Episode 129: The Attacker Mindset: Maxie Reynolds on Red Teaming, Underwater Data Centers, and Human Nature
OODAcast
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...
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Episode 128: The Money Trap: Alok Sama on SoftBank, Mega Bets, and Life Beyond Wall Street
OODAcast
In this episode of the OODAcast, host Matt Devost is joined by Alok Sama, author of , 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...
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Episode 127: Chris Wysopal on Reducing Attack Surface in the Age of AI
OODAcast
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...
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Episode 126: John Boyd, Maneuver Warfare, and the Future of the Marine Corps – A Conversation with Ian Brown
OODAcast
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...
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Episode 125: Unmasking Cyber Threats: Trevor Hilligoss’s Mission to Disrupt Criminal Networks
OODAcast
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...
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Episode 124: The History and Future of Cyberwar with Matt Devost
OODAcast
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...
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Episode 123: Forging Leadership: Admiral Studeman on Intelligence, National Security, and Proactivity
OODAcast
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...
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Episode 122: Embracing the Future: Insights from Brandon Jones
OODAcast
In this episode of the OODAcast, Bob Gourley sits down with Brandon Jones, CEO of , 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...
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Episode 121: Dr. Bilyana Lilly on Russian Information Warfare and Navigating Future Risks
OODAcast
In this OODAcast, Matt interviews Dr. Bilyana Lilly who is an expert on Russian information warfare and geo-political risk. Bilyana is also the author of the book Russian Information Warfare and the novel Digital Mindhunters. Dr. Lilly shares her fascinating origin story and how she emerged as one of the premiere experts on Russian information warfare and geopolitical dynamics. Bilyana has worked tracking international arms and weapons supply chains, conflict zones, and other geo-political dynamics in academia, the private sector, and at internationally renowned think tanks. She shares...
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Episode 120: Leadership and Innovation with Former NASA CIO and Current Executive Leader Renee Wynn
OODAcast
In this episode of the OODAcast, Bob Gourley interviews Renee Wynn, former Chief Information Officer (CIO) of NASA. Renee Wynn’s career trajectory is a testament to the unpredictable yet rewarding nature of professional journeys. Starting with a Bachelor of Arts in Economics from a liberal arts college, Renee navigated through various roles, ultimately becoming the CIO of NASA. She emphasizes the importance of focusing on capabilities rather than specific job titles, a mindset that allowed her to seize unexpected opportunities. The Value of Liberal Arts in Technology Renee underscores the...
info_outlineCharity Wright is a Cyber Threat Intelligence Analyst with over 15 years of experience at the US Army and the National Security Agency, where she translated Mandarin Chinese. Charity now specializes in dark web cyber threat intelligence, counter-disinformation, and strategic intelligence at Recorded Future. Her analysis has provided deep insights into a variety of incidents, activities and strategic moves by well resourced adversaries, primarily actors operating in China.
In July 2021 she led production of a report on China’s digital colonialism, surfacing aspects of espionage, surveillance and manipulation campaigns that were staggering in scope. China’s Digital Silk Road (DSR) initiative, announced in 2015, is an expansive global data infrastructure that does far more than serve users. It has been proven to have a dark side that includes exporting surveillance technologies to dictators and authoritarian regimes throughout the developing world, in some cases trading technology for access to sensitive user data and facial recognition intelligence. Domestically, China uses this type of technology to assert authority over its citizens, censor the media, quell protests, and systematically oppress religious minorities. Now, over 80 countries are enabled to do the same with Chinese surveillance technology.
In this OODAcast we examine Charity’s approach to analysis and review some of the key elements of her reporting on China’s Digital Silk Road. As we do we also examine ways that open societies can work together to help mitigate these threats.
We also examine Charity’s views on other global cyber threats and seek insights that can help any intelligence analyst continue to improve their craft.
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