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.

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

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, every significant event has cyber implications, making it imperative for leaders to recognize and act upon the symbiosis between geopolitical and cyber risks. See The Cyber Threat

Challenges in Cyber “Net Assessment”: While leaders have long tried to gauge both cyber risk and security, actionable metrics remain elusive. Current metrics mainly determine if a system can be compromised, without guaranteeing its invulnerability. It’s imperative not just to develop action plans against risks but to contextualize the state of cybersecurity concerning cyber threats. Despite its importance, achieving a reliable net assessment is increasingly challenging due to the pervasive nature of modern technology. See: Cyber Threat

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 fascinating insights from her time attending a Russian military conference with top leaders, her activities tracking information warfare and influence campaigns and then the conversation shifts to current geo-political risks including the conflict in Ukraine and what we can expect by way of targeting during the upcoming US election cycle.

Official Bio:

Dr. Bilyana Lilly is the chair of the cyber track at the Warsaw Security Forum and an adjunct researcher at the RAND Corporation. Dr. Lilly helps clients to detect and respond to ransomware threats and information warfare activities. Bilyana led a team that developed a threat-based risk assessment framework to prioritize vulnerabilities in critical infrastructure which the U.S. Department of Homeland Security now uses in all 50 states. She is a speaker at DefCon, CyCon, Executive Women's Forum, and the author of two books and a dozen publications, translated in Russian and Chinese. Dr. Lilly has been cited in the Wall Street Journal, Foreign Policy, and ZDNet. She has been denounced by Russia’s Ministry of Foreign Affairs. Lilly has a Ph.D. from Pardee RAND Graduate School, and master’s degrees from Oxford University (distinction) in England and the Graduate Institute in Switzerland.

Additional Resources:

• Connect with Dr. Lilly on LinkedIn
• Russian Information Warfare: Assault on Democracies in the Cyber Wild West

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 significance of her liberal arts education in her professional life. Her studies honed her writing skills, critical thinking, and ability to organize arguments—skills essential for effective communication and policy defense in public service. This foundation proved invaluable in her roles at the Environmental Protection Agency (EPA) and NASA, where she often had to articulate complex technical concepts to diverse audiences.

Renee’s tenure at the EPA was marked by her passion for the agency’s mission—ensuring clean air, water, and safe land use. Her role evolved with the advent of computers, sparking her interest in how technology can enhance mission delivery. This experience laid the groundwork for her transition to NASA, where she faced the challenges of managing a vast and complex IT infrastructure supporting global and off-world operations.

At NASA, Renee encountered a culture of profound dedication and love for the agency’s mission. She detailed the complexities of NASA’s operations, which include managing data from global and space-based sources. A significant part of her role involved ensuring the cybersecurity of these operations, particularly the International Space Station, where a cyber incident could have international repercussions.

Renee highlights the innovative integration of art and science in NASA’s projects. For instance, the James Webb Space Telescope’s sun shields, inspired by origami, demonstrate how artistic concepts can solve engineering challenges. This convergence of disciplines not only facilitates technical advancements but also fosters creativity and out-of-the-box thinking.

The conversation delves into the burgeoning space economy, where new opportunities such as space mining, in-orbit servicing, and space tourism are emerging. Renee points out the dual nature of these advancements—each new capability also presents potential risks, particularly in cybersecurity and ethical considerations.

Since retiring, Renee has embraced a portfolio career, serving on corporate and advisory boards, consulting, and engaging in public speaking. Her diverse roles keep her connected to cutting-edge technology and allow her to contribute her expertise to various sectors, including marketing and nonprofit organizations.

Renee Wynn’s journey from a liberal arts graduate to the CIO of NASA exemplifies the profound impact of a well-rounded education on a career in technology. Her insights into the integration of liberal arts and technical disciplines highlight the value of diverse perspectives in solving complex problems. As the space economy continues to evolve, her experiences and foresight offer valuable lessons for the future of technology and exploration.

