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by Matt Devost & Bob Gourley
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- May 27, 202553 min
Episode 129: The Attacker Mindset: Maxie Reynolds on Red Teaming, Underwater Data Centers, and Human Nature
In this OODAcast episode, host Matt Devost sits down with Maxie Reynolds, author of The Art of the Attack, to explore the evolution of her unique career from offshore oil rigs to elite red teaming and cybersecurity innovation. Maxie shares how her unconventional path, working a decade in oil and gas, earning degrees while on remote rigs, and eventually breaking into cybersecurity at PwC, shaped her approach to physical and digital security. Her journey led to the creation of a company that builds underwater data centers, a novel fusion of her industrial and red teaming experiences. She discusses the rising interest in submerged infrastructure, particularly after China's moves in the space and the demands of modern AI-driven cooling systems. The conversation dives deep into what it means to adopt an "attacker mindset", seeing opportunities where others see obstacles and using architecture, human psychology, and environment as vectors for access. Maxi outlines how her social engineering engagements hinge on understanding perception, psychology, and pretext creation rather than just technical exploits. She offers real-world stories of infiltrating secure facilities and engaging high-stakes targets using layered personas and misdirection. Through it all, she emphasizes the role of self-awareness, stress management, and emotional discipline in high-pressure operations, often drawing parallels between red teaming and stoicism. Maxie and Matt also examine how to responsibly deliver red team results to leadership, balancing candor with empathy to ensure organizations grow stronger without shame or defensiveness. They reflect on the future of AI in security, the persistence of physical threats, and the irreplaceable value of human judgment. The episode wraps with a powerful reading list and a shared love of books, highlighting titles that explore geopolitics, materials science, and the ungoverned world of the open ocean. This episode is packed with insight, storytelling, and practical wisdom for cybersecurity professionals, technologists, and leaders looking to understand how adversaries think—and how to outsmart them. Additional Links: The Art of Attack: Attacker Mindset for Security Professionals by Maxie Reynolds Maxie on Twitter/X Book Recommendations: How the World Really Works: The Science Behind How We Got Here and Where We're Going by Vaclav Smil The Outlaw Ocean: Journeys Across the Last Untamed Frontier by Ian Urbina Prisoners of Geography: Ten Maps That Explain Everything About the World by Tim Marshall Chip War: The Fight for the World's Most Critical Technology by Chris Miller Stuff Matters: Exploring the Marvelous Materials That Shape Our Man-Made World by Mark Miodownik
- May 12, 202551 min
Episode 128: The Money Trap: Alok Sama on SoftBank, Mega Bets, and Life Beyond Wall Street
In this episode of the OODAcast, host Matt Devost is joined by Alok Sama, author of The Money Trap, for a compelling conversation about Sama's journey from modest beginnings in India to leading some of the most ambitious investment efforts in tech history. Sama recounts his early days in Delhi, the unlikely path to Wharton, and his time at Morgan Stanley before stepping into the eye of the storm as President and CFO of SoftBank. Alongside Masayoshi Son, he helped deploy the groundbreaking Vision Fund, a $100B initiative that forever changed the scale of tech investing. Sama offers behind-the-scenes insights into the wild ride of investing in giants like Uber, WeWork, and ARM, reflecting on how bold vision and massive capital shaped, and sometimes distorted, the future of technology. es candid lessons from massive wins and public missteps, including the now-infamous WeWork saga. He also delves into how a high-stakes smear campaign impacted his health and priorities, offering an unflinching look at the personal costs of operating at the top of global finance. Throughout the episode, Sama's honesty, humor, and humility shine, echoing the voice that made his book so impactful. Beyond business, the conversation turns deeply personal. Sama reflects on what really matters after decades of chasing financial success. He opens up about regrets around time lost with loved ones, the role of humility in leadership, and how ancient Indian philosophy helped him reframe his priorities. Now entering a new chapter focused on writing, mentoring, and giving back, Sama offers timeless advice for entrepreneurs, investors, and anyone navigating high-pressure careers. This episode is a must-watch for those curious about the intersection of power, capital, and purpose. Additional Links: Alok on X Book Recommendation: The Rings of Saturn by W.G. Sebald
- Mar 24, 202551 min
Episode 127: Chris Wysopal on Reducing Attack Surface in the Age of AI
