities of online dating, the impact of technology on communication, and the darker aspects of digital interactions, including sextortion and misinformation. They explore the psychological implications of smartphone use, the role of AI in modern communication, and the rise of extremist ideologies in the digital age. Dr. Fox Hamilton emphasizes the need for further research in these areas as technology continues to evolve.TakeawaysOnline dating can be a mixed experience, requiring resilience.People use dating apps for various reasons beyond romance.Women often face more harassment on dating platforms than men.Sexting can be a normal part of sexual development but poses risks.Sextortion is a growing problem, particularly for young people.Smartphone addiction is not a clinical diagnosis but can lead to problematic use.AI can influence how people interact and perceive reality.Misinformation often spreads through mainstream media and social media.The Manosphere promotes harmful ideologies that can lead to radicalization.Understanding the psychology behind online behavior is crucial for addressing these issues.Sound Bites"It's not always the most fun experience.""There's a lot that people can get out of it.""It's a crime to share those images.""It's definitely a problem.""It's a much more empowering way.""We can no longer trust our eyes.""It was a really nice conversation."
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The Dark Art of Money Laundering with Matthew Hedger
In this episode of the Entropy podcast, host Francis Gorman interviews Matthew Hedger, a veteran intelligence officer and financial operations specialist. Matthew shares his extensive background in covert operations, including his experience laundering money and working with organized crime. The conversation delves into the intricacies of social pattern recognition, the insider threats within financial institutions, and the evolving landscape of money laundering in the digital age. Matthew discusses the impact of AI on criminal activities and the importance of understanding human behavior in cybersecurity. He also offers advice for aspiring intelligence officers and highlights the need for vigilance in the face of emerging threats.TakeawaysMatthew Hedger has over 17 years of experience in intelligence operations.He laundered over a hundred million dollars while working undercover.Social pattern recognition is crucial for survival in dangerous environments.Insider threats are a significant vulnerability in financial institutions.COVID-19 has exacerbated human vulnerabilities in organizations.Criminals are increasingly using innovative methods for money laundering.Digital platforms like Roblox can be exploited for illicit activities.AI is transforming the landscape of criminal activity and intelligence gathering.The future of cryptography may lead to less privacy and security.Aspiring intelligence officers should seek knowledge and learn from experienced professionals.Sound Bites"I laundered over a hundred million dollars cumulatively.""You can pocket millions of dollars and walk across borders.""We're natural BS detectors as people.""Criminals are nothing if not adaptive.""They know what they're talking about.""Roblox is a billion dollar economy a year.""AI has taken scams to the next level.""How do you trust anything that you can really keep private?""Learn from those who have done extraordinary things."
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Inside The Mind Of A CIA Operative with James Lawler
In this episode, host Francis Gorman interviews James Lawler, a former CIA operations officer with 25 years of experience in espionage. James shares his journey into the CIA, the motivations behind espionage, and his role in dismantling the A.Q. Khan nuclear smuggling ring. He discusses current nuclear threats, the evolution of espionage in the digital age, and the importance of understanding the human element in insider threats. James also reflects on his transition from intelligence operations to becoming a published author, highlighting the storytelling aspect of his novels.TakeawaysJames Lawler's journey into the CIA began unexpectedly during law school.The role of a CIA operations officer involves manipulating individuals for espionage.Motivations for espionage often include personal grievances and financial needs.The A.Q. Khan nuclear smuggling ring was dismantled through strategic operations.Current nuclear threats are significant, particularly concerning Iran's potential capabilities.AI and social media have transformed the landscape of espionage and targeting.Understanding the human element is crucial in identifying insider threats.Compassion and support in organizations can prevent insider threats.Lawler's novels are inspired by his real-life experiences in espionage.Writing serves as a creative outlet for Lawler post-CIA career.Sound Bites"I enjoyed the hell out of it.""Revenge is absolutely one of the purest motivations for espionage.""AI makes targeting much easier.""I was looking for people going through divorce.""I can create books where I live vicariously through my characters.""I call that my psychological dividends.""It's a way to keep the neurons firing in the brain.""You're a great interviewer and a great host."
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Building Trust In The Digital Age with Robin Dreeke
In this episode of the Entropy Podcast, host Francis Gorman speaks with Robin Dreeke, a former FBI special agent and expert in human behavior. They discuss the importance of trust in building relationships, the journey of Robin from the Marine Corps to the FBI, and the art of recruiting spies. The conversation also delves into the impact of technology on trust, strategies for fostering team cohesion, and the five principles of trust outlined in Robin's work. In this conversation, Robin Dreeke discusses the importance of kindness, generosity, and effective communication in building trust and unforgettable connections with others. He emphasizes the need to embrace challenges as opportunities for growth and the significance of understanding human behavior, especially in the context of trust and violence. Robin also addresses the current geopolitical climate and its impact on trustworthiness, providing insights on how to navigate these complexities in personal and professional relationships.TakeawaysTrust is the number one skill set in building alliances.The foundation of healthy relationships is trust.Recruiting spies is about understanding their challenges.Technology can erode trust if not used wisely.We thrive in deprivation mode, not in comfort.Teams need to understand the overarching 'why' to be effective.People need to be seen and heard in conversations.Seek the thoughts and opinions of others to foster collaboration.Ego suspension is crucial for healthy dialogue.Generosity in communication fosters better relationships. Start with kindness and generosity in interactions.Being generous with time can create meaningful connections.To be unforgettable, focus on how you make others feel.Embrace challenges as opportunities for growth.Trust can be rebuilt, but it requires effort and time.In a chaotic world, simplicity in relationships is key.Understanding the arc of behavior helps predict actions.People do not suddenly become violent; it's an escalation.Healthy relationships are free from drama and chaos.Open communication and transparency are essential for trust.Sound Bites"It all starts around that age.""I wanted to become an astronaut.""You really don't recruit a spy.""Start with kindness and generosity.""Be generous with your time.""Every day is a great gift.""It's all about the arc of behavior."
Nibble Knowledge is delighted to bring you "The Entropy Podcast"—hosted by Francis Gorman. The Entropy Podcast centers on cybersecurity, technology, and business, featuring conversations with accomplished professionals who share real-world knowledge and experience. Our goal is simple: to leave you better informed and inspired after every episode.We chose the name “Entropy” because it symbolizes the constant flux and unpredictability in cybersecurity, technology, and business. By understanding the forces that drive change and “disorder,” we can create better strategies to adapt and thrive in an ever-evolving technology and geo political landscape.You can also check out our YouTube Channel here: https://youtube.com/@nibbleknowledge-v7l?feature=sharedDisclaimer: The views and opinions expressed on all episodes of this podcast are solely those of the host and guests, based on personal experiences. They do not represent facts and are not intended to defame or harm any individual or business. Listeners are encouraged to form their own opinions.
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