Connect with Renee Wynn on LinkedIn

In this episode of OODAcast, Megan Jaffer joins the conversation to discuss her journey in the intelligence community and the creation of Iron Butterfly Media Group. Megan also discusses the expansion of Iron Butterfly Media, including new podcast series and a documentary on women in intelligence.

Megan shares her background, including her studies in international relations and her experiences in South Korea. She highlights the origins of the Iron Butterfly podcast, which began as a small project during COVID-19 and has grown significantly, becoming influential in both academia and intelligence agencies. The Iron Butterfly podcast aims to share stories of women in the intelligence community, documenting their contributions and leadership.

Throughout the podcast, Megan has shared numerous impactful stories. For instance, Carmen Medina’s insights on leadership, emphasizing the importance of avoiding humiliation in interactions, and Maria Whitcup’s emotional recount of engaging with a murderer, highlighting the necessity of understanding even the darkest aspects of human behavior.

Future Endeavors

Looking ahead, Iron Butterfly Media is expanding. The team has grown, and the podcast has moved to video format. They are also launching a new podcast, “Women in the Arena,” focusing on military women. Moreover, they are in post-production for a documentary on women in the intelligence community, aiming for completion by the end of the year.

Building a Supportive Community

In addition to the media group, Megan has founded the Iron Butterfly Foundation. This 501c3 organization aims to provide resources and support for women to develop and execute their ideas, fostering a community of creators.

Megan Jaffer’s journey is a testament to the power of determination, networking, and passion. Her work through the Iron Butterfly podcast and foundation continues to inspire and support women in the intelligence community, ensuring their stories and contributions are recognized and remembered.

For more insights and to support Iron Butterfly Media, visit their website and follow them on LinkedIn and Instagram.

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, every significant event has cyber implications, making it imperative for leaders to recognize and act upon the symbiosis between geopolitical and cyber risks. See The Cyber Threat

Challenges in Cyber “Net Assessment”: While leaders have long tried to gauge both cyber risk and security, actionable metrics remain elusive. Current metrics mainly determine if a system can be compromised, without guaranteeing its invulnerability. It’s imperative not just to develop action plans against risks but to contextualize the state of cybersecurity concerning cyber threats. Despite its importance, achieving a reliable net assessment is increasingly challenging due to the pervasive nature of modern technology. See: Cyber Threat

In this episode of OODAcast, Bob Gourley interviews Laura Thomas, a deep tech consultant and former CIA officer. Laura discusses her journey from a small town in North Carolina to a career in the CIA, where she served as a case officer. She emphasizes the importance of critical thinking and decision-making under uncertainty, and how these skills have translated to her work in deep tech.

Laura also highlights the potential of quantum computing and fusion energy, stressing the need for innovation and strategic investment in these transformative technologies.

Laura’s refreshing comments underscore why healthy debate is absolutely critical to good organizational decisions. She says “Disagree with me, I want to hear it, and don’t hold back!”

She provides some frameworks that can help leaders seeking to assess the dynamic geopolitical world we live in today. Her advice: “Zoom out.” Look at the bigger picture. And think through multiple scenarios. She is a huge fan of scenario planning.

Anyone who claims they know the future, she says, is likely a charlatan. Be very careful when you hear someone trying to tell you they know exactly what comes next.

We talk about Deep Tech.

Laura publishes online at Lauraethomas.com. Her writings there include expert insights into topics like how to engage technical experts at US national labs, agencies and academia to land your next role, things to know about national security deep tech, unique insights into transitioning to the private sector, and fact based observations on espionage and sex.

Find Laura on linkedin at: Laura Thomas

Allan Friedman is a senior strategist at CISA (the Cyber Security and Infrastructure Security Agency) where he coordinates all of their cross-sector activities on the topic of SBOM: The Software Bill of Materials.