In this OODAcast, Chris Wysopal shares his insights from decades in cybersecurity, detailing his journey from the early hacking collective "The L0pht" to co-founding Veracode. Wysopal reflects on the evolution of cybersecurity, highlighting his early contributions to vulnerability research and advocating the importance of adversarial thinking in security practices. He emphasizes the transition from traditional vulnerability testing to comprehensive application risk management, recognizing the increased reliance on third-party software and the escalating complexity of securing modern applications. Wysopal also discusses how generative AI technologies are significantly accelerating application development but simultaneously creating substantial security challenges. He stresses that while AI-generated applications multiply rapidly, their vulnerability density remains comparable to human-written code. To manage this growing risk, Wysopal underlines the necessity of integrating automated, AI-driven vulnerability remediation into the software development lifecycle. Looking forward, Wysopal advocates for embedding security deeply within the application creation process, anticipating that AI will eventually assist in producing inherently secure software. However, he also underscores the enduring threat of social engineering attacks, urging enterprises to prioritize comprehensive security awareness programs to bolster their overall cybersecurity posture and resilience. The conversation examines some very interesting correlations between the mindset of the great hackers and the success of great entrepreneurs. Both take a good bit of grit, an ability to focus and be creative and perhaps most importantly: Persistence. Learn more about Chris Wysopal's approaches and the company he founded at Veracode. For insights into reducing your organization's attack surface see: State of Software Security 2025
- Mar 7, 202548 min
Episode 126: John Boyd, Maneuver Warfare, and the Future of the Marine Corps – A Conversation with Ian Brown
In this episode of the OODAcast, Bob Gourley speaks with Ian Brown, retired Marine Corps officer and author of A New Conception of War, which explores the influence of John Boyd on the Marine Corps and the evolution of maneuver warfare. Ian shares insights from his 20-year career in the Marines, including his experiences as a CH-53 helicopter pilot, forward air controller, and operations officer at the Brute Krulak Center for Innovation and Future Warfare. The conversation dives into the history and adaptability of the Marine Corps, Boyd's impact on military strategy, and how maneuver warfare became central to Marine Corps doctrine. Ian discusses Boyd's unique ability to synthesize knowledge from multiple disciplines, his contributions beyond the well-known OODA loop, and his lasting influence on competitive decision-making across military and business environments. Ian also previews his next book project, which will compile full transcripts of Boyd's recorded presentations, offering a deeper look into his strategic thinking. The discussion touches on leadership, decision-making, and the importance of adapting mental models for success—principles that apply beyond warfare to business, strategy, and national security. Whether you're a military historian, strategist, or business leader, this episode provides valuable insights into the enduring relevance of Boyd's ideas. To get the book see: A New Conception of War For a directory of all OODAcasts see: https://oodaloop.com/oodacasts/
- Feb 14, 202541 min
Episode 125: Unmasking Cyber Threats: Trevor Hilligoss's Mission to Disrupt Criminal Networks
In this OODAcast, Bob Gourley interviews Trevor Hilligoss from SpyCloud, diving into his career trajectory from the U.S. Army to cybercrime intelligence. Hilligoss shares his unconventional path, starting as a forward observer in the Army before transitioning to law enforcement and later working with the FBI's Joint Ransomware Task Force. He explains how his investigative experience led him to SpyCloud, a company dedicated to collecting intelligence on cybercriminals and using it to prevent attacks. The discussion highlights how cyber threats evolve and why proactive intelligence is crucial in countering criminal activities. Hilligoss explains SpyCloud's unique role in cyber defense, which involves infiltrating underground forums and gathering stolen data to identify vulnerabilities before criminals can exploit them. He emphasizes the growing challenge of session hijacking, malware-driven credential theft, and the commoditization of cybercrime, where even low-skilled actors can execute sophisticated attacks using readily available tools. He underscores the importance of disrupting cybercriminals by exposing their identities and dismantling their infrastructure, rather than solely relying on traditional law enforcement methods. The conversation also explores how enterprises, governments, and small businesses can leverage SpyCloud's intelligence to protect their networks. The episode concludes with a discussion on fraud, particularly scams targeting elderly victims, and the need for stronger industry-wide defenses. Hilligoss expresses optimism about the future of cybersecurity, citing increased collaboration between public and private sectors and innovative disruption techniques, such as name-and-shame campaigns and cybercriminal takedowns. He encourages a mindset of making cybercrime as difficult and costly as possible for bad actors, reinforcing the importance of staying ahead of evolving threats. For more on SpyCloud see: SpyCloud.com
- Dec 17, 20241h 1m
Episode 124: The History and Future of Cyberwar with Matt Devost
In this episode of the OODAcast we turn the microphone over to Dr. Bilyana Lily, the world renowned cyber and geopolitical expert, who interviews OODA's CEO and co-founder Matt Devost. The session provides insights which can benefit any entrepreneur, board member, investor or cybersecurity practitioner. Bilyana reviews Matt's journey from a small-town in Vermont to becoming a global leader in cybersecurity, counterterrorism, and risk management and then dives into Matt's work founding groundbreaking companies like FusionX and the Terrorism Research Center, his insights into AI and cyber defense, and even his contributions to Hollywood films like Blackhat. Matt also explores the evolving hacker community, the future of augmented reality, and why exponential technological change will reshape our world. This is a must-watch for anyone interested in the nexus of technology, security, and innovation.
- Dec 17, 202446 min
Episode 123: Forging Leadership: Admiral Studeman on Intelligence, National Security, and Proactivity
In this OODAcast, Bob Gourley interviews retired Admiral Mike Studeman, a leader with over 35 years of experience in operational intelligence and national security. Admiral Studeman shares his journey, from joining the Navy at the close of the Cold War to serving as the Director of Intelligence for Southern Command and Indo-Pacific Command, and ultimately as the Commander of the Office of Naval Intelligence. He offers deep insights into the evolving nature of intelligence, emphasizing the importance of operational intelligence in driving informed decision-making at all levels. Admiral Studeman discusses key lessons from his career, the value of continual learning, and his perspective on leadership—highlighting the importance of proactive action, integrity, and inspiring others. He also explores challenges facing America today, including leadership crises and the strategic implications of global shifts, particularly with respect to China. The discussion delves into his new book, Mind of the Chain: Forging Leaders of Iron Integrity, where he shares stories and reflections from his career, offering valuable advice to leaders at all stages of their journey. Admiral Studeman's message is clear: effective leadership requires constant learning, discernment, and a commitment to shaping a better future. For more see: MikeStudeman.com Might of the Chain: Forging Leaders of Iron Integrity
- Sep 13, 202441 min
Episode 122: Embracing the Future: Insights from Brandon Jones
In this episode of the OODAcast, Bob Gourley sits down with Brandon Jones, CEO of Throughline, to explore his career journey, the importance of liberal arts in technology, and the innovative work of Throughline. The conversation highlights the value of a diverse educational background and the pivotal role of communication and storytelling in driving organizational success. Brandon Jones shares his foundational story, emphasizing the impact of his time at St. Mary's College in Maryland, where he graduated with a computer science degree while also engaging deeply with liberal arts. His experience playing basketball and becoming the all-time leading scorer for men's basketball at St. Mary's taught him valuable lessons in teamwork and decision-making. This liberal arts background fostered a creative spark that later influenced his leadership style. Jones and Gourley discuss the importance of blending science and liberal arts education. Jones highlights the critical thinking skills developed through studying philosophy and other liberal arts subjects. He emphasizes the need for understanding problems deeply before jumping to solutions, a principle that has guided his career and approach to leadership. After graduating, Jones began his career at Electronic Data Systems (EDS), where he worked on the Navy Marine Corps Internet at the Pentagon. This role exposed him to high-level operations and decision-making within the Navy. His transition to public service came when he joined the Naval Facilities Engineering Systems Command (NAVFAC), where he ultimately served as the Chief Information Officer (CIO). As the CIO of NAVFAC, Jones faced numerous challenges, including cybersecurity threats and the need for application rationalization. He successfully reduced the number of applications from 3,000 to 200 and secured significant funding to enhance cybersecurity for naval facilities. His proactive approach and ability to communicate complex issues through compelling storytelling were crucial in achieving these milestones. Jones underscores the importance of storytelling in leadership. At NAVFAC, he used visual storytelling to convey the critical need for cybersecurity measures, which resulted in securing $100 million in funding and 100 full-time equivalents (FTEs) for cybersecurity efforts. This approach demonstrated the power of combining technical expertise with effective communication. Throughline, an enterprise design and strategy firm, blends creative agency capabilities with management consulting. Jones describes Throughline as the "Amazon of Storytelling," helping organizations communicate their strategies, visualize progress, and align talent with organizational goals. The firm's mission is to help human beings win, leading to organizational success. Jones acknowledges the competitive landscape but emphasizes Throughline's unique approach, rooted in a blend of IT and creative expertise. He highlights the importance of continuous learning, both personally and for his team. Jones reads extensively and invests in professional development to stay ahead in a rapidly evolving industry. The conversation also touches on the future of space exploration and technology, drawing on insights from Dr. Thomas PM Barnett's book, "America's New Map." Jones discusses the importance of understanding global trends and taking strategic actions to build a desirable future. Throughline's collaboration on the book exemplifies their commitment to shaping the future through innovative thinking and strategic foresight. Brandon Jones' journey from a liberal arts college to leading Throughline demonstrates the value of a diverse educational background, the power of storytelling in leadership, and the importance of continuous learning. His insights provide valuable lessons for leaders and organizations navigating the complexities of today's technological landscape. Connect with Brandon on LinkedIn. Related Reading: Technology Convergence and Market Disruption: Rapid advancements in technology are changing market dynamics and user expectations. See: Disruptive and Exponential Technologies. Corporate Board Accountability for Cyber Risks: With a combination of market forces, regulatory changes, and strategic shifts, corporate boards and their directors are now accountable for cyber risks in their firms. See: Corporate Directors and Risk Geopolitical-Cyber Risk Nexus: The interconnectivity brought by the Internet has made regional issues affect global cyberspace. Now, e
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