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...

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...

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 fro...

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...

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 Spy...

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 cybe...

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 In...

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 h...

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...

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...

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...

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...

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 vu...

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 serv...

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 Di...

Charles Clancy has successfully led technology efforts in government, industry, academia and continues to lead and innovate in his current position as Senior Vice President and GM of MITRE Labs. He is MITRE's Chief Futurist. His role in technology leadership and his tracking of tech across multiple domains made for an incredibly insightful OODAcast. We review Charles' insights into: Quantum Comput...

Mark McGrath has applied the teachings of John Boyd to a career that began in the Marine Corps, included leadership positions in financial services firms and consulting with businesses with a need to learn to thrive in volatile, uncertain, complex and ambiguous (VUCA) environments. He co-founded the consultancy AGLX and serves as its Chief Learning Officer. He is the co-host of the popular podcast...

Serene is a hacker in the truest sense of the word. She's applied a hacker mindset to learn coding, piano, and blend art and engineering in fascinating ways. You'll find her collaborating on-stage with Grimes one night and coding censorship resistant technologies the next day. As a self-taught coder she was the first engineer hired into Google Ideas when she was just a teenager. At Google she pion...

Andy Bochman is the Senior Grid Strategist-Defender for Idaho National Laboratory's National and Homeland Security directorate. In this role, Andy provides strategic guidance on topics at the intersection of grid security and climate resilience to INL leadership as well as senior U.S. and international government and industry leaders. Andy is a frequent speaker, writer, and trainer who has testifi...

Spencer Ante is the author or "Creative Capital: Georges Doriot and the Birth of Venture Capital", which was on my Top 10 book list for 2022. In fact, I found Doriot's story so compelling that a portrait of him hangs on the wall at the Hack Factory start-up studio in Reston, VA. Doriot is a compelling figure with an incredible story as told in Spencer's book.  He was a Harvard Business School prof...

ob Zukis is a man on a mission to improve the ability of corporate America to succeed in a complex digital world, even when under constant cyber attack. Bob is the CEO and founder of the Digital Directors Network, the global pioneer in helping corporate directors advance their understanding of systemic risk. We consider Bob to be the world's leading advocate for improving cybersecurity governance....

Adam Shostack is widely known in the cybersecurity world for his pioneering work on disclosing and discussing computer vulnerabilities (the CVE  (common vulnerabilities and exposures) list). He also helped formalize and train leading approaches to threat modeling and wrote the foundational book on the subject ( Threat Modeling: Designing for Security ). In this OODAcast we seek lessons from Adam's...

Sebastian Mallaby joined the OODAcast for a discussion about the Power Law in venture capital and the rise of the global hedge fund and private equity industries. Sebastian's book "The Power Law: Venture Capital and the Making of the New Future" is one of the most insightful books on the venture capital industry I've read to date and was included in my  Top 10 Security, Technology & Business books...

Neil Wiley has lead some of the US Intelligence Community's most important analytical functions. His career in intelligence began as a Naval Intelligence Officer in an operational intelligence center focused on support to critical operational naval missions. He would later serve joint intelligence missions in Europe, would rise to lead all analytical activities at the Defense Intelligence Agency a...

This OODAcast features a fascinating conversation with Michael Gibson, the author of the book "Paper Belt on Fire" who is also the co-founder of the Thiel Fellowship program and the 1517 Fund, both of which focus on identifying unconventional ideas and individuals that can drive disruptive innovation in technology, arts, and science. In this interview we dive into the establishment of the Thiel Fe...