Allan is widely known as a change agent in both the public and private sector. In government he led initiatives that created positive change in major community-wide initiatives around vulnerability disclosure and vulnerability management. He also championed efforts that made dramatic improvements in the ability to reduce risk due to the proliferation of Internet of Things devices including championing ways to keep these devices patched in the field. Now at CISA his SBOM efforts have produced action across a sector that few other initiatives have.

We discuss:

- What executive leaders need to know about SBOM and how to explain its benefits to any non-technical executive.

- How a small team can establish a vision and make change across government, industry and academia.

- What new initiatives may be coming that will support needs of the security and technology communities.

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, every significant event has cyber implications, making it imperative for leaders to recognize and act upon the symbiosis between geopolitical and cyber risks. See The Cyber Threat

Challenges in Cyber “Net Assessment”: While leaders have long tried to gauge both cyber risk and security, actionable metrics remain elusive. Current metrics mainly determine if a system can be compromised, without guaranteeing its invulnerability. It’s imperative not just to develop action plans against risks but to contextualize the state of cybersecurity concerning cyber threats. Despite its importance, achieving a reliable net assessment is increasingly challenging due to the pervasive nature of modern technology. See: Cyber Threat

Joe Sullivan has been at the forefront of managing security risk in rapidly growing high tech companies over the past 20 years serving as the Chief Security Officer at Facebook from early start-up through the IPO, CSO of Uber and CloudFlare, and as a security leader at eBay/PayPal. Joe was also involved in a landmark legal case for a breach at Uber which resulted in a criminal conviction that serves as a precedent for executive liability in cybersecurity going forward.

In this OODAcast we discuss:

• Joe's early career and how he got interested and involved in technology and started his career as a federal prosecutor focused on cyber crime.
• The transition into serving as a technology company CSO and his experiences at eBay/PayPal, Facebook, Uber and Cloudflare.
• Lessons learned from building and managing highly functional security teams in dynamic environments.
• Frameworks for managing risk at companies like Facebook and Uber.
• His experiences being prosecuted and convicted surrounding circumstances associated with a 2016 incident at Uber.
• How the courts will handle future cases like this and the associated liability for C-suite executives.
• His current work focused on supplying technology for remote learning to displaced children in Ukraine.

Official Bio:Joe Sullivan is CEO of Ukraine Friends and President of Joe Sullivan Security LLC. Previously, Joe had served as the Chief Security Officer of Cloudflare since July (2018 - 2022). Prior to that, Joe was employed as Chief Security Officer at both Uber (2015 - 2017) and Facebook (2008 - 2015). His first private sector experience was in senior security and legal roles at eBay and PayPal (2002 - 2008). He also held the position of Commissioner for the United States Presidential Commission on Enhancing National Cybersecurity in 2016 and spent the first eight years of his career with the US Department of Justice, including as a federal prosecutor focused on cyber crime. Joe also advises a number of companies on security practices and mentors a number of developing security leaders.

Recommended Books:

Russia: Revolution and Civil War, 1917-1921

Beneath A Scarlet Sky

Joe Tranquillo is a Professor of Biomedical Engineering at Bucknell University and a provost at the school.

He is also and author and speaker with a knack for helping make new and at times complex subjects understandable. In this OODAcast we discuss many aspects of the revolution in biological sciences with Joe including topics like:

• New ways of delivering medicines that target specific tissues
• Discovery of the structure of almost every human protein
• Methods to synthesize biomolecules, which can result in ways to manufacture a wide range of materials like therapeutics, flavors, fabrics, food, fuels.
• New ways of growing food that are more productive and take fewer pesticides and fertilizers.

We also discuss the concept of complex systems and lessons from complex systems theory that apply not only to biological sciences and engineering but to many complex human activities and creations. We examine ways leaders can improve their ability to think in terms of complex systems, ways that technologists can use systems thinking to better communicate with non-technical people, and insights for executives on where the revolution in biological sciences is taking